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Step into this beautiful 1924 cedar shake home in Homewood where original character meets thoughtful modern additions and upgrades. This is not a flipped home – one household has lived here for 30 years. It has been meticulously maintained, updated and restored. Almost 1500 square feet of living on one floor provides unexpected space and flow. This doesn’t include a finished basement. The original part of the home is charming and well preserved. It has beautiful plaster walls and ceilings with no cracks – it has been skillfully skim coated throughout. The original Douglas Fir floors have been recently sanded and refinished. French doors divide the dining room and living room, along with a pocket door. The full bath is a reflection of the timeless style of the era, with pedestal sink, black and white tile floor and floating cabinet with custom walnut top, designed by a master craftsman. The tiled walls align this jack and jill bathroom separating 2 bedrooms. The dining room leads to the heart of the home – a one-of-a-kind, custom modern kitchen with Brazilian quartzite countertops, high gloss cabinetry, custom built ins, hand cut porcelain backsplash, skylight, new stainless steel appliances, and custom hand-built fan hood. Attached to the kitchen is a gorgeous, intimate, boutique bar, which adjoins the family room, offering an open living space. The kitchen, bar and family room have unique short-planked 3/4 tongue and groove maple floors. Off the family room are large glass doors, leading to the deck. Next, the large master suite with its own full bathroom, featuring a soaking tub, tile floors, walls and double vanity. The spacious master bedroom features 3 closets and ¾” tongue and groove oak floors. The finished basement adds flexible space for a media room and office or guest suite. The full bathroom features tile floors, a stand alone shower and vanity. The basement also includes finished laundry area, storage room and pantry. The roof was recently inspected and is in good shape. A large unfinished attic, that spans the entire home, offers endless storage space. The entire home has been updated with dimmable LED recessed lighting, providing multiple lighting options in every room. HVAC consists of Trane A/C until and Carrier gas furnace. The beautiful mature, landscaped double lot adds tremendous value to this homestead. It is a private retreat with a beautiful canopy of well-established trees, a large low maintenance composite deck, and separate flagstone patio. The outdoor space is quiet and serene, offering plenty of room to dine, entertain, garden and gather. A cottage-style cedar shake detached garage completes the package. The highly desired Homewood neighborhood is hard to beat. Lined with trees, it’s a short distance to the historic Annapolis waterfront, Navy stadium, and a wide selection of lively restaurants and bars. This home has easy access to Washington DC or Baltimore or the Bay Bridge. Don’t miss the opportunity to own this rare gem! Note: no photos are taken with a wide angle lens – they accurately represent the space.

3 Beds ⋅ 2 Baths

Step into this beautiful 1924 cedar shake home in Homewood where original character meets thoughtful modern additions and upgrades. This is not a flipped home – one household has lived here for 30 years. It has been meticulously maintained, updated and restored. Almost 1500 square feet of living on one floor provides unexpected space and flow. This doesn’t include a finished basement. The original part of the home is charming and well preserved. It has beautiful plaster walls and ceilings with no cracks – it has been skillfully skim coated throughout. The original Douglas Fir floors have been recently sanded and refinished. French doors divide the dining room and living room, along with a pocket door. The full bath is a reflection of the timeless style of the era, with pedestal sink, black and white tile floor and floating cabinet with custom walnut top, designed by a master craftsman. The tiled walls align this jack and jill bathroom separating 2 bedrooms. The dining room leads to the heart of the home – a one-of-a-kind, custom modern kitchen with Brazilian quartzite countertops, high gloss cabinetry, custom built ins, hand cut porcelain backsplash, skylight, new stainless steel appliances, and custom hand-built fan hood. Attached to the kitchen is a gorgeous, intimate, boutique bar, which adjoins the family room, offering an open living space. The kitchen, bar and family room have unique short-planked 3/4 tongue and groove maple floors. Off the family room are large glass doors, leading to the deck. Next, the large master suite with its own full bathroom, featuring a soaking tub, tile floors, walls and double vanity. The spacious master bedroom features 3 closets and ¾” tongue and groove oak floors. The finished basement adds flexible space for a media room and office or guest suite. The full bathroom features tile floors, a stand alone shower and vanity. The basement also includes finished laundry area, storage room and pantry. The roof was recently inspected and is in good shape. A large unfinished attic, that spans the entire home, offers endless storage space. The entire home has been updated with dimmable LED recessed lighting, providing multiple lighting options in every room. HVAC consists of Trane A/C until and Carrier gas furnace. The beautiful mature, landscaped double lot adds tremendous value to this homestead. It is a private retreat with a beautiful canopy of well-established trees, a large low maintenance composite deck, and separate flagstone patio. The outdoor space is quiet and serene, offering plenty of room to dine, entertain, garden and gather. A cottage-style cedar shake detached garage completes the package. The highly desired Homewood neighborhood is hard to beat. Lined with trees, it’s a short distance to the historic Annapolis waterfront, Navy stadium, and a wide selection of lively restaurants and bars. This home has easy access to Washington DC or Baltimore or the Bay Bridge. Don’t miss the opportunity to own this rare gem! Note: no photos are taken with a wide angle lens – they accurately represent the space.

113 Mckendree Ave, Annapolis

Listing courtesy of Homecoin.com. Contact:

$2,100,000

Homes this charming and inviting located on Horn Point in Eastport don't come on the market that often! This delightful home exudes classic elegance and modern comfort. Updates are already completed so you don't have to do a thing but move right in. The open floor plan with immaculate hard wood flooring invites you to relax or entertain. The kitchen and family room "great room" and gas fireplace overlook the private patio and gardens. A huge bonus is the large, primary bedroom suite on the main level. Loads of natural light everywhere in this home. Beautiful renovation with four spacious bedrooms and two and a half baths, the layout is designed for both relaxation and entertaining. The heart of the home features a family room that flows seamlessly into the kitchen, complete with an inviting island and upgraded countertops. Enjoy cozy evenings by the fireplace, adorned with glass doors and a classic mantel. The hardwood floors throughout add warmth, while built-ins provide both style and functionality. The unfinished basement offers potential for customization, with walkout stairs leading to the landscaped yard, perfect for outdoor gatherings. This urban gem is just blocks from the Severn River, where you can enjoy leisurely walks or hop on a boat and enjoy the Chesapeake Bay. The community is vibrant, with local parks, shops, and dining options that foster a friendly atmosphere. There's ample space for gardening or play. Parking is a breeze with a driveway and on-street options. This home is not just a property; it's a place where memories are made, surrounded by a welcoming community that truly feels like home.

4 Beds ⋅ 3 Baths

Homes this charming and inviting located on Horn Point in Eastport don't come on the market that often! This delightful home exudes classic elegance and modern comfort. Updates are already completed so you don't have to do a thing but move right in. The open floor plan with immaculate hard wood flooring invites you to relax or entertain. The kitchen and family room "great room" and gas fireplace overlook the private patio and gardens. A huge bonus is the large, primary bedroom suite on the main level. Loads of natural light everywhere in this home. Beautiful renovation with four spacious bedrooms and two and a half baths, the layout is designed for both relaxation and entertaining. The heart of the home features a family room that flows seamlessly into the kitchen, complete with an inviting island and upgraded countertops. Enjoy cozy evenings by the fireplace, adorned with glass doors and a classic mantel. The hardwood floors throughout add warmth, while built-ins provide both style and functionality. The unfinished basement offers potential for customization, with walkout stairs leading to the landscaped yard, perfect for outdoor gatherings. This urban gem is just blocks from the Severn River, where you can enjoy leisurely walks or hop on a boat and enjoy the Chesapeake Bay. The community is vibrant, with local parks, shops, and dining options that foster a friendly atmosphere. There's ample space for gardening or play. Parking is a breeze with a driveway and on-street options. This home is not just a property; it's a place where memories are made, surrounded by a welcoming community that truly feels like home.

513 First St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$965,000

OPEN SUN 11-1pm! Welcome to 46 Lafayette Avenue, nestled in the heart of Murray Hill, one of Annapolis' most desirable and walkable neighborhoods! Perfectly situated in this charming historic community, this exceptional home is within walking distance to Lafayette Waterfront park, and a little more than a block from the vibrant shops and restaurants on West Street and all the excitement of Downtown Annapolis. Rich in character and thoughtfully updated, this beautiful home seamlessly blends historic charm with modern conveniences. Original pine floors welcome you inside, leading to a stunning gourmet Kitchen featuring a gorgeous marble center island, stainless appliances, and classic subway tile backsplash. The Kitchen flows effortlessly into the inviting dining and living spaces,, creating the perfect setting for everyday living and entertaining. Attention to detail is evident with custom plantation shutters, upgraded lighting, convenient main level laundry, and a charming covered front porch, ideal for relaxing and enhjoy the neighborhood atmosphere. Offering 3 finished levels this home features four BR's, a cozy sitting area, and a dedicated home office, providing wonderful flexibility for today's lifestyle. Step outside to your private backyard patio and garden, an inviting retreat perfect for gatherings. There is a full unfinished basement providing convenience and dry storage. Significant improvements since 2018 include updates to the roof, HVAC and exterior adding to this home's appeal. This is your opportunity to own in Murray Hill and enjoy the charm, character and walkable lifestyle of Annapolis.

4 Beds ⋅ 2 Baths

OPEN SUN 11-1pm! Welcome to 46 Lafayette Avenue, nestled in the heart of Murray Hill, one of Annapolis' most desirable and walkable neighborhoods! Perfectly situated in this charming historic community, this exceptional home is within walking distance to Lafayette Waterfront park, and a little more than a block from the vibrant shops and restaurants on West Street and all the excitement of Downtown Annapolis. Rich in character and thoughtfully updated, this beautiful home seamlessly blends historic charm with modern conveniences. Original pine floors welcome you inside, leading to a stunning gourmet Kitchen featuring a gorgeous marble center island, stainless appliances, and classic subway tile backsplash. The Kitchen flows effortlessly into the inviting dining and living spaces,, creating the perfect setting for everyday living and entertaining. Attention to detail is evident with custom plantation shutters, upgraded lighting, convenient main level laundry, and a charming covered front porch, ideal for relaxing and enhjoy the neighborhood atmosphere. Offering 3 finished levels this home features four BR's, a cozy sitting area, and a dedicated home office, providing wonderful flexibility for today's lifestyle. Step outside to your private backyard patio and garden, an inviting retreat perfect for gatherings. There is a full unfinished basement providing convenience and dry storage. Significant improvements since 2018 include updates to the roof, HVAC and exterior adding to this home's appeal. This is your opportunity to own in Murray Hill and enjoy the charm, character and walkable lifestyle of Annapolis.

46 Lafayette Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$450,000

SIMULCAST AUCTION. Online pre-bidding begins November 17, 2026 at 10:00 AM ET. Live bidding begins November 19, 2026 at 1:00 PM ET, both on-site at 316 Chester Ave and online through the Ashland Auction Group bidding platform. List price is the suggested opening bid. A 10% buyer’s premium will be added to the high bid. On-site bidders must bring a $10,000 cashier’s check. Online bidders must register and complete the required credit card authorization. Pre-auction offers may be accepted. Built in 1920, this detached Eastport home offers 2 bedrooms and 2 full bathrooms. Inside, the home features a living room, dining room, hardwood floors, and an interior staircase. The outdoor space includes a patio and rear yard on approximately 0.07 acres. Butler’s Marina is nearby on Chester Avenue, and the Annapolis Maritime Museum’s waterfront campus is on Second Street. Eastport’s restaurants and marinas are nearby, with downtown Annapolis and City Dock across the Spa Creek Bridge. The property needs updates and is sold as-is.

2 Beds ⋅ 2 Baths

SIMULCAST AUCTION. Online pre-bidding begins November 17, 2026 at 10:00 AM ET. Live bidding begins November 19, 2026 at 1:00 PM ET, both on-site at 316 Chester Ave and online through the Ashland Auction Group bidding platform. List price is the suggested opening bid. A 10% buyer’s premium will be added to the high bid. On-site bidders must bring a $10,000 cashier’s check. Online bidders must register and complete the required credit card authorization. Pre-auction offers may be accepted. Built in 1920, this detached Eastport home offers 2 bedrooms and 2 full bathrooms. Inside, the home features a living room, dining room, hardwood floors, and an interior staircase. The outdoor space includes a patio and rear yard on approximately 0.07 acres. Butler’s Marina is nearby on Chester Avenue, and the Annapolis Maritime Museum’s waterfront campus is on Second Street. Eastport’s restaurants and marinas are nearby, with downtown Annapolis and City Dock across the Spa Creek Bridge. The property needs updates and is sold as-is.

316 Chester Ave, Annapolis

Listing courtesy of Ashland Auction Group LLC. Contact:

$459,900

Opportunity awaits at 711 Melrose Street, directly across from Navy-Marine Corps Memorial Stadium in one of Annapolis’s most sought-after locations. This original home is ready for a full renovation, making it an ideal project for investors, builders, or buyers looking to create something truly their own. The current layout offers 2 bedrooms, 1 full bath, and a partially finished basement with room to expand living space. Outside, enjoy a generous backyard with a storage shed, plus a newly installed driveway with parking for 2+ cars, a rare convenience in this area. Just minutes from the U.S. Naval Academy, downtown Annapolis, and the waterfront, this location offers lasting value in the heart of Anne Arundel County. Bring your vision and make the most of this exceptional setting. Property is being sold strictly as-is.

2 Beds ⋅ 1 Baths

Opportunity awaits at 711 Melrose Street, directly across from Navy-Marine Corps Memorial Stadium in one of Annapolis’s most sought-after locations. This original home is ready for a full renovation, making it an ideal project for investors, builders, or buyers looking to create something truly their own. The current layout offers 2 bedrooms, 1 full bath, and a partially finished basement with room to expand living space. Outside, enjoy a generous backyard with a storage shed, plus a newly installed driveway with parking for 2+ cars, a rare convenience in this area. Just minutes from the U.S. Naval Academy, downtown Annapolis, and the waterfront, this location offers lasting value in the heart of Anne Arundel County. Bring your vision and make the most of this exceptional setting. Property is being sold strictly as-is.

711 Melrose St, Annapolis

Listing courtesy of Next Step Realty. Contact:

$1,795,000

Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

4 Beds ⋅ 4 Baths

Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

830 Chester Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$599,000

Charming Homewood cottage with numerous recent updates! This property is located on a partially secluded lot bordering city-owned, undevelopable land encompassing the headwaters of College Creek. Enjoy a peaceful setting on the back deck with a sense of privacy, all while being conveniently located near downtown Annapolis, shopping, dining, and local amenities. Recent improvements include a newer hot water heater, HVAC system, appliances, windows, newly renovated bathroom, insulation, asphalt driveway, hardscape walkway and retaining wall. A detached finished shed with dedicated electric offers flexible space with the potential to serve as a private home office, studio, or hobby space. This delightful cottage combines classic charm, thoughtful updates, and a convenient Annapolis location! Don't miss this one!

2 Beds ⋅ 1 Baths

Charming Homewood cottage with numerous recent updates! This property is located on a partially secluded lot bordering city-owned, undevelopable land encompassing the headwaters of College Creek. Enjoy a peaceful setting on the back deck with a sense of privacy, all while being conveniently located near downtown Annapolis, shopping, dining, and local amenities. Recent improvements include a newer hot water heater, HVAC system, appliances, windows, newly renovated bathroom, insulation, asphalt driveway, hardscape walkway and retaining wall. A detached finished shed with dedicated electric offers flexible space with the potential to serve as a private home office, studio, or hobby space. This delightful cottage combines classic charm, thoughtful updates, and a convenient Annapolis location! Don't miss this one!

30 Woodlawn Ave, Annapolis

Listing courtesy of Compass. Contact:

$700,000

Stunning, updated home on a spacious .6-acre lot located just 2 miles from historic downtown Annapolis. The main level boasts beautifully refinished hardwood floors, updated eat-in kitchen, and a separate dining room. The bright living room with a wood-burning fireplace flows effortlessly toward outdoor living, featuring a spacious screened-in porch that exits to a large back deck. A desirable main-floor bedroom with a full ensuite bathroom offers ultimate convenience. Upstairs, you will find three additional hardwood-floored bedrooms sharing a tastefully updated full bathroom. The versatile basement provides a flexible space perfect for a rec room or fifth bedroom, complete with a full bath, laundry, and ample storage. The expansive, private backyard completes this property with a detached one-car garage and an additional separate storage shed.

5 Beds ⋅ 3 Baths

Stunning, updated home on a spacious .6-acre lot located just 2 miles from historic downtown Annapolis. The main level boasts beautifully refinished hardwood floors, updated eat-in kitchen, and a separate dining room. The bright living room with a wood-burning fireplace flows effortlessly toward outdoor living, featuring a spacious screened-in porch that exits to a large back deck. A desirable main-floor bedroom with a full ensuite bathroom offers ultimate convenience. Upstairs, you will find three additional hardwood-floored bedrooms sharing a tastefully updated full bathroom. The versatile basement provides a flexible space perfect for a rec room or fifth bedroom, complete with a full bath, laundry, and ample storage. The expansive, private backyard completes this property with a detached one-car garage and an additional separate storage shed.

1925 Fairfax Rd, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

$314,900

2 Beds ⋅ 1 Baths

208 Admiral Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

$2,199,000

Welcome to one of Annapolis’ most sought-after water-access communities, where timeless character meets extensive, thoughtful improvements. Since 2022, the sellers have invested extensively in enhancing the home's living spaces, major systems, and outdoor setting, while carefully preserving its original character. Major improvements include a beautifully reimagined kitchen, renovated primary and secondary baths, updated bedrooms, custom millwork and library built-ins, upgraded electrical and lighting, and extensive interior and exterior painting. Additional enhancements include updates to the home's heating systems, whole-house water filtration, and a thoughtfully redesigned family room with an inviting stove and improved flow throughout the main level. Outside, the transformation is equally impressive. Extensive professional landscaping and hardscaping have created a private, beautifully designed setting featuring a stone patio, firepit, landscape lighting, lush gardens, and multiple spaces for outdoor entertaining. A garage provides coveted off-street parking, with ample street parking available for guests. The list of improvements goes well beyond what can be captured here. This is a home that truly deserves to be experienced in person to appreciate the care, attention, and investment that have gone into it. Living in Wardour is about much more than the home. Residents enjoy access to private community beaches, kayak storage, wooded trails, and waterfront pathways—all just minutes from the heart of Annapolis. The neighborhood offers an exceptional combination of convenience and lifestyle, with a Blue Ribbon elementary school, coffee shop, ice cream shop, brewery, café, grocery store, upscale dining, and numerous neighborhood restaurants close by. Downtown Annapolis and Navy-Marine Corps Memorial Stadium are both within walking distance, while nearby Route 50 provides easy access to Washington, D.C., Baltimore, and the Eastern Shore. Beautifully updated, meticulously landscaped, and ideally located, this is a wonderful opportunity to enjoy the best of the Annapolis lifestyle in one of its most desirable communities.

3 Beds ⋅ 3 Baths

Welcome to one of Annapolis’ most sought-after water-access communities, where timeless character meets extensive, thoughtful improvements. Since 2022, the sellers have invested extensively in enhancing the home's living spaces, major systems, and outdoor setting, while carefully preserving its original character. Major improvements include a beautifully reimagined kitchen, renovated primary and secondary baths, updated bedrooms, custom millwork and library built-ins, upgraded electrical and lighting, and extensive interior and exterior painting. Additional enhancements include updates to the home's heating systems, whole-house water filtration, and a thoughtfully redesigned family room with an inviting stove and improved flow throughout the main level. Outside, the transformation is equally impressive. Extensive professional landscaping and hardscaping have created a private, beautifully designed setting featuring a stone patio, firepit, landscape lighting, lush gardens, and multiple spaces for outdoor entertaining. A garage provides coveted off-street parking, with ample street parking available for guests. The list of improvements goes well beyond what can be captured here. This is a home that truly deserves to be experienced in person to appreciate the care, attention, and investment that have gone into it. Living in Wardour is about much more than the home. Residents enjoy access to private community beaches, kayak storage, wooded trails, and waterfront pathways—all just minutes from the heart of Annapolis. The neighborhood offers an exceptional combination of convenience and lifestyle, with a Blue Ribbon elementary school, coffee shop, ice cream shop, brewery, café, grocery store, upscale dining, and numerous neighborhood restaurants close by. Downtown Annapolis and Navy-Marine Corps Memorial Stadium are both within walking distance, while nearby Route 50 provides easy access to Washington, D.C., Baltimore, and the Eastern Shore. Beautifully updated, meticulously landscaped, and ideally located, this is a wonderful opportunity to enjoy the best of the Annapolis lifestyle in one of its most desirable communities.

102 Melvin Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$859,000

NEWLY UPDATED! NEW BATHROOMS, GARAGE, and A BONUS 3rd FLOOR ROOM. Boasting 1,670 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized 0.26-acre lot! Offering space and flexibility nearly impossible to find this close to City Dock. While the main house charms with high ceilings, refinished hardwoods, and a light-filled 3-seasons wrap-around porch, the true crown jewel is the backyard oasis. Surrounded by stunning, mature trees and a double oversized lot as well as a brand NEW GARAGE WITH ELECTRICITY! Walk to the Navy Stadium, local cafes, and the Poplar Trail. Note on Square Footage: Finished square footage has been updated to 1,670 sq. ft. based on recent agent measurements. Public tax records currently reflect inaccurate historical data (1,442 sq. ft.) and do not fully capture the complete finished living area.

3 Beds ⋅ 2 Baths

NEWLY UPDATED! NEW BATHROOMS, GARAGE, and A BONUS 3rd FLOOR ROOM. Boasting 1,670 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized 0.26-acre lot! Offering space and flexibility nearly impossible to find this close to City Dock. While the main house charms with high ceilings, refinished hardwoods, and a light-filled 3-seasons wrap-around porch, the true crown jewel is the backyard oasis. Surrounded by stunning, mature trees and a double oversized lot as well as a brand NEW GARAGE WITH ELECTRICITY! Walk to the Navy Stadium, local cafes, and the Poplar Trail. Note on Square Footage: Finished square footage has been updated to 1,670 sq. ft. based on recent agent measurements. Public tax records currently reflect inaccurate historical data (1,442 sq. ft.) and do not fully capture the complete finished living area.

21 Woodlawn Ave, Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

$1,700,000

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U.S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is equally inviting, with a private patio and lush turf yard overlooking Cumberland Court—an ideal setting for morning coffee, al fresco dining, summer gatherings, or simply enjoying the charm of downtown living. Surrounded by the history, culture, shops, restaurants, and waterfront that make the Historic District so special, this distinctive home offers an authentic Annapolis lifestyle, blending historic charm, modern comfort, exceptional walkability, and an unusually generous amount of private parking.

3 Beds ⋅ 3 Baths

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets modern comfort. Built in 1900, this inviting residence captures the quintessential charm of Annapolis while offering thoughtful updates and the conveniences of contemporary living. Steps away from the welcoming front porch you'll find boutique shops, waterfront dining, historic landmarks, and the U.S. Naval Academy. Inside, original hardwood floors and classic architectural details create a warm and inviting atmosphere. The layout features three bedrooms, two full bathrooms, and a half bath. The main level offers comfortable living and entertaining spaces along with a welcoming kitchen, while a carefully renovated room addition provides valuable additional living space. The primary bathroom has been beautifully styled with a luxurious spa-like feel, creating a peaceful retreat at the end of the day. Outdoor living is equally inviting, with a private patio and lush turf yard overlooking Cumberland Court—an ideal setting for morning coffee, al fresco dining, summer gatherings, or simply enjoying the charm of downtown living. Surrounded by the history, culture, shops, restaurants, and waterfront that make the Historic District so special, this distinctive home offers an authentic Annapolis lifestyle, blending historic charm, modern comfort, exceptional walkability, and an unusually generous amount of private parking.

219 King George St, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,675,000

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

5 Beds ⋅ 3 Baths

Ideally situated on the corner of Prince George & College Ave(across from St Johns College), this distinguished residence is tucked in the heart of Historic Downtown Annapolis. This exceptional home offers the charm of an Historic home built circa 1800's with modern conveniences. Soaring ceilings and windows create sun-drenched rooms with beautiful views of the grounds at St. Johns College. This home was built for entertaining. It has amazing flow to entertain your guests for a dinner party. Take a short walk to outdoor dining on West Street during "Dinner Under the Stars" or host friends for all the amazing Downtown events like Midnight Madness. This home is in the heart of it all! The electrical and plumbing was updated in 1990, new hot water heater in 2024, 2 heat pumps in 2025 and new Shake Shingle roof in 2026. There are 4 bedrooms and 2 full baths on the second floor with a bonus room on the third floor great for guests or office. All this just 1.5 blocks from the Naval Academy and steps to the shops and amazing restaurants Annapolis has to offer! There is driveway with private parking for 2 cars and plenty of street parking for guests. Walk to City Dock for morning coffee and watch the boats pass by or sit in the morning room and enjoy your coffee looking over the grounds of St. Johns. This is an amazing house in an amazing location with all that Annapolis has to offer.

250 Prince George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,395,000

Highly desirable Eastport location just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

4 Beds ⋅ 5 Baths

Highly desirable Eastport location just a short walk to Historic Annapolis, the U.S. Naval Academy, vibrant restaurants, boutique shops, and multiple marinas. This rare offering features essentially two separate homes on one property, creating an exceptional opportunity for multi‑generational living, guest accommodations, potential rental income, or a private studio/office retreat. The beautifully updated three‑level Cape Cod has been thoughtfully expanded and modernized. It features a gourmet kitchen, hardwood floors, two generous bedrooms, and 2.5 bathrooms. The main level office provides flexibility and can easily function as an additional bedroom. Every level blends comfort with style, offering bright spaces and quality finishes throughout. At the rear of the property sits an eclectic secondary structure with two cozy bedrooms and two full baths. Its lower level includes garage space and abundant storage ideal for bikes, paddleboards, tools, or seasonal items. Outdoor living shines here: a spacious deck and stone patio create inviting spaces for entertaining, grilling, or unwinding in a peaceful setting. With numerous exterior upgrades and a location that captures the best of Eastport living, this property is truly one of a kind.

1030 Boucher Ave, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$1,300,000

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

5 Beds ⋅ 4 Baths

A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind.

135 Conduit St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$2,795,000

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

3 Beds ⋅ 3 Baths

Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home.

113 Bay Dr, Annapolis

Listing courtesy of Krauss Real Property Brokerage. Contact:

$1,875,000

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

4 Beds ⋅ 4 Baths

***Owner financing available at 6%*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best.

400 Jefferson St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

$1,495,000

A significant price reduction has been made on this stunning home! Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek and parking on both sides of street, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

3 Beds ⋅ 3 Baths

A significant price reduction has been made on this stunning home! Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek and parking on both sides of street, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation and completely fenced in. Features 2 ensuite Bedrooms and a 3rd enclosed Bedroom easily adapted into a private home office or gym while still preserving the home's architectural flow. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living.

100 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$540,000

Price adjusted to reflect market response. AND it's open 10/31 & 11/1 ! There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

3 Beds ⋅ 2 Baths

Price adjusted to reflect market response. AND it's open 10/31 & 11/1 ! There's history here. In the 1940s, the Meade family built a number of homes on President Street and in Hillsmere — Meade Street bears their name. For the first time, the family will be passing on this home, one of the last one still in family hands, to new owners. Original wood trim, high ceilings, and wood floors pair with a surprisingly open floor plan for its age. The third bedroom and kitchen were added in the 1960's. The daughters' bedroom was the upper level for many years. A detached garage with an attached screened porch is perfectly positioned for outdoor entertaining. The yard is large and fenced. This home only needs the new owner's personal touches to make it once again a forever home!

1309 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$550,000

Eastport! Eastport! Eastport! Corner lot that consists of 9,240 square feet. Off street parking and street parking. Stainless steel refrigerator, washer and dryer, and storage in lower level off the kitchen and in the upper level. New 10 foot by 15 foot shed. Separate dining room. Back porch 21 feet by 7 feet. Partially fenced back yard. Upstairs bedroom has unique wood ceiling. Freshly painted living room, 2 bedrooms, and dining room. Lot has room for expansion. Close to downtown, Quiet Waters Park, and Eastport Shopping Center. Easy access to main streets.

3 Beds ⋅ 1 Baths

Eastport! Eastport! Eastport! Corner lot that consists of 9,240 square feet. Off street parking and street parking. Stainless steel refrigerator, washer and dryer, and storage in lower level off the kitchen and in the upper level. New 10 foot by 15 foot shed. Separate dining room. Back porch 21 feet by 7 feet. Partially fenced back yard. Upstairs bedroom has unique wood ceiling. Freshly painted living room, 2 bedrooms, and dining room. Lot has room for expansion. Close to downtown, Quiet Waters Park, and Eastport Shopping Center. Easy access to main streets.

1311 President St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$700,000

Welcome to 1025 Hanson Street, offering nearly 2,880 sq. ft. of exceptionally flexible living space across three finished levels in the heart of Annapolis! Perfect for a multi-generational family. Thoughtfully improved and meticulously maintained, this turn-key home provides a rare combination of space, versatility, parking and major system upgrades. The main and upper levels feature 4 bedrooms, a full bath, a bright and open living area, an updated kitchen with granite countertops and tile backsplash, and dedicated laundry with front-loading washer and dryer, utility sink and additional storage. The fully finished ground level creates an incredible second living space featuring 2 additional bedrooms, a den/office, full bath, stunning secondary kitchen (minus stove/oven) with granite countertops, stainless steel appliances and tile backsplash, a second laundry setup with utility sink, and new LVP flooring throughout. A private side entrance, new fencing, paver walkway and patio access provide tremendous flexibility for multi-generational living, extended guests, a home office setup or simply additional space to spread out. Outside, you'll find features that are especially hard to come by in Annapolis—including dual driveways with parking for 6+ vehicles and/or boats, along with a two-story detached shed offering excellent storage and convenient yard and street access. Extensive improvements provide peace of mind, including a NEW 2025 roof on both the home and shed with transferable warranty, updated HVAC including heat pump and indoor coil, 60-gallon hybrid high-efficiency water heater, 200-amp electrical service, Tesla EV charger, French drain and stormwater management system, sump pump, updated attic insulation with spray foam, Nest thermostats, updated siding, additional ground-level egress, ceiling fans, fresh paint and much more. With three finished levels, two distinct living areas, exceptional parking and storage, and numerous major capital improvements already completed, 1025 Hanson Street offers the kind of versatility that's difficult to find in Annapolis. Whether you're looking for room for a growing household, multi-generational living, extended guests, midshipman sponsor hosting, or simply a home that provides plenty of space to live, work and entertain—this one is a 10/10!

6 Beds ⋅ 3 Baths

Welcome to 1025 Hanson Street, offering nearly 2,880 sq. ft. of exceptionally flexible living space across three finished levels in the heart of Annapolis! Perfect for a multi-generational family. Thoughtfully improved and meticulously maintained, this turn-key home provides a rare combination of space, versatility, parking and major system upgrades. The main and upper levels feature 4 bedrooms, a full bath, a bright and open living area, an updated kitchen with granite countertops and tile backsplash, and dedicated laundry with front-loading washer and dryer, utility sink and additional storage. The fully finished ground level creates an incredible second living space featuring 2 additional bedrooms, a den/office, full bath, stunning secondary kitchen (minus stove/oven) with granite countertops, stainless steel appliances and tile backsplash, a second laundry setup with utility sink, and new LVP flooring throughout. A private side entrance, new fencing, paver walkway and patio access provide tremendous flexibility for multi-generational living, extended guests, a home office setup or simply additional space to spread out. Outside, you'll find features that are especially hard to come by in Annapolis—including dual driveways with parking for 6+ vehicles and/or boats, along with a two-story detached shed offering excellent storage and convenient yard and street access. Extensive improvements provide peace of mind, including a NEW 2025 roof on both the home and shed with transferable warranty, updated HVAC including heat pump and indoor coil, 60-gallon hybrid high-efficiency water heater, 200-amp electrical service, Tesla EV charger, French drain and stormwater management system, sump pump, updated attic insulation with spray foam, Nest thermostats, updated siding, additional ground-level egress, ceiling fans, fresh paint and much more. With three finished levels, two distinct living areas, exceptional parking and storage, and numerous major capital improvements already completed, 1025 Hanson Street offers the kind of versatility that's difficult to find in Annapolis. Whether you're looking for room for a growing household, multi-generational living, extended guests, midshipman sponsor hosting, or simply a home that provides plenty of space to live, work and entertain—this one is a 10/10!

1025 Hanson St, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

$835,000

The ideal Murray Hill home with a little bit of everything: one-level living, a private driveway, lovely yard, and fully updated. A wonderful single-family home and an appealing alternative to condo living, with your own outdoor space and parking right outside your door. This stylish home is fully renovated and truly move-in ready, with dramatic open-beam ceilings that give the interior a style all its own. The most recent improvements include new quartz countertops, newly reconfigured front steps with new railings, a widened and expanded driveway, and a new skylight that brings even more natural light inside. The screened front porch is a great spot for a morning cup of coffee and to enjoy the neighborhood. Inside, hardwood floors run throughout, complemented by stainless steel appliances, beautifully tiled showers, and great custom details. The kitchen offers exceptional storage, including a custom appliance garage with built-in power outlets to keep countertops clean and uncluttered. Outside, beautiful seasonal landscaping surrounds the home. An elegant iron gate opens to the rear yard, where a wide paver walkway leads to the spacious shed with its handsome wood door. There is also a large deck with plenty of room for outdoor furniture and a grill! Approximately 1,100 square feet. Tax records do not reflect the actual square footage. All of this in sought-after Murray Hill, within walking distance of Downtown Annapolis, restaurants, shops, the waterfront, and everything that makes in-town living so special.

3 Beds ⋅ 2 Baths

The ideal Murray Hill home with a little bit of everything: one-level living, a private driveway, lovely yard, and fully updated. A wonderful single-family home and an appealing alternative to condo living, with your own outdoor space and parking right outside your door. This stylish home is fully renovated and truly move-in ready, with dramatic open-beam ceilings that give the interior a style all its own. The most recent improvements include new quartz countertops, newly reconfigured front steps with new railings, a widened and expanded driveway, and a new skylight that brings even more natural light inside. The screened front porch is a great spot for a morning cup of coffee and to enjoy the neighborhood. Inside, hardwood floors run throughout, complemented by stainless steel appliances, beautifully tiled showers, and great custom details. The kitchen offers exceptional storage, including a custom appliance garage with built-in power outlets to keep countertops clean and uncluttered. Outside, beautiful seasonal landscaping surrounds the home. An elegant iron gate opens to the rear yard, where a wide paver walkway leads to the spacious shed with its handsome wood door. There is also a large deck with plenty of room for outdoor furniture and a grill! Approximately 1,100 square feet. Tax records do not reflect the actual square footage. All of this in sought-after Murray Hill, within walking distance of Downtown Annapolis, restaurants, shops, the waterfront, and everything that makes in-town living so special.

122 Smith Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$385,000

AUCTION! Occupied property and inspections NOT available - sold as-is. No for sale sign. Contact with occupants is prohibited. No financed offers/bids as there is NO access. Property is being sold occupied with any and all occupants in AS IS/WHERE IS condition. Neither the seller nor the listing broker can verify the existence of any lease agreement, either written or verbal, nor any rental amount being paid, due or owing. Please DO NOT disturb the occupants. Access for inspections or other purposes is NOT available. Buyer is assuming ALL responsibility for any necessary eviction action. Do not email any offers as the property is being sold via auction and all bids are to be submitted online during auction period. The sale will be subject to a 5% buyers premium pursuant to the Auction Terms & Conditions (minimums may apply). All auction bids will be processed subject to seller approval. Property information provided is estimated and not guaranteed (this includes condo fee/bedroom/bathroom count). Cash bids only as you cannot access the unit. The buyer's agent is to pay a $200 plus sales tax offer management fee at closing of an accepted offer. BIDDING STARTS Aug 24 and ENDS Aug 26.

3 Beds ⋅ 1 Baths

AUCTION! Occupied property and inspections NOT available - sold as-is. No for sale sign. Contact with occupants is prohibited. No financed offers/bids as there is NO access. Property is being sold occupied with any and all occupants in AS IS/WHERE IS condition. Neither the seller nor the listing broker can verify the existence of any lease agreement, either written or verbal, nor any rental amount being paid, due or owing. Please DO NOT disturb the occupants. Access for inspections or other purposes is NOT available. Buyer is assuming ALL responsibility for any necessary eviction action. Do not email any offers as the property is being sold via auction and all bids are to be submitted online during auction period. The sale will be subject to a 5% buyers premium pursuant to the Auction Terms & Conditions (minimums may apply). All auction bids will be processed subject to seller approval. Property information provided is estimated and not guaranteed (this includes condo fee/bedroom/bathroom count). Cash bids only as you cannot access the unit. The buyer's agent is to pay a $200 plus sales tax offer management fee at closing of an accepted offer. BIDDING STARTS Aug 24 and ENDS Aug 26.

208 Parker Ave, Annapolis

Listing courtesy of Northrop Realty. Contact:

1979 Baltimore Annapolis Blvd, Annapolis

$3,000,000

A truly extraordinary opportunity awaits in one of Annapolis' most coveted waterfront locations. Situated in the historic Ferry Farms neighborhood, 1979 Baltimore Annapolis Boulevard is one of only thirteen homes positioned directly across the Severn River from the U.S. Naval Academy, offering uninterrupted panoramic views that have captivated generations. Imagine enjoying the Blue Angels soaring overhead each May from your own front lawn or dock—an experience few will ever call home. Rich in architectural character, the residence showcases the craftsmanship and charm of its era, including original hardwood floors, a classic wood-burning fireplace, vintage kitchen, inviting sunroom, screened porch, and period details that create a warm sense of history. The home's generous square footage spans three levels, blending the original residence with a substantial 2015 addition that expanded both its living space and functionality while preserving its unique personality. For buyers with vision, this property presents an exceptional opportunity to create a landmark waterfront residence tailored to today's lifestyle. Architectural renderings, renovation plans, a professional landscape design, and contractor cost estimates are available to help bring that vision to life, allowing the next owner to build upon an already remarkable foundation. The original home includes a main-level bedroom and full bath, while the upper level offers four additional bedrooms, including a primary suite with a private balcony overlooking the water. The 2015 addition introduced a spacious three-car garage, an expansive loft, and an additional bedroom perfect for guests, a home office, or a studio. A future bathroom has already been considered, with a rough-in located beneath the connecting section of the second floor. The lower level offers even more possibilities, featuring a second wood-burning fireplace, laundry area, utility space, and an impressive workshop with soaring ceilings and direct access to the garage and backyard—ideal for craftspeople, hobbyists, or future finished living space. Outside, the waterfront amenities are equally compelling. The private deep-water pier and bulkhead, completed in 2003, feature approximately 10 feet of water depth, a 40,000-pound boat lift, a 15,000-pound lift, and two 1,500-pound personal watercraft lifts, making this an outstanding property for serious boaters. A built-in outdoor barbecue and expansive waterfront setting invite effortless entertaining and relaxed evenings watching sailboats drift past the Academy. Properties of this caliber, location, and potential rarely become available. Whether thoughtfully restoring its historic character, executing the available renovation plans, or creating a legacy waterfront estate of your own design, this is a once-in-a-generation opportunity to own an irreplaceable piece of Annapolis waterfront in one of its most prestigious and tightly held neighborhoods.

5 Beds ⋅ 2 Baths

A truly extraordinary opportunity awaits in one of Annapolis' most coveted waterfront locations. Situated in the historic Ferry Farms neighborhood, 1979 Baltimore Annapolis Boulevard is one of only thirteen homes positioned directly across the Severn River from the U.S. Naval Academy, offering uninterrupted panoramic views that have captivated generations. Imagine enjoying the Blue Angels soaring overhead each May from your own front lawn or dock—an experience few will ever call home. Rich in architectural character, the residence showcases the craftsmanship and charm of its era, including original hardwood floors, a classic wood-burning fireplace, vintage kitchen, inviting sunroom, screened porch, and period details that create a warm sense of history. The home's generous square footage spans three levels, blending the original residence with a substantial 2015 addition that expanded both its living space and functionality while preserving its unique personality. For buyers with vision, this property presents an exceptional opportunity to create a landmark waterfront residence tailored to today's lifestyle. Architectural renderings, renovation plans, a professional landscape design, and contractor cost estimates are available to help bring that vision to life, allowing the next owner to build upon an already remarkable foundation. The original home includes a main-level bedroom and full bath, while the upper level offers four additional bedrooms, including a primary suite with a private balcony overlooking the water. The 2015 addition introduced a spacious three-car garage, an expansive loft, and an additional bedroom perfect for guests, a home office, or a studio. A future bathroom has already been considered, with a rough-in located beneath the connecting section of the second floor. The lower level offers even more possibilities, featuring a second wood-burning fireplace, laundry area, utility space, and an impressive workshop with soaring ceilings and direct access to the garage and backyard—ideal for craftspeople, hobbyists, or future finished living space. Outside, the waterfront amenities are equally compelling. The private deep-water pier and bulkhead, completed in 2003, feature approximately 10 feet of water depth, a 40,000-pound boat lift, a 15,000-pound lift, and two 1,500-pound personal watercraft lifts, making this an outstanding property for serious boaters. A built-in outdoor barbecue and expansive waterfront setting invite effortless entertaining and relaxed evenings watching sailboats drift past the Academy. Properties of this caliber, location, and potential rarely become available. Whether thoughtfully restoring its historic character, executing the available renovation plans, or creating a legacy waterfront estate of your own design, this is a once-in-a-generation opportunity to own an irreplaceable piece of Annapolis waterfront in one of its most prestigious and tightly held neighborhoods.

1979 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$4,600,000

140 SPA DRIVE YOUR HOME. YOUR MARINA. YOUR ANNAPOLIS. A PRIVATE 14-SLIP MARINA IN YOUR OWN BACKYARD—ON SPA CREEK IN ANNAPOLIS. An exceptionally rare opportunity to own a waterfront residence with its own 14-slip marina on one of Annapolis’ most treasured waterways. Set along approximately 90 feet of Spa Creek waterfront, 140 Spa Drive combines an extraordinary boating lifestyle with a distinctive total five-bedroom residence, panoramic water views and dockside parking—all in a residential setting. For the serious boater, yachtsman or family who wants room for more than one boat, this is a property unlike almost anything else in Annapolis. Step from your home to your marina, welcome friends and family by water, or simply enjoy watching life on Spa Creek from nearly every level of the residence. The Nantucket-inspired home is designed around the water, with walls of glass and more than 100 windows filling the interiors with natural light and capturing sweeping Spa Creek views. Multiple balconies and an expansive waterside terrace create wonderful spaces for entertaining, dining outdoors or simply enjoying the ever-changing waterfront. The home offers approximately 5,095 square feet of finished living space, including approximately 3,295 square feet above grade and an additional approximately 1,800-square-foot finished lower level. Five bedrooms, generous living spaces and flexible guest or in-law accommodations make the property equally suited to everyday living and extended family gatherings. Outside, the marina becomes an extension of the home. Fourteen slips, approximately 90 feet of waterfront, dockside parking and a waterside workshop create an exceptional setting for those whose life revolves around the water. Located at the protected upper reaches of Spa Creek, the property is just a few minute boat ride from downtown Annapolis Harbor. This isn’t simply a waterfront home. It’s an opportunity to own an Annapolis boating lifestyle that would be extraordinarily difficult to duplicate. 140 Spa Drive — where your backyard is your marina.

5 Beds ⋅ 4 Baths

140 SPA DRIVE YOUR HOME. YOUR MARINA. YOUR ANNAPOLIS. A PRIVATE 14-SLIP MARINA IN YOUR OWN BACKYARD—ON SPA CREEK IN ANNAPOLIS. An exceptionally rare opportunity to own a waterfront residence with its own 14-slip marina on one of Annapolis’ most treasured waterways. Set along approximately 90 feet of Spa Creek waterfront, 140 Spa Drive combines an extraordinary boating lifestyle with a distinctive total five-bedroom residence, panoramic water views and dockside parking—all in a residential setting. For the serious boater, yachtsman or family who wants room for more than one boat, this is a property unlike almost anything else in Annapolis. Step from your home to your marina, welcome friends and family by water, or simply enjoy watching life on Spa Creek from nearly every level of the residence. The Nantucket-inspired home is designed around the water, with walls of glass and more than 100 windows filling the interiors with natural light and capturing sweeping Spa Creek views. Multiple balconies and an expansive waterside terrace create wonderful spaces for entertaining, dining outdoors or simply enjoying the ever-changing waterfront. The home offers approximately 5,095 square feet of finished living space, including approximately 3,295 square feet above grade and an additional approximately 1,800-square-foot finished lower level. Five bedrooms, generous living spaces and flexible guest or in-law accommodations make the property equally suited to everyday living and extended family gatherings. Outside, the marina becomes an extension of the home. Fourteen slips, approximately 90 feet of waterfront, dockside parking and a waterside workshop create an exceptional setting for those whose life revolves around the water. Located at the protected upper reaches of Spa Creek, the property is just a few minute boat ride from downtown Annapolis Harbor. This isn’t simply a waterfront home. It’s an opportunity to own an Annapolis boating lifestyle that would be extraordinarily difficult to duplicate. 140 Spa Drive — where your backyard is your marina.

140 Spa Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$524,999

Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath residence offers approximately 1,600 finished square feet across two levels, combining a functional layout with quality finishes and extensive upgrades throughout. The main level features a bright living room and an updated kitchen with quartz countertops, shaker cabinetry, stainless steel appliances, and a dining area. A main-level bedroom and full bath provide flexibility for guests or a home office. A dedicated laundry and utility space leads to the rear addition, where the private primary suite includes vaulted ceilings, a walk-in closet, and an en-suite bath with double vanities, custom tile, and a walk-in shower. The upper level offers a finished attic suite with a third bedroom, full bath, and bonus flex space suitable for an office or additional living area. Interior features include durable flooring, recessed lighting, and a cohesive, modern design. Exterior highlights include a fully fenced backyard with new sod and a concrete patio, ideal for outdoor enjoyment. The property also features professional landscaping, a new asphalt driveway for off-street parking, and durable exterior materials including Hardie Plank siding, Andersen 200 Series windows, and a new architectural shingle roof. Major system upgrades include 200-amp electric service, new plumbing, dual-zone HVAC, and a whole-house sprinkler system. Conveniently located near restaurants, marinas, parks, downtown Annapolis, and Truxton Park.

3 Beds ⋅ 3 Baths

Welcome home to this thoughtfully redesigned home in Eastport just blocks from Spa Creek and minutes to downtown Annapolis. This beautifully updated 3-bedroom, 3-bath residence offers approximately 1,600 finished square feet across two levels, combining a functional layout with quality finishes and extensive upgrades throughout. The main level features a bright living room and an updated kitchen with quartz countertops, shaker cabinetry, stainless steel appliances, and a dining area. A main-level bedroom and full bath provide flexibility for guests or a home office. A dedicated laundry and utility space leads to the rear addition, where the private primary suite includes vaulted ceilings, a walk-in closet, and an en-suite bath with double vanities, custom tile, and a walk-in shower. The upper level offers a finished attic suite with a third bedroom, full bath, and bonus flex space suitable for an office or additional living area. Interior features include durable flooring, recessed lighting, and a cohesive, modern design. Exterior highlights include a fully fenced backyard with new sod and a concrete patio, ideal for outdoor enjoyment. The property also features professional landscaping, a new asphalt driveway for off-street parking, and durable exterior materials including Hardie Plank siding, Andersen 200 Series windows, and a new architectural shingle roof. Major system upgrades include 200-amp electric service, new plumbing, dual-zone HVAC, and a whole-house sprinkler system. Conveniently located near restaurants, marinas, parks, downtown Annapolis, and Truxton Park.

1210 President St, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$2,950,000

Just steps from the gates of the United States Naval Academy, 238 King George Street offers an exceptional opportunity to enjoy the beauty, history and cherished traditions of Annapolis from one of its most desirable addresses. Beautifully renovated and thoughtfully expanded, this distinguished residence offers approximately 3,750 square feet of elegant living space across four finished levels, complemented by the extraordinary convenience of private parking for three cars. There is something magical about life in Annapolis. The sound of the Naval Academy Chapel bells, the excitement of Navy football Saturdays, the pageantry of Commissioning Week and leisurely evenings strolling to exceptional restaurants, charming boutiques and the waterfront. For Naval Academy graduates, it's an opportunity to reconnect with treasured memories and traditions. For others, it's an invitation to experience a lifestyle unlike any other. Inside, timeless architecture and sophisticated finishes create a home that is both elegant and wonderfully inviting. Rich hardwood floors, exquisite millwork, beautiful natural light and gracious gathering spaces provide the perfect setting for everyday living and memorable entertaining. Imagine Thanksgiving dinners surrounded by family, Christmas celebrations beside a glowing fireplace and intimate evenings with friends before a stroll through the beautifully illuminated streets of downtown. The beautifully appointed gourmet kitchen features a generous island, six-burner cooking and lovely finishes, making everything from quiet mornings to elaborate holiday entertaining a pleasure. The luxurious primary suite offers a peaceful retreat with a sitting area, soaking tub, separate shower and heated bathroom floors. The exceptional finished lower level, complete with a fireplace, heated floors, wet bar and private walk-out entrance, is perfectly suited for Navy football gatherings, movie nights or relaxed entertaining. An inviting upper-level loft offers flexible living space and views of the iconic Naval Academy Chapel dome, while outdoor terraces and balconies provide lovely places to enjoy morning coffee or an evening glass of wine. Extensive improvements, including a new roof, updated HVAC systems, water heater and numerous interior enhancements, complement the home's beautiful renovations. Offered substantially furnished, with limited exclusions, this exceptional property is equally appealing as a distinguished primary residence or an elegant Annapolis retreat. And then there is the luxury that cannot be recreated: the location. Walk to the Naval Academy, enjoy dinner downtown without moving your car, watch the Blue Angels during Commissioning Week or experience the magic of Annapolis during the holidays. With its private three-car driveway, the convenience of downtown living becomes truly effortless. For those who have always loved Annapolis, this is an opportunity to come home. For those discovering its charm, it's an invitation to become part of something extraordinary. 238 King George Street — where timeless Annapolis traditions meet exceptional living.

4 Beds ⋅ 5 Baths

Just steps from the gates of the United States Naval Academy, 238 King George Street offers an exceptional opportunity to enjoy the beauty, history and cherished traditions of Annapolis from one of its most desirable addresses. Beautifully renovated and thoughtfully expanded, this distinguished residence offers approximately 3,750 square feet of elegant living space across four finished levels, complemented by the extraordinary convenience of private parking for three cars. There is something magical about life in Annapolis. The sound of the Naval Academy Chapel bells, the excitement of Navy football Saturdays, the pageantry of Commissioning Week and leisurely evenings strolling to exceptional restaurants, charming boutiques and the waterfront. For Naval Academy graduates, it's an opportunity to reconnect with treasured memories and traditions. For others, it's an invitation to experience a lifestyle unlike any other. Inside, timeless architecture and sophisticated finishes create a home that is both elegant and wonderfully inviting. Rich hardwood floors, exquisite millwork, beautiful natural light and gracious gathering spaces provide the perfect setting for everyday living and memorable entertaining. Imagine Thanksgiving dinners surrounded by family, Christmas celebrations beside a glowing fireplace and intimate evenings with friends before a stroll through the beautifully illuminated streets of downtown. The beautifully appointed gourmet kitchen features a generous island, six-burner cooking and lovely finishes, making everything from quiet mornings to elaborate holiday entertaining a pleasure. The luxurious primary suite offers a peaceful retreat with a sitting area, soaking tub, separate shower and heated bathroom floors. The exceptional finished lower level, complete with a fireplace, heated floors, wet bar and private walk-out entrance, is perfectly suited for Navy football gatherings, movie nights or relaxed entertaining. An inviting upper-level loft offers flexible living space and views of the iconic Naval Academy Chapel dome, while outdoor terraces and balconies provide lovely places to enjoy morning coffee or an evening glass of wine. Extensive improvements, including a new roof, updated HVAC systems, water heater and numerous interior enhancements, complement the home's beautiful renovations. Offered substantially furnished, with limited exclusions, this exceptional property is equally appealing as a distinguished primary residence or an elegant Annapolis retreat. And then there is the luxury that cannot be recreated: the location. Walk to the Naval Academy, enjoy dinner downtown without moving your car, watch the Blue Angels during Commissioning Week or experience the magic of Annapolis during the holidays. With its private three-car driveway, the convenience of downtown living becomes truly effortless. For those who have always loved Annapolis, this is an opportunity to come home. For those discovering its charm, it's an invitation to become part of something extraordinary. 238 King George Street — where timeless Annapolis traditions meet exceptional living.

238 King George St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$3,449,000

A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends timeless architectural beauty with sophisticated modern livability. The main property features 4,474 square feet of refined above-grade living space, complemented by a fully legal, licensed lower-level apartment that offers immense versatility for multi-generational living or premium rental income. In total, the property features six bedrooms, 4.5 bathrooms, and beautifully curated living spaces defined by rich period details, soaring ceilings, and remarkable craftsmanship. Six fully rebuilt, functional wood-burning fireplaces (three equipped with gas starters) serve as stunning architectural focal points throughout the home. Equally captivating are the enchanting outdoor spaces. Here, manicured grounds, lush landscaping, vibrant flower beds, and a serene koi pond create a private garden retreat rarely found downtown. Set on a prime 7,324-square-foot lot along one of the city’s most coveted historic streets, the property offers tranquility just moments from the waterfront and bustling downtown scene. Zoned as a two-family residence, this remarkable property represents a rare, premium investment or a luxurious private estate. Residents will enjoy an unmatched lifestyle, surrounded by boutique shopping, acclaimed waterfront dining, art galleries, historic landmarks, and the unmistakable charm of Annapolis Harbor. Elegant, iconic, and rich with history, 16 Maryland Avenue represents downtown Annapolis living at its absolute finest.

6 Beds ⋅ 5 Baths

A truly exceptional historic residence is now available in the heart of downtown Annapolis. Welcome to 16 Maryland Avenue, a distinguished circa-1830 Greek Revival home masterfully restored in collaboration with the renowned Hammond-Wilson Architects. Perfectly positioned just steps from State Circle and the United States Naval Academy, this iconic three-story brick property seamlessly blends timeless architectural beauty with sophisticated modern livability. The main property features 4,474 square feet of refined above-grade living space, complemented by a fully legal, licensed lower-level apartment that offers immense versatility for multi-generational living or premium rental income. In total, the property features six bedrooms, 4.5 bathrooms, and beautifully curated living spaces defined by rich period details, soaring ceilings, and remarkable craftsmanship. Six fully rebuilt, functional wood-burning fireplaces (three equipped with gas starters) serve as stunning architectural focal points throughout the home. Equally captivating are the enchanting outdoor spaces. Here, manicured grounds, lush landscaping, vibrant flower beds, and a serene koi pond create a private garden retreat rarely found downtown. Set on a prime 7,324-square-foot lot along one of the city’s most coveted historic streets, the property offers tranquility just moments from the waterfront and bustling downtown scene. Zoned as a two-family residence, this remarkable property represents a rare, premium investment or a luxurious private estate. Residents will enjoy an unmatched lifestyle, surrounded by boutique shopping, acclaimed waterfront dining, art galleries, historic landmarks, and the unmistakable charm of Annapolis Harbor. Elegant, iconic, and rich with history, 16 Maryland Avenue represents downtown Annapolis living at its absolute finest.

16 Maryland Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$1,295,000

PRICE IMPROVEMENT! RARE OPPORTUNITY TO OWN A REMARKABLE PIECE OF ANNAPOLIS HISTORY! The Patrick Creagh House c. 1740 (also known as 160 Prince George Street) is an architecturally significant residence with a gambrel roof structure and features header and English bond brick walls. This property has been thoughtfully adapted for modern living while preserving its timeless character and craftsmanship. Ideally located in the heart of Annapolis just one block from the US Naval Academy Gate 1, City Dock, Main Street and the Maryland State House, this exceptional home offers the best of historic charm and downtown convenience. A welcoming center hall introduces spacious living and dining rooms designed for both elegant entertaining and comfortable everyday living. The private patio and garden create a serene outdoor extension of the home’s living spaces. Upstairs, the home features a primary suite with full bath, two additional bedrooms, a second full bath, and convenient laundry. The lower level provides ideal space for a wine cellar, storage, or additional utility needs. The property’s kitchen, baths and wiring have been updated and the home is move-in ready! This distinguished 18th-century property has been extensively researched and documented and is listed on the NATIONAL REGISTER OF HISTORIC PLACES for its architectural importance and contribution to local history. Patrick Creagh was a man of many skills and was considered an important person in the community. He is mostly known for building the Old Treasury c. 1737 on the Maryland State House Grounds, the oldest public building in the state that was fully restored and opened to the public this year. ***NOTE: FURNISHINGS REMOVED AND INTERIOR WALLS HAVE BEEN PAINTED. Some photos have been virtually staged/AI generated to illustrate the property's design potential only. ***

3 Beds ⋅ 3 Baths

PRICE IMPROVEMENT! RARE OPPORTUNITY TO OWN A REMARKABLE PIECE OF ANNAPOLIS HISTORY! The Patrick Creagh House c. 1740 (also known as 160 Prince George Street) is an architecturally significant residence with a gambrel roof structure and features header and English bond brick walls. This property has been thoughtfully adapted for modern living while preserving its timeless character and craftsmanship. Ideally located in the heart of Annapolis just one block from the US Naval Academy Gate 1, City Dock, Main Street and the Maryland State House, this exceptional home offers the best of historic charm and downtown convenience. A welcoming center hall introduces spacious living and dining rooms designed for both elegant entertaining and comfortable everyday living. The private patio and garden create a serene outdoor extension of the home’s living spaces. Upstairs, the home features a primary suite with full bath, two additional bedrooms, a second full bath, and convenient laundry. The lower level provides ideal space for a wine cellar, storage, or additional utility needs. The property’s kitchen, baths and wiring have been updated and the home is move-in ready! This distinguished 18th-century property has been extensively researched and documented and is listed on the NATIONAL REGISTER OF HISTORIC PLACES for its architectural importance and contribution to local history. Patrick Creagh was a man of many skills and was considered an important person in the community. He is mostly known for building the Old Treasury c. 1737 on the Maryland State House Grounds, the oldest public building in the state that was fully restored and opened to the public this year. ***NOTE: FURNISHINGS REMOVED AND INTERIOR WALLS HAVE BEEN PAINTED. Some photos have been virtually staged/AI generated to illustrate the property's design potential only. ***

158 Prince George St, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$1,549,000

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

5 Beds ⋅ 2 Baths

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!

202 Wardour Dr, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

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