Refine Search
Map
Sort by
$1,595,000
4 Beds ⋅ 5 Baths
COMING SOON - expected on the market September 30th. Enjoy the historic and neighborhood charm of Lower Eastport in this beautifully renovated, turn-key home on a peaceful, tree-lined street just blocks from the water, parks, shops, and restaurants. The property features a three-bedroom, three-and-a-half-bath main house and a one-bedroom cottage at the rear of the property, providing an additional bedroom and full bath along with the privacy and independence of a separate dwelling. The current owners have invested more than $100,000 in renovations since 2024. The main house, built in 2007, is thoughtfully designed for entertaining with an open kitchen, adjoining living room, separate dining space, front and back porches with seating areas, and a fully fenced backyard. Upstairs, the spacious ensuite primary bedroom overlooks the backyard and features a large walk-in closet and adjoining bath. A second bedroom and hallway full bath complete the upper level. The lower level is currently used as a family room and third bedroom and includes a full bath, laundry, additional storage, and a private outside entrance. Custom plantation shutters throughout enhance the aesthetic appeal of the home, offer excellent light control, and provide privacy. At the rear of the property, the cottage is a valuable addition with an upstairs bedroom, full bath, kitchen, living and dining area, and laundry. It is ideal for housing family members or guests or generating rental income. The cottage has its own electric meter and is licensed for rental; current owners have generated nearly $36,000 in rental income over the past 12 months from long-term tenants. With its prime Lower Eastport setting, quality updates, and separate cottage, this property offers exceptional flexibility for family, guests, or rental income. This combination is uncommon in Annapolis and offers a truly distinctive opportunity. Note: Finished square footage and bedroom and bathroom totals reflect the combined main house and cottage. The main house has 2,344 finished square feet plus 86 unfinished square feet; the cottage has 667 finished square feet.

123 Chesapeake Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,025,000
3 Beds ⋅ 3 Baths
Welcome to 98 Monticello Avenue, a charming Murray Hill residence that captures the character and ease of the Annapolis lifestyle. From the moment you step inside, a welcoming entryway sets the tone for a home filled with warmth, natural light and thoughtful spaces throughout. The main level offers a comfortable living room centered around a beautiful fireplace, creating an inviting place to gather and unwind. The adjacent kitchen is bright and beautifully appointed with hardwood flooring, a cooktop and a cozy breakfast nook. A convenient half bath completes the main level, while a spacious deck extends the living space outdoors and overlooks the fully fenced backyard- an ideal setting for morning coffee, entertaining, or enjoying time outdoors. Upstairs, three generously sized bedrooms share a full bath, offering comfortable accommodations for family and guests. Continue to the upper level to discover additional flexible space that can easily adapt to your lifestyle—whether used as a home office, playroom, creative space or additional storage. The lower level adds even more versatility with a full bathroom, laundry area and abundant storage, providing valuable functionality rarely found in a home of this character. Set in the highly desirable Murray Hill neighborhood, this water-oriented location offers easy access to Spa Creek and the waterfront lifestyle that makes Annapolis so special, while remaining just moments from downtown. Enjoy convenient access to the Naval Academy, local restaurants, shops, parks and the many experiences that define the Annapolis lifestyle. A home with timeless charm, flexible living spaces, outdoor living and an exceptional location, all within one of Annapolis' most beloved neighborhoods. PHOTO DISCLOSURE: Photo #1 has been AI-enhanced for marketing purposes. The fireplace flames were digitally added and are not intended to represent or warrant the condition, functionality, or operability of the fireplace.

98 Monticello Ave, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$2,650,000
5 Beds ⋅ 5 Baths
A rare opportunity in the heart of Murray Hill! Welcome to 8 Brooke Avenue, a stunning 2015 Traynor Brothers-built Craftsman offering nearly 5,000 square feet of beautifully finished living space just steps from Downtown Annapolis. Combining timeless architecture, exceptional craftsmanship, and the space and amenities today's luxury buyer desires, this extraordinary home features 5 bedrooms, 5 full baths, a main-level office/optional 6th bedroom, three finished levels, and an oversized 2-car garage all on a flat 0.18-acre lot. The attention to detail begins at the curb with HardiePlank siding, AZEK trim, cultured stone, tapered Arts & Crafts columns, hand-built wood brackets, a Brazilian cherry front porch, and brick-paver driveway and walkway. Step inside to a light-filled, open floor plan showcasing white oak flooring, plantation shutters, custom hardwood trim and moldings, wainscoting, coffered ceilings, and a striking gas fireplace with custom architectural mantel. Designed for entertaining, the gourmet kitchen centers around a generous granite island and features high-end stainless appliances, oversized subway tile, and a Bertazzoni 36" six-burner gas range with wok burner. A walk-in butler's pantry with custom hardwood shelving and barn-style door provides exceptional storage, while the spacious mudroom with built-in cubbies makes everyday living effortless. Just beyond, a screened porch creates the perfect setting for morning coffee, dinner with friends, or relaxing outdoors. Upstairs, the luxurious primary suite feels like a private retreat with a vaulted ceiling, two generous walk-in closets with custom built-ins, and a spa-inspired bath featuring a soaking tub, double vanity, and oversized three-head shower. Three additional bedrooms and two additional full baths complete the sleeping quarters. Even the laundry room has been thoughtfully designed—a large, updated, light-filled space with higher ceilings, generous storage, and a utility sink, making everyday functionality feel anything but ordinary. The finished walk-out lower level adds another dimension to the home with a spacious recreation area, additional bedroom, full bath, flex/play space, abundant storage, and direct access to a shaded brick-paver patio. An additional outdoor firepit gathering area creates yet another inviting place to entertain, unwind, and enjoy evenings with family and friends. And then there is the location. Walk to Downtown Annapolis, the U.S. Naval Academy, waterfront, restaurants, shops, and everything that makes this city so special. At the end of the street, enjoy access to Old Woman's Cove and Spa Creek, grab your kayak or paddleboard and be on the water in minutes. Few homes in Murray Hill and the surrounding area offer this combination of nearly 5,000 finished square feet, newer Craftsman construction, exceptional architectural detail, garage parking, multiple outdoor living spaces, water access, and walkability. Come experience 8 Brooke Avenue and discover a home and an Annapolis lifestyle that is truly something special.

8 Brooke Ave, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,295,000
4 Beds ⋅ 3 Baths
Welcome to your future home in water-privileged Beacon Hill, where coastal living meets quality new construction. Set on a half-acre lot with a circular driveway, this to-be-built residence will be finished with durable Hardie Plank siding and architectural shingles for lasting beauty and low maintenance. The inviting design features a beautiful porch that wraps around to create a lovely seating area just outside the family room. Inside, 10-foot ceilings and luxury vinyl plank flooring create an airy, elegant main level with an open floor plan made for easy living and more formal entertaining if desired. The gourmet kitchen will inspire any home chef with quartz countertops, stainless steel appliances, and a generous pantry. A main-level bedroom offers flexibility for guests, multi-generational living, or single-level convenience. Upstairs, the primary suite is an oasis, complete with a gas fireplace, a luxurious bath, a walk-in closet, and private access to the veranda, the perfect spot for morning coffee or evening relaxation. Two additional bedrooms share a full bath, while an upstairs library provides a quiet space to read, work, or unwind. The laundry is conveniently located upstairs. A large shed adds valuable storage for kayaks, paddleboards, tools, and more. Don't miss the chance to tweak the options on the home you've been dreaming of in this exceptional waterside neighborhood! Beacon Hill has two access points for the Chesapeake Bay, and one is directly across from this property. It’s an easy commute into downtown Annapolis as well as to commute routes 50 and 97. Schools include Cape St. Claire elementary, Magothy River middle, and Broadneck high school.

1546 Shipsview Rd, Annapolis

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

$1,650,000
4 Beds ⋅ 3 Baths
Waterfront living with a private pier in Annapolis at an exceptional price in gated Epping Forest! Mid-century modern waterfront sanctuary rises above Saltworks Creek on a quiet protected cove all on a .34 Acre lot—where timeless design meets an ethereal, peaceful connection to the water and outside. Originally built in 1978, the almost 3600 sq. ft residence recently underwent a comprehensive renovation inside and out while honoring Mid-Century authenticity and maintaining an effortless flow and contemporary preference. From the street side, the home presents a timeless silhouette with a recent 70K Elevator with ramp that serves as a secondary entrance servicing 2 out of the 3 levels. Waterside, the home is the ultimate expression of blurring the line between nature and interior with floor to ceiling glass walls, 8' sliding glass doors and unobstructed water views from the deck. This home wasn't designed to look at the water but rather live with it. A massive stone central fireplace is the heart of the living area creating a cozy architectural retreat. Tasteful modernization but true to its mid-century roots, every element of the home has been considered preserving the architectural integrity while offering the comfort and convenience expected today. More than a home, this is a rare opportunity to own a piece of design history- reimagined for modern waterfront living. Current Owners invested 925K on restoration since purchase including elevator, brand new private pier, brand new Kitchen and all 3 Full Baths, selecting high end finishes throughout to create a setting for exceptional everyday living. Epping Forest is a Gated Waterfront Community on the Severn River with a community beach, waterfront clubhouse with restaurant and bar, tennis/pickleball and marina (new marina is currently under construction) Strong neighborhood connections where neighbors treat each other like family and fun happens weekly! Year around community events codify friendships, 4th of July Fireworks, Oyster & Bull Roast, Boat Club, Summer Volleyball League, community chapel, yoga & summer camps. Come experience the best Chesapeake Bay Maritime Annapolitan Lifestyle around! Epping Forest Inc is a special benefit tax district with bylaws and binding rules and regulations. Please see virtual house showcase listing from Zillow and read house bio in documents.

1739 Vineyard Trl, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,085,000
4 Beds ⋅ 6 Baths
Bright, spacious and beautifully appointed, this impressive home offers exceptional living and entertaining space on three finished levels. A dramatic 2-story foyer, hardwood floors and 9' ceilings welcome you inside. The main level features formal living and dining rooms, a family room with fireplace, private library and a gourmet kitchen with oversized island, granite counters, abundant cabinetry, stainless appliances, double ovens and organized pantry. The adjoining morning room adds even more light and living space. Upstairs, retreat to the private primary suite with sitting room, fireplace, walk-in closet and luxurious bath with soaking tub and separate shower. Three additional bedrooms each offer their own private ensuite bath. The finished lower level is made for fun and relaxation with a spacious family/game room with fireplace, exercise room, full bath with walk-in sauna and plenty of storage. Outside, two patios/terraces overlook a beautifully landscaped, fenced backyard backing to trees for added privacy. Spacious, inviting and ready to enjoy!

2700 Windswept Ln, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$2,995,000
3 Beds ⋅ 4 Baths
A rare waterfront setting just off the Severn River, 1800 River Watch Lane is positioned on a private peninsula with more than 450 feet of shoreline along Luce Creek, offering exceptional privacy, sweeping water views and approximately 8 feet of protected deep water at the pier. From here, the Severn River is moments away and downtown Annapolis is an easy boat ride, an extraordinary setting for anyone who wants to make the Chesapeake Bay lifestyle part of everyday life. Approached by a long private drive and circular pea-stone courtyard, the extensively renovated residence sits high above the water, surrounded by mature trees and landscaping. Designed primarily on one level, the home takes full advantage of its elevated setting, with water views filling nearly every room and expansive outdoor living spaces overlooking the creek. At the center of the home, the dramatic living room pairs a wood-paneled cathedral ceiling with a floor-to-ceiling stone fireplace and an entire wall of glass facing the water. Doors open to a broad Ipe deck spanning the waterside of the home, creating a natural extension of the living space. Morning coffee overlooking the creek, dinner outside with friends or an evening in the hot tub all unfold against the backdrop of the water. The open layout continues into the dining and family areas, where cathedral ceilings, a gas fireplace and panoramic views create relaxed spaces equally suited to entertaining and everyday living. The adjoining chef's kitchen features marbled Silestone countertops, an extensive suite of Miele appliances, including double wall ovens, warming drawer and induction cooktop, along with a large walk-in pantry. The home's private spaces are equally thoughtful. A dedicated office with built-ins and an adjoining den or bedroom offer flexibility for working from home or accommodating guests. An architecturally distinctive, skylit hexagon hall leads to the bedroom wing and the waterside primary suite, a serene retreat with a gas fireplace, tray ceiling and oversized walk-in closet. The spa-inspired primary bath features a soaking tub positioned toward the view, large walk-in shower, double vanity and private sauna. Two additional bedrooms, including one ensuite, another full bath, separate laundry room and powder room complete the living spaces. Hardwood flooring, generous windows and clean contemporary finishes carry throughout the home, while a well-appointed mudroom connects to the oversized two-car garage. Outside is where the property becomes truly exceptional. The elevated homesite provides privacy and long views across Luce Creek, while a private funicular makes the trip from the house to the shoreline effortless. At the water, a substantial private pier with two boat lifts and approximately 8 feet MLW provides the kind of deep-water access that is increasingly difficult to find. The protected waters of Luce Creek offer an ideal home base for your boat, with the Severn River just beyond and the Chesapeake Bay easily accessible. Spend the morning on the water, cruise into downtown Annapolis for lunch or dinner, or simply enjoy the activity along the creek from the deck above. Despite its remarkably private setting, 1800 River Watch Lane remains convenient to downtown Annapolis as well as major routes to Baltimore, BWI, Washington, D.C. and the Eastern Shore. With its combination of substantial shoreline, protected deep water, immediate Severn River access, privacy and proximity to Annapolis, 1800 River Watch Lane offers a waterfront lifestyle that is increasingly hard to replicate.

1800 River Watch Ln, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,279,000
Welcome to 1112 Little Magothy View, a rare waterfront opportunity in the highly sought-after Cape St. Claire community, where exceptional waterfront living meets remarkable flexibility for today's lifestyle and tomorrow's vision. Perfectly positioned along approximately 80 feet of private waterfront on the Little Magothy River, this property offers expansive water views, a private pier, and direct access to the Magothy River and Chesapeake Bay. Whether your vision is to move in and enjoy the home today, thoughtfully renovate over time, or create a custom waterfront home tailored to your vision, this property offers possibilities rarely found in one offering. Unlike many waterfront properties purchased solely for the land, 1112 Little Magothy View provides a substantial existing home with nearly 2,900 square feet, an attached garage, expansive circular driveway, an in-ground pool, generous pool decking, mature landscaping, and existing site improvements that create an outstanding foundation for whatever your future plans may be. The home's floor plan is one of its greatest strengths. Four bedrooms are conveniently located on the main level, providing the increasingly desirable option of one-level living. Upstairs, a spacious guest bedroom is complemented by a large waterside family room, creating exceptional flexibility for future reconfiguration into a luxurious primary suite, guest retreat, home office, or additional entertaining space. Buyers looking to renovate will appreciate the home's generous footprint and layout, offering an excellent canvas for modernizing while preserving many of the features today's buyers desire. Those considering new construction will appreciate the value of an already improved waterfront homesite with a substantial existing footprint and site improvements. One of the property's most unique features is the privacy it enjoys. The northern property line borders a community-owned waterfront park, where a wooded buffer creates a natural separation from neighboring homes, providing an uncommon sense of space and privacy rarely found on waterfront properties. The protected waters of the Little Magothy provide an ideal setting for kayaking, paddleboarding, canoeing, swimming, fishing, and sailing, while a marked channel offers convenient access to the open waters of the Chesapeake Bay. Spend the morning paddleboarding on the calm waters of the Little Magothy, enjoy an afternoon sail within sight of home, or cruise directly into the Chesapeake Bay for a day on the water—all from your private pier. End the day relaxing beside the pool or entertaining family and friends while taking in beautiful views across the Little Magothy River. Cape St. Claire offers an unmatched waterfront lifestyle with community beaches, marinas, boat ramps, fishing and crabbing piers, playgrounds, waterfront parks, year-round community events, and nearby shopping and dining, all just minutes from downtown Annapolis and convenient commuter routes. Rarely does a waterfront property offer this combination of protected waterfront, privacy, lifestyle, and long-term flexibility. Whether enjoyed exactly as it is or transformed over time, 1112 Little Magothy View presents an exceptional opportunity in one of Annapolis' most desirable waterfront communities. Property is being sold As-Is.

1112 Little Magothy Vw, Annapolis

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

$1,700,000
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: 4433727171
$1,400,000
5 Beds ⋅ 6 Baths
Welcome to this stately five-bedroom Colonial in the sought-after Olde Bloomfield community, offering approximately 5,198 square feet of beautifully designed living space across multiple levels, along with community water privileges and access to the South River.” A gracious, columned entrance opens to a light-filled foyer featuring rich hardwood flooring, crown molding, detailed millwork, and elegant architectural accents. The formal dining room is enhanced by a tray ceiling, creating an impressive setting for dinners and special occasions. Designed for everyday living and entertaining, the spacious gourmet kitchen features granite countertops, abundant wood cabinetry, a large center island with seating, stainless steel appliances, a gas cooktop, and double wall ovens. A large butler’s pantry provides valuable additional storage and serving space, while the conveniently located wet bar features a sink, glass-front cabinetry, and a wine refrigerator. The sun-filled breakfast area is surrounded by bay windows overlooking the landscaped yard, and the adjoining family room is anchored by an impressive stone fireplace. The home offers five generously sized bedrooms, each with its own full bathroom—an exceptional feature providing comfort and privacy for household members and overnight guests. The spacious primary suite includes a walk-in closet and a private bathroom with dual vanities and a soaking tub. The finished lower level expands the home’s versatility, offering plenty of room for recreation, entertaining, relaxing, or creating a home theater or game room. Interior and exterior access make this level especially convenient. The unfinished fourth level is ready for your creativity, with exciting possibilities for a future home office, studio, recreation room, fitness area, or additional storage. Outside, enjoy a wide, level backyard with established landscaping, a deck, and a patio—providing plenty of space to entertain, garden, play, or simply unwind. An attached two-car garage and spacious driveway provide ample parking. Located within walking distance of the South River, Olde Bloomfield residents may enjoy access to the community’s private dock for fishing and peaceful river views. Use of the dock and other waterfront amenities is limited to eligible community residents and is subject to HOA authorization, rules, and availability. This exceptional home combines generous living space, timeless architectural details, private bedroom suites, outdoor enjoyment, and the appeal of living near the South River—all within one distinctive community.

2902 Good Luck Ln, Annapolis

Listing courtesy of RE/MAX Executive. Contact:

$1,700,000
4 Beds ⋅ 3 Baths
Come see this beautiful one-of-a-kind WATERFRONT property! Complete waterfront view from both levels of this home and every room. True master bedroom and large enough to fit a king-size bedroom suite and private bathroom. Covered patio to enjoy the view in every weather type! Large windows throughout the home brings in natural light while keeping the waterfront setting front and center. There are fireplaces on each level. Swim all year round with this heated indoor pool and hot tub. Dock rental slips are available for owners for a $500 fee for deep water (6ft) or lower water slips for $200 (3ft) with electricity. This property can have a personal pier added not to mention Just steps away from the community beach and docks. Arundel on the Bay also offers a community beach and an established waterfront neighborhood just minutes from everything Annapolis has to offer.

1323 Magnolia Ave, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000
$1,279,000
3 Beds ⋅ 3 Baths
Set along one of Annapolis’ most picturesque tree-lined streets, this beautifully remodeled (2016) residence offers a rare combination of timeless character, sophisticated finishes, and exceptional privacy in the heart of the city. Classic semi-circle brick steps create a gracious approach to the front entrance, setting the tone for the nearly 2,000 finished square feet within. Inside, warm hardwood floors ground the home throughout all the living areas and bedrooms while abundant natural light and refined architectural details create an inviting atmosphere. At the heart of the residence is a beautifully renovated gourmet kitchen featuring elegant granite countertops, Viking appliances, generous amounts of cabinet space, and a large island well suited to everyday living and entertaining. Just off the kitchen, is a generous and open living space with fireplace. Additionally, there is a large mud-laundry room with detailed storage, cubbies and hangers for all your belongings. From the kitchen, french doors open to a handsome brick patio framed by a lush canopy of mature trees. Remarkably private for such a central Annapolis location, this outdoor retreat is ideal for summer dinners, weekend barbecues, entertaining friends, or simply enjoying a quiet afternoon beneath the trees. Upstairs, the second level includes a sun-filled primary bedroom with a beautifully appointed tile bath and charming views over the surrounding streetscape. Two additional bedrooms and a very well appointed full bath are located just down the hall. The rooms are filled with natural light and overlook the private patio and treetops beyond. The third level provides an exceptionally versatile flex space, perfect as an additional guest bedroom, private home office, fitness/artist studio, reading room, or quiet retreat allowing the home to adapt effortlessly to a variety of lifestyles. The lower level offers generous storage along with excellent space for a workshop, hobby area, or projects—an especially valuable feature for anyone who appreciates having room to create, build, or stay organized. Perhaps most compelling is the location. Just moments from Dock Street, Spa Creek, Eastport, and the Annapolis Yacht Club, this home places some of the city’s most celebrated waterfront destinations within easy reach. West Street and Murray Hill are also conveniently accessible, providing an ideal balance between downtown energy and the privacy and warmth of an established residential neighborhood. Elegant, comfortable, and distinctly Annapolis, this is a home that offers the charm of historic city living with the thoughtful updates and outdoor privacy desired for modern life. *Some of the images in this listing have been lightly visually enhanced.

132 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,105,000
5 Beds ⋅ 5 Baths
507 Sunwood Lane – Where Luxury, Comfort & Location Come Together Welcome to 507 Sunwood Lane, a stunning home nestled in the sought-after Rosewood community and located within the highly acclaimed Broadneck School District. Offering exceptional living spaces, resort-style outdoor amenities, and a flexible floor plan, this home truly has it all. Step inside to find a private home office, perfect for remote work, and an elegant formal dining room that flows seamlessly into a versatile bonus room off the kitchen. The heart of the home is the beautifully appointed kitchen featuring newer stainless steel appliances, granite countertops, a center island, and a sunny breakfast area. Just beyond, the inviting family room (new carpeting) showcases a cozy fireplace and provides the perfect setting for everyday living and entertaining. Outdoor living reaches a new level with a spacious Trex deck overlooking your own private backyard Oasis! The fully fenced yard is highlighted by a beautifully landscaped 35,000 Gallon in-ground heated saltwater pool, relaxing hot tub, and plenty of space to enjoy summer gatherings with family and friends. Upstairs, the expansive owner's suite is a true sanctuary, featuring cathedral ceilings, a private sitting room, walk-in closet, double vanities, and a separate shower. Bedroom two offers a private en-suite bath, while bedrooms three and four share a convenient Jack-and-Jill bathroom. The finished walkout lower level provides incredible flexibility with a fifth bedroom, new LVP flooring, full-size windows, full kitchen setup, sliding glass door access to the rear patio, and an ideal layout for an in-law suite or extended guest accommodations. Additional unfinished storage space and a dedicated workshop room complete the lower level. Conveniently located near the Bay Bridge, Downtown Annapolis, the U.S. Naval Academy, Bay Dale Shopping Center, Cape Saint Claire, Severna Park, and major commuter routes to Washington, D.C. and Baltimore, this exceptional home combines luxury, convenience, and top-rated schools, including Windsor Farm Elementary, Severn River Middle, and Broadneck High School. If you've been searching for the perfect place to call home, your search ends here. Welcome to 507 Sunwood Lane—where memories are waiting to be made.

507 Sunwood Ln, Annapolis

Listing courtesy of RE/MAX Aspire. Contact: (443) 574-1071
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to 313 Fourth St, one of only three townhomes at The Tecumseh and a rare opportunity in one of Eastport’s most distinctive waterfront communities. Completed in 1968 on the site of a former boatyard, The Tecumseh was Annapolis’s earliest condominium communities, designed around the boating lifestyle that continues to define Eastport today. Set directly on Spa Creek, the community offers a 72-slip private marina, waterfront swimming pool and deck, and gated private parking. Located at the corner of Fourth St and Severn Ave, this three-story, approximately 2,700-square-foot residence offers three bedrooms, two-and-a-half baths, expansive third-floor bonus space, charming Eastport street appeal, and a private rear courtyard. The main level is filled with character, featuring charming arched details, a newly renovated powder room, spacious kitchen with breakfast nook, dining area, walk-in butler’s pantry, and custom built-in bookshelves surrounding a gas fireplace. A generous living area opens through sliding glass doors to a private courtyard with a paved patio—perfect for dining al fresco and entertaining. Upstairs, the second floor features a spacious primary suite with an ensuite bath and two closets, plus two additional bedrooms that share a full bath. The third floor surprises with vaulted ceilings, a large finished bonus room, additional unfinished space, and a laundry area—offering tremendous flexibility for a home office, gym, playroom, studio, or additional living space. Just beyond your back door is direct access to The Tecumseh’s waterfront amenities, including its marina and waterfront swimming pool. For the boater, ownership also includes a 40-foot boat slip entitlement. What truly sets this property apart is the lifestyle. Step outside and you’re moments from Spa Creek and just steps from Eastport’s Restaurant Row, while downtown Annapolis is easily accessible across the bridge. Rarely available, 313 Fourth St offers the opportunity to become part of a waterfront community cherished for its history, location, boating lifestyle, and enduring connection to Annapolis’s maritime heritage. The Tecumseh Condominium has a 15-day first right of refusal.

313 Fourth Street, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,675,000
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: 4102638686
$1,395,000
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:

$1,750,000
4 Beds ⋅ 4 Baths
If you love a home that breathes history, you’ll fall in love with this one. Ideally situated at 102 Duke of Gloucester Street, the property rests along one of the area’s most historic streets—named in the late 1600s in honor of Prince William, The Duke of Gloucester. Some of the images in this listing have been lightly visually enhanced. Set on one of the most desirable stretches of the street, this classic Annapolis home is one where history, character, and everyday livability come together beautifully. Directly across from St. Mary’s Church, this four-bedroom, 3.5-bath residence offers just under 3,000 square feet perched on a generous lot with ample private parking. Its location places you within effortless walking distance of Spa Creek, Main Street, Ego Alley, the Annapolis Yacht Club, and Eastport—an extraordinary position that puts the very best of Annapolis at your doorstep. From the moment you cross the threshold, the charm is unmistakable. This home is filled with warm natural light and the energy of a true Annapolis residence that has been has been lived in, loved, and appreciated in its time. Rich wood, original details, and an authentic sense of place create an atmosphere that simply cannot be replicated in a new build. Among its most beautiful details are the original panes of glass showcased at the front of the home, along with rare, old-growth Georgia hard-pine edge-grain floors, and an original letter box—craftsmanship and materials that are increasingly difficult, if not impossible, to find today. The second floor showcases an especially inviting primary suite with a huge bath filled with warm morning light— a peaceful place to begin each day surrounded by the character of historic Annapolis. An additional full bath and bedrooms right down the hall. A bright and spacious grand room crowns the 3rd floor to be used as you like for an additional bedroom, exercise, and artist haven, office - you decide! The lower level is fitted with the original brick floors and offers a private full suite—an exceptional space for guests, extended family, or separate living arrangement. Additionally it includes its own secluded workshop, a rare and charming feature for someone who enjoys working with their hands, tackling projects, or simply having a dedicated place to create. Easily accessed from the kitchen breakfast area, the rear yard is one of the property’s most unexpected treasures. This generous outdoor space, not often found in downtown, offers privacy, a place to garden, entertain or simply letting the dog run and play. You will have your own highly desired and remarkably convenient parking for downtown living with room for two full-size vehicles or up to three compact cars, complemented by additional ample street parking. A fire-suppression system adds an additional layer of peace of mind to this historic residence. The sewer line was updated within the last 8 years and the roof was replaced in 2016 with 50 year rated shingles. But perhaps what makes this home most special is what cannot be measured in square footage. It has soul. The wood is rich. The light is warm. The architecture carries the imprint of another era. And the location is nearly impossible to duplicate. For those who appreciate the romance of an old home—the imperfections, the craftsmanship, the history, and the stories embedded within its walls—102 Duke of Gloucester Street offers something increasingly rare: a genuine piece of Annapolis that still still feels like a home.

102 Duke Of Gloucester St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,300,000
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: (410) 280-5600
$3,375,000
5 Beds ⋅ 7 Baths
Nestled in the serene enclave of Cape St. John, this exquisite coastal residence offers a harmonious blend of luxury and comfort, perfectly designed for an elevated lifestyle. Built in 2012, this stunning detached home showcases timeless architectural elegance with its brick and HardiPlank exterior, inviting you into a world of sophistication. Step inside to discover an expansive open floor plan adorned with rich hardwood and tile flooring, creating a warm and inviting atmosphere. The gourmet kitchen is a chef's dream, featuring a commercial-grade range, stainless steel appliances, and a spacious island, perfect for culinary creations and entertaining. The butler's pantry adds an extra touch of convenience, while the adjoining dining area flows seamlessly into the living space, highlighted by an elegant gas fireplace that provides a cozy ambiance. Waterfront views from every room.The primary suite is a true sanctuary, boasting breathtaking views and a luxurious en-suite bathroom complete with a soaking tub and walk-in shower. Each of the five bedrooms is generously sized with ensuite baths offering ample space for relaxation and privacy. Thoughtful details such as crown moldings, recessed lighting, and wainscoting enhance the home's refined aesthetic. Venture to the fully finished daylight basement, where natural light pours in through large windows, creating an inviting space for recreation or relaxation. This versatile area includes a wet/dry bar, perfect for hosting gatherings or enjoying quiet evenings at home, another bedroom and 2 full baths. Outside, the property is a true oasis. The extensive hardscape is complemented by lush landscaping and an underground lawn sprinkler system, ensuring a vibrant outdoor space year-round. Enjoy evenings on the screened porch or patio, where you can take in the tranquil views of the South River. With private access to the water, indulge in boating, fishing, or simply basking in the beauty of your surroundings. A standout waterfront designed for the boating lifestyle, featuring a 6' × 115' private pier with a spacious 10' × 20' platform and 3' × 12' finger pier - a total of 125 ft. length from the MHWL at the bulkhead. With approximately 10 feet of water at Mean Low Water (MLW) at the slips, the property offers exceptional deep-water access, along with a 12' × 14' boat lift with guide pole and an approximately 18' × 50' mooring slip. A timber bulkhead and riprap-protected shoreline complete this impressive waterfront setting—offering outstanding access to the Chesapeake and everything that comes with life on the water. The pier also includes a dock box, kayak rack, and lighthouse-style power pedestal. Additional features include a two-car attached garage with inside access, energy-efficient appliances, and a comprehensive water treatment system, ensuring comfort and convenience at every turn. This home is not just a residence; it's a lifestyle, offering the perfect blend of luxury, comfort, and natural beauty. Experience the best of coastal living in this remarkable property, where every detail has been thoughtfully curated for your enjoyment.

203 Cape St John Rd, Annapolis

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

$2,499,500
6 Beds ⋅ 6 Baths
There are houses that simply check the boxes, and then there are houses that have a sense of place. Tucked away at the end of a quiet street in the coveted Wardour neighborhood, this beautifully crafted custom home is filled with the details that make a house memorable: gorgeous millwork, custom built-ins, gracious rooms, beautiful gardens and spaces designed for both gathering and retreat. At the heart of the home is a stunning chef’s kitchen that opens seamlessly to the spacious family room and screened porch, equally suited to busy mornings, relaxed weekends and a house full of friends. Custom built-ins surround the breakfast area, while formal living and dining rooms offer elegant spaces for entertaining without feeling overly formal. Upstairs, the expansive primary suite feels like a true retreat, with an oversized walk-in closet and spa-inspired bath featuring dual vanities, a soaking tub and separate shower. Two additional bedroom suites, a generous bonus room perfect for a family room, library, playroom or home office, and a large laundry room complete the second level. The third floor adds two more bedrooms and a full bath, offering tremendous flexibility for guests, work or hobbies. The lower level adds another layer of versatility, with its own private entrance, living room, full kitchen, bedroom, full bath and separate laundry. Ideal for extended family, an au pair or long-term guests, this completely independent apartment has also historically rented for $2,100 per month. Outside, the grounds are every bit as special as the home itself. Beautifully established English-style gardens surround the property, with professional landscaping, lush plantings and masses of mature hydrangeas creating a setting that feels almost Nantucket-like in the summer. The screened porch overlooks this private garden retreat and may quickly become your favorite room in the house. A circular driveway provides generous off-street parking, while the oversized two-car garage includes custom built-in storage. Significant recent improvements include three new HVAC systems installed approximately three years ago, along with an upgraded sprinkler system. And perhaps the most Annapolis detail of all: step outside in the morning and you can hear reveille from the U.S. Naval Academy; in the evening, taps carries through the air. Downtown Annapolis, the Naval Academy, marinas, restaurants and shopping are all just minutes away, with easy access to Route 50 making commuting simple and convenient. As an added benefit, the entire home has historically rented for approximately $16,000 during Naval Academy Commissioning Week, an exceptional opportunity unique to this sought-after Annapolis location. Beautifully built, wonderfully livable and unmistakably Annapolis, this is a home with room for everyone, and then some.

4 Ridge Rd, Annapolis

Listing courtesy of Cummings & Co Realtors. Contact: 4108230033
$9,500,000
6 Beds ⋅ 10 Baths
Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed!

3285 Harness Creek Rd, Annapolis

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

$2,795,000
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: (410) 804-7921
$1,900,000
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: (410) 280-5600
$1,250,000
4 Beds ⋅ 4 Baths
Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5-minute walk from the Naval Academy Marine Corps Stadium, this beautifully renovated 2026 home offers the rare combination of privacy, convenience and Annapolis charm. Set on a generous .598-acre tract, the property backs-up to Tawes Gardens, that gives the home a tranquil and private setting. The home has been completely renovated in 2026, both inside and out, offering thoughtful updates while maintaining the integrity of the community. Enjoy the best of Annapolis, all within walking distance or true city living just a short drive away. Welcome home to 700 Miller Road.

700 Miller Rd, Annapolis

Listing courtesy of Cottage Street Realty LLC. Contact:

$1,595,000
2 Beds ⋅ 3 Baths
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, 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. 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: 4102638686
$1,875,000
4 Beds ⋅ 5 Baths
There is something unmistakably special about life in Eastport—and 820 Bay Ridge Ave captures it beautifully. Set within coveted Sailor’s Quay, this exceptional residence offers more than 4,000 square feet of sophisticated living across four beautifully finished levels, combining timeless architecture, thoughtful customization, and an effortless coastal sensibility just moments from the heart of Annapolis. Behind the white picket fence, manicured landscaping and gracious brick front porch create a picture-perfect welcome. Inside, rich hardwood floors, 9-foot ceilings, elegant millwork, tray ceilings, and plantation shutters establish a refined yet relaxed atmosphere. Unlike many homes in the community, this residence was thoughtfully customized during construction with numerous builder upgrades, enhanced electrical features, and details designed to improve both everyday living and long-term functionality. At the heart of the home, the beautifully appointed kitchen features honed granite countertops, premium appliances, abundant cabinetry, and a generous center island that opens seamlessly to the family room and its upgraded gas fireplace. The formal dining room, illuminated by a striking chandelier, is made for memorable dinners, while the adjoining sitting room or study is equally suited to a favorite book, working from home, or an evening bourbon. Outdoor living is woven beautifully into the home. Enjoy coffee on the charming front porch overlooking the flower garden, dinner in the private English courtyard, or cocktails on the second-floor terrace. Ceiling fans enhance both outdoor spaces, while a dedicated natural gas line makes grilling effortless and provides the opportunity for a future fire feature. Professionally enhanced landscaping and a thoughtfully improved yard complete this private outdoor retreat. The primary suite is serene and exceptionally spacious, with a custom walk-in closet, spa-inspired bath, and expansive private sitting room. A generous junior suite with its own bath offers wonderful privacy for family or guests, while two additional vaulted-ceiling bedrooms share a beautifully appointed full bath. The finished third-floor loft provides additional inviting spaces for a home office, fitness studio, media room, and guest retreat. The finished lower level adds a large family room and full bath, creating remarkable flexibility for entertaining, overnight guests, or multigenerational living. The home was also designed with the future in mind, with a framed elevator shaft allowing for the addition of an elevator without compromising its architecture or thoughtful floor plan. And then there is the location. This is the kind of Annapolis address where so much of daily life can happen on foot. St. Mary’s School, City Dock, neighborhood cafés, restaurants, boutiques and shopping are all within walking distance, as are the Annapolis Yacht Club and Eastport Yacht Club. Stroll to Eastport’s waterfront restaurants and marinas, cross the Spa Creek Drawbridge into Historic Downtown Annapolis, or take the water taxi home after an evening downtown. The United States Naval Academy, galleries, parks, sailing, and the unmistakable energy of the Chesapeake are all part of the lifestyle. Morning coffee at a neighborhood café. An afternoon on the water. Dinner in Eastport. A walk across the bridge for ice cream at City Dock. School, sailing, dining, shopping and downtown Annapolis—all without having to get in the car. This is polished Eastport living at its best: gracious but never fussy, luxurious yet wonderfully livable, and perfectly positioned to enjoy one of Annapolis’ most sought-after neighborhoods. With more than 4,000 square feet, four finished levels, exceptional outdoor spaces, extensive custom upgrades, future elevator capability, and an enviable Sailor’s Quay address, 820 Bay Ridge Ave offers a rare opportunity to enjoy Annapolis exactly as it was meant to be lived.

820 Bay Ridge Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,349,000
5 Beds ⋅ 2 Baths
Just steps from Spa Creek in the Annapolis Historic District, 8 Revell Street is a distinctive 1903 home offering more than 3,600 square feet across three finished levels, with 5 bedrooms and 2 full baths. Beautiful original character, mature gardens and an exceptional downtown location set the stage. With its classic wood-shingle exterior, recently resurfaced standing-seam metal roof and freshly painted interior, the home presents an opportunity to thoughtfully update its spaces while preserving the details that make it so memorable. An elevated front porch sits above the street and offers a charming glimpse of Spa Creek—a lovely perch for enjoying the refreshing breezes off the water. Inside, hardwood floors, generous room sizes, original built-ins, distinctive tilework, classic radiators and an unforgettable stained-glass window are among the details that give this home its remarkable charm. The third floor is one of the home’s most beautiful spaces. The fifth bedroom, currently staged as an elegant office, is a light-filled retreat with elevated views of Spa Creek. An adjoining full bath and access to generous attic storage add tremendous versatility to this special level of the home. Outside, a large terraced brick patio offers wonderful space for dining, entertaining and relaxing. Mature gardens surround the patio, while established wisteria climbs the trellis to provide natural shade and a beautiful sense of enclosure. A garden shed provides additional outdoor storage. And then there is the location. From Revell Street, stroll to City Dock, St. Mary’s, the shops and restaurants of Main Street, the waterfront and so much of downtown Annapolis. Walk to the end of the street and catch a water taxi to explore Annapolis from the water. A morning paddle on Spa Creek, downtown dining and shopping, historic streets and the Chesapeake Bay lifestyle are all within easy reach. With its generous scale, original architectural details, beautiful outdoor spaces, Spa Creek views and exceptional location within the Annapolis Historic District, 8 Revell Street offers a rare combination of history, character and possibility. Enjoy what makes it special today while thoughtfully making it your own for its next chapter. Property is being sold As-Is.

8 Revell St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,285,000
4 Beds ⋅ 3 Baths
Experience the best of the Annapolis lifestyle at 1610 Ridout Road, where beautifully updated interiors, exceptional outdoor living, and coveted water access come together in one inviting home. Inside, an open and comfortable floor plan is designed for the way people actually live. The kitchen opens to a sun-filled bar and dining area, where a sliding door provides direct access to the backyard and creates an easy connection between indoor and outdoor living. Two gas fireplaces, one in the living room and another in the family room, bring warmth and character to the main level, while the finished lower level provides additional flexible living space and storage. Upstairs, the spacious primary suite with an ensuite bath and three additional bedrooms sharing a full hall bath, offer comfortable space for family and guests. An attached two-car garage completes the home’s practical conveniences. Outside is where this property truly distinguishes itself. Framed by lush landscaping, the expansive, fully fenced backyard unfolds as a series of thoughtfully created outdoor living spaces. The in-ground pool, hot tub, generous patio space, and pergola-covered dining area area designed for long summer days and effortless entertaining, while the broad lawn offers plenty of room to play, garden, or simply unwind. And the lifestyle extends well beyond the property line. Amberley is one of the Broadneck Peninsula’s sought-after water-privileged communities, with three private community piers along Whitehall and Ridout Creeks and 45 slips accommodating both power and sailboats. Residents also enjoy a boat ramp, kayak and paddleboard storage, and a launch pier for smaller watercraft. More than 15 acres of community forest and open space, along with over 3 miles of paved roads and walking trails, contribute to Amberley’s peaceful, established character. Just minutes from Downtown Annapolis, Broadneck schools, and convenient routes to Washington, D.C., Baltimore, and the Eastern Shore, this private oasis offers something increasingly difficult to find: space to spread out, a backyard built for living, and easy access to the Chesapeake Bay lifestyle.

1610 Ridout Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$1,350,000
6 Beds ⋅ 6 Baths
New construction from acclaimed local builder, Sturbridge Homes! This spectacular home offers over 3,900 square feet of finished space in the heart of Annapolis's Homewood neighborhood, close to all of the entertainment and enjoyment available in our historic town. Located near the new Annapolis Public Library, Maryland Hall, Annapolis Town Center, and the Naval Academy Stadium, this home is situated for you to enjoy the best of in-town life, yet relax in a tree-lined neighborhood environment. This home is excellently upgraded with 9-foot ceilings on all three levels, quartz countertops, ceramic tile, stainless appliances, and more! The main level features a flexible den/office/bedroom with an attached full bathroom, so guests and family can have private space. The primary suite is a luxurious oasis with plenty of space to enjoy with a huge customizable walk-in closet. The lower level features a separate entrance, a bedroom and a full bathroom, and a large rec room, making it perfect for entertaining guests, caregiving, or multi-generational living. The builder has included many thoughtful touches throughout. The front porch is a perfect spot to savor your morning coffee, and the backyard with deck offers endless possibilities. The home comes with green building features, a package of smart home features, and a 10-year limited warranty. Enjoy the low-maintenance lifestyle of a new construction home for many years to come!

3 Rusty Red Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,495,000
5 Beds ⋅ 5 Baths
OPEN HOUSE SATURDAY SEPT 26th 11am to 1pm. Welcome to your castle on the hill! Introducing an extraordinary custom-built estate with brand new roof, privately nestled on more than 2+ WOODED ACRES along the B&A Trail in a quiet cul-de-sac setting, just minutes from downtown HISTORIC ANNAPOLIS and convenient to the Rt. 50 corridor. Located in the sought-after Broadneck School District, this exceptional property also includes deeded mooring rights to Cool Spring Cove. Chase Creek Swim Club nearby for summer pool fun! Designed for both elegant entertaining and comfortable everyday living, the home showcases a dramatic two-story great room highlighted by an impressive 18-foot stone fireplace and expansive windows that fill the space with natural light. The OPEN-CONCEPT layout seamlessly connects the living, dining, and gourmet kitchen areas, with quartz countertops and a gas range with double ovens create the perfect culinary setting. Tailored for MAIN-LEVEL LIVING, the spacious primary suite offers a private retreat complete with a spa-inspired bath featuring a walk-in shower/steam room, jacuzzi tub, and oversized walk-in closet. The main floor also includes a flexible guest bedroom or office, a half bath, and an expansive laundry/mudroom adjoining the oversized three-car garage and workshop with custom cabinetry. A stunning curved open staircase leads to the upper level, where a second primary suite provides ideal MULTI-GENERATIONAL LIVING accommodations, accompanied by two additional bedrooms connected by a Jack-and-Jill bath. The FINISHED LOWER LEVEL significantly expands the home’s living space with a large recreation room centered around an 11-foot stone fireplace, along with a custom bar, gaming area, bonus room or optional sixth bedroom, luxury full bath, and extensive storage and wine cellar space. OUTDOOR LIVING is equally exceptional, featuring a sprawling illuminated patio designed for year-round entertaining. The fully equipped outdoor kitchen includes a pizza oven, burners, sink, mini refrigerator, and adjoining firepit area. Thoughtful upgrades throughout — including a whole-house generator — complete this truly one-of-a-kind property.

1603 Waters Ridge Ct, Annapolis

Listing courtesy of Keller Williams Flagship. Contact: