Annapolis Single Family Properties for Sale

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:

$949,000

Annapolis Turnkey Luxury Colonial - Coastal Elegance, Timeless Charm & Exceptional Privacy in Anchorage: Welcome to 1130 Mainsail Drive, a beautifully renovated Colonial nestled in a tranquil corner of Anchorage, one of Annapolis’ sought-after waterfront communities. Set on 0.55 acres along a peaceful, low-traffic street, this exceptional 3-bedroom, 2.5-bath residence offers approximately 2,300 square feet of thoughtfully designed living space, plus a basement and attached garage. Surrounded by mature landscaping and an expansive private backyard backing to woods, the property offers a rare combination of tranquility, privacy, and the distinctive waterfront-community lifestyle of Anchorage. From the moment you arrive, the home’s classic colonial architecture and inviting character set the tone. Inside, a fully renovated, stunning open floor plan with kitchen, family, living and dining areas that blends timeless craftsmanship with sophisticated modern finishes. Hardwood floors extend throughout the main and upper levels, complemented by elegant pine ceilings and an abundance of recessed LED lighting. At the heart of the home is a spectacular gourmet chef’s kitchen, thoughtfully designed for both entertaining and everyday living. The custom renovation features soapstone countertops, a marble mosaic backsplash, a dramatic 7.5’ x 4.5’ marble-topped island illuminated by nautical-inspired pendant lighting, and elegant Martha Stewart Hampton cabinetry with soft-close drawers. Stainless steel appliances and a five-burner gas range complete this beautifully appointed culinary space. The home’s living spaces are equally inviting. The living room features a gas fireplace framed by mosaic tile and elegant built-ins, accented by sophisticated sconces and plantation shutters. The family room offers a second gas fireplace and opens naturally to the screened-in porch, creating an ideal setting for relaxed gatherings or enjoying the peaceful, wooded surroundings. The owner’s suite is a private retreat, complete with a comfortable sitting area, crown molding, and generous closet space. The luxurious en-suite bath evokes a true spa experience with a walk-in marble-tile shower, soaking tub overlooking the private backyard, double vanity with marble countertops and undermount sinks, soft-close mirrored cabinets, recessed lighting, and a refined marble-and-slate floor. Thoughtful design continues throughout the home with a welcoming foyer featuring slate flooring and a beautifully organized mudroom with pine built-ins, hooks, and cubbies. A dedicated laundry room includes a convenient mop sink. Outside, the expansive private yard is one of the property’s defining features. Backing to woods and extending beyond the fenced area toward the electrical utility corridor, the grounds create an unusually spacious and secluded setting. Whether entertaining on the screened porch, enjoying morning coffee, gardening, or simply taking in the peaceful natural surroundings, the property offers a wonderful sense of retreat. Enjoy Chesapeake-area evenings around the inviting fire pit, an ideal setting for cocktails, conversations and outdoor gatherings. Beyond the home’s exceptional aesthetics, the property has been extensively updated for comfort and efficiency. Notable improvements include a whole-house reverse-osmosis water system with a 300-gallon tank, gas water heater replaced in 2022, sewer line replaced with PVC in 2022, and a full-capacity generator. Located within Anchorage, residents enjoy the unique character of an established waterfront community with access to a 49-slip deep-water marina on Lake Ogleton, a boat ramp, a swimming pool, racks for kayaks and paddleboards, and the Chesapeake Bay lifestyle, while remaining conveniently close to downtown Annapolis, 35-miles from Washington DC and 32-miles from Baltimore. Please note Owners would like to sell all furniture! The furniture is NOT included in the listed price!

1130 Mainsail Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$859,000

OPEN HOUSES: FRI 9/25 4-6pm, SAT 9/26 12-2pm ---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: 8554500442

$799,000

Welcome home to lucky number 777 with over 3,000 finished square feet. You will fall in love with this very well maintained four bedroom, two & a half bath, colonial with a two car garage in sought after Cape St Claire. This property is made for entertaining large gatherings, with so much space to spread out! Wood floors throughout most of the main level, from the foyer to the spacious living room with a fireplace, into the formal dining room, and through the eat in kitchen. The cozy family room sits off from the kitchen and dining room. And, from the dining room step out to a wonderful enclosed porch with access to decks from both sides of the room. Upstairs find four ample sized bedrooms, with a huge primary bedroom with not only an attached bath and two walk-in closets, but a very large bonus room with so many options for use. The other three bedrooms share a the hall full bath, and the laundry is on the bedroom level for convenience. The back yard is fully fenced and ready to accommodate a large gathering or just enjoy the private setting as you relax in the fully functioning hot tub. New in summer of 2026 - roof, two HVAC system, and water heater****** Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to Ft Meade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore

777 Windgate Dr, Annapolis

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

$575,000

2 Beds ⋅ 2 Baths

Welcome to this lovely single-family home nestled in a peaceful, private setting, backing to mature trees in the desirable Heritage Harbour 55+ community. Offering comfortable one-level living, this home features a spacious living room with a gas fireplace, dining room, kitchen, family room, two bedrooms, two full baths, and a versatile den/office. An attached two-car garage provides added convenience. Step outside to the deck and enjoy the peaceful setting and wooded views. This home offers a wonderful opportunity to add your own personal touches and truly make it your own. Heritage Harbour offers an exceptional array of amenities and activities, including golf, tennis, pickleball, canoeing, kayaking, and so much more. Conveniently located in Annapolis with easy access to Baltimore, Washington, DC, and BWI Airport, this home combines a tranquil setting with an active 55+ lifestyle.

856 Boatswain Way, Annapolis

Listing courtesy of Boyle & Kahoe Real Estate. Contact: 4104491301

$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:

$525,000

Pristine and move-in ready, 2 Silopanna Court offers just over 2000 square feet of flexible living space inside Annapolis city limits, minutes from Eastport and historic downtown. A well-planned addition expanded the home to include a spacious upstairs primary suite and a separate family room with an adjoining office area on the main level. The primary suite features a walk-in closet and a private bath, with sliding doors that open to its own balcony. Three additional generously sized bedrooms share a second full bath, keeping all four bedrooms together upstairs. A main-level powder room adds convenience for guests. A full wall of built-in shelving and cabinetry gives the living room character and ample storage. The kitchen features white cabinets and stainless steel appliances and opens to a dining area with sliding doors to the backyard patio. The family room provides space to spread out, while the adjoining office or sitting area accommodates working from home. Outside, the fenced backyard offers room to garden or play beneath mature trees. A broad paver patio extends the living space outdoors, with plenty of room for dining and gathering. A separate shed keeps tools and outdoor equipment neatly stored and out of sight. Just steps from the house, a wooded trail leads toward Spa Creek for waterside walks and opportunities to spot herons and turtles. Nearby waterfront parks include Amos Garrett, where a pier and water taxi pickup offer another way to enjoy Annapolis and reach Eastport or downtown. In the opposite direction, a footbridge connects to Truxtun Park and the city’s public pool. Maryland Hall is a short walk away, with West Street cafes and local restaurants close by. Historic downtown Annapolis offers shopping and live theater, along with waterfront dining and community events throughout the year. Welcome Home!

2 Silopanna Ct, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425

$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

$675,000

AN EXCEPTIONAL OPPORTUNITY TO ASSUME THE EXISTING 4.75% Discover the charm and flexibility of the 3 - bedroom, 2.5 bath Coastal haven in Oyster Harbor, one of Annapolis most desirable water - privileged communities. AnThoughtfully designed for comfortable everyday living and the Chesapeake Bay lifestyle, the home offers inviting indoor spaces, outdoor entertaining areas, and access to exceptional community amentiies. Fresh updates - including interior paint make the home feel refreshed and ready to enjoy. On first level two bedrooms with adjoining Jack and Jill bathroom plus 1/2 bath and laundry room. Handsome hardwoods add warmth and character throughout the main living areas. A Wood burning fireplace creates a cozy focal point for cool evenings and relaxed gatherings. A large pantry provides valuable kitchen storage and everyday convenience. The spacious primary suite includes a private ensuite bath and an upper-level deck, offering a peaceful place to enjoy morning coffee or unwind outdoors. The second floor flex space can serve as a home office, sitting room, dressing area, nursery, or an opportunity to enlarge the primary bath. A screened porch extends the living space outdoors - ideal for dining, entertaining, or enjoying the quite surroundings. The fenced backyard offers privacy and room for pets, play, gardening, or outdoor entertaining. A dedicated grilling station makes hosting summer cookouts easy. The spacious garage includes a workshop area plus attic storage, with room for tools, bikes, paddle boards, boating gear, outdoor equipment, and Chesapeake Lifestyle essentials. Security system. Life here extends beyond the property lines. Oyster Harbor is a water- privileged community with access to a community marina, kayak rack, and beach, both a short stroll from the home. Enjoy boating, kayaking, fishing, swimming, or simple taking in the waterfront atmosphere without giving up the convenience of being minutes from downtown Historic Annapois. The community amenities are included through Oyster Harbor's tax district, helping make the neighborhood's recreational features part of the homeownership experience. Va Assumable loan @ 4.75% may be available. This home is more coastal charm - it is an opportunity to embrace the casual, connected, water oriented lifestyle of Annapolis

1339 Fishing Creek Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$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.

219 King George St, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4433727171

$560,000

Welcome to 1182 Bay Highlands Drive in Annapolis! This solid home offers a great opportunity for buyers looking to make a property their own in an established Annapolis community. The major systems have been replaced within the past few years, providing a strong foundation for future improvements. The home is ready for updating and TLC, including cosmetic improvements to the kitchen, baths, flooring, and finishes. With the major systems already addressed, buyers can focus on renovations and personal touches to bring out the home's full potential. The asking price is reflective of the home's current condition and the updates needed. Property is being sold strictly "AS IS." Seller will make no repairs. A great opportunity for buyers with vision who want to customize a solid home and build equity in Annapolis.

1182 Bay Highlands Dr, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

$520,000

Beautifully appointed rancher in the sought-after Cape St. Claire community of Annapolis, just one block from the Magothy River and the Chesapeake Bay! Step inside to a spacious main level featuring gleaming hardwood floors and a bright, open living room centered around a tile-surround wood-burning fireplace with a reclaimed-style mantle and custom open shelving. The flowing layout leads seamlessly into the dining area, offering ample storage and direct access to a screened-in deck, perfect for indoor-outdoor living. The kitchen is thoughtfully designed with granite countertops, a classic subway tile backsplash, 36” cabinetry, and stainless steel appliances. The primary suite provides a comfortable retreat with crown molding, a generously sized closet with an organization system, and a private en-suite bath complete with a walk-in shower and updated vanity. Two additional bedrooms and a well-appointed hall bath complete the main level. The finished lower level expands your living space with plush carpeting, built-in shelving, a dedicated workshop, gym area, and a utility space featuring a convenient powder room, ideal for guests, a home office, or multigenerational living. Enjoy outdoor living in the fully fenced yard with a patio and secure storage, perfect for entertaining or relaxing. Conveniently located near major commuter routes, including US-50 and I-97, for easy access to Annapolis, Baltimore, and beyond.

1030 Mountain Top Dr, Annapolis

Listing courtesy of Northrop Realty. Contact: 4105310321

$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:

$1,249,000

An exceptional offering in the heart of the Annapolis Historic District, 100 Conduit Street captures the timeless elegance and effortless lifestyle that make downtown Annapolis so coveted. Set along one of the city’s most charming historic streets, this distinctive three-four bedroom, two-and-a-half-bath residence pairs beautiful architectural character with an extraordinary location just moments from the waterfront. Inside, gracious living spaces are defined by gorgeous wood floors, rich millwork, custom built-ins, and thoughtful architectural details that lend warmth, character, and a wonderful sense of place. A chef's kitchen and separate dining room provide an elegant setting for everything from intimate dinners to holiday gatherings, while the inviting side porch offers the perfect spot for morning coffee, an evening glass of wine, or simply watching the rhythm of downtown life unfold. The home feels equally suited to comfortable everyday living and sophisticated entertaining, with carefully considered updates complementing its historic character. Beyond the interiors, established gardens create a private and enchanting retreat—an increasingly rare luxury in the heart of downtown. Just outside the front door, the best of Annapolis is yours to enjoy on foot. Stroll to Main Street and City Dock, dine at celebrated restaurants, browse boutiques and galleries, walk along the waterfront, or enjoy the traditions and energy surrounding the U.S. Naval Academy. There is an undeniable romance to life in the Historic District—the architecture, brick-lined streets, waterfront evenings, and the ability to leave the car behind and simply experience the city. 100 Conduit Street offers a rare opportunity to become part of that story, with the charm of historic Annapolis and the sophistication of downtown living beautifully intertwined.

100 Conduit St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$975,000

Experience resort like living in the water-oriented community of Oyster Harbor! Why choose between elegance and Chesapeake living when you can have both?! This stunning property offers the perfect blend of style and comfort with the ease of access to a plethora of sought after water-oriented community amenities! The main level features a beautiful, open kitchen with walk-in pantry, stainless steel appliances, center island, and large eat-in space. The living room is truly the heart of the home featuring a cozy gas/propane fireplace- perfect for gathering for cozy evenings at home. The upper floor is home to all four bedrooms- two of which have attached bathrooms and walk-in closets- and the upper level laundry adds convenience to daily living. The attached garage, with space for two vehicles and additional storage, provides practicality without compromising on style with a large driveway making it easy for guest parking. One of the standout features of this property is the spacious deck and large backyard- indoor/ outdoor living at its finest! The community of Oyster Harbor offers an exclusive lifestyle for water enthusiasts, with opportunities for boating, fishing, and enjoying the natural beauty of the bay. Enjoy easy access to many community amenities including: a large beach with gazebo, two tot lots (one on the beach!), three community marinas, boat ramp, fishing pier, kayak storage, and more! This home is not just a residence; it's a gateway to a lifestyle of luxury and leisure. Experience the perfect blend of modern amenities and serene surroundings in this exceptional Oyster Harbor property.

1326 Harbor Rd, Annapolis

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

$1,700,000

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

$599,000

4 Beds ⋅ 2 Baths

Located in the sought-after water-privileged community of Beechwood on the Burley, this two-level home offers comfortable living, a spacious outdoor setting, and an ideal Broadneck Peninsula location just minutes from downtown Annapolis and with easy access to Route 50. The established community offers water access, a marina, playground, and peaceful neighborhood setting, with convenient back-road access to downtown Annapolis. Inside, the home has been well maintained and thoughtfully updated with refinished hardwood floors, fresh paint, updated lighting, and new carpet. The upper level features a comfortable open-concept layout with a living room that flows into the dining area and kitchen. Granite countertops, beautiful cabinetry, and a center island with seating create a welcoming kitchen with plenty of workspace. Sliding glass doors open to a composite deck overlooking the flat, fully fenced backyard, where mature landscaping provides privacy and a lovely backdrop for outdoor living. The primary suite features a private ensuite bath, accompanied by two additional bedrooms and a full hall bath. The lower level adds valuable living space with a family room centered around a propane gas fireplace, an office/fourth bedroom, laundry room, and access to the attached garage. Ample storage throughout adds to the home's everyday functionality. Beechwood on the Burley is a voluntary HOA community with access to a waterfront park, community dock with slips, playground, and picnic area along the water. The neighborhood's quiet roads and surrounding farmland create a peaceful setting for walking, running, and cycling, while the home's location provides easy access to Annapolis, Broadneck schools, shopping, dining, and major commuter routes.

626 Edwards Rd, Annapolis

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 906-3848

$1,279,000

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

$879,000

Welcome Arundel on the Bay - a water oriented lifestyle community offering access to kayaking, paddle-boarding, beach and playground. All this with close proximity to shopping, restaurants, parks and downtown Annapolis. The quiet and calm neighborhood offers an island-like feeling. And this striking 3-story home is absolutely MOVE-IN READY! Gracious and plentiful windows leave you appreciating the timeless perennial gardens, majestic trees and peeks at Fishing Creek from multiple locations. As Fall arrives the "peeks" will become relaxing and lovely views! A bright and open floorplan features architectural lines and high ceilings which enhance the home's airy, gallery-like feel. Stunning wood floors offer warmth and continue the feeling of openness. We hope you like to cook and entertain - this Kitchen makes it not only possible but inviting and engaging. Extend your morning or evening and take a step out to the private back Deck tucked in to give you an intimate feeling with a lovely pergola and hanging lights. And it is only one of three Decks. The Primary Suite is magazine worthy - morning coffee on your Deck with lovely views or an evening toast to the day. Two more very spacious Bedrooms and updated Bath complete the 2nd Floor. And then the 3d Floor is worthy of the term "RETREAT". A wall of floor to ceiling windows with a side view of Fishing Creek and views of the trees and gardens below is icing on the cake! Amazing Community Features: Magnolia Avenue Beach, Newport Avenue Community Pier, Linden Avenue Recreational Pier, Redwood Avenue launching pier/boat ramp, and playgrounds.

3401 Saratoga Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$974,990

Construction is underway — and something truly special is taking shape! Schaefer Homes is proud to present this stunning newly constructed Colonial in the prestigious Oyster Harbor community, with a target completion date of November 2026. From the moment construction began, every detail has been thoughtfully considered to deliver a home that is as beautiful as it is livable. Set on a sprawling 0.62-acre lot, this exceptional residence offers the kind of space and privacy that is increasingly rare — plenty of room to create the outdoor oasis you've always envisioned, whether that's a garden retreat, entertaining terrace, or simply wide open space to enjoy the beauty of your surroundings. Inside, the elegant Colonial layout unfolds beautifully across a thoughtfully designed floor plan featuring 4 spacious bedrooms and 2.5 elegantly appointed bathrooms. The showstopping gourmet kitchen is the heart of the home, outfitted with upgraded design features and premium finishes that will inspire everything from weeknight dinners to unforgettable gatherings with family and friends. From its classic vinyl siding exterior to its sophisticated interior appointments, this home strikes the perfect balance between timeless architectural charm and the fresh, modern feel of new construction. Every finish, every detail, and every design choice reflects the quality and craftsmanship that Schaefer Homes is known for throughout Maryland. Oyster Harbor is more than a community — it's a lifestyle. Serene, exclusive, and truly one of a kind, this is the kind of neighborhood where neighbors become friends and every day feels like a retreat. This is your opportunity to plant roots in one of the area's most sought-after addresses. Don't wait — opportunities like this don't come around often. Schedule your private appointment today and take the first step toward making this dream home yours!

3268 Kitty Duvall Dr, Annapolis

Listing courtesy of Blackwell Real Estate, LLC. Contact: 4432214120

$850,000

Welcome to 327 Beach Drive, a beautifully updated 4-bedroom, 3-bath home located in the sought-after Hillsmere Shores community of Annapolis. Thoughtfully renovated with an emphasis on quality craftsmanship and timeless finishes, this home is truly move-in ready. The main level features brand-new natural birch flooring throughout, solid wood interior doors, crown molding, and recessed lighting in every bedroom. At the heart of the living room, a custom shiplap fireplace creates a warm and inviting focal point. The beautifully finished hall bathroom features custom details and an elevated design. A fully permitted addition created an impressive primary suite complete with a luxury private bath, providing a spacious and relaxing retreat. The finished lower level adds valuable flexibility with a home office and fourth bedroom, perfect for guests, working from home, or additional living space. The exterior is equally impressive with crisp white board-and-batten siding, an architectural-shingle roof, and great curb appeal. Step outside to a large, flat, fully fenced backyard offering plenty of space for entertaining, pets, play, and gardening. A low-maintenance Trex patio provides the perfect spot for outdoor dining, grilling, or relaxing. Located in desirable Hillsmere Shores, this thoughtfully renovated Annapolis home combines custom finishes, flexible living space, a fantastic backyard, and the coastal community lifestyle buyers are looking for.

327 Beach Dr, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

$626,000

5 Beds ⋅ 4 Baths

Welcome to 1976 Dominoe Road—an expansive, beautifully updated five-bedroom, four-full-bath home offering exceptional space, versatility, and income potential in a convenient Annapolis location. The bright, open-concept upper level features luxury vinyl plank flooring, recessed lighting, crown molding, and attractive built-ins. At the heart of the home is a spacious kitchen featuring Quartz countertops, stainless steel appliances, an electric stove, an over-the-range microwave, and a large center island with seating. An oversized window fills the space with natural light and offers peaceful backyard views, while glass doors open directly onto the elevated deck—perfect for outdoor dining, entertaining, or relaxing. The adjoining living room features a large picture window, a cozy fireplace, and plenty of room for family and friends to gather. This level also includes three generously sized bedrooms and two full bathrooms, including a primary suite with a private bathroom. A conveniently located stackable washer and dryer completes the upper level. The fully finished lower level significantly expands the home’s possibilities. It features a spacious family room with a ventless electric fireplace and built-in shelving, two additional bedrooms, two full bathrooms—including a second primary suite—a kitchenette, and a separate stackable washer and dryer. This versatile space is ideal for extended family, guests, a home office, or a potential income-producing suite, subject to applicable local requirements. Outside, the fully fenced backyard offers ample space for entertaining, gardening, children, pets, or peaceful relaxation. Enjoy evening gatherings, meals on the screened porch and elevated deck, and the privacy of your own outdoor retreat. A private driveway provides convenient off-street parking. New Roof, New Bathroom upgrade, New Front railings, Kitchen upgraded, New floorings, upgraded lightings. upgraded windows, New Water Heater and much more in 2026. HVAC system is just 3 years old. Conveniently located near shopping, dining, recreation, major commuter routes, downtown Annapolis, and everything the area has to offer, this spacious and adaptable home presents a rare opportunity. Whether you need room for a growing household, multigenerational living, or potential rental income. Schedule your private showing today!

1976 Dominoe Rd, Annapolis

Listing courtesy of Accord Realty Inc.. Contact:

$725,000

1 Beds ⋅ 2 Baths

A unique mixed-use opportunity in the heart of Annapolis! Located in the Arts District, 232 West Street offers the flexibility of commercial and residential use in a convenient location close to Downtown Annapolis, Navy-Marine Corps Memorial Stadium, and the U.S. Naval Academy. Renovated in 2018, the property is currently configured for residential use with one bedroom and one and a half baths. Skylights and abundant natural light create a bright, welcoming feel throughout. The updated kitchen features white cabinetry, stainless steel appliances, a subway tile backsplash, and an island with seating, while hardwood floors add warmth and character. The spacious primary bedroom offers two closets and direct access to a private deck. The adjoining bathroom features a dual-sink vanity and a shower with dual shower heads. A separate studio in the rear provides additional flexible space with a variety of potential uses. The fenced yard adds privacy and creates a nice connection between the property, outdoor space, and the studio, while a shed provides additional storage. In-home laundry and a tankless water heater add to the property's conveniences. Situated on an approximately 2,700-square-foot lot, the property also offers potential for future expansion, subject to applicable zoning and approvals. Enjoy a prime West Street location with easy access to Downtown Annapolis, City Dock, restaurants, and shops, along with convenient access to Routes 50 and 97. A versatile property with a unique combination of location, character, and flexibility.

232 West St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767

$624,900

There's a version of Annapolis living where you don't have to choose between being close to everything and having room to enjoy being home. This updated 3-bedroom, 2-bath home sits in a residential setting just minutes from downtown Annapolis, the Naval Academy, Eastport, marinas, restaurants, and shopping, while offering something that can be hard to find this close to the city: real outdoor space. Step outside and the fully fenced backyard speaks for itself. A covered deck flows to the patio and firepit, creating a space for morning coffee, dinner outside, a quiet evening by the fire, or hosting when you want to. Inside, the home balances comfort and function. Both baths feature updated showers, and the fireplace anchors the main living area. The partially finished basement with a bar adds flexible space for entertaining, movie nights, or whatever fits the way you live. The updates go beyond cosmetic. The covered deck and roofs on both the home and garage were replaced in 2021, the fence was added in 2024, and a new front porch, mailbox, walkway, and water heater followed in 2025. The detached garage adds parking and storage, with room for a workshop. Close to the energy of Annapolis, with plenty of room to unwind when you get home.

1033 Hyde Park Dr, Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact: 8554500442

$725,000

Coming Soon! Welcome to 2567 Forest Knoll, a charming rancher tucked away on a cul-de-sac in the beloved 55+ community of Heritage Harbour in Annapolis. Offering three bedrooms and two full bathrooms, this single-level home provides easy, comfortable living in a peaceful setting. The furnace and HVAC system were replaced approximately three years ago. Heritage Harbour offers an amenity-rich lifestyle with pools, clubhouse facilities, tennis, golf, boating access to the South River, and a variety of clubs, activities, and social opportunities. More details and professional photography coming soon!

2567 Forest Knl St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$995,000

A long private lane beneath a canopy of mature trees leads to a distinctive mid-century modern retreat that feels worlds away, yet is just minutes from the restaurants, shopping, and everyday conveniences of Annapolis. Tucked into the woods in the sought-after Downs on the Severn, this four-season sanctuary offers the best of both worlds, the privacy and escape of a secluded setting paired with the community and resort-style amenities of one of the area’s most desirable water-privileged neighborhoods. Each season brings a different backdrop. Spring arrives with an explosion of color throughout the surrounding landscape, summer fills the property with lush greenery, fall transforms the tree canopy, and winter reveals the quiet architectural beauty of the home and its wooded setting. The result is a property that feels deeply connected to nature throughout the year. The natural setting is truly part of the experience here. A stream winds through the landscape to a beaver pond, becoming increasingly visible as the leaves begin to fall and adding another beautiful dimension to the views. Wildlife is a regular part of daily life, with deer, wild turkeys, birds, ducks on the pond, and more making frequent appearances. Summer evenings bring the sounds of bullfrogs, while owls can often be heard among the trees. For anyone who appreciates nature and wildlife, the property offers an ever-changing view and soundtrack throughout the seasons. Inside, the home blends contemporary style with the warmth and character of its mid-century roots. Vaulted wood ceilings, exposed beams, brick accents, expansive windows, and multiple skylights create a vintage-meets-modern aesthetic while filling the interiors with natural light. The open floor plan feels relaxed and inviting, with a dramatic brick fireplace anchoring the main gathering spaces. The gourmet kitchen flows easily into the living and dining areas, while walls of glass frame the trees beyond and reinforce the home's connection to its surroundings. Outdoor living is equally inviting. An expansive rear deck stretches across the back of the home, creating a private perch among the trees for morning coffee, outdoor dining, entertaining, or simply taking in the peaceful setting. Below, the walkout lower level opens to a spacious patio and offers additional light-filled living space with a family room, two bedrooms, and a full bath. Large windows continue the connection to nature on both levels. The property also offers a two-car garage that can accommodate most standard sedans, along with a detached two-car carport providing additional covered parking. Recent improvements include a new refrigerator (2026), arborist inspection and tree trimming (September 2026), resurfaced asphalt driveway with one-year warranty (September 2026), new wood floors in the primary bedroom (September 2026), upgraded exterior outlets (2026), septic system service (2026), flue and chimney service and cleaning (2026), new washing machine (2025), exterior painting and repairs (2025), rear deck reinforcement and staining (2024), interior painting throughout (2023), and more. Beyond the privacy of home, Downs on the Severn offers a wonderful sense of community with a deep-water marina, a clubhouse, swimming pool, and tennis/pickleball courts. This special property offers the character of a true Annapolis neighborhood with the feeling of a secluded retreat, an architectural sanctuary in the woods with waterfront recreation and the conveniences of town just minutes away. Welcome Home!

1707 Trinity Pl, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$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:

$675,000

Welcome to 953 Mastline Drive, a spacious ranch style home in the highly sought after 55+ community of Heritage Harbour. Offering just under 2,000 square feet, three bedrooms, two full bathrooms, and a two car garage, this home provides easy single level living with plenty of space to enjoy. Inside, fresh paint and brand new carpet give the home a clean, refreshed feel throughout. Generous living and dining areas offer flexibility for everyday life and entertaining, while the primary suite features its own private bathroom. Updated windows and HVAC, along with new insulation, add to the improvements already completed, allowing you to move right in while still having the opportunity to personalize the home over time. Heritage Harbour offers an impressive collection of amenities, including indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine hole golf course, community Lodge, library, and an extensive calendar of clubs, activities, and social opportunities. Shopping, dining, healthcare, and everyday conveniences are nearby, with easy access to Routes 50 and 97 and Historic Downtown Annapolis just a short drive away. Combining a spacious ranch layout, valuable updates, and the active lifestyle of one of the Annapolis area’s most established 55+ communities, 953 Mastline Drive is ready to welcome its next owner.

953 Mastline Dr, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact: 4439012200

$755,000

Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level and stairs feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50

303 Riding Ridge Rd, Annapolis

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

$1,750,000

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

$825,000

Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

2691 Claibourne Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$534,000

4 Beds ⋅ 2 Baths

A Dutch Colonial home on a cul-de-sac inside the Annapolis city line, for $534,000. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. 1017 Hyde Park Drive was built in 1984 in Wilshire. Three bedrooms and a full bath sit upstairs, a fourth bedroom and a second full bath on the main level, with central air for August. Its 1,272 square feet on the top two levels sit over a finished basement, with room for a rec room, a gym or an office. Out back, a deck looks over a yard of your own. The address does the rest. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, and from the restaurants of Eastport, the Annapolis Maritime Museum and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore and the Eastern Shore within reach, for the commute or for the weekend.

1017 Hyde Park Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$995,000

2 Beds ⋅ 2 Baths

Highly Desirable Eastport Peninsula! Experience the best of the Eastport lifestyle in this charming home, ideally located in the heart of the peninsula. Relax on the inviting front porch and watch the world go by, or step out your door and walk to Eastport’s renowned restaurants, lively bars, boutique shopping, marinas, yacht clubs, and the water taxi to historic downtown Annapolis. Inside, beautiful heart pine floors add warmth and character. The spacious rear yard is a rare find in Eastport and offers plenty of room for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. The chef’s kitchen features Viking refrigerator and stainless steel appliances, creating a wonderful space for both everyday cooking and entertaining. Thoughtful improvements and major updates throughout the years make this home truly move-in ready while still offering the opportunity to add your own personal touches. Notable improvements include: * Pella rear sliding glass door — 2025 * Carrier first-floor HVAC — 2025 * Washer & dryer — 2024 * Viking refrigerator — 2024 * New roof — 2023 * First-floor bathroom remodeled — 2018 * Front porch replaced and metal roof added — 2018 * First-floor floors and stairs refinished by Beers — 2017 * Rinnai tankless water heater — 2016 * Upstairs bathroom and closet remodeled by Gate One Builders — 2011 * HardiePlank siding — 2009 * Fence — 2005 * Brick foundation repointed — 2004 * Shed — 2003 * Renovation and rear addition — 1998 A wonderful opportunity to own a piece of Eastport—move right in, enjoy the lifestyle, and make it your own.

412 Third St, Annapolis

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000

$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:

$610,000

Welcome to this beautifully updated ranch-style home in Hillsmere Estates... where modern comfort meets serene living. Located on a spacious corner lot with ample driveway parking, this warm and charming retreat boasts four bedrooms and three full bathrooms and is designed to accommodate all your lifestyle needs. The open well-appointed kitchen is ready for your culinary adventures boasting plenty of sleek counter space along with an abundance of cabinets. Gather around the roomy kitchen island or the bright and cheerful dining area for your social events or comforting traditional meals. Cozy up to the newly updated fireplace in the living room that creates the perfect ambiance for quiet evenings or festive gatherings. Hardwood flooring on the main floor adds to the appeal of this home. The inviting sunroom is ready when you need extra space for game time adventures or a moment to lean back with your feet up to revel in your comfy quiet world. The fully finished basement offers plenty of room for your bedroom/office along with a family room for entertainment and the added convenience of a full bathroom. It also features a kitchenette space that can easily be converted to a full kitchen with a laundry area to create an accommodating in-law suite. Not only are there endless options in the basement living areas, this generous space includes plentiful storage room for your handy tools and treasured keepsakes. Stepping out to the back yard, the WOW feature continues as you gaze out to the fully fenced and expansive 0.32-acre flat lot where your options are limitless. A picturesque atmosphere where you can be the host of a special occasion or unwind in your private outdoor oasis. As nature smiles in this abundant space, a large shed has been gently nestled in allowing you to organize some well-deserved lounging furniture, gardening implements as well as your entertaining games and toys for all your pleasures. As you venture out from the sanctuary of your lovely home, the amenities for the Hillsmere Shores community are ready to be enjoyed. Feel the charm as you walk down Hillsmere Drive beneath a canopy of historic cypress trees. Treat yourself with exclusive access to a private marina on the South River, a sandy beach, waterfront pavilions, a community pool, and multiple playgrounds. Potential adventures abound in a community where you are within easy walking distance to Quiet Waters Park sharing its nature trails, dog beach and playgrounds. For water enthusiasts, you are only 2 miles from the South River, providing easy access for boating, fishing and kayaking. Multiple slips are available by lease making your aquatic adventures just a stone's throw away. Embrace the lifestyle you've always wanted in a community that offers both tranquility and recreational opportunities and is conveniently located near schools, a library along with dining and shopping experiences. This is more than just a house... it is your home and community where you can create lasting memories. Don't miss your chance to make this home your own!

301 Cedar Ln, Annapolis

Listing courtesy of ExecuHome 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.

113 Bay Dr, Annapolis

Listing courtesy of Krauss Real Property Brokerage. Contact: (410) 804-7921

$750,000

Welcome to 580 Pinedale Dr, a spacious 4-bedroom, 2.5-bath home set on a beautiful 1.8-acre lot in Annapolis. Offering a comfortable blend of character, functionality, and privacy, this home provides plenty of space for everyday living and entertaining. The impressive lofted living room is filled with natural light and features skylights that create an open, airy atmosphere. The inviting family room offers a propane fireplace, providing a cozy gathering space for relaxing evenings. The spacious kitchen offers plenty of cabinet and counter space, providing a functional and inviting setting for preparing meals and gathering with family and friends. A convenient half bath completes the main level. The spacious primary bedroom features its own ensuite bathroom and private laundry, creating a comfortable retreat with added convenience. Three additional bedrooms provide flexibility for family, guests, a home office, or hobby space. Outside, the expansive 1.8-acre property offers room to enjoy the outdoors and plenty of privacy, while the attached 2-car garage provides ample parking and storage. With its generous lot, versatile floor plan, lofted living space, and sought-after Annapolis location, 580 Pinedale Dr offers an opportunity to enjoy both space and convenience.

580 Pinedale Dr, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

$575,000

4 Beds ⋅ 2 Baths

Welcome to this beautifully updated split-foyer home nestled on a gorgeous corner lot in the sought-after Cape St. Claire community of Annapolis. Offering an exceptional combination of modern updates, thoughtful improvements, and outstanding community amenities, this move-in ready home has been meticulously maintained inside and out. Inside, you'll enjoy modern fixtures, recessed lighting, granite countertops, and an updated kitchen featuring stainless steel appliances, including a refrigerator, dishwasher, and electric range replaced in 2022. The kitchen flows seamlessly onto a brand-new wood deck (2023, freshly stained in 2026), creating the perfect space for outdoor dining, entertaining, or simply relaxing. The inviting living room is centered around a beautifully renovated wood-burning fireplace (2023), while major system upgrades provide added peace of mind, including a new HVAC system (2024) and a whole-house humidifier (2025) for year-round comfort. The main level offers three bedrooms, including a primary suite with a private bath and two additional bedrooms with a shared hall bath. The finished lower level features a spacious flex area that can easily serve as a recreation room, home office, workout space, guest area, or potential fourth bedroom, along with a dedicated laundry area and convenient side-entry mudroom. Step outside and discover extensive outdoor improvements completed between 2022 and 2024. The property has been professionally regraded and enhanced with retaining walls, a stone walkway, additional gravel parking, and a completely restructured driveway offering improved functionality and expanded parking. An engineered drainage system, including underground front-yard downspouts and a complete backyard French drain, helps keep the property dry and functional throughout the seasons. Thoughtfully selected native, non-invasive flowers and shrubs provide beautiful color and interest throughout the year. Located in the highly desirable Cape St. Claire community of Annapolis, Maryland, residents enjoy access to outstanding neighborhood amenities, including a private community beach, community marina, boat ramp, fishing and crabbing pier, playgrounds, parks, and community events throughout the year. Conveniently located just minutes from downtown Annapolis, Broadneck Park, Sandy Point State Park, the Chesapeake Bay, the U.S. Naval Academy, shopping, dining, waterfront attractions, and everyday conveniences. Commuters will appreciate easy access to Route 50, I-97, Baltimore, Washington, D.C., Fort Meade, and BWI Airport. Whether you're looking for a beautifully updated home, a move-in ready property with major system upgrades, or the lifestyle that comes with living in one of Annapolis' premier water-access communities, this exceptional Cape St. Claire home offers the perfect opportunity to enjoy the very best of Maryland's Chesapeake Bay lifestyle.

1178 Glenwood Dl, Annapolis

Listing courtesy of Redfin Corp. Contact: 3016586186

$1,900,000

***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.

400 Jefferson St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$1,250,000

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

$924,999

5 Beds ⋅ 4 Baths

Nestled in the charming Admiral Heights neighborhood, this stunning split-level home exudes warmth and character, inviting you to experience its unique design and craftsmanship. Built with everyone in mind, this residence boasts timeless appeal with its classic brick-and-vinyl siding exterior, harmoniously blending with the lush surroundings. Step inside to discover a spacious layout that offers both comfort and functionality. With five generous bedrooms and three and a half bathrooms, this home is perfect for those who appreciate space and versatility. The heart of the home features a cozy fireplace, creating an inviting atmosphere for gatherings and quiet evenings alike. The partially finished basement provides endless possibilities, whether you envision a workshop, a play area, or additional storage. The expansive lot offers ample outdoor space for relaxation and recreation, while the community pool adds a refreshing touch for those warm summer days. Parking is a breeze with an attached carport and additional driveway space, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where cherished memories are made. Experience the perfect blend of classic design and modern living in this delightful Admiral Heights gem. Don't miss the opportunity to make this house your home!

13 Rickover Ct, Annapolis

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

$750,000

RARE OPPORTUNITY! TWO HOMES ON ONE LOT IN EASTPORT! This versatile property offers an exceptional combination of character, functionality, and flexibility with a renovated 2-bedroom, 1.5-bath main home PLUS a separate 1-bedroom, 1-bath guest house. The main residence features gleaming hardwood floors, a cozy fireplace, and a spacious kitchen with abundant counter space, a large peninsula, and stainless-steel appliances. The inviting layout provides comfortable living spaces while retaining the charm and character buyers love. The detached guest house is a standout feature, offering a private bedroom, full bath, living room, washer/dryer, and separate utilities. Ideal for guests, extended family, a private home office, or other flexible living arrangements. Enjoy the outdoors in the pleasant, tree-lined backyard, enclosed by a privacy fence. A 1+ car garage and shed provide plenty of room for parking, storage, hobbies, and outdoor equipment. Located conveniently to the restaurants, shops, waterfront, and attractions of Eastport and Downtown Annapolis, this property puts you close to everything while offering the flexibility of two separate living spaces. Notable recent improvements include: New roof and skylights (2023) New driveway (2022) Guest house electrical wiring (2022) New dishwasher (2024) Two homes. One lot. Endless possibilities. A unique opportunity in a highly desirable Annapolis location!

906 Jackson St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$879,990