Annapolis 3 Bedroom Properties for Sale

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

113 Mckendree Ave, Annapolis

Listing courtesy of Homecoin.com. Contact:

$1,795,000

EXPANSIVE WATERVIEWS OF THE SEVERN RIVER!!!! Charming home overlooking fantastic waterviews!! Extensive renovation took place in 2019 included second floor Primary suite addition(includes full bath and walkin closet), beautiful new kitchen, Hardwood floors throughout, new windows, new powder room, new main level laundry, renovated main level full bath, new architectual shingle roof, new electric and HVAC heat pump with gas backup. Whole house generator! recent improvement include new patio pavers and walkway,exterior just painted with new composite shutters and garage door. This home has great curb appeal. Once inside the waterviews are fantastic!! Beautiful kitchen with granite counters opens to the sun filled family room. Hardwood floors are stunning. The Primary addition is a private oasis and again you won't take your eyes off of the WATERVIEWS!! The community offer a beach on the Severn River and community docks. Minutes by car or boat to downtown Annapolis. Perfect party house for Blue Angles!! This truely is a MUST SEE!!

219 Riverside Dr, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

$725,000

Welcome to 123 Maple Drive in sought-after, amenity-rich Hillsmere Estates! This updated 3-bedroom, 3-full-bath home features a spacious main-level bedroom, new windows, new LVP flooring on the main level, and new carpet on the stairs and upper level. The updated kitchen offers new quartz countertops, stainless steel appliances, and a new stove and microwave. The primary ensuite has been completely renovated, and the other two full baths have also been updated. A new sliding glass door leads to the large, new custom-built deck overlooking a spacious, flat, fenced rear yard—plenty of room for entertaining, playing, or relaxing outdoors. A two-car garage with a new garage door adds convenience and storage. Enjoy all that Hillsmere has to offer, including a community pool, beach, boat ramp, volleyball court, frisbee golf, pavilion, and more, plus adjacent access to Quiet Waters Park. Located approximately a 5-minute walk to Hillsmere Elementary and a 3-minute drive to Key School, this home combines thoughtful updates, great outdoor space, and an incredible Annapolis location!

123 Maple Dr, Annapolis

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

$700,000

An incredible, rare opportunity in a peaceful and sought-after Annapolis community! Tucked away on a quiet cul-de-sac and set on a lush 0.76-acre lot, 1085 Carriage Hill Court is a charming English Cotswold cottage reproduction offering endless potential for investors, renovators, or buyers looking to build sweat equity. Sold entirely AS-IS, this home is ready for a complete refresh or total transformation. The existing layout boasts strong architectural bones, including a family room with vaulted ceilings and a stacked stone fireplace, a primary suite with a sitting area/loft, and a bonus room over the garage. Outside, the sprawling, peaceful lot backs to trees, offering a private refuge ready for your personal touch. Residents enjoy fantastic neighborhood amenities including basketball courts, tennis and pickleball courts, a playground, and open green space. All of this is ideally located just minutes from historic downtown Annapolis, local dining, shopping, and major commuter routes (I-97 & Route 50). Bring your vision, and capitalize on a premier Annapolis location!

1085 Carriage Hill Ct, Annapolis

Listing courtesy of Compass. Contact:

$530,000

YOUR ANNAPOLIS LIFESTYLE STARTS HERE! Discover move-in-ready comfort, thoughtful updates, and Chesapeake Bay living in the sought-after Cape St. Claire community! Beautifully maintained, this 4-bedroom, 2-bath home offers approximately 1,828 square feet of flexible living space on a welcoming corner lot. Inside, enjoy an inviting living room with a beautifully renovated wood-burning fireplace, an updated kitchen featuring granite countertops and stainless steel appliances, and easy access to the newer wood deck, perfect for morning coffee or weekend entertaining. Three main-level bedrooms and a finished lower level provide plenty of flexibility for everyday living, guests, a home office, or recreation space. MAJOR IMPROVEMENTS ALREADY COMPLETED! Highlights include a newer HVAC system (2024), whole-house humidifier (2025), updated kitchen appliances, renovated fireplace, newer deck, and extensive exterior improvements including professional grading, drainage, retaining walls, walkways, and expanded parking. LOVE WHERE YOU LIVE! Cape St. Claire offers a wonderful Chesapeake Bay lifestyle with neighborhood beaches, marinas, boat access, parks, playgrounds, and community activities. Enjoy nearby Sandy Point State Park, downtown Annapolis, waterfront dining, shopping, and convenient access to Route 50. Beautifully updated, meticulously maintained, and ready for its next chapter! Come experience the home, the neighborhood, and the lifestyle for yourself. Schedule your private tour today! *** Some photos are virtually staged.***

1178 Glenwood Dl, Annapolis

Listing courtesy of Redfin Corp. Contact:

$370,000

Welcome to this freshly painted 3-bedroom, 1.5-bath townhouse in Annapolis’s sought-after Whispering Woods community, located in the Blue Ribbon Broadneck school district. The updated kitchen features generous cabinetry, and new GE Café appliances, including an induction stove and dishwasher. LVT flooring flows throughout, and new carpet on the stairs, a new water heater, and new gutters add comfort and peace of mind. A screened-in sunroom and adjoining deck create inviting spaces to relax or entertain while enjoying views of the fenced backyard. The outdoor space also includes a concrete patio and storage shed. Residents can enjoy two separate children’s play areas within the community. Everyday conveniences and local destinations are close by. Broadneck Park and its dog park are about five minutes away, as is Bay Hills Shopping Center, with dining and grocery options. Annapolis Town Center and Annapolis Mall are about 10 minutes away, while Downtown Annapolis, the Naval Academy, and the stadium are roughly 15 minutes away. Marinas and yacht clubs are nearby, and the Bay Bridge is about 10 minutes away. Enjoy comfortable indoor-outdoor living with shopping, dining, recreation, and the Chesapeake Bay all within easy reach. *** Some photos are virtually staged.***

329 Charred Oak Ct, Annapolis

Listing courtesy of Redfin Corp. Contact:

$995,000

Epic Home in the Waterfront Community of Epping Forest! Post and Beam Tree House with 6 Levels of Interior/Exterior Living Space plus an additional lower level with utility room and bonus storage in basement. The perfect location in one of Annapolis's prime waterfront communities! Contemporary log home design with custom built ins and windows everywhere bringing the surrounding peace of nature inside. Intimate spaces uniquely designed within an open floorplan. Custom cabinetry, soaring pine plank ceilings, walls of Anderson windows, Pine wide plank flooring and over 1,000 square feet of outside multi level deck space. Imagine spending a quiet Fall Saturday in this glorious property curled up with a book in the loft library surrounded by woods and nature. Anderson Windows, 15K Panoramic Forever Sliding Doors to access upper deck in loft and new roof in 2024. Recent 20K in Improvements including large parking area retaining wall. Epping Forest is a Gated Waterfront Community on the Severn River with a communal beach, waterfront Clubhouse with restaurant and bar, tennis/pickleball and Marina. Your neighbors will become your best friends and better than family. The very best you can find in Annapolis! Year around activities include 4th of July Fireworks, Oyster & Bull Roast, Boat Club, Summer Volleyball League, Kayaks & summer camps. Come experience the best Chesapeake Bay Maritime Annapolitan Lifestyle around! Lead Free Certificate available, contact agent for more details!

1760 Birdbrook Trl, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$725,000

Beautifully renovated from top to bottom, this stunning rancher in the sought-after 55+ Heritage Harbour community offers stylish, single-level living with an open floor plan, thoughtfully selected finishes, and inviting indoor and outdoor spaces. Situated on a beautifully landscaped corner lot in a quiet cul-de-sac, the home features fresh paint, new luxury plank flooring, updated light fixtures, ceiling fans, and multiple skylights that fill the interior with natural light. Welcoming landscaping leads to the front entrance, where a spacious foyer opens to the beautifully reimagined kitchen, dining area, and family room. The renovated kitchen showcases 42-inch white soft-close cabinetry, stainless steel appliances, and striking waterfall granite countertops with a breakfast bar. The adjoining dining area and family room create a seamless setting for everyday living and entertaining. On the opposite side of the kitchen, the inviting living room features a cozy fireplace, custom built-ins, and convenient access to the laundry room and the two-car garage. From here, step into the delightful four-season sunroom, complete with a dedicated heating and cooling wall unit and picturesque backyard views. A patio just outside extends the living space outdoors, while an underground irrigation system helps maintain the beautifully landscaped grounds. Tucked away in the bedroom wing, the primary suite offers a generous wall of closets and a beautifully renovated en-suite bath featuring an elegant vanity, stylish finishes, and a tiled shower with a glass door. Two additional bedrooms share an updated full hall bath with coordinating marble-look tile finishes. Heritage Harbour offers an exceptional resort-style lifestyle with indoor and outdoor pools, a fitness center, nine-hole golf course, tennis and pickleball courts, bocce ball, and scenic paths. The community Lodge features a library, auditorium, billiards, woodworking shop, and gathering spaces. Additional amenities include RV parking and storage, South River waterfront access with a pier and boat slips, kayaking opportunities, and an abundance of clubs and organized activities. Historic downtown Annapolis, shopping, dining, and commuter routes are just minutes away. A one-time $2,100 recreation fee is payable by the buyer to Heritage Harbour at settlement. Please note: some photos have been virtually staged.

848 Deerwood Ct, Annapolis

Listing courtesy of Northrop Realty. Contact:

$795,000

Welcome to Admiral Heights. Perched proudly, this beautifully maintained home at 405 Halsey Road, is where pride of ownership shines throughout. Ideally located just minutes from downtown Annapolis, the U.S. Naval Academy stadium, and major commuter routes to Washington, D.C., Northern Virginia, and Baltimore, this home offers the perfect blend of comfort, convenience, and lifestyle. Featuring 3 bedrooms and 2.5 bathrooms, the home offers a thoughtfully designed layout with inviting spaces for everyday living and entertaining. The main level features a kitchen that opens to the dining area and family room, complete with a cozy wood-burning fireplace. From here, step into the enclosed sunporch and out to the deck, creating a wonderful flow for indoor-outdoor living. A separate formal dining room and convenient powder room complete the main level. Upstairs, the spacious primary suite offers a large walk-in closet, a comfortable sitting area, and a private full bathroom. Two additional generously sized bedrooms and a full hall bathroom provide plenty of room for family, guests, or a home office. Major updates include a new roof and replacement windows, offering added peace of mind. The lower level provides excellent potential to create additional living space tailored to your needs, whether you envision a recreation room, home gym, theater, or hobby space. Outside, enjoy the lovely backyard, perfect for summer barbecues, entertaining friends, or simply relaxing at home. With this homes wonderful location, inviting living spaces, and meticulous care, this Admiral Heights home is ready for its next chapter. Come discover all it has to offer.

405 Halsey Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$250,000

Opportunity awaits! Fully updated: Annapolis home being sold in an ONLINE AUCTION. The auction closes Tuesday, November 24, 2026, at 2:00 PM EST. Fully updated three-bedroom, three-full-bath brick-and-siding split-foyer in Cape St. Claire on approximately 0.21 acre. Features include an expansive primary bedroom, an updated kitchen with new appliances, living and dining areas, a lower-level recreation room and third bedroom, laundry and mechanical rooms, a rear deck, driveway parking, central air, a private well, a public sewer, and one fireplace. Original list price: $585,000; opening bid: $250,000. Open house viewing and inspection opportunities: Sunday, November 1, 2:00–4:00 PM; Thursday, November 12, 11:00 AM–1:00 PM; Sunday, November 22, 10:00 AM–12:00 PM EST. Register at Prime Auction Solutions. Review complete auction terms, documents, buyer's premium, deposit requirements, and property documents before bidding. The final price to be set at auction. Excellent investor and investment opportunity. Register and bid your price at Prime Auction Solutions. Contact the agent for more specific information. Watch video.

721 Fairway Dr, Annapolis

Listing courtesy of Keller Williams Realty. Contact:

$599,900

3 Beds ⋅ 5 Baths

****VA ASSUMABLE LOAN OPTION AT AN INCREDIBLE 4.75% INTEREST RATE! **** Welcome to 135 Lejeune Way, a four-level Admirals Square townhome with 3 bedrooms, 5 bathrooms (3 full, 2 half), a den, an attached garage, and a rooftop deck. The second level is made for entertaining. Sunlit open-plan living and dining flow into a gourmet kitchen with stainless steel appliances and an oversized center island, with room for everyone to gather. An upgraded electric fireplace anchors the living area, so the space feels warm and inviting in any season. Upstairs, the large primary suite has a recently renovated bathroom. A second bedroom with its own full bath is on the same level. The top floor adds a third bedroom with a full bath and a loft that opens to the rooftop deck, a good spot for morning coffee or an evening unwind. The half baths have also been recently renovated. The entry level has a den that works as a home office, gym, or guest space, plus a half bath and direct access to the attached garage. The location is hard to beat. The U.S. Naval Academy and the brick streets, restaurants, and waterfront of downtown Annapolis are minutes away. Annapolis Town Center is nearby for shopping and dining, and Routes 50 and 97 enable easy access to Naval Support Activity Annapolis and Fort Meade.

135 Lejeune Way, Annapolis

Listing courtesy of Willow Oaks Realty, LLC.. Contact:

$585,000

Beautifully renovated and tucked away on a cul-de-sac in the desirable Stonecreek community, this contemporary home offers stylish living spaces, inviting outdoor retreats, and an exceptional Annapolis location. Extensive improvements include a renovated kitchen and bathrooms, newly finished basement, newly installed whole-house sprinkler system, new flooring and a new electrical panel. A neutral color palette and luxury vinyl plank flooring create a fresh, cohesive feel throughout the home. The renovation includes closed electric, plumbing, building, mechanical, and sprinkler permits. Step inside to discover a spacious living room with a soaring vaulted ceiling that creates an open, airy atmosphere. The living room flows seamlessly into the adjoining dining room, providing an inviting setting for everyday meals and entertaining. Beyond the dining area, the beautifully renovated kitchen showcases crisp white soft-close cabinetry, granite countertops, stainless steel appliances, and an extra-long breakfast bar offering generous seating and preparation space. Open to the kitchen, the comfortable family room features a cozy fireplace and a sliding glass door leading to the screened porch, creating an effortless connection between indoor and outdoor living. Three bedrooms occupy the main level, beginning with the primary suite, where a vaulted ceiling adds architectural interest. A walk-in closet provides ample storage, while the beautifully renovated en-suite bath features a striking floor-to-ceiling tiled shower. Two additional bedrooms share an updated hall bath appointed with modern fixtures and stylish finishes. The finished lower level expands the home's versatility with a spacious recreation room featuring recessed lighting, an updated full bath, and a flexible bonus room ideal for a home office, guest accommodations, exercise room, or hobby space. Outside, the screened porch and tiered deck offer multiple areas for relaxing and entertaining, while the fenced backyard provides additional space to enjoy the outdoors. A storage shed offers convenient space for tools and outdoor equipment, while a greenhouse provides an ideal setting for gardening enthusiasts. The roof was replaced in 2023, per the previous owner. Residents of Stonecreek enjoy access to a community swimming pool and tennis courts, along with proximity to Quiet Waters Park and Truxtun Park for additional outdoor recreation. Historic downtown Annapolis is just minutes away, offering waterfront dining, boutique shopping, and the charm of City Dock. Convenient access to Forest Drive, Route 50, and major commuter routes completes this appealing location. Please note: some photos have utilized virtual staging.

14 Landings Ct, Annapolis

Listing courtesy of Northrop Realty. Contact:

$315,000

SPACIOUS THREE-LEVEL LIVING JUST MINUTES FROM DOWNTOWN ANNAPOLIS! Looking for ways to lower your interest rates? Discover exceptional value in this refreshed townhome-style condo, offering 1,600+ sq. ft. of space with the convenience of condo living and the possibility to assume the owner's FHA loan. Freshly painted and finished with stylish luxury vinyl plank flooring on all three levels, this home has a cohesive, modern look that is easy to maintain. The roomy main level offers an eat-in kitchen, a great room for everyday living and entertaining, a convenient powder room, and access to a brick patio overlooking tranquil open green space. The second level features two generously sized bedrooms and a full bath, offering flexibility for guests or a home office. The entire top level is dedicated to an expansive Owner’s Suite, creating a private retreat complete with an oversized walk-in closet and a spacious ensuite bath featuring a soaking tub, separate shower, and double vanity. Enjoy low-maintenance living, with condo fees covering roof maintenance, fencing, lawn care, and access to the community pool and fitness center. Additional highlights include an HVAC system replaced in 2022, one reserved parking space, and an additional parking permit. LOCATION, SPACE, AND VALUE! Just minutes from the restaurants, shopping, waterfront attractions, and vibrant lifestyle of Historic Downtown Annapolis, this home offers an outstanding opportunity to enjoy generous living space without the upkeep of a traditional single-family home.

50-H Hearthstone Ct Unit H, Annapolis

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

$560,000

Also for Rent, Listing ID MDAA2150578. Welcome to 104 Vanguard, a bright and spacious 3 level townhome in the heart of Annapolis, nestled in the gated community of Village Greens. Enjoy shopping, dining and entertainment just steps from your front door. This beautifully maintained home is perfect for everyday living and entertaining alike. The entry level features a two car garage, a half bath, and flex space perfectly suited for a home office or recreation room. The main level includes a gourmet kitchen with granite countertops, stainless steel appliances, a large island with breakfast bar, and dining room that leads to a deck that is perfect for grilling, entertaining, or just relaxing. Rounding out this level is a family room that overlooks the community recreation area and an additional half bath. Upstairs are two generously-sized guest bedrooms, a guest bath, a laundry closet, and a sumptuous primary suite with spacious walk in closet and primary bath with dual vanities. Minutes from Eastport, Annapolis, the Naval Academy, and Quiet Waters Park, this home offers an unparalleled lifestyle with the added comfort of a gated community. Easy access to Rtes. 50 and 97 gives you plenty of commuting options to the Baltimore and DC areas. Come enjoy all that Annapolis has to offer. Your new lifestyle awaits! Welcome Home!

104 Vanguard Ln, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$469,932

Welcome to 2006 Puritan Terrace in the desirable Windgate community of Annapolis! This spacious three-level townhome offers 3 bedrooms, 2.5 baths, and approximately 1,800+ square feet of finished living space, providing the perfect combination of comfort, functionality, and convenience. The main level features an inviting living room and a generous eat-in kitchen with a center island, adjoining dining area, and sliding glass doors leading to a spacious rear deck overlooking a wooded setting and community walking path. Upstairs, you'll find three comfortable bedrooms, including a primary suite with a private bath and walk-in closet. The finished lower level provides additional living and entertaining space with a cozy gas fireplace, along with a separate laundry area and storage space. Two assigned parking spaces add everyday convenience. Enjoy the Windgate community's walking paths and playground, all within easy reach of downtown Annapolis, shopping, restaurants, major commuter routes, and everything the Annapolis lifestyle has to offer. A wonderful opportunity to enjoy spacious townhome living in a convenient Annapolis location. Schedule your showing and come see the possibilities!

2006 Puritan Ter, Annapolis

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

$375,000

Welcome to 19 Belvedere, an inviting end-unit townhome ideally situated in the desirable Copperwood community in The Landings. Offering three bedrooms, two full baths, and one half bath, this home combines comfortable living with an exceptional Annapolis location. Fresh paint and new carpeting provide a bright, refreshed interior, while a wood-burning fireplace adds warmth and character to the living space. The true highlight is the location and lifestyle. Residents of The Landings enjoy great community amenities, including two swimming pools, pickleball courts, and walking trails complete with convenient dog waste stations. Just beyond the neighborhood, Truxtun Park and the Pip Moyer Recreation Center offer even more opportunities for outdoor recreation, fitness, and leisure. Enjoy the convenience of strolling to nearby Clock Tower Place, home to neighborhood favorites including Grapes Wine Bar, Tastings Gourmet Market, and Sweet Hearts Pâtisserie. Whether meeting friends for a glass of wine, picking up gourmet provisions, or enjoying a morning pastry, some of Annapolis’s favorite local destinations are steps from your doorstep. Just minutes from historic Downtown Annapolis, shopping, dining, and major commuter routes, The Landings offers the perfect balance of neighborhood charm, recreation, and everyday convenience. An outstanding opportunity to enjoy the best of the Annapolis lifestyle in a welcoming, amenity-rich community.

19 Belvedere Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$269,000

Welcome home to Fairwinds of Annapolis! *Updates: LVP Flooring 2023, Furnace 2023, Fully Painted 2026* This spacious three bedroom, two bathroom condo offers the perfect combination of comfort, convenience, and easy living in the heart of Annapolis. Step inside to discover an inviting, light filled living room featuring attractive flooring and plenty of space to relax or entertain. The adjoining dining area provides a wonderful setting for everyday meals or gathering with friends and family. The thoughtfully designed kitchen offers abundant cabinetry, generous counter space, and a functional layout that makes meal preparation a breeze. The spacious primary bedroom provides a comfortable retreat, complete with its own private bathroom and three closets. Two additional bedrooms offer incredible flexibility for guests, a home office, or whatever suits your lifestyle. Enjoy the convenience of in-unit laundry and the added bonus of a private, covered patio, perfect for enjoying your morning coffee or unwinding after a busy day. Water and gas are included in the condo fee. Fairwinds condo has amenities for everyone to enjoy. The playground, pool, and tennis courts are all steps away from the condo. From here, you are close to everything in Annapolis! You will be walkable to grocery stores, shops, restaurants, and beautiful Quiet Waters Park. Downtown Annapolis is just a short car ride away. Commuting is a breeze as you are close to major interstate routes, USNA, Ft. Meade, Baltimore, DC, and BWI. Make an appointment to see this one today.

21 Silverwood Cir Unit 3, Annapolis

Listing courtesy of Compass. Contact:

$355,000

Price Improvement!! Discover the charm of this townhouse in the serene Whispering Woods community. This is a great opportunity to own a beautiful townhouse in Annapolis! It offers a perfect blend of comfort and functionality, making it an ideal retreat for modern living. Step inside to find a spacious layout featuring 3 inviting bedrooms, updated full bath and 1/2 bath in the basement. Enjoy a spacious updated eat in kitchen with crown molding and plenty of room to cook, gather and dine! Crown molding throughout the large living room/dining room combo. The fully finished basement, complete with a walkout entrance, provides additional living space, ideal for a home office, playroom, or cozy den. Brand new roof and attic insulation! Conveniently located near Route 50, charming downtown Annapolis with water views, shopping and dining. Don't miss the opportunity to make this charming residence your own!

303 Wood Hollow Ct, Annapolis

Listing courtesy of Maryland Residential Management Co. Contact:

$285,000

Mid-Level Condo Available Now in the Sought After Annapolis Overlook Community. This 3 Bedroom 2 Full Bath Condo offers an Open Living Space and Balcony showing a Beautiful Wooded Backdrop to give a sense of Privacy. Features of this Home include Brand New LVP Flooring, Brand New Carpet in Bedrooms, Brand New Renovated Hall Bathroom, Freshly Painted, Stainless Steel Appliances in the Kitchen, Wood Burning Fireplace, and So Much More!!! The Annapolis Overlook Community offers a Community Center, Fitness Center, In-ground Pool, and More. Located Minutes from Downtown Annapolis.

20 Amberstone Ct Unit H, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$570,000

Nestled in the prestigious gated community of Village Greens, this exquisite Colonial townhouse offers a harmonious blend of luxury and comfort. Built in 2016, this meticulously maintained residence spans 2,000 square feet, showcasing high-end finishes including a newly updated kitchen and thoughtful design throughout. Step inside to discover a warm and inviting atmosphere, where rich hardwood floors flow seamlessly through the main living areas. The spacious living room, anchored by a cozy fireplace for your indoor and outdoor enjoyment, invites relaxation and gatherings with loved ones. With three generously sized bedrooms, including a serene master suite with an ensuite bath, this home provides ample space for rest and rejuvenation. The two full and two half baths are beautifully appointed, offering both style and functionality. Enjoy the convenience of an attached finished rear-entry garage and driveway parking, ensuring easy access and ample space for guests. The low-maintenance outdoor area allows for leisurely afternoons spent soaking up the sun or enjoying a quiet evening under the stars. Experience the exclusive lifestyle that Village Greens has to offer, with its serene surroundings and proximity to local amenities. This stunning townhouse is not just a home; it's a sanctuary where luxury meets everyday living. Embrace the opportunity to make this exceptional property your own.

1612 Belle Dr, Annapolis

Listing courtesy of O'Brien Realty ERA Powered. Contact:

$350,000

Rarely available end-unit townhome in sought-after Whispering Woods! Brand New 50 yr architectural roof! This move-in ready 3 bedroom, 1.5 bath home offers privacy and charm surrounded by mature trees. Enjoy spacious living areas, and a fenced rear yard perfect for relaxing or entertaining. Private shed provides additional storage. Conveniently located near shopping, restaurants, parks, and major commuter routes with easy access to Downtown Annapolis, Route 50, and I-97.

1503 Lodge Pole Ct, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact:

$535,000

NEW ROOF- 50 year shingle! Welcome to this spacious Colonial in the sought after water privileged community of Cape St. Claire. Step inside to a bright and inviting main level filled with natural light. The spacious living room opens to the updated kitchen featuring a new island with seating for three, new quartz countertops, freshly painted cabinetry, and a cozy breakfast nook overlooking the rear yard. A dining room addition provides plenty of space for gathering and entertaining with direct access to the rear deck and yard. A full bath on this level adds extra convenience. Upstairs, you will find three bedrooms and two full baths. The primary suite features vaulted ceilings, a walk in closet, and a private ensuite bath complete with a soaking tub and separate stall shower. Outside, the property has been freshly landscaped with a new parking pad and fresh grass seed throughout. The rear yard offers plenty of space to enjoy the outdoors, along with a large shed for additional storage. Cape St. Claire offers a sought after waterfront lifestyle just minutes from Annapolis. This established community along the Chesapeake Bay features community several beaches, parks, playgrounds, three marinas, boat ramps, and opportunities for boating, kayaking, fishing, and enjoying life on the water. Known for its strong sense of community, Cape St. Claire hosts neighborhood events throughout the year and offers convenient access to local shopping, dining, schools, and major commuter routes. It is a wonderful setting for buyers looking to enjoy the relaxed Chesapeake Bay lifestyle while remaining close to Annapolis and everything Anne Arundel County has to offer.

1161 Green Holly Dr, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

$719,000

This immaculate 3 bedroom, ranch-style residence built in 1995 boasts 1,795 sq. ft. of luxurious living space on the main level + a finished basement. Step inside to find an open floor plan adorned with crown moldings and gleaming wood floors creating an inviting atmosphere perfect for entertaining. The gourmet kitchen, complete with an island and table space, is a culinary enthusiast's dream. Host friends and family for Thanksgiving where you can serve large parties in your formal dining room. The main living area is huge, with high ceilings, built-in shelves and a cozy fireplace. Enjoy the private backyard from the enclosed brick patio room. The fully finished, walk out basement gives you even more space for relaxation or hobbies. Heritage Harbour is a 55+ community that is located close to shopping, AAMC, historic Annapolis and major commuter routes ad offers endless amenities, activities and groups to keep you busy having fun, making friends and staying active. Embrace the exclusive amenities that define this community, including an art studio, fitness center, and multiple pools-both indoor and outdoor. Engage in friendly competition on the pickleball courts or enjoy leisurely strolls along the scenic jog/walk paths. With private access to the South River, indulge in water activities like canoeing or kayaking just a mile away. The meticulously maintained grounds and community features, including a clubhouse and library, foster a sense of belonging and camaraderie. Experience the perfect blend of luxury and leisure in this exceptional property, where every day feels like a retreat.

2548 Mission Hills Ct, Annapolis

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

$695,000

Enjoy a gracious foyer with gleaming hardwood floors open to an expansive living room with a gas burning fireplace and custom built-ins. Soak up the sun in the morning room wrapped in floor to ceiling windows overlooking mature trees, creating a serene retreat. The custom chef inspired gourmet kitchen features 42 inch solid wood cabinetry, granite countertops, a five burner KitchenAid gas cooktop, stainless steel appliances a French door refrigerator and ceramic tile floor. The spacious primary suite offers a cozy reading alcove, two walk-in closets and a luxurious ensuite bath with dual vanities and a separate shower. Nine foot ceilings, abundant natural light, hardwood floors, ample closet space and privacy complete the home.This wonderful 55+ community offers something for everyone, with indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine-hole par-3 golf course, and a waterfront clubhouse known as The Lodge. Residents can enjoy time on the South River with access to a community dock and boat slips, along with a variety of clubs and social activities throughout the year. Condo and HOA fees include access to the community amenities, making for an easy, low-maintenance lifestyle. With garage parking and historic downtown Annapolis just a short drive away, shopping, dining, and entertainment are all within easy reach. All just minutes from historic downtown Annapolis.

940 Astern Way Unit 508, Annapolis

Listing courtesy of Compass. Contact:

$869,000

Enjoy the convenience and charm of Eastport living at 827 Bay Ridge, just a short walk to local restaurants, shops, marinas, parks, and downtown Annapolis. This updated and well-maintained 3-bedroom, 3-full-bath home offers comfortable, flexible living space. The main level features two bedrooms and two full baths, inviting living areas, hardwood floors, and an updated kitchen with white cabinetry, granite countertops, and stainless steel appliances. Just off the living and dining areas, the screened porch overlooks the private backyard, creating the perfect spot to relax or entertain. The lower level provides additional living space with a third bedroom and full bath, ideal for guests, a private retreat, or a home office. Outdoor features include a welcoming front porch, rear patio, private backyard, and a driveway conveniently located behind the home, along with a storage shed. Whether you’re looking for a full-time residence or a weekend getaway, this turnkey home has everything that makes coastal living so desirable!

827 Bay Ridge Ave, Annapolis

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

$554,990

Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the community beach, take a walk through Quiet Waters Park, or be in downtown Annapolis in minutes. This is the lifestyle that makes Hillsmere Shores so special. Set near the Chesapeake Bay and the mouth of the South River, this updated 3-bedroom, 2.5-bath home blends comfort, character, and flexibility in one of Annapolis’s most loved waterfront communities. Inside, a thoughtful renovation created spaces that feel open, warm, and easy to enjoy. The expanded kitchen features a center island, eat-in area, custom tile backsplash, solid wood cabinetry, and plenty of room to gather. The primary suite was also expanded and now offers a sitting area, large walk-in closet, brand-new carpeting, and a beautifully renovated bath. But the room you may never want to leave is the four-season sunroom. Fresh paint, new luxury vinyl plank flooring, and views of the fenced backyard make it the perfect place to relax in every season.The finished lower level gives you even more room to spread out. Use it as a recreation room, office, gym, creative space, or potential fourth bedroom. A classic brick fireplace with an insert creates the perfect backdrop for cozy evenings, and a half bath adds extra convenience. Outside, the backyard offers privacy, trees, and room to enjoy the outdoors. And then there’s Hillsmere Shores itself: a private marina, boat ramps, kayak and canoe launch, community beach, swimming pool, playgrounds, picnic areas, and recreation spaces—all just minutes from downtown Annapolis, Key School, and Quiet Waters Park. This isn’t just Annapolis living. This is Chesapeake Bay living at its best.

416 Walnut Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$2,199,000

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

102 Melvin Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$499,999

Welcome to this beautifully renovated 3-bedroom, 2-full-bath single-family home in the desirable Arundel on the Bay community. This move-in-ready home features a spacious kitchen with quartz countertops, stainless steel appliances, upgraded cabinetry, and coffered ceilings complemented by abundant recessed lighting. The property sits on a 7,300-square-foot lot with a nice-sized yard and a Trex deck, perfect for outdoor entertaining and relaxing. The home is conveniently located just steps from a large community playground, making it especially convenient for families. Enjoy the benefits of this water-privileged community, including access to the beach and boat slips. The HOA is voluntary, providing flexibility while still offering access to community amenities.

3458 Newport Ave, Annapolis

Listing courtesy of RE/MAX Galaxy. Contact:

$399,900

COMPLETELY RENOVATED & MOVE-IN READY IN CEDAR RIDGE! After 30 years of thoughtful ownership and meticulous care, this beautifully updated 3-bedroom, 2½-bath townhouse is ready for its next chapter. The pride of ownership is evident throughout, with updates made over the years and the home continually improved and maintained. The improvements begin with replacement windows installed in 2000 and continue to today with a beautifully updated kitchen featuring newer cabinetry, countertops, and appliances. All three bathrooms have been updated, and the HVAC system and hot water heater have both been replaced within the past four years. One of the home's standout features is the incredible amount of storage. The current owner made exceptional use of The Container Store's organizing systems throughout the home, maximizing virtually every inch of available space. Even the full-size stacked washer and dryer provide additional room and functionality. One bedroom is currently being used as a home office and features a Murphy bed that easily accommodates overnight guests. Step through the kitchen's sliding glass door and you'll discover a completely private, fenced rear yard with a beautiful patio—perfect for grilling, entertaining, or simply enjoying your own outdoor space. The kitchen's location directly off the patio makes indoor/outdoor entertaining easy. And then there's Cedar Ridge! Enjoy the convenience of an HOA that takes care of the exterior maintenance, including the roof and siding, helping provide greater predictability for homeowners. The community also offers a swimming pool and Tot Lot. Best of all, you're within walking distance of Eastport and downtown Annapolis, with its wonderful restaurants, shops, waterfront, and everything that makes the Annapolis lifestyle so special. This is a home that has been lovingly cared for, thoughtfully updated, and designed for comfortable living. Truly move-in ready—just unpack and enjoy! Schedule your private showing today. This one won't last long!

1045 Cedar Ridge Ct, Annapolis

Listing courtesy of Academy Realty Inc.. Contact:

$859,000

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

21 Woodlawn Ave, Annapolis

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

$2,995,000

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:

$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:

$540,000

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. Price is reflective of the current condition of the home. 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:

$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:

$614,900

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. With a VA assumable loan at an interest rate of approximately 2.7%–2.8%, qualified buyers may also have an opportunity to secure financing at a rate that's difficult to find in today's market. 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. VA loan assumption is subject to loan servicer approval, buyer qualification, and applicable requirements.

1033 Hyde Park Dr, Annapolis

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

$1,250,000

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

313 Fourth St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$327,500

Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table space, making it a cozy spot for casual meals. The home features three spacious bedrooms, including a primary suite that encompasses the entire third floor, with a luxurious walk-in closet and an en-suite bathroom. Additional highlights include a laundry room, a second-floor bathroom, updated lighting, ceiling fans for added comfort, and plush carpeting that enhances the inviting atmosphere throughout. The stainless steel refrigerator and gas range, washer, dryer, carpet, and heat pump have all been updated within the past 5 years. The home has a brand-new storm door and bay window at the front of the house). Homeowners and investors will appreciate the low-maintenance lifestyle this property offers, with an association fee that includes lawn maintenance and snow removal. The community amenities include outdoor common grounds, a refreshing pool, and a fitness center. Parking is hassle-free with two parking permits included -one parking place is assigned and located directly in front of the townhome. An additional car can be parked (with permit), in the "Permit Required" spaces. The community's prime location (close proximity to Quiet Waters Park, Downtown Annapolis, the US Naval Academy, and shopping) ensures easy access to local amenities and attractions. Whether you're looking to buy or invest, this Annapolis Overlook property is a fantastic opportunity. With its blend of modern features, community amenities, and strategic location, it stands ready to deliver both comfort and value for years to come. Don't miss your chance to purchase this delightful home!

40 Ironstone Ct Unit B, Annapolis

Listing courtesy of RE/MAX One. Contact:

$650,000

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:

$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:

2104 Chesapeake Harbour Dr E Unit 202, Annapolis

$669,000

Welcome to resort-style coastal living at 2104 Chesapeake Harbour Dr E #202, a turnkey waterfront home in Annapolis' premier gated community. Enjoy serene water views and high-end upgrades from top to bottom. The open, light-filled layout features stylish new LVP flooring (Oct 2024) and contemporary lighting throughout (2024). Cook and entertain in the updated kitchen with custom cabinetry and quartz countertops (Dec 2024), plus brand-new appliances (Jan 2025). Relax in the primary suite with its custom Closet America walk-in closet (Sept 2025). Living in Chesapeake Harbour gives you direct access to a deep-water marina, private beach, pools, tennis courts, 24/7 security, and an on-site waterfront restaurant, all just minutes from historic Downtown Annapolis.

2104 Chesapeake Harbour Dr E Unit 202, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$275,000

NEW PRICE and MOVE-IN READY! Top-floor 3 bed, 2 full bath condo in Fairwinds of Annapolis. Offering low-maintenance living and an unbeatable location just minutes from Downtown Annapolis. This large floorplan home features a bright, open layout and a private balcony. The updated kitchen features new flooring, gas cooking, ample cabinet storage, and a new refrigerator. Bathrooms have been refreshed with newly installed floors and lighting. The HVAC system was replaced in 2022, providing added peace of mind. The spacious primary bedroom features a private full bath and two closets, including a large walk-in closet. Two generously sized secondary bedrooms share an additional full bath. Enjoy the convenience of gas heating, hot water, and cooking, along with access to the community pool and tennis courts. Reserved off-street parking is available for a fee through the condo association. This new price and location are hard to beat! Walking distance to grocery stores, coffee shops, and restaurants. Easy access to shopping, Downtown Annapolis, Eastport, the Naval Academy, and major commuter routes. Schedule a tour today!

142 Georgetown Rd Unit 9, Annapolis

Listing courtesy of Redfin Corp. Contact:

$1,495,000

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

100 Market St, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$569,000

The one you've been waiting for. An elegant townhouse which offers a harmonious blend of luxury and comfort, perfectly suited for those who appreciate low maintenance living with thoughtful upgrades, designed for an effortless, comfortable lifestyle. Meticulously maintained and upgraded by both the previous and current owners, the residence spans 2,088 square feet and showcases a traditional architectural style, enhanced by the brick front. Step inside to discover a warm and inviting interior with high-end finishes. The spacious living area features rich wood floors, crown moldings, floor to ceiling windows, plantation shutters, beautiful paneled walls, all the details that create a beautifully curated home with an atmosphere of quiet luxury. The gourmet kitchen is a culinary enthusiast's dream, equipped with stainless steel appliances, including a five-burner gas cooktop and double ovens. The expansive island and table space invite gatherings, while recessed lighting adds a touch of modern elegance. The home boasts three generously sized bedrooms, including a luxurious primary suite complete with a walk-in closet and beautifully appointed en-suite bathroom with a soaking tub and shower. An additional full bath upstairs is shared by the two other bedrooms and enjoy the convenience of a bedroom level laundry room. The cozy fireplace in the lower living area is a focal point, serving as the perfect retreat for relaxing evenings or a private home office. Outside, the property backs to trees and the deck offers an ideal space for outdoor relaxation or entertaining. The attached rear-entry garage with additional parking in front provides convenience for you and your guests. Adding to peace of mind, the roof is one year old, new washer, nearly new dryer, hot water heater in 2022 and brand new garage door and opener. This residence is more than just a home; with a prime location, easy access to commuter routes, and move in ready appeal, it embodies a lifestyle of comfort, where every detail has been thoughtfully curated. Experience the perfect blend of welcoming elegance in this exceptional property, where you can create lasting memories in a truly inviting setting.

2604 Foremast Aly, Annapolis

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

2161 Scotts Crossing Ct Unit 302, Annapolis

$349,999

Step into this beautifully maintained top-floor 3-bedroom, 2-bath condo in the desirable Scott’s Crossing Condominiums, offering over 1,320 square feet and a prime location just minutes from the vibrant charm of downtown Annapolis. As you enter, you're welcomed by fresh paint throughout (2026), a foyer with a convenient coat closet, and elegant column accents that open into a bright and airy main living space. The kitchen features warm wood cabinetry, granite countertops, a tiled backsplash, and stainless steel appliances, along with a cozy breakfast nook framed by a bay window overlooking peaceful wooded views. Entertain with ease or unwind at the end of the day in the well-appointed living and dining areas, complete with hardwood floors, 9+ ft ceilings, a cozy gas fireplace, and access to a private patio that offers a serene setting to relax and take in the views. The primary suite is a true retreat, showcasing a vaulted ceiling with a lighted fan and a charming bay window, perfect for a reading nook or sitting area with a tranquil backdrop. Two spacious closets and an ensuite bath with a dual sink vanity and tub/shower combo complete the space. Two secondary bedrooms, each with ample closet space, are thoughtfully positioned for added privacy and versatility, whether used as guest rooms or an in-home office, and share a full bath with a large walk-in shower. A dedicated laundry room with additional storage and a full-sized washer and dryer adds everyday convenience. Recent updates include a newer HVAC (2021), water heater (2022), and plush new carpet (2026). Parking is a breeze in the off-street parking lot. Beyond the community, enjoy the nearby Bestgate Park, Trader Joe’s and Annapolis Mall, plus easy access to major highways for a quick commute to Baltimore, DC, and more. Don’t miss this rare find! Save thousands via an interest rate buydown or reduced closing costs by taking advantage of the following special lender program. Lender credit equal to 1.50% of the loan amount or amount allowed per program guidelines available to an eligible buyer financing the purchase of this property through Maddox Mortgage Group Powered By Atlantic Bay (DBA) of Atlantic Bay Mortgage Group, L.L.C. Terms and availability are subject to change at any time.

2161 Scotts Crossing Ct Unit 302, Annapolis

Listing courtesy of Keller Williams Capital Properties. Contact:

$650,000

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:

$639,900

JUST REDUCED - AN INCREDIBLE VALUE ON THE BROADNECK PENINSULA! Welcome home to 525 Deep Creek View, where nearly 3,000 finished square feet, a 2-car garage, and a flexible floor plan offer the space you want with the ease of low-maintenance living. Located in sought-after Deep Creek Village, this spacious 3-bedroom, 3 full and 1 half bath home lives much larger than you might expect. Hardwood floors and abundant natural light welcome you to the open main level, where a spacious dining and sitting area flows into the heart of the home. The designer kitchen features an oversized center island, granite countertops, stainless steel appliances, gas cooktop, wall oven, pantry, and abundant cabinetry. An expanded morning room provides even more living space and opens through French doors to the rear deck, perfect for grilling, entertaining, or relaxing outdoors. Upstairs, the generous owner's suite offers two walk-in closets, a spa-inspired bath, and a separate sitting area ideal for a home office, reading nook, or fitness space. Two additional bedrooms, a full hall bath, and upper-level laundry complete this floor. The finished lower level gives you even more flexibility, with a large recreation room, custom built-ins, a full bath, and direct access to the 2-car garage. Use it as a media room, home gym, office, guest space, playroom, or simply another comfortable place to spread out. And the lifestyle extends beyond the home. Deep Creek Village offers walking trails, green spaces, a tot lot, and neighborhood social gatherings, all just minutes from downtown Annapolis, shopping, dining, parks, marinas, and Route 50. Enjoy easy access to Washington, D.C., Baltimore, and the Eastern Shore while coming home to the relaxed lifestyle of the Broadneck Peninsula (yes, it is in the Broadneck School District!) If you've been looking for more space without more maintenance, 525 Deep Creek View may be exactly what you've been waiting for.

525 Deep Creek Vw, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$540,000