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$875,000
4 Beds ⋅ 3 Baths
Coming soon....fully renovated open concept....hardwood floors and finished basement. Residents have access to a private sandy beach overlooking the Chesapeake Bay, a private marina with boat slips and direct access to the South River, boat ramps, a community swimming pool, waterfront pavilions, playgrounds, volleyball courts, picnic areas, and an active calendar of events that creates a genuine sense of community. Quiet Waters Park, Hillsmere Elementary School, the library, shopping, restaurants, Eastport, Historic Downtown Annapolis, and City Dock are all just minutes away, giving you the perfect blend of convenience, recreation, and coastal charm.

109 Sunset Dr, Annapolis

Listing courtesy of Winning Edge. Contact: 4434636009
$1,285,000
4 Beds ⋅ 3 Baths
Discover elegance at 1227 Cross Road in Annapolis, Maryland, a stunning 2023-built home in the water-privileged Oyster Harbor community, elevated by upgrades made by the current owner since purchase. Enter through grand double doors into an open foyer with hickory hardwood floors, soaring ceilings, and crown molding. The great room impresses with a coffered ceiling, ceiling fan, fireplace, and large windows that flood the space with natural light. The gourmet kitchen is an entertainer’s dream, featuring a 5-foot quartz island, double oven, prep sink, breakfast nook, expansive walk-in pantry, and a butler’s pantry/wet bar upgraded by the owner for effortless hosting. The formal dining room, with its trey ceiling and designer windows, adds sophistication. A main-level office or in-law suite includes a full bath, ceiling fan, and custom California Closets added post-purchase for enhanced organization. Ascend the stunning, light-filled staircase, a true architectural centerpiece to the second floor. Here, a versatile loft/flex space is perfect for a family room, home office, or play area. Two additional bedrooms with ceiling fans and owner-installed California Closet systems offer comfort, with one boasting private bath access and a walk-in closet. The primary suite is a retreat, featuring recessed lighting, a trey ceiling, a spacious dressing/sitting area, a luxurious 6x6 shower, and a large walk-in closet with a California Closet upgrade. A laundry center, enhanced by the owner with custom cabinetry, granite countertops, and a Blanco sink, adds convenience. The oversized 2-car garage features 12-foot ceilings, an owner-applied epoxy floor, and a 240V electric vehicle hookup. A mudroom with custom storage cabinetry, added post-purchase, welcomes you from the garage. Additional owner upgrades include gutter guards, Cat6 wiring, pre-installed security system wiring, and a 1,500 sq ft conditioned crawl space for storage. Outdoors, relax on the 13x10 screened porch with recessed lighting, a thoughtful owner addition. Recent updates in 2026 include new kitchen floor, kitchen backsplash subway tile, wet bar backsplash subway tile, fireplace surround and painting throughout. Enjoy Oyster Harbor’s waterfront amenities, including a boat ramp, pier, private beach, and opportunities for kayaking, fishing, and paddleboarding. With the current owner’s thoughtful upgrades since 2023, this Annapolis gem combines modern luxury with unparalleled functionality. View the full HD Video Tour and contact listing agent for a private in person tour.

1227 Cross Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (703) 745-1212
$439,000
3 Beds ⋅ 3 Baths
Welcome to 7 Harbour Heights Drive #7, where comfort, convenience, and the Annapolis lifestyle come together! Located in the desirable Seabreeze community, this spacious townhome-style condominium features 3 bedrooms, 2 full bathrooms upstairs, and a convenient half bath on the main level. Step inside to a bright and inviting interior with a comfortable, flowing floor plan designed for both everyday living and entertaining. The fireplace in the kitchen area adds warmth and character, creating a cozy setting for casual meals, morning coffee, or gathering with family and friends. Generously sized living spaces provide plenty of room to relax, entertain, or create the perfect work-from-home space. Upstairs, you’ll find three bedrooms and two full bathrooms, offering a functional layout with plenty of space and privacy. The location is hard to beat—just minutes from Downtown Annapolis, the U.S. Naval Academy, Anne Arundel Medical Center, Annapolis Town Centre, shopping, dining, and entertainment, with convenient access to Routes 50 and 97 for commuting to Washington, D.C., Baltimore, and beyond. Enjoy the ease of low-maintenance living while being close to everything Annapolis has to offer. Welcome home to 7 Harbour Heights Drive #7!

7 Harbour Heights Dr Unit #7, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$1,250,000
4 Beds ⋅ 3 Baths
Set on 2.5 beautifully landscaped acres in the desirable community of The Meadows, this distinctive three-sided brick home offers an impressive combination of privacy, spacious one-level living, custom features, and exceptional indoor and outdoor entertaining spaces. With four generously sized bedrooms and three full baths on the main level, the home provides a versatile floor plan rarely found today. At the heart of the home is a beautifully appointed chef's kitchen designed for both serious cooking and casual gatherings. Features include stainless steel appliances, granite countertops, an oversized island with seating, two separate convection ovens, gas cooking, and quality KraftMaid cabinetry with a double pantry, pull-out storage, and under-lit glass-front cabinets. A custom wet/dry bar with wine cooler, wine rack, oversized sink, and instant hot water creates a dedicated entertaining area. The kitchen opens to the inviting family room with gas fireplace, while the elegant living and dining rooms feature beautiful stone flooring and an oversized bay window that brings abundant natural light into the home. Plantation shutters add both architectural character and privacy. A spacious main-level laundry and mudroom with rear entrance, garage access, custom shelving, and generous storage makes everyday living exceptionally convenient. The main-level primary suite is truly a private retreat. An extraordinary 12' x 12' walk-in closet professionally organized by California Closets provides exceptional storage. The spa-inspired primary bath features dual vanities, an air-soaking tub, an oversized separate shower, a private water closet with a bidet, and marble tile flooring. The finished lower level dramatically expands the home's possibilities. An expansive clubroom with built-in cabinetry and bookshelves offers plenty of space for a pool table, media center, gaming area, or large gatherings. A separate room currently serves as a home gym but could easily be converted into an office, craft room, or additional flexible space. Multiple exterior entrances provide convenient access to the grounds. A custom hobby/utility area with specialized wiring and a commercial-size sink is ideal for pottery, creative projects, gardening needs, or even a dog-washing station. An additional conditioned storage area with heat and air provides valuable year-round storage. The outdoor spaces are equally impressive. Stone paver walkways lead to an expansive 1,407-square-foot multi-level stone patio, creating a spectacular setting for entertaining, dining, or relaxing outdoors. A Trex deck directly off the kitchen is ideal for grilling, while professionally landscaped gardens and an underground sprinkler system enhance the 2.5-acre setting. An oversized 613-square-foot side-entry two-car garage features a custom organization system, and an additional parking pad provides ample space for guests or oversized vehicles. An owned propane tank supplies the gas range, fireplace, and whole-house generator, providing additional comfort and peace of mind. Dual-zone HVAC includes one unit replaced in 2024. Additional features include public water, a septic system, and a voluntary HOA. Conveniently located for access to Annapolis, Baltimore, and Washington, D.C., this exceptional Meadows property offers a rare opportunity to enjoy acreage and privacy without sacrificing accessibility.

1812 Millridge Ct, Annapolis

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

$585,000
3 Beds ⋅ 3 Baths
Welcome to 1055 Sun Valley Drive, a beautifully cared‑for Colonial in Cape St. Claire that blends thoughtful updates, flexible living space, and Broadneck Peninsula convenience. This 3BR/2.5BA home offers approximately 2,050 finished square feet. Built in 1989, the property is newer than many surrounding homes and features public water/sewer, electric heat, and an attached garage. The heart of the home is the fully remodeled kitchen (2021), designed with marble counters, custom wood cabinetry, and a Fisher & Paykel dishwasher drawer. An open‑concept redesign creates a seamless flow into an oversized dining room with French doors to the backyard—ideal for everyday living and entertaining. The living room was updated in 2024 with custom built‑in cabinetry and bookcases, and new flooring (2021) runs throughout the first level. Three spacious bedrooms and two full bathrooms make up the second floor. The primary bedroom’s ensuite bath includes a new vanity top (2026) and a refinished tub. Outdoor highlights include professional landscaping, a new fence (2026) fully enclosing the backyard, a main shed built in 2020, and a smaller side shed added in 2026. Enjoy the seasonal reward of a productive strawberry patch each summer. Near Broadneck schools, parks, shopping and commuter routes, this home is a rare find for buyers seeking a move‑in‑ready home in a highly desirable Annapolis location. Cape St. Claire’s HOA provides water privileges—including a beach, marina access, and waterfront recreation—for just $10 per year.

1055 Sun Valley Dr, Annapolis

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

$599,000
4 Beds ⋅ 3 Baths
Welcome to Heritage, a sought-after Annapolis community where space, comfort, and convenience come together! This beautifully refreshed three-level Colonial offers four bedrooms, multiple living spaces, a huge fully fenced backyard, and an impressive list of recent updates—making it truly move-in ready. Step inside to fresh paint, new carpet and LVP flooring, updated fixtures and hardware, and a bright, welcoming layout designed for everyday living and entertaining. The updated kitchen features freshly painted cabinetry and a brand-new refrigerator and opens to the family room for an easy, connected flow. Formal living and dining rooms provide additional space to gather, while the fully enclosed sunroom with casement windows offers a wonderful spot to relax and enjoy views of the backyard. A convenient half bath and mudroom with laundry hookups complete the main level. Upstairs, you’ll find four generously sized bedrooms. The spacious primary bedroom features two closets, while the second and third bedrooms share a Jack-and-Jill bath with a brand-new shower. An additional full hall bath adds even more flexibility for busy mornings and overnight guests. The lower level expands your living space with a partially finished recreation room featuring new drywall and recessed lighting—ready for movie nights, a game room, home gym, office, or whatever suits your lifestyle. A large storage and utility room includes additional laundry facilities, and a waterproofing system installed in 2023 comes with a lifetime warranty for added peace of mind. Outside, the expansive fully fenced backyard is ready for entertaining, gardening, play, or simply enjoying more room to spread out. A composite deck and storage shed add even more functionality. Additional improvements include replacement windows and a roof replaced within approximately the last 10 years. And then there’s the location! Heritage residents enjoy access to community amenities including a pool, clubhouse, fields, and a footbridge over Spa Creek—all while being conveniently located near the shops, restaurants, waterfront, and unmistakable charm of Downtown Annapolis. With its generous space, extensive updates, fantastic backyard, and Annapolis location, this is a home you’ll want to experience in person. Welcome home!

402 South Cherry Grove, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425
$725,000
4 Beds ⋅ 3 Baths
This charming Colonial-style home in the desirable Riva Trace community offers a perfect blend of comfort and convenience. Set on a spacious 0.27-acre lot, the well-maintained yard features a side yard and a rear yard with an inground pool, ideal for gardening or entertaining. Inside, the home boasts four bedrooms and two and a half bathrooms, providing ample space for relaxation. The cozy family room is enhanced by a fireplace with glass doors, perfect for creating a warm ambiance during cooler months. The family room also leads to an enclosed porch that also leads to the pool and rear yard. The unfinished basement with a walkout entrance offers potential for customization, whether for additional living space or storage. Enjoy the luxury of a personal pool, perfect for summer gatherings or quiet afternoons. The property is conveniently located near Ginger View Creek, offering a tranquil water feature for nature enthusiasts. Riva Trace is known for its strong community spirit, with nearby parks and recreational facilities that promote an active lifestyle. Residents benefit from access to quality schools and essential public services, ensuring a well-rounded living experience. With easy access to local amenities and a welcoming neighborhood atmosphere, this home is a fantastic opportunity for those seeking a vibrant community. This is the Cardiff model with many wonderful features. The price reflects TLC needed.

236 Autumn Chase Dr, Annapolis

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

$550,000
4 Beds ⋅ 3 Baths
Coming Soon in Cape St. Claire! This beautiful home pairs updated features with a flexible layout design in one of the area’s most sought-after communities. Inside, you’ll find hardwood floors, a gorgeous kitchen, a spacious primary suite with cathedral ceiling and private bath, plus a finished lower level offering even more room to spread out. Connects to an attached one car garage with interior access and huge storage space off the back of the garage. Outside, enjoy a fenced backyard and rear deck, all just minutes from Cape St. Claire’s beaches, boat ramp, playgrounds and community amenities. **OPEN HOUSE Saturday August 15th 10AM-12PM**

1280 Cape St Claire Rd, Annapolis

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$1,279,000
5 Beds ⋅ 3 Baths
Welcome to 1112 Little Magothy View, a rare waterfront opportunity in the highly sought-after Cape St. Claire community, where exceptional waterfront living meets remarkable flexibility for today's lifestyle and tomorrow's vision. Perfectly positioned along approximately 80 feet of private waterfront on the Little Magothy River, this property offers expansive water views, a private pier, and direct access to the Magothy River and Chesapeake Bay. Whether your vision is to move in and enjoy the home today, thoughtfully renovate over time, or create a custom waterfront home tailored to your vision, this property offers possibilities rarely found in one offering. Unlike many waterfront properties purchased solely for the land, 1112 Little Magothy View provides a substantial existing home with nearly 2,900 square feet, an attached garage, expansive circular driveway, an in-ground pool, generous pool decking, mature landscaping, and existing site improvements that create an outstanding foundation for whatever your future plans may be. The home's floor plan is one of its greatest strengths. Four bedrooms are conveniently located on the main level, providing the increasingly desirable option of one-level living. Upstairs, a spacious guest bedroom is complemented by a large waterside family room, creating exceptional flexibility for future reconfiguration into a luxurious primary suite, guest retreat, home office, or additional entertaining space. Buyers looking to renovate will appreciate the home's generous footprint and layout, offering an excellent canvas for modernizing while preserving many of the features today's buyers desire. Those considering new construction will appreciate the value of an already improved waterfront homesite with a substantial existing footprint and site improvements. One of the property's most unique features is the privacy it enjoys. The northern property line borders a community-owned waterfront park, where a wooded buffer creates a natural separation from neighboring homes, providing an uncommon sense of space and privacy rarely found on waterfront properties. The protected waters of the Little Magothy provide an ideal setting for kayaking, paddleboarding, canoeing, swimming, fishing, and sailing, while a marked channel offers convenient access to the open waters of the Chesapeake Bay. Spend the morning paddleboarding on the calm waters of the Little Magothy, enjoy an afternoon sail within sight of home, or cruise directly into the Chesapeake Bay for a day on the water—all from your private pier. End the day relaxing beside the pool or entertaining family and friends while taking in beautiful views across the Little Magothy River. Cape St. Claire offers an unmatched waterfront lifestyle with community beaches, marinas, boat ramps, fishing and crabbing piers, playgrounds, waterfront parks, year-round community events, and nearby shopping and dining, all just minutes from downtown Annapolis and convenient commuter routes. Rarely does a waterfront property offer this combination of protected waterfront, privacy, lifestyle, and long-term flexibility. Whether enjoyed exactly as it is or transformed over time, 1112 Little Magothy View presents an exceptional opportunity in one of Annapolis' most desirable waterfront communities. Property is being sold As-Is. Coming Soon status may change to Active status prior to date noted in MLS.

1112 Little Magothy Vw, Annapolis

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

$685,000
3 Beds ⋅ 3 Baths
Welcome to coastal living at its finest in Annapolis’ gated Chesapeake Harbour community! Enjoy sweeping marina views, fantastic people watching, and resort style amenities including 2 pools, tennis/pickleball courts, kayak access, walking trails, beaches, cocktails and entertainment at the dock bar and waterfront dining at The Beacon Restaurant. This sun drenched 3 bedroom, 3 full bath condo boasts high ceilings and a seamless floor plan made for entertaining. The upper level loft doubles as a flexible 3rd bedroom or home office, offering an airy, open concept layout that overlooks the main living area to maximize light and space. Don't miss this coastal gem!

2102 Chesapeake Harbour Dr E Unit #202, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425
$770,000
3 Beds ⋅ 3 Baths
Welcome to Eastport. This three-bedroom, three-full-bath home is a beautifully maintained, turn-key Cape Cod offering over 2,000 square feet of fully finished living space; including a lower-level den that easy serves as an on-suite. Originally transformed during a massive, studs-out 2017 remodel, this home offers ultimate peace of mind with entirely replaced core systems and premium finishes throughout. The chef’s kitchen is fully equipped with Saint Cecilia granite countertops, an expansive island breakfast bar, premium stainless steel appliances, a mosaic tile backsplash, and soft-close cabinetry. The open floor plan main level also includes 2 bedrooms and a full bathroom. Upstairs, a massive second-story addition houses a luxurious primary suite with a custom glass shower, a walk-in closet, and a sitting area. The lower level offers a family room with a storage area and a "DEN" with a full bath. No detail was spared in the renovation, which features gleaming new hardwood floors, energy-efficient double-pane tilt-in windows, and updated insulation. Enjoy worry-free living with a comprehensive HVAC setup including a gas furnace and central A/C, updated plumbing, new electrical panels, a new water heater, and a fully integrated, code-compliant interior fire sprinkler system. The exterior shines with architectural roof shingles, low-maintenance vinyl siding, new gutters, and a spacious gravel driveway. Outside, enjoy outdoor entertaining in the fully fenced, private backyard. Perfectly situated moments from historic downtown Annapolis, Eastport restaurants, and local waterways. Move right in and enjoy seamless coastal living!

907 Monroe St, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$415,000
3 Beds ⋅ 3 Baths
This 3 bedroom, 2.5-bath home with a large finished basement provides great value. Located in The Landings, this Annapolis home has been loved and had money spent on it on things that matter. NEW ROOF in 2025. Updated high-end efficient windows. Updated sliding doors. Updated bathroom vanities. Updated HVAC. New flooring throughout. Updated cedar siding. The main level provides wonderful living and entertaining space filled with natural light and features a cozy log burning fireplace. The upper level offers THREE bedrooms with wonderful natural light. The primary bedroom features a vaulted ceilings and its own en-suite bathroom; it is bright and spacious. The basement level includes large laundry room and a large living area that could easily be used as a media room or home office. The rear of the home offers a private deck looking out to a community greenspace which is perfect for relaxing or entertaining. The front of the home offers spacious parking. Ideally located, this home has easy access to Routes 50 and 97 but yet is minutes from downtown Annapolis’s shopping, dining, and waterfront attractions. Community amenities are substantial and include two pools, four pickleball courts and two tennis courts. The community cuts the grass and maintains the grounds... this is carefree living. This townhome is a must see!

6 Tiburon Ct, Annapolis

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

$655,000
3 Beds ⋅ 3 Baths
COMING SOON!!!!!! One of the nicest lots in Heritage.

1302 Homewood Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$875,000
3 Beds ⋅ 3 Baths
Experience the ultimate waterfront lifestyle in the prestigious Harbour Village Marina at Chesapeake Harbour, where panoramic marina views and exceptional amenities create one of Annapolis' most sought-after communities. This beautifully updated 3 bedroom 3 bath waterfront condominium offers an inviting blend of elegance, comfort, and coastal charm. Wake each morning to tranquil marina views from your private balcony, spend your afternoons enjoying the private sandy beach, waterfront pool, tennis and pickleball courts, or simply watch the boats come and go from one of the area's premier marinas. Whether you're an avid boater or simply appreciate life on the water, this is waterfront living at its finest. Inside, the spacious floor plan is designed for both everyday living and effortless entertaining. The living room and primary suite each feature a gas fireplace, creating warm and inviting spaces to unwind. Multiple balconies capture beautiful marina vistas, while the updated kitchen showcases granite countertops, stainless steel appliances, and generous workspace for preparing meals or gathering with family and friends. Thoughtful upgrades throughout the home provide both style and peace of mind, including fresh interior paint, engineered hardwood flooring, updated granite countertops, designer bathroom vanities with quartz countertops, newer interior doors with brushed bronze hardware and glass door knobs, LED ceiling lighting, Lutron switches, modern 15-amp outlets with USB and USB-C charging ports, and numerous electrical improvements. The oversized two-car garage with EV charging capability adds convenience for today's lifestyle. Residents of Chesapeake Harbour enjoy an unmatched collection of waterfront amenities, including a private beach, marina, waterfront swimming pools, tennis and pickleball courts, walking paths, and the popular Beacon Waterfront Galley & Bar...all within the gated community. No other condominium community in Annapolis offers this unique combination of waterfront recreation, boating, dining, and resort-style living. Whether you're searching for a full-time residence, an elegant weekend retreat, or the perfect lock and leave waterfront home, this exceptional condominium offers a rare opportunity to enjoy the Chesapeake Bay lifestyle in one of Annapolis' most exclusive waterfront communities.

7038 Clinton Ct Unit #11B, Annapolis

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

$349,000
2 Beds ⋅ 3 Baths
Come home to the Tidewater Colony community! This amazingly updated 2 bedroom / 2.5 bathroom upper unit features an open floor-plan, gleaming new flooring and many upgrades throughout. This meticulously maintained 2 level unit has a private balcony and tons of storage. Enjoy the incredible community pool, fitness center, clubhouse, tennis courts, playgrounds, walk/bike paths, picnic area, and ample green space for outdoor sports. The location is unbeatable - within minutes of the activities, restaurants, and shopping that Downtown Annapolis has to offer!!

2002 Peggy Stewart Way Unit #205, Annapolis

Listing courtesy of Keller Williams Capital Properties. Contact:

$380,000
2 Beds ⋅ 3 Baths
PRICE IMPROVEMENT - If you overlooked this home - Look Again! Welcome to 6 Belvedere Court ideally situated in the sought-after Copperwood community within The Landings. This recently updated home offers a fantastic townhome in a wonderful neighborhood close to all things Annapolis. Newly updated kitchen with all new appliances. New luxury vinyl plank on the main level. New carpet on stairs and upper level bedrooms. Two brand new and updated full baths upstairs. Brand new and updated powder room on the main level. **Please note that the virtually staged photos are not exact dimensions** Steps from community amenities, including two swimming pools with toddler pools and two tennis courts. The neighborhood also provides easy access to Route 50 and Route 97, making commuting a breeze. Outdoor enthusiasts will love being within walking distance of Truxton Park, while nearby attractions such as the Naval Academy, Quiet Waters Park, BWI Airport, Washington, DC, and Fort Meade add to the home's convenience and appeal. Don’t miss this opportunity!

6 Belvedere Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$500,000
4 Beds ⋅ 3 Baths
This 4-bedroom, 2.5-bath detached Colonial in Hillsmere Estates offers a spacious three-level layout with an eat-in kitchen, family room, sunroom, fenced backyard, and partially finished walkout lower level. Additional features include a primary suite with a private bath and sitting area, a wood-burning fireplace, hardwood flooring, an asphalt driveway, and access to community beaches, picnic areas, a playground, boat ramp, and marina.

318 Beach Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$995,000
3 Beds ⋅ 3 Baths
Live the ultimate Downtown Annapolis lifestyle at 8 Constitution Square. Tucked away on a quiet, neighborly cul-de-sac in Murray Hill, this home offers a seamless blend of tranquility and effortless downtown walkability. Skip the parking headaches of historic downtown. Here, you'll enjoy your own private driveway on a low traffic street, giving you a true neighborhood feel right in the heart of the 21401 zip code. Stroll just one block to Maryland Hall to see a local art exhibit or concert, launch a kayak from Amos Garrett Park, take a short walk to Navy-Marine Corps Memorial Stadium on game day, or head down to West Street and City Dock for world-class dining, shops, and waterfront nightlife. Inside, this meticulously updated home shines with light-filled, open living spaces wrapped in gleaming hardwood floors. The main-level family room impresses with dramatic cathedral ceilings, bright skylights, and gorgeous gas fireplace, the ideal focal point for crisp autumn evenings. Step through the main living area directly out to your expansive, fully fenced backyard oasis, a rare find in downtown living. Whether you are hosting a pre-game tailgate, entertaining friends after a night out in Eastport or Downtown, or simply unwinding around the fire pit under the stars, this private outdoor haven delivers space you rarely find this close to the water. Offering single-family privacy without sacrificing walkable luxury, this is a unique, turn key, Annapolis gem. *Buyer to verify square footage

8 Constitution Sq, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425
$475,000
3 Beds ⋅ 3 Baths
This bright, updated end-unit townhome offers an open layout, plenty of natural light, and a convenient Annapolis location. Fresh paint, natural wood-tone luxury vinyl plank flooring, and coastal-inspired details give the home a clean and welcoming feel. The living room features a floor-to-ceiling sliding glass door that brings in lots of sunlight and opens to the front patio. The kitchen includes white 42-inch cabinets, granite countertops, stainless steel appliances, a subway tile backsplash, a large island with seating, and a pantry. A powder room and access to the garage are also located on the main level. Upstairs, the primary bedroom includes large windows, a board-and-batten accent wall, a walk-in closet, and a private bathroom with a double vanity, soaking tub, and tiled shower. Two additional bedrooms each have balcony access and share a full hall bathroom. The laundry room is also conveniently located upstairs. As an end unit, the home receives natural light throughout all three levels. A rear-loading one-car garage provides secure parking and additional storage. Admirals Square offers landscaped common areas, a central green space, a fountain, and a fire pit gathering area. The community is located minutes from Historic Downtown Annapolis, the U.S. Naval Academy, Annapolis Town Center, Westfield Annapolis Mall, parks, marinas, restaurants, shopping, and waterfront attractions. Easy access to Route 50 and Route 2 makes commuting to Baltimore, Washington, D.C., and surrounding areas convenient.

527 Leftwich Ln, Annapolis

Listing courtesy of Northrop Realty. Contact: 4104651770
$429,000
3 Beds ⋅ 3 Baths
A rare find in the heart of Annapolis! This truly move-in ready home features three bedrooms, two and half baths, and a modern kitchen with new electric range and generous living space throughout. Many major improvements have been completed for you within the past five years, providing added peace of mind. These include a new roof, LVP flooring throughout the main level, a basement waterproofing system, sump pump, and hot water heater, along with a new balcony and lower deck spaces. You’ll find exceptional storage space across all three levels, including a partially floored attic and fenced deck space in back for kayaks, toys and more. The finished basement is added living space, and has a flexible use space, ideal for a workshop or hobbies. Enjoy the wooded back view and lower level access, and in the summertime relax at the community pool. All of this is just minutes from West street, local parks, trails, and the best of downtown Annapolis, making it an outstanding opportunity to enjoy city living. Welcome home!

73 Gentry Ct, Annapolis

Listing courtesy of Homecoin.com. Contact: 8884002513
$2,250,000
4 Beds ⋅ 3 Baths
Set back off the road on a quiet cul-de-sac in the coveted Saefern community, this contemporary home offers peaceful water views, a private wooded setting, and endless potential to make it your own. Whether you're looking to move right in and enjoy the home as it is or reimagine the space into your dream retreat, this property presents an incredible opportunity in one of Annapolis' most sought-after waterfront communities. Designed to embrace its natural surroundings, the home is filled with light and features soaring ceilings, warm wood architectural details, and expansive windows that bring the outdoors in. The dramatic living room is anchored by a striking brick fireplace and flows into the dining area and kitchen, creating an inviting space for gathering. Three sets of sliding glass doors open to the expansive balcony, seamlessly blending indoor and outdoor living while framing peaceful water and woodland views. Just beyond, the enclosed porch with vaulted ceilings provides a year-round place to relax while taking in the peaceful water and woodland views. The thoughtfully designed main level offers two bedrooms, including a spacious primary suite with a private sitting area and ensuite bath, along with a second bedroom that is served by a full hall bath, ideal for guests, family, or a home office. The walkout lower level expands the living space with a generous family room featuring a second fireplace, a built-in bar area, and access to the adjoining sunroom and patio, creating the perfect setting for entertaining. Two additional bedrooms are located on this level, including one with a private ensuite bath and private patio. An additional bedroom offers flexible accommodations for guests or multigenerational living. Life in Saefern is about much more than the home itself. Membership in the renowned Saefern Saddle & Yacht Club (SSYC) includes a boat slip, marina, swimming pool, tennis and pickleball courts, horse stables, dog park, playground, and an active community lifestyle. Just minutes from Historic Annapolis, the U.S. Naval Academy, shopping, dining, and convenient commuter routes to Washington, D.C. and Baltimore, this is a rare opportunity to invest in a home with outstanding bones, water views, and the chance to create something truly special. Welcome Home!

500 Sara Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$625,000
2 Beds ⋅ 3 Baths
Welcome to the sought-after waterfront community of Chesapeake Harbour! This beautiful 2-bedroom, 2.5-bath end unit condo offers a spacious, light-filled floor plan with a rare combination of features. Transom windows above sliding doors and windows in the living and dining rooms adds even more light. The updated kitchen is designed for both everyday living and entertaining, showcasing granite countertops, a center island, stainless steel appliances, under cabinet lighting, and a built-in wine fridge. Expansive living room with vaulted ceiling has an electric fireplace for added ambiance. The loft, complete with custom built-in shelves, provides the perfect space for a home office, family room, or guest retreat. The half bath in the loft area is a great plus. Primary bedroom with huge walk-in closet and primary bath with double vanity & large walk in shower. Enjoy outdoor living on the expansive wraparound deck, ideal for morning coffee, outdoor dining, or simply relaxing. Located in one of Annapolis' premier gated waterfront communities, Chesapeake Harbour offers exceptional amenities, including a private beach, two swimming pools, tennis & pickleball courts, walking trails, a marina, and the popular Beacon Waterfront Galley & Bar, all just minutes from Historic Downtown Annapolis. Outdoor enthusiasts will appreciate the opportunity to join the Canton Kayak Club, offering convenient access to kayaks and launch sites throughout the region, including a resident-access launch within Chesapeake Harbour.

7048 Harbour Village Ct Unit #202, Annapolis

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

$356,000
3 Beds ⋅ 3 Baths
Welcome home to 1041 Cedar Ridge Ct, a well-maintained property offering comfort, convenience, and an exceptional community setting. This home is in good condition and features a private patio and privacy fence Located adjacent to the community pool, residents can enjoy easy access to seasonal recreation and outdoor relaxation just steps from their front door. Conveniently situated near shopping, dining, commuter routes, and everyday amenities, this property presents an excellent opportunity for buyers seeking both value and lifestyle.

1041 Cedar Ridge Ct, Annapolis

Listing courtesy of Maryland Realty Connection. Contact: admin@mdreoconnection.com
$595,000
4 Beds ⋅ 3 Baths
Nestled in the charming Cape St. Claire community, this exquisite split foyer home offers a perfect blend of comfort and luxury. With 2,168 square feet of thoughtfully designed living space, this residence features four spacious bedrooms including a massive owners suite and three full bathrooms, ensuring ample room for relaxation and entertaining. Step inside to discover a warm and inviting atmosphere, highlighted by an open floorplan that seamlessly connects the kitchen and dining areas. The kitchen, complete with electric appliances and generous table space, is perfect for culinary enthusiasts. Enjoy cozy evenings by the fireplace, where natural light pours in. The fully finished basement offers endless possibilities, whether you envision a home gym, office, or additional living space. Outside, sits on the perfect corner lot, providing a unique outdoor experience. Just a short stroll away, indulge in the community's exceptional amenities, including access to the beautiful Chesapeake Bay and Magothy River. Imagine sipping your morning coffee on the porch while taking in serene water views, or spending weekends at the nearby beach and boat dock. This property is not just a home; it's a lifestyle, offering a perfect blend of tranquility and recreation. Experience the best of waterfront living in this exclusive community, where every day feels like a vacation.

994 Hillendale Dr, Annapolis

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$925,000
4 Beds ⋅ 3 Baths
Welcome to Ketch Court, tucked away in the highly sought-after waterfront community of Annapolis Cove. With four bedrooms, two-and-a-half bathrooms, a finished basement with brand-new flooring, and a huge backyard, this home offers the space and flexibility to fit just about any stage of life. Hardwood floors create a warm, welcoming feel throughout the main level, while the family room fireplace makes the perfect gathering spot on chilly evenings. Whether you're hosting family for the holidays, watching the big game with friends, or simply enjoying a quiet night at home, this is a house that's meant to be lived in. The finished basement adds even more living space and can easily become a media room, playroom, home gym, office, or guest retreat. Upstairs, you'll find four spacious bedrooms, giving everyone a place to unwind at the end of the day. Step outside and you'll discover one of the home's best features, a backyard that's hard to find in Annapolis. There's plenty of room for cookouts, yard games, pets, gardening, or simply relaxing on the deck with your morning coffee before the day begins. It's the kind of outdoor space you'll use every chance you get. One of the biggest reasons people love Annapolis Cove is the neighborhood itself. Neighbors gather for happy hours at the marina, movie nights, and the community's annual Fourth of July parade. Kids ride bikes together, friends stop to chat on evening walks, and there's a true sense of community that's becoming harder and harder to find. Residents also enjoy access to the private marina, playground, green spaces, and the opportunity to join the waterfront Bay Ridge Pool. Just minutes from Historic Downtown Annapolis, Quiet Waters Park, shopping, restaurants, and commuter routes, you'll enjoy the best of Annapolis while coming home to one of its most welcoming neighborhoods. This is more than a beautiful house, it's a place to put down roots, make memories, and enjoy a lifestyle that keeps people in Annapolis Cove for years. Welcome home!

1286 Ketch Ct, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$659,000
4 Beds ⋅ 3 Baths
Experience the perfect blend of modern luxury and waterfront living at 1412 Ellis Road in the highly sought-after, water-privileged community of Oyster Harbor. This beautifully renovated home offers exceptional style, flexible living spaces, and outstanding indoor and outdoor entertaining—all just minutes from downtown Annapolis. The main residence features 3 spacious bedrooms and 2 full bathrooms, thoughtfully updated with today's finishes and designed for comfortable everyday living. The gourmet kitchen is the heart of the home, showcasing sleek cabinetry, premium appliances, and generous prep space, making it ideal for everything from casual family meals to hosting friends. A standout feature of this property is the detached studio suite, complete with its own kitchen, full bathroom, and washer and dryer. Perfect as a guest house, private home office, creative studio, or space for extended family. Does someone need a place to stay when visiting the Naval Academy. $$ This would work. The inviting living area offers a warm, welcoming atmosphere year-round. During the cooler months, relax in the cozy interior spaces, and when the weather warms up, step outside to enjoy two expansive rear decks that seamlessly extend your living space outdoors. Whether you're grilling, dining under the stars, or simply unwinding with family and friends, these outdoor spaces were designed to be enjoyed in every season Beyond the home, Oyster Harbor provides an exceptional Chesapeake Bay lifestyle with community amenities that include a private beach, boat ramp, fishing pier, kayak launch, playground, and picnic area. Here, you'll enjoy the charm of waterfront living while remaining just minutes from Historic Annapolis, shopping, restaurants, and major commuter routes.

1412 Ellis Rd, Annapolis

Listing courtesy of Compass. Contact: (443) 873-3585
$1,285,000
3 Beds ⋅ 3 Baths
Nestled in the heart of Eastport, this thoughtfully designed 3-bedroom, 2.5-bath home offers the perfect combination of comfortable living, modern updates, and one of Annapolis' most sought-after walkable locations. Complete with a rare detached two-car garage, this is an exceptional opportunity to enjoy the Eastport lifestyle in an established neighborhood that continues to attract significant investment and enduring demand. The main level features hardwood flooring throughout, a spacious living room, separate dining room, and an inviting family room with a wood-burning fireplace that opens directly to the kitchen—creating an ideal space for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, a gas cooktop, and a separate main-level laundry/mudroom for added convenience. A spacious three-season porch extends the living space and creates a wonderful transition to the beautifully landscaped backyard, complete with a flagstone patio, attractive stone retaining wall, and detached two-car garage—ideal for relaxing or entertaining. Upstairs, the spacious primary suite offers a walk-in closet and private bath, along with two additional bedrooms and a full bathroom. The unfinished lower level provides abundant storage, a dedicated workshop area, and exterior access to the rear yard. Recent improvements include a new HVAC system (2024), newer garage doors, and a low-maintenance composite front porch. Step outside and enjoy everything that makes Eastport one of the most desirable waterfront communities in the region. Walk or bike to neighborhood restaurants, coffee shops, marinas, the Annapolis Athletic Club, Spa Creek, multiple yacht clubs, and Historic Downtown Annapolis via the Eastport Bridge. Hop aboard the Water Taxi, spend afternoons on the waterfront, or simply enjoy the vibrant coastal lifestyle that surrounds you. Opportunities to purchase in established Eastport neighborhoods continue to become more limited as significant investment and redevelopment enhance the surrounding area. Whether you're looking for a wonderful place to call home or a long-term investment in one of Annapolis' most coveted communities, 1105 Boucher Avenue offers both lifestyle and lasting value.

1105 Boucher Ave, Annapolis

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

$1,550,000
3 Beds ⋅ 3 Baths
Price Improvement and Exceptional Value! A rare opportunity to own over 2 private acres in one of Annapolis’ most desirable waterfront communities. Complete with a private tennis court and backing to a sprawling horse farm, this exceptional property offers the perfect blend of privacy, recreation, and the Chesapeake lifestyle. Nestled in the sought-after Whitehall Beach neighborhood, residents enjoy community water access, a fishing pier, and the relaxed coastal lifestyle this special enclave is known for. Lovingly maintained by the same owners for many years, this custom home has been exceptionally cared for and thoughtfully preserved. Offering the best of both worlds, it combines tranquil country living with the convenience of being just minutes from downtown Annapolis, waterfront dining, marinas, Route 50, and the highly regarded Broadneck school district. Inside, you’ll find a warm and inviting floor plan with high ceilings, abundant natural light, and timeless custom built-ins that create an inviting main living area. The spacious unfinished lower level provides endless possibilities for future living space, a home gym, workshop, or additional storage. The expansive grounds offer plenty of room to entertain, garden, or simply enjoy your own private retreat, with potential space for a future pool or additional outdoor amenities, subject to buyer verification and all applicable approvals - making this an exceptional offering where privacy, community, and the Chesapeake lifestyle come together. Schedule your private tour today!

718 Whitehall Beach Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$959,000
4 Beds ⋅ 3 Baths
Beautifully updated and thoughtfully designed, this four-bedroom home offers exceptional indoor and outdoor living in the prestigious Annapolis waterfront community of Epping Forest. Where waterfront living and exceptional amenities combine to create an unparalleled lifestyle. This sought-after, water-privileged neighborhood features a new deep-water marina, wooded trails, a clubhouse overlooking the Severn River, tennis, pickleball and basketball courts, parks, and two sandy beaches perfect for swimming, relaxing, or launching your next adventure on the water. Inside, this beautifully designed home offers four spacious bedrooms, including a convenient main-level bedroom, ideal for guests, multigenerational living, or a private home office. The open, light-filled floor plan welcomes you with abundant natural light, effortless flow, and oak hardwood floors throughout, creating inviting spaces for both everyday living and entertaining. The chef’s kitchen is thoughtfully appointed with premium GE Café appliances, striking Blue-Eyed granite countertops, and abundant cabinetry, making meal preparation both functional and enjoyable. Just beyond, the inviting living room is anchored by a charming enclosed wood-burning fireplace, creating a warm and welcoming atmosphere throughout the seasons. The spacious dining area opens directly to the side patio, seamlessly extending indoor living and entertaining outdoors. Upstairs, the luxurious primary suite serves as a private retreat, featuring an expansive walk-in closet and a spa-inspired ensuite bath designed for relaxation. A charming Juliet balcony offers the perfect spot to enjoy a cool evening breeze or a quiet morning coffee. Two additional bedrooms and a well-appointed full bathroom provide comfortable accommodations for family and guests. The bright, finished lower level offers exceptional flexibility, with generous space for a recreation room, fitness area, media room, or home office. A large utility room with walk-out access to the rear patio adds both convenience and functionality. Outdoor living is equally impressive. The private patio provides an ideal setting for al fresco dining, morning coffee, or relaxing at the end of the day. Gather around the inviting fire pit on cool evenings, while the charming garden shed keeps outdoor essentials neatly organized. Beyond, a second secluded garden creates a peaceful retreat with plenty of room for family, friends, and pets to enjoy. The professionally landscaped and hardscaped grounds provide season-long color, beauty, and privacy, creating a tranquil outdoor oasis. Combining timeless style, thoughtful design, and the unmatched lifestyle of Epping Forest, this exceptional home offers a rare opportunity to experience the very best of Annapolis waterfront living. Epping Forest is a Special Tax District with an annual assessment of $2,003 and is governed by community Rules and Regulations.”

1724 Robinhood Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$745,000
4 Beds ⋅ 3 Baths
There are homes that impress you. Then there are homes that make you imagine a completely different way of living. Imagine ending your workday with a walk to the beach to watch the sun set over the Chesapeake Bay. Weekend mornings begin with coffee on your deck surrounded by mature trees, afternoons are spent boating on the South River, swimming at the community pool, or exploring Quiet Waters Park, and evenings end with neighbors gathering for concerts, celebrations, and waterfront sunsets. This is the lifestyle that has made Hillsmere one of Annapolis' most cherished waterfront communities for generations—and it's waiting for you at 104 Groh Lane. Beautifully updated from top to bottom, this home offers the perfect balance of modern style and everyday comfort. Every room reflects a fresh, timeless aesthetic with thoughtful finishes, abundant natural light, and a warm, welcoming feel that allows you to simply move in and begin enjoying life from day one. The beautifully renovated kitchen is designed for those who love to cook. Whether you're preparing fresh Maryland crab cakes after a day on the water, perfecting your favorite family recipes, baking holiday desserts, or creating an elegant dinner for friends, this is a space where great meals become lasting memories. The adjoining dining and living areas flow effortlessly together, making entertaining feel natural while allowing everyone to stay connected long after dessert has been served. Step outside and discover one of this property's greatest assets—a lush, private, level backyard that's becoming increasingly difficult to find in Annapolis. This exceptional homesite offers endless possibilities, with room for the custom pool you've always envisioned, vibrant gardens, an outdoor kitchen, a fire pit, or simply a wide expanse of green lawn where children and pets can run freely. Host summer barbecues on the spacious deck, celebrate birthdays beneath the stars, enjoy quiet mornings listening to the birds, or spend peaceful evenings surrounded by the beauty of your own backyard sanctuary. The finished lower level provides the flexibility today's lifestyles demand, offering the perfect space for a recreation room, media lounge, fitness studio, home office, guest accommodations, or a combination of all four. Whether you're working from home, hosting overnight guests, or creating a place for everyone to spread out, this home easily adapts to the way you live. But what truly sets this property apart is what lies beyond your front door. Hillsmere is far more than a neighborhood—it's a true waterfront community where neighbors know one another and every season brings new opportunities to enjoy the outdoors. Residents have access to a private sandy beach overlooking the Chesapeake Bay, a private marina with boat slips and direct access to the South River, boat ramps, a community swimming pool, waterfront pavilions, playgrounds, volleyball courts, picnic areas, and an active calendar of events that creates a genuine sense of community. Quiet Waters Park, Hillsmere Elementary School, the library, shopping, restaurants, Eastport, Historic Downtown Annapolis, and City Dock are all just minutes away, giving you the perfect blend of convenience, recreation, and coastal charm. Finding a beautifully updated home is easy. Finding one on a lush, level lot in one of Annapolis' most beloved waterfront communities is not. 104 Groh Lane offers more than beautiful spaces and thoughtful updates. It offers morning walks to the water, evenings filled with laughter on the deck, lifelong friendships, unforgettable gatherings, and the simple joy of coming home to a place that feels exactly where you're meant to be.

104 Groh Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686