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$835,000
3 Beds ⋅ 3 Baths
Tucked into Homewood, just beyond the brick sidewalks of Historic Downtown Annapolis, 16 Woodlawn Avenue is a residence taken down to the studs and rebuilt in 2019, blending all the comforts of modern design with the historic charm of Homewood. A traditional front porch, turned white columns and soft buttery siding announce the home from the street while a long driveway offers the rare luxury of off street parking in one of Annapolis's most walkable in-town pockets. Inside, tall ceilings and recessed lighting set an airy tone against gorgeous oak flooring on the main level and the beautifully refinished original pine flooring on the stairs and level two. The classic period moldings that run throughout remind you that this home has been here for a time as the updates make it seem like a much newer build. The kitchen anchors the main level: white shaker cabinetry, stainless appliances, and granite countertops surround a center island with room for a kitchen table, while a separate formal dining room sits just off the living room for more considered entertaining. A main level powder room, a rare find in homes of this era, provides ease buyers rarely expect from an in-town address. A mudroom tucked off the kitchen doubles as an office also providing space for the pantry, a laundry closet and access to the unfinished basement and backyard. Upstairs, three bedrooms include a primary suite that is bright, generously scaled, and appointed with an ensuite bath and stall shower. The hall bath is an ode to the age of the home with a refurbished black and white clawfoot tub (with shower) set beneath classic wainscoting. A third floor of floored attic space stands ready as flexible storage today, or a defining feature tomorrow for an owner who wants to finish it into additional living space. Outside, the large, flat, fully fenced yard is anchored by a side patio off the mudroom for grilling and framed by fig trees, with a gate to a rear fenced area and a large storage shed beyond. The location is a defining feature in its own right. Walk to Navy games, boat shows, Wednesday night's "Dinner Under the Stars, and pickup pickleball on West Street, or take a short drive to the boat ramps at Amos Garrett Park or West Annapolis to launch your paddle board or kayak. 16 Woodlawn Avenue isn't just a renovated in-town home. It stands as a premier expression of Chesapeake Bay living at its most walkable and most alive. Be sure to check out the virtual walk through tour!

16 Woodlawn Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$795,000
4 Beds ⋅ 3 Baths
Perfectly positioned in the heart of sought-after Admiral Heights, 290 Halsey Road offers a wonderful combination of timeless character, comfortable one-level living, and beautifully flexible space. Hardwood floors bring warmth and elegance throughout the main level, while the inviting living room is centered around a gas fireplace, creating a sophisticated yet comfortable place to gather. The kitchen is appointed with stainless steel appliances, and the light-filled sunroom provides a beautiful extension of the living space—ideal for morning coffee, casual entertaining, or simply enjoying the changing seasons. Designed with versatility in mind, the home offers the ease of one-level living, complemented by a spacious walk-out lower level that can effortlessly accommodate a family room, private guest suite, home office, fitness space, or recreation area. Three full bathrooms further enhance the home’s functionality and flexibility. All of this is set within one of Annapolis’ most desirable established neighborhoods, just moments from Downtown Annapolis, West Annapolis, the Navy-Marine Corps Memorial Stadium, Route 50, shopping, dining, and everyday conveniences. An exceptional opportunity to enjoy the charm and lifestyle of Admiral Heights with inviting interiors, flexible living spaces, and an outstanding Annapolis location.

290 Halsey Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$799,000
1 Beds ⋅ 1 Baths
Welcome to waterfront living at The Point, one of Annapolis’ most desirable communities on Spa Creek. Thoughtfully designed to showcase the water, this one-bedroom, one-bath condo features beautiful hardwood floors, stunning Spa Creek views, and two private balconies, perfect for taking in the waterfront scenery. The updated kitchen features high end appliances and upgraded countertops, creating a clean, seamless look. The Point offers an exceptional Annapolis lifestyle with a waterfront pool, marina with boat slips for power and sailboats, tennis and pickleball courts, clubhouse, and access for kayaking and other water activities. Enjoy the convenience of walking to downtown Annapolis and Eastport for restaurants, shops, marinas, and waterfront fun. The unit also includes assigned storage and dedicated bicycle space on the ground floor. Whether you’re looking for a full-time home or an easy Annapolis getaway, this is waterfront living with downtown fun just a short walk away.

5 President Point Dr Unit #A2, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,299,900
3 Beds ⋅ 4 Baths
Historic Character. Elevated luxury. Unparalleled location. Step into history and experience the timeless elegance of Two Eleven King George Street, a distinctive condominium in the heart of Historic Annapolis. The property adjoins the Historic Paca Gardens This extraordinary three-level residence seamlessly blends 18th-century charm with sophisticated modern living. Residence features 3 bedrooms, 3 1/2 baths, and an elevator provides effortless access to all three levels directly from the private parking garage-an exceptional convenience in the historic district. Rich hardwoods. Elegant living and dining spaces. Wood Burning Fireplace. Office/den/family room. Charming breakfast nook off kitchen. Enjoy finished lower level that maybe your 3rd bedroom/office/den along with separate laundry room. Enjoy seasonal view of the magnificent William Paca Gardens, while being just steps away from the United States Naval Academy, City Dock, charming shops, acclaimed restaurants, and the Annapolis Harbor. Energy-efficient construction with rooftop solar hot water. "Few residences in Annapolis can tell a story spanning nearly a century of hospitality. Before becoming one of only three luxury residences, Two King George Street welcomed visitors as the beloved Blue Lantern Inn and later the Red Coach Inn. Today, it continues that tradition of gracious living, thoughtfully redesigned as an exclusive condominium overlooking the historic William Paca Gardens in the heart of historic Annapolis. The condominium owners have the right of first refusal. Today, residents enjoy private, elevator access, secure garage parking, addition to garage parking space you are also eligible for 1 street parking space. Timeless architecture in one of Annapolis' most coveted locations and the charm of Maryland's Capitol.

211 King George St Unit #A, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$1,050,000
5 Beds ⋅ 4 Baths
Discover the Space, Style & Lifestyle You’ve Been Waiting For in Mulberry Hill! Welcome to an exceptional 4-bedroom, 3.5-bath Colonial nestled on a spacious corner lot in sought-after Mulberry Hill. Offering an impressive blend of timeless elegance, modern updates, expansive living spaces, and incredible versatility, this is a home that truly stands apart. From the moment you arrive, the charming covered front porch sets the tone. Step inside to a beautifully appointed main level featuring beautiful hardwood floors, fresh paint, French doors, elegant crown molding, and recessed lighting. The thoughtfully designed floor plan offers the perfect balance of refined entertaining spaces and comfortable everyday living, with a formal living room, formal dining room, and inviting family room anchored by a cozy gas fireplace. The updated kitchen is sure to be the heart of the home, featuring granite countertops, a center island, new stainless steel appliances, and a sun-filled breakfast nook framed by a beautiful bay window. It’s an ideal space for everything from quiet morning coffee to lively gatherings with family and friends. Upstairs, retreat to the spacious primary suite, complete with hardwood floors, a private bath, and a versatile bonus room that can easily adapt to your lifestyle. Two additional bedrooms with new carpeting share a full bath and offer generous space for family, guests, or a home office. Then there’s the finished walk-up lower level—an incredible bonus that expands the possibilities even further. With a large recreation room, an additional flexible room, and a full bath, this level is perfectly suited for a guest suite, home office, gym, media room, playroom, or private retreat. Outside, the spacious corner-lot setting provides room to relax and entertain, while the rear deck creates an inviting spot for outdoor gatherings. The oversized three-car garage and expansive driveway offer exceptional convenience, with abundant parking, storage, and room for vehicles, hobbies, recreational equipment, or all the extras that come with everyday life. Location is the finishing touch. Tucked into a quiet and desirable community, you’re just minutes from the Naval Academy, Naval Academy golf, dining, shopping, recreation, and everything that makes the Annapolis area so special—including its iconic waterfront lifestyle. Spacious. Flexible. Ideally located. This home offers the room you need, the updates you want, and the lifestyle you’ve been waiting for—all with plenty of opportunity to make it uniquely yours. Don't miss it!

1825 Johnson Rd, Annapolis

Listing courtesy of Curtis Real Estate Company. Contact:

$439,500
2 Beds ⋅ 3 Baths
More info and photos coming soon!

2700 Summerview Way Unit #304, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

$975,000
5 Beds ⋅ 4 Baths
Welcome to this stunning Colonial in the highly sought-after Bowen Manor community of Annapolis, offering over 4,500 square feet of beautifully appointed living space. This is a fantastic opportunity to own one of the biggest, and most private lots in the neighborhood. Perfectly positioned with desirable southeast exposure, this exceptional home is bathed in natural sunlight from morning through early evening. Step inside the grand foyer and discover an open-concept floor plan featuring soaring ceilings, rich Brazilian tigerwood hardwood flooring, elegant architectural columns, custom plantation shutters, and extensive decorative moldings. The formal dining room is designed to impress with a tray ceiling, crown molding, and chair rail, while the adjacent living room is filled with natural light from expansive windows. At the heart of the home is the gourmet kitchen, complete with a large center island with breakfast bar seating, granite countertops, Viking microwave and dishwasher, French door refrigerator, walk-in pantry, and a sun-filled breakfast room with direct access to the expansive rear deck. The adjoining family room showcases a dramatic floor-to-ceiling stone fireplace, creating the perfect gathering space. A private home office and powder room complete the main level. Retreat upstairs to the luxurious primary suite featuring a tray ceiling, oversized walk-in closet, and a beautifully remodeled spa-inspired bath with dual granite vanities, jetted soaking tub, frameless tiled shower with built-in seating and decorative inlay, private water closet, and tray ceiling. Spacious secondary bedrooms provide generous accommodations for family and guests. The fully finished lower level offers exceptional flexibility with a large recreation and entertainment area, fifth bedroom, a renovated full bath, utility/storage room with durable epoxy flooring, and access to the garage. Outdoor living is equally impressive. Relax or entertain on the expansive tiered deck featuring Bose outdoor speakers and smart under-deck lighting, then step down to the custom stone patio overlooking a private, fully fenced backyard surrounded by mature trees and open green space. An 11-zone irrigation system services the front flower beds and both front and rear lawns for effortless landscaping. Thoughtful updates and premium features include a Trane two-stage HVAC system (2024), Hot Water Heater (2026), smart Yale front door lock, dual smart thermostats, Wi-Fi-enabled garage door opener, epoxy garage flooring, 5.1 surround sound ceiling speakers in the living room, GE Smart washer and dryer (2021), and a professionally soft-washed exterior completed in 2026. Enjoy an unbeatable location just minutes from Routes 50 and 97, Mike's Crab House, South River marinas, Annapolis Town Center, Festival at Riva, Annapolis Mall, multiple grocery stores, restaurants, and more. Outdoor enthusiasts will appreciate being just minutes from Riva Park, Quiet Waters Park, and Davidsonville Park. Luxury finishes, modern smart-home technology, an exceptional outdoor living experience, and one of Annapolis' most convenient locations combine to make this remarkable Bowen Manor residence truly one of a kind. This home won't last long!

206 Bowen Ct, Annapolis

Listing courtesy of Redfin Corp. Contact: 4102028454
$899,900
3 Beds ⋅ 4 Baths
Originally built as the community’s model home with over 3,300 finished sq ft, this 3 bedroom, 3.5 bath home features tray ceilings, a built-in speaker system, and abundant natural light throughout the main level. The spacious kitchen overlooks the living and dining areas and features granite countertops, stainless steel appliances, and a large pantry. The living room features a gas fireplace with stone surround, along with direct access to the back deck. Plantation shutters add a finished touch throughout. The primary suite features a walk-in closet and en suite bath with a soaking tub and walk-in shower. Two additional bedrooms and upper-level laundry complete the bedroom level. The fully finished basement expands the living space even further, with windows bringing in natural light, a full bathroom, and plenty of room for a media space, gym, office, or additional living area. Outside, a large, low-maintenance back deck overlooks a tree lined yard, creating a private setting for relaxing or entertaining. An attached two-car garage features an epoxy-coated floor and electric vehicle charger. The location makes it easy to enjoy so much of what Annapolis has to offer, with Quiet Waters Park, Riva Park, Downtown Annapolis, Eastport, the U.S. Naval Academy, local marinas, waterfront dining, shops, and restaurants all within easy reach. Spend a day on the Chesapeake Bay, explore downtown, catch a Navy game, or head across the Bay Bridge for a day on the Eastern Shore. Route 50 and I-97 also provide convenient connections throughout the region. Meticulously maintained and beautifully finished, 108 Marquise Lane offers the opportunity to own the home originally designed to showcase the best of the community.

108 Marquise Ln, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600
$309,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully updated two level penthouse condo featuring three bedrooms, two full baths, and a thoughtfully designed open concept layout. The living and dining areas flow seamlessly together, while soaring ceilings and abundant natural light create a bright, spacious atmosphere. A cozy wood-burning fireplace adds warmth and charm. The elegant primary suite features a private en suite bath and direct access to a peaceful blacony overlooking mature trees. The perfect setting for morning coffee or evening relaxation. With modern finishes and thughtful upgrades throughout, this home is move in ready. Conveniently located near shopping, dining, public transportation, Washington, D.C., ad major commuter routes, this stylish penthouse condo offers the perfec t combination of comfort, convenience, and contemporty living. Condo living at its' best.

30 Sandstone Ct, Annapolis

Listing courtesy of Keller Williams Preferred Properties. Contact:

$625,000
2 Beds ⋅ 2 Baths
Discover a luxurious lifestyle in this exquisite 2-bedroom, 2-bathroom residence nestled in the prestigious Grandview at Annapolis Towne Centre. This contemporary corner "Davenport" unit boasts an open floor plan with 10' ceilings, enhanced by elegant crown moldings and recessed lighting, creating a warm and inviting atmosphere. The gourmet kitchen features upgraded countertops and high-end appliances, including a built-in microwave, wall oven, and sleek Miele Induction cooktop, perfect for culinary enthusiasts. There is also a den that makes a great home office or flex space. Step onto the private balcony to enjoy serene views or unwind in the community's rooftop pool or elegant bar. The building offers exceptional amenities, including a fitness center, concierge service, and a stylish bar/lounge. Enjoy the convenience of in-unit laundry and assigned parking with electric vehicle charging stations available. With its prime location (easy access to shopping, dining, downtown Annapolis, Naval Academy, marinas etc.) and luxurious features, this home is a perfect blend of comfort and sophistication, inviting you to embrace an exclusive lifestyle. Experience the best of modern living in this exceptional property.

1915 Towne Centre Blvd Unit #303, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$481,900
4 Beds ⋅ 2 Baths
Fully Renovated Rancher in a Highly Desired Neighborhood! Welcome to this beautifully renovated rancher, featuring 4 bedrooms, 2 full bathrooms, and a fully finished basement. The main level offers beautiful hardwood floors and a completely updated kitchen featuring 42-inch cabinets, quartz countertops, a separate island, and stainless steel appliances. The spacious finished basement provides a large family room, a fourth bedroom, and a full bathroom—perfect for guests, a home office, or additional living space. Enjoy the private backyard and new deck, ideal for outdoor entertaining and relaxing. Located on a quiet street in a highly sought-after neighborhood, the home is conveniently close to major routes, shopping, and everyday amenities. All required permits have been obtained for the renovations. Recent updates include: New siding; New roof; New windows; New gas furnace; New central A/C; New hot water heater; New sump pump; New deck; Fully renovated kitchen; Finished basement with bedroom and full bathroom. Nothing to do but move in and enjoy!

105 Rosecrest Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$385,000
3 Beds ⋅ 1 Baths
AUCTION! Occupied property and inspections NOT available - sold as-is. No for sale sign. Contact with occupants is prohibited. No financed offers/bids as there is NO access. Property is being sold occupied with any and all occupants in AS IS/WHERE IS condition. Neither the seller nor the listing broker can verify the existence of any lease agreement, either written or verbal, nor any rental amount being paid, due or owing. Please DO NOT disturb the occupants. Access for inspections or other purposes is NOT available. Buyer is assuming ALL responsibility for any necessary eviction action. Do not email any offers as the property is being sold via auction and all bids are to be submitted online during auction period. The sale will be subject to a 5% buyers premium pursuant to the Auction Terms & Conditions (minimums may apply). All auction bids will be processed subject to seller approval. Property information provided is estimated and not guaranteed (this includes condo fee/bedroom/bathroom count). Cash bids only as you cannot access the unit. The buyer's agent is to pay a $200 plus sales tax offer management fee at closing of an accepted offer. BIDDING STARTS Aug 24 and ENDS Aug 26.

208 Parker Ave, Annapolis

Listing courtesy of Northrop Realty. Contact: 4105310321
$1,199,000
3 Beds ⋅ 4 Baths
Welcome to 145 Prince George St., a distinctive historic home that blends classic architectural character with thoughtful modern updates. From its welcoming front porch and slate roof to its original wood details and spacious interior, this home offers a rare combination of charm, character, and versatility. The main level features beautiful wood floors and an inviting floor plan designed for both everyday living and entertaining. The spacious kitchen offers abundant cabinetry and storage, including a built-in pantry cabinet, along with an island and granite countertops. Stainless steel appliances include a dishwasher and microwave, a new four-burner gas range/oven and new French-door refrigerator provide. Just off the kitchen, the large dining room offers plenty of space for gatherings and features a mini-split ductless heating and cooling system, chandelier, crown molding, and architectural columns that provide an elegant transition into the living room. The living room is highlighted by a brick fireplace with marble hearth and gas fireplace, creating a warm and inviting focal point. Windows throughout the main level feature classic shutters. The original staircase adds even more character, with beautiful wood steps and traditional wood balusters leading to the upper levels. The first upper level offers two bedrooms, including a spacious primary bedroom with its own private bath, along with a hall bathroom. Continue to the second upper level, where a flexible loft space provides additional sleeping or living space and is currently arranged with multiple twin beds. This versatile area could serve a variety of purposes depending on the needs of the new owner. The unfinished basement provides valuable storage and utility space and includes a convenient half bath, washer and dryer, gas-fired boiler, gas water heater, and exterior access. Outside, the rear yard is fenced and features a six-person hot tub, creating a private space for relaxing or entertaining. The front of the home features a welcoming porch with a brick-tile surface, while the exterior showcases a combination of stucco, cedar, and slate that adds to the property’s distinctive historic character. With its original architectural details, spacious rooms, flexible upper-level living space, updated kitchen appliances, private fenced rear yard, and inviting front porch, 145 Prince George St. offers a unique opportunity to own a home with character that is difficult to replicate. Some photos may feature virtual staging.

145 Prince George St, Annapolis

Listing courtesy of RE/MAX Aspire. Contact: (443) 574-1071
$550,000
4 Beds ⋅ 3 Baths
Welcome to 785 Rolling View Drive… If you’ve been waiting for a home that gives you space, outdoor living, community amenities, and access to the water without the waterfront price tag, this is it!!! 4-bedroom, 2.5-bath split foyer sits in one of the Broadneck Peninsula’s most recognizable water-privileged communities. Off-street parking, covered front porch, and a comfortable layout designed for everyday living and entertaining. The main level features an open living room and dining room combination, with a separate kitchen equipped with stainless steel appliances, including a newer refrigerator, stove, microwave, and dishwasher. From the dining area, step outside onto the oversized deck—the perfect spot for summer gatherings, morning coffee, grilling, or simply enjoying the peaceful setting. Three bedrooms are located on the main level, including a primary bedroom with a walk-in shower, along with a full bath. The lower level includes a fourth bedroom, family/rec room with wood-burning fireplace, separate laundry room, half bath, and walkout access to the rear yard. The backyard offers a private, secluded feel backing to a ravine, creating a natural buffer and peaceful outdoor setting. Major updates include: newer roof, Central A/C, flooring and updates throughout (2026). Cape St. Claire. This isn’t just a neighborhood—it’s a lifestyle. Residents enjoy access to multiple community beaches, three marinas, boat ramps, parks, recreation facilities, piers, and countless ways to enjoy the water. Go boating, launch a kayak, spend the afternoon at the beach, fish from the pier, or simply enjoy everything this unique community has to offer. Shopping and restaurants are conveniently located within the community, while Annapolis is just a short drive away. Perfect for commuters; convenient access to Washington, D.C., Baltimore, and Fort Meade. Come see why 785 Rolling View Drive is more than just an affordable Annapolis home—it’s an opportunity to live the Cape St. Claire lifestyle. Schedule a private showing today!!!

785 Rolling View Dr, Annapolis

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$385,000
3 Beds ⋅ 3 Baths
PHOTOS COMING . This sun-filled home is located in the lovely Harbour Heights. Awaiting your special touch, this home features hardwood floors, crown molding, granite kitchen counters, stainless steel appliances and a deck that backs to trees. The Owner's suite has vaulted ceilings and a spacious walk-in closet. Close to restaurants and shopping, Rt 50 and minutes from downtown Annapolis and Navel Academy.

95 Harbour Heights Dr Unit #95, Annapolis

Listing courtesy of Samson Properties. Contact: 3018500255
$895,000
6 Beds ⋅ 3 Baths
From the street, its charm is immediate, but step inside and the amount of space, functional layout and flexibility of the home quickly become the surprise. Well loved and carefully improved, it balances original character with meaningful updates throughout. A welcoming entry foyer sets the tone with a custom built-in bench and storage, adding character while keeping everyday comings and goings organized. From here, the home opens into the fully renovated kitchen, where upscale finishes pair with a functional layout and easy connection to the dining area. The open-concept dining and large family room create a natural flow for both everyday living and entertaining, with the family room anchored by an ashlar-cut sandstone fireplace with a raised flagstone hearth and a large bay window overlooking the front yard. Down the hall is the primary suite, which includes a beautifully renovated en suite bath, while two additional bedrooms share a large bathroom with convenient double-sink vanity. The lower level is where the home's versatility really comes into focus. It has comfortably served as a long-term guest suite, with a quasi-kitchenette, full bathroom and dedicated home office space. The oversized living room and adjacent living space were just renovated in 2026, creating even more room to gather, work, host guests or spread out. There is a 6th bedroom adjacent to the kitchenette that has a myraid of potential uses: home gym, hobby room, home theater space or storage. A full walkout leads directly to the patio, where overhead string lights make it an inviting extension of the living space. Set on a rare double lot just shy of a half acre, 296 Halsey offers a generous amount of outdoor space and established landscaping that changes with the seasons. Mature flowering pink magnolias fill with blossoms in the spring, followed by crepe myrtles bringing color later in the year. There is something intentional and worth noticing in every season, whether viewed from the bay window, beneath the front-yard tree swing or from the backyard patio. Since purchasing the home, the current owners have invested significantly in 296 Halsey while taking great care of the character that was already here. The result is a home that feels genuinely well loved: spacious without losing its charm, updated without losing its personality, and far more expansive than its first impression suggests. Updates worth noting for any savvy home buyer: HVAC replaced (2026), Basement Renovation (2026), Roof (2022) and Kitchen + Primary Suite full renovation (2022).

296 Halsey Rd, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425
$875,000
4 Beds ⋅ 3 Baths
Welcome to 109 Sunset Drive, a beautifully fully renovated 4-bedroom, 3-full-bath home offering approximately 2,500 finished square feet in the highly desirable Hillsmere Shores community of Annapolis. Thoughtfully renovated from top to bottom, this impressive home combines a bright open-concept floor plan, extensive 2026 improvements, a finished lower level & a fabulous fenced backyard retreat complete w/ a refreshing private pool, exceptional privacy & peaceful tree-lined views. Step inside to discover an inviting open layout enhanced by beautifully refinished natural hardwood floors, fresh paint, new interior trim, new interior & exterior doors & new lighting fixtures throughout. The completely refreshed kitchen features new finishes, tile flooring & new appliances and flows seamlessly into the adjoining living & dining spaces, creating an ideal setting for both everyday living & entertaining. Updated bathrooms feature new finishes & tile flooring, while the finished lower level provides additional flexible living space w/ new LVP flooring, perfect for a family room, recreation area, home office, guest space or gym. The extensive 2026 renovations go well beyond the beautiful interior and include a new architectural-shingle roof, new blown-in cellulose insulation throughout the attic, whole-home draft sealing, new HVAC system, new water softener/filter system, new sump pump motor, new kitchen & laundry appliances, new interior & exterior doors, new trim package & new lighting fixtures throughout. Outdoor improvements are equally impressive, including new bluestone front & rear patios w/ custom steel railings. The backyard is designed for relaxation & entertaining, offering a refreshing private pool surrounded by a fenced setting, mature trees & peaceful views. The pool has been professionally opened & serviced, recently fully drained, updated w/ new tile & caulking at the coping & includes a new robotic cleaner. A large tree on the property has also been professionally pruned & assessed for health & safety. And then there is the Hillsmere Shores lifestyle. Residents have access to a private sandy beach overlooking the Chesapeake Bay, private marina w/ boat slips & direct access to the South River, boat ramps, community swimming pool, waterfront pavilions, playgrounds, volleyball courts, picnic areas & an active calendar of events that creates a genuine sense of community. Whether spending summer days at the beach or pool, launching a boat for an afternoon on the water or gathering with neighbors along the waterfront, this is a community designed to enjoy the very best of Annapolis living. There is a voluntary HOA of just $25 annually for those wishing to use the Association. Quiet Waters Park, Hillsmere Elementary School, the library, shopping, restaurants, Eastport, Historic Downtown Annapolis & City Dock are all just minutes away, giving you the perfect blend of convenience, recreation & coastal charm. With 4 bedrooms, 3 full baths, approximately 2,500 finished square feet, extensive renovations, a finished lower level, private pool, fenced backyard retreat & incredible access to the Chesapeake Bay & South River, 109 Sunset Drive is a rare opportunity to enjoy move-in-ready living and the quintessential Annapolis lifestyle. ***PLEASE SEE DISCLOSURES FOR A FULL LIST OF 2026 IMPROVEMENTS***

109 Sunset Dr, Annapolis

Listing courtesy of Winning Edge. Contact: 4434636009
$675,000
3 Beds ⋅ 2 Baths
This adorable split level home is located on a cul-de-sac in ROLLING HILLS! The sellers just had the interior painted, carpets replaced on the main and upper levels, and the vanity replaced in the primary bath—all on top of existing updates throughout. A generous asphalt driveway and meandering paver walkway create a wonderful first impression. Once inside, you'll find hardwood floors, a bright interior, generous room sizes, and a seamless layout. The wood-burning fireplace anchors the lower-level recreation room, creating an inviting, cozy space. The laundry and utility area provides convenient access to the rear yard, which boasts a composite deck, a large double-door shed, and a lush, gently rolling lawn dotted with shade trees. Just wait until you see this one—you're going to love it!

1838 Brett Ct, Annapolis

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

$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 include 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:

$414,999
3 Beds ⋅ 2 Baths
Welcome home to this charming 3-bedroom, 1.5 bath home conveniently located near Downtown Annapolis! Featuring beautiful hardwood floors and a finished basement, this home offers comfortable living with plenty of additional space to make your own. Step outside to a large, fully fenced backyard perfect for entertaining, pets, gardening, or simply relaxing outdoors. Move in and enjoy as-is or bring your personal touches and create a space that truly reflects your style. With its convenient location, flexible living space, and inviting outdoor area, this home is full of opportunity. Don’t miss your chance to make it yours!

200 Woods Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$669,900
2 Beds ⋅ 2 Baths
Welcome to easy, active living in Heritage Harbour! This beautifully maintained villa offers a desirable open floor plan with hardwood floors, 2 bedrooms plus a versatile den that can easily serve as a 3rd bedroom, office, or guest space. The spacious screened-in porch is the perfect place to enjoy your morning coffee, relax with a good book, or entertain friends while overlooking the beautifully landscaped grounds. A 2-car garage provides plenty of room for vehicles, bikes, golf cart, and extra storage. All this in Heritage Harbour, Annapolis’ premier 55+ community, offering an incredible array of amenities including golf, pools, tennis, pickleball, fitness facilities, clubs, activities, and so much more. Come see why Heritage Harbour is such a wonderful place to call home!

847 Rudder Way, Annapolis

Listing courtesy of Academy Realty Inc.. Contact: (410) 263-9105
$424,900
3 Beds ⋅ 2 Baths
Located in the sought after Revell Downs community and blue ribbon Broadneck School District, this move in ready home features tasteful updates throughout and is just minutes from waterfront parks, marinas, shopping, dining, and historic Annapolis. It provides the perfect balance of neighborhood charm, everyday convenience, and the Chesapeake Bay lifestyle! The solar panels are owned by the seller and will convey with a warranty until 2042. Reap the benefit of EXTREMELY low utility costs! See the July invoice in the Documents section. Outdoor entertaining is provided by a large fenced rear yard with huge newer concrete patio and direct access to a tot lot. The current owner is willing to sell the existing furnishings to the prospective buyer for a nominal price. Don't delay...this home will sell very quickly!

1622 Secretariat Dr, Annapolis

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

$1,349,000
5 Beds ⋅ 5 Baths
Rare Opportunity to own a newer home tucked away on a private cul-de-sac just a short stroll from everything Downtown Annapolis has to offer. Completed in 2022, this exceptional home showcases top of the line finishes throughout. Designer kitchen with Quartz countertops, custom cabinetry and high end GE Cafe appliances. Wide Plank hardwood floors throughout the main and upper levels. 9 foot ceilings and custom moldings. Recessed lights throughout the home. Low Maintenance Hardie Plank siding and Anderson Windows. Main level has an open floor plan with office area perfect for those that work from home. Upper level features 4 generous sized bedrooms. Primary Bedroom has cathedral ceilings, massive his and her walk in closets. Lower level is finished with indestructible Luxury Vinyl Plank floors. In the lower level there is a room perfect for a gym or 5th bedroom (there is an egress window). The .25 acre lot has community space next to it that provides extra yard space for kids to use. 2 Car attached garage with a rough in for EV Charger. Sellers recently installed Solar Panels. Energy costs are VERY minimal. Terrapin Station is a prime location. The Navy Stadium is just around the corner. Walkable to Historic Annapolis, US Naval Academy and tons of restaurants. Steps from the Poplar Path which has numerous playgrounds and the Michael Busch Annapolis Library off it. Come live the Annapolis lifestyle!

111 Ellershaw Ct, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$449,000
2 Beds ⋅ 1 Baths
Beautifully updated and meticulously cared-for condo in the sought-after Dreams Landing community, offering coastal charm and the best of the Annapolis waterfront lifestyle! In excellent condition and truly move-in ready, this home is filled with bright natural light and features hardwood floors throughout, fresh paint, and an updated kitchen with quartz countertops, stainless steel appliances, white cabinetry, and backsplash. The updated full bathroom features shiplap detailing, a new vanity, light fixture, and hardware, plus the convenience of an in-unit stackable washer and dryer installed July 2026. Enjoy beautiful evening sunsets, a waterside community pool, kayak storage, and fantastic access to the Severn River. Launch your kayak or hop on your boat for a ride into Downtown Annapolis! Additional conveniences include an exercise room in the building and a private lower-level storage unit with built-in shelving, perfect for bikes, boating gear, and extra storage. Perfect as a full-time residence, weekend getaway, or easy Annapolis retreat, conveniently located near Downtown Annapolis, the U.S. Naval Academy, shopping, dining, and all that Annapolis has to offer. Just unpack and start enjoying life by the water! Schedule your private tour today, you won't want to miss this opportunity!

1204 Dreams Landing Way Unit #1204, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$520,000
3 Beds ⋅ 4 Baths
Welcome to this beautiful and thoughtfully updated townhome in the sought-after community of Windgate! Offering 3 spacious bedrooms, 2 full and 2 half baths, a 1-car garage, three finished levels, and a desirable bump-out, this home combines comfort, style, and convenience. The remodeled eat-in kitchen features crisp white cabinetry, granite countertops, stainless steel appliances, gas cooking, and a bright breakfast area. The adjoining dining area opens to a large rear deck—perfect for grilling, entertaining, or simply relaxing. Plantation shutters, numerous built-ins, and beautifully upgraded flooring throughout add even more character and appeal, including engineered hardwood, luxury vinyl tile, ceramic tile, and carpet. Upstairs you'll find three generously sized bedrooms, including a spacious primary suite featuring vaulted ceilings and a large walk-in closet. The finished lower level provides even more living space with a large recreation room, half bath, and walk-out access to the patio and fully fenced backyard. This home has been exceptionally well maintained with numerous recent improvements, including a NEW HVAC system, hot water heater, kitchen appliances, and flooring in 2023; NEW garage door and openers in 2025; plus a roof installed in 2019 with 50-year shingles—providing added peace of mind for the next owner. Location is another standout! Enjoy convenient access to Downtown Annapolis, the U.S. Naval Academy, Annapolis Mall, Anne Arundel Medical Center, and an incredible selection of restaurants, shopping, entertainment, and everyday conveniences. Commuters will appreciate the easy access to major routes connecting Annapolis, the Eastern Shore, Washington, D.C., and Baltimore. Beautifully updated, spacious, and ideally located—this wonderful Windgate townhome is ready to welcome its next owner!

706 Howards Loop, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$564,900
2 Beds ⋅ 2 Baths
Discover this charming 2-bedroom, 2-bathroom unit in the desirable Park Place community, built in 2007. This mid-rise Luxury Condominium building, located in Annapolis, features a spacious 1,056 sq. ft. layout, perfect for modern living. Enjoy the convenience of stainless steel appliances, including a built-in microwave, gas oven/range, and dishwasher. The community offers exceptional amenities, including a refreshing outdoor pool, gym, party room and a dog park, outdoor patio with grills, catering to an active lifestyle. With 24-hour security and reserved parking in an underground garage, peace of mind is paramount. Located near vibrant local shops and dining options, Park Place is ideal for those seeking a blend of comfort and convenience. The association fee covers essential services, trash removal and snow removal, gas, water, sewer, ensuring a hassle-free living experience. Embrace the lifestyle this community offers, where every day feels like a retreat.

5 Park Pl Unit #414, Annapolis

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

$379,000
2 Beds ⋅ 2 Baths
Welcome to Creekside Cove! This beautifully maintained, multi-level end-unit condo offers the perfect blend of convenience, comfort, and privacy in a tucked-away community just minutes from everything Annapolis has to offer. Inside, you are greeted with an open-concept layout features hardwood floors, crown molding, and a gourmet kitchen with stainless steel appliances, 42" maple cabinetry, and granite countertops. Fresh paint & carpet as well! Stay comfortable year-round because the HVAC and water heater were both replaced within the last two years. The spacious primary suite provides a relaxing retreat with a whirlpool tub. Enjoy the ease of condo living with no yard work or weekend maintenance to worry about, giving you more time to relax, entertain, and enjoy the Annapolis lifestyle. A one-car garage plus driveway parking provides added convenience and plenty of space for your vehicle and guests. Tucked away in the peaceful Creekside Cove community yet conveniently close to Anne Arundel Medical Center, Downtown Annapolis, the U.S. Naval Academy, Annapolis Mall, and Route 50, this home puts everything within easy reach. Come home, unwind, and enjoy the best of Annapolis without the upkeep of a traditional home!

2144 Hideaway Ct Unit #29, Annapolis

Listing courtesy of RE/MAX One. Contact: 4105356291