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962 Woodland Cir, Annapolis
$749,999
5 Beds ⋅ 4 Baths
Welcome home to this charming Waterview colonial in sought after Cape St Clarie community. Enjoy your morning coffee or an evening beverage on your expansive deck while taking in the views of the Little Magothy River. This home has so many wonderful features. The main level as you enter the home has a separate living area with a dining area right off that. The large gourmet kitchen will be the heart of the home with the sprawling open floor plan. Off the family room you step out to the spacious deck and enjoy the river views year-round. The upper level boasts 3 ample sized bedrooms, with the primary enjoying its own primary bath. If that wasn't enough, the lower level has another whole separate living area, with a kitchen, full bath, laundry, 2 bedrooms, a living room and its own separate entrance from the main level of the house. The exterior has a great, fenced yard for the family and the pets to enjoy, there is even an above ground pool for summertime enjoyment. The community has a beach, clubhouse and boat slips available for an additional fee. Don't miss out for a chance to own in this community!

962 Woodland Cir, Annapolis

Listing courtesy of Rosendale Realty. Contact:

3349 Arundel On The Bay Rd, Annapolis
$670,000
4 Beds ⋅ 3 Baths
Welcome to your turn-key coastal retreat in the highly sought-after water-privilege community of Oyster Harbor! Situated on a rare double lot, this beautiful 4-bedroom, 3-full-bath home offers the perfect blend of modern updates and outdoor flexibility. The main level shines with refinished hardwood floors, a freshly painted interior, and a bright, open-concept kitchen, living, and dining area. Step through the glass doors onto the elevated wrap-around deck—an entertainer's dream perfect for catching cool breezes off the Chesapeake Bay. Retreat to the private primary suite addition, featuring a cozy stone fireplace, dual closets, with a private bath. The fully finished lower level boasts brand-new wall-to-wall carpet, a spacious family room, a full bath, a fourth bedroom, den, and ample storage space. Outside, the expansive double lot provides endless possibilities for a garage, boat storage, or custom gardens. Enjoy premier community amenities including a private beach, playground, and boat slips. Don't miss this incredible opportunity to live the Coastal Annapolis Lifestyle!

3349 Arundel On The Bay Rd, Annapolis

Listing courtesy of Engel & Volkers Annapolis. Contact:

173 Williams Dr, Annapolis
$1,749,000
4 Beds ⋅ 4 Baths
Stress melts away the moment you pull into the driveway. Set on 1.06 peaceful acres in sought-after Admiral Heights, this mid-century modern home offers expansive views of Weems Creek in both directions, with a resident bald eagle that has called the neighborhood home for more than a decade. The house was fully renovated to the studs in 2022, with new windows, doors, chef's kitchen, design-grade bathrooms, insulation and flooring throughout. Inside are 4 bedrooms and 3.5 baths across 2,382 square feet, with numerous windows designed to take in the water views and the quiet setting. Recent updates continue outside: the exterior was painted in 2025, and the front yard was fully redone and the upper roof replaced in 2026. The work is done, so you can move in and enjoy it. The property includes an approximately 0.2-acre subdivided buildable lot, which offers room for a second home, a guest house for extended household or relatives, or a future investment. This waterfront location is ready to finish, so bring your dock designer/builder and complete the picture. Admiral Heights is a popular water-privileged community with a voluntary improvement association, a neighborhood pool with membership options, several community-owned docks, and a local boat club. You’re minutes from downtown Annapolis and the Navy-Marine Corps Memorial Stadium, with easy access to Route 50 for commuting to DC, Baltimore and beyond. A rare chance to own a renovated, private retreat on Weems Creek, with space to grow.

173 Williams Dr, Annapolis

Listing courtesy of Homecoin.com. Contact:

830 Chester Ave, Annapolis
$1,795,000
4 Beds ⋅ 4 Baths
Priced to Sell! This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centrally located for easy access to shopping and restaurants in Eastport, as well as a quick trip to downtown Annapolis. Offering 4bedrooms (one on main level), 3.5 baths, a dedicated mudroom with a wet sink, a finished basement with storage, bar, and half bath. Hardwood flooring throughout. The original garage and car port are located on the rear alley. Sellers are offering completed architectural plans for an ADU - ready for submission. The front of the home (new sod) is the original bungalow with all of its charm, and a formal living room with an updated wood burning fireplace (2019). The fourth bedroom and full bath are on the main level. The upper level has a generously sized primary bedroom with a vaulted ceiling, multiple closets, and space for a desk, workout studio or expanded closets. The additional two bedrooms and bath on the upper level are generously sized and have hardwood flooring. Laundry is on the bedroom level. The main-level, hand-scraped white oak floors were re-sanded and given a matte finish in Oct 2026. Central to the rear addition in the gorgeous kitchen and great room with space for dining, two sitting rooms and a gas fireplace. The sizeable, fenced, backyard includes a large patio for entertaining, a detached finished game room/office that could be converted back to 2-car garage, and a car port and driveway with parking for 2-3 cars. Please note that the rear yard has an astro-turf product on it that was professionally installed for wear and proper drainage.

830 Chester Ave, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1207 Mcguckian St, Annapolis
$1,475,000
4 Beds ⋅ 4 Baths
Luxury New Construction | A Lifestyle of Walkability, Elegance & Annapolis Charm. Don’t miss this exceptional opportunity to own a stunning new-construction home in the highly desirable Homewood neighborhood of Annapolis! With permits in hand and construction about to begin, there is still time to personalize select finishes and make this beautiful home your own. Offering three finished levels of thoughtfully designed living space, this residence delivers more than luxury living, it offers a lifestyle centered around comfort, connection, and the best of Annapolis right outside your door. Inside, 9-foot ceilings on every level and a bright, open-concept floor plan create an inviting sense of space. The gourmet kitchen is designed to impress, featuring 42-inch custom cabinetry, quartz countertops with a coordinating backsplash, stainless steel appliances, and an oversized island that seamlessly connects the dining area and spacious family room. A cozy gas fireplace creates a warm and welcoming gathering space, while sliding glass doors open to a private deck, perfect for morning coffee, evening cocktails, or entertaining friends. A stylish powder room and convenient mudroom with laundry space complete the main level. Upstairs, the expansive primary suite offers a peaceful retreat, complete with a generous walk-in closet and spa-inspired bath featuring a double vanity, soaking tub, and glass-enclosed shower. Two additional bedrooms and a well-appointed full bath provide comfortable accommodations for family and guests. The finished lower level expands the possibilities with a spacious recreation room, fourth bedroom, and full bath, ideal for hosting overnight guests, accommodating extended family, or creating a flexible space for work and leisure. Set along a charming, tree-lined street, this home captures the character of Homewood while offering the style, comfort, and convenience of modern construction. Here, the lifestyle is just as special as the home itself. Enjoy a leisurely walk to downtown Annapolis for waterfront dining, boutique shopping, coffee with friends, and evenings spent exploring the city’s vibrant historic district. With inviting green spaces, a welcoming neighborhood atmosphere, and convenient access to major commuter routes, you can enjoy the perfect balance of urban convenience and residential charm. With its exceptional design, flexible living spaces, and coveted walkable location, this is more than a place to call home, it’s an opportunity to embrace the Annapolis lifestyle. And with construction just getting underway, you may still have the opportunity to add your own personal touch.

1207 Mcguckian St, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

1820 Baltimore Annapolis Blvd, Annapolis
$1,895,000
6 Beds ⋅ 5 Baths
Welcome to an exceptional private estate in St. Margaret's, where sophisticated living meets effortless indoor-outdoor entertaining. Tucked behind a gated entrance and set on beautifully landscaped grounds, this expansive residence offers an impressive blend of luxury, versatility, and thoughtful design. The main level welcomes you with a grand foyer, solid red oak hardwood floors, and a stunning two-story living room featuring a gas fireplace and custom built-ins. The gourmet kitchen is truly the heart of the home, showcasing Wolf and Sub-Zero appliances, quartz countertops, marble backsplash, Miele dishwasher, beverage refrigerator, walk-in pantry, and abundant custom storage. The adjacent all-seasons room, complete with a wood-burning stove, provides a warm and inviting space to relax year-round. The main-level primary suite is a private retreat with its own gas fireplace, dual custom walk-in closets, built-in safe, and spa-inspired bath featuring a jetted soaking tub, oversized glass shower with dual shower heads and body sprayers, and dual marble vanities. A flexible additional room on the main level offers endless possibilities as an office, guest room, or additional bedroom. Above the oversized two-car garage, a separate bonus suite with full bath and closet provides exceptional flexibility for guests, an au pair, home gym, private office or additional bedroom Upstairs, a spacious loft-style lounge provides additional entertaining space, while three generously sized bedrooms offer walk-in closets and access to private or Jack-and-Jill baths. The lower level is designed for fun and entertaining, featuring a large open recreation area with polished concrete floors, indoor rock-climbing wall, built-in dartboard, beverage refrigerator, and a wood-paneled office/media room with custom built-ins and wet bar. Extensive unfinished storage, multiple utility-floored storage rooms, and a secure storage room with built-in safe and passcode entry provide an abundance of space. Outside, enjoy a custom paver patio with built-in gas grill, dedicated entertaining area, separate stone fire pit, private garden with raised planting beds, expansive side yard, and built-in basketball hoop. The property offers three garage bays, a circular driveway with auto court and five additional parking spaces, plus an attached storage shed. Recent updates include HVAC system improvements to both first and second-floor HVAC systems. A natural gas generator provides backup power for the tankless water heater, primary living spaces, and network/Wi-Fi infrastructure. With its gated privacy, remarkable entertaining spaces, luxury finishes, flexible living arrangements, extensive storage, and exceptional mechanical updates, 1820 Baltimore Annapolis Boulevard offers a truly distinctive lifestyle in sought-after Annapolis.

1820 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

7 Landings Ct, Annapolis
$625,000
5 Beds ⋅ 4 Baths
Beautifully Updated 5-Bedroom Home in The Landings of Annapolis! Welcome to 7 Landings Court, where spacious living, modern updates, and fantastic community amenities come together! This beautifully updated home offers 5 bedrooms, 3.5 bathrooms, and approximately 2,500 square feet of finished living space across three levels. Step inside to discover a thoughtfully designed floor plan featuring a convenient main-level bedroom, perfect for guests, a home office, or flexible living arrangements. The brand-new kitchen showcases all-new cabinetry and appliances, creating a fresh, inviting space for everyday living and entertaining. Upstairs, you’ll find three generously sized bedrooms and two full bathrooms, including a private primary suite. The finished lower level provides even more versatile living space, complete with a fifth bedroom, full bathroom, and plenty of room for recreation, entertaining, or relaxation. Enjoy outdoor living at its finest with a charming covered front porch, an expansive approximately 40-foot-wide rear deck, and a spacious, fully fenced backyard offering endless possibilities for entertaining, gardening, or simply unwinding. A two-car driveway provides convenient off-street parking. Located in the desirable Landings community, residents enjoy access to wonderful amenities, including a swimming pool, tennis courts, and pickleball courts, with an HOA fee of $140/Month. With five bedrooms, extensive updates, flexible living spaces, and outstanding community amenities, this Annapolis home offers an exceptional opportunity. Make sure to book your showing before its gone!

7 Landings Ct, Annapolis

Listing courtesy of Alberti Realty, LLC. Contact:

584 Wayward Ct, Annapolis
$544,000
4 Beds ⋅ 2 Baths
Nestled in the serene community of Rolling Knolls, this exquisite split foyer home offers a harmonious blend of modern luxury and timeless comfort. With a major renovation completed in 2019, every corner of this residence has been thoughtfully designed to create an inviting atmosphere that feels like home. Step inside to discover a spacious layout that seamlessly integrates living and dining areas, perfect for both intimate gatherings and entertaining guests. The heart of the home features a well-appointed kitchen with ample table space, ideal for casual meals or morning coffee. The kitchen is equipped with high-end stainless appliances, including a sleek electric oven/range, a dishwasher for effortless cleanup, and convenient upgrades, ensuring that every need is met with ease. Natural light pours through the thoughtfully placed windows, double sliders to the back yard add greenery inside, enhanced by an elegant bay window, that add a touch of light and breeze. The large family room in the lower level has a fireplace and a 4th bedroom, currently an office. The mantel provides a perfect spot for personal touches, making this space truly your own. Primary bath with a tub shower serves the primary bedroom. Outside, the property is situated on a peaceful cul-de-sac, offering a sense of privacy and tranquility. The outdoor space includes a charming patio, perfect for al fresco dining or simply enjoying the beauty of nature. With off-street parking available, convenience is at your fingertips. Experience the perfect blend of modern amenities and classic charm in this charming Rolling Knolls residence. The elementary school is right up the street, making it a breeze to get there in a jiffy, or walk there. Annapolis boasts water sports, parks & recreation are within the community, and you'll enjoy the lifestyle here!

584 Wayward Ct, Annapolis

Listing courtesy of Executive Choice Realty. Contact:

204 S Villa Ave, Annapolis
$1,395,000
4 Beds ⋅ 4 Baths
Discover an exceptional blend of sophisticated design, resort-inspired living, and everyday convenience in this beautifully appointed Annapolis residence. Tucked along a quiet street yet remarkably close to everything that makes Annapolis so desirable, this distinctive home offers the perfect balance of privacy and accessibility. From the vibrant restaurants, boutiques, and waterfront attractions of Historic Downtown Annapolis to the charm of nearby neighborhoods and marinas, the very best of the Annapolis lifestyle is just moments away. Designed with both elegant entertaining and comfortable everyday living in mind, the home welcomes you with striking architectural details, beautifully curated finishes, and thoughtfully designed spaces throughout. The main level features gracious formal living and dining areas, complemented by a butler's pantry that makes hosting effortless. At the heart of the home, a beautifully appointed kitchen opens seamlessly to the casual dining area and inviting family room, where accordion glass doors overlook the backyard retreat with serene pool as the focal point The outdoor living experience is truly exceptional. A stunning private pool serves as the centerpiece of a beautifully designed backyard, framed by lush landscaping and mature greenery that create a wonderful sense of seclusion. An expansive covered patio with comfortable lounging and dining areas, ceiling fans, and a fully equipped outdoor kitchen provides the perfect setting for everything from leisurely summer afternoons to memorable evenings entertaining family and friends. The seamless connection between the interior living spaces and poolside retreat creates an atmosphere reminiscent of a private luxury resort. Upstairs, an open loft with a bar area provides an additional gathering space, ideal for relaxing or entertaining or can easily be transformed into an additional bedroom and bath. The luxurious primary suite offers a peaceful escape, complete with an expansive walk-in closet and beautifully appointed spa-inspired bath featuring a curbless walk-through shower. A private balcony overlooking the pool adds another inviting place to unwind. Two additional bedrooms share a well-appointed full bath, offering comfortable accommodations for family or guests. The finished lower level provides remarkable versatility, with a spacious living room, kitchenette, bedroom, and full bath creating an ideal arrangement for extended family, overnight guests, or multigenerational living. A dedicated wine cellar adds a sophisticated touch, while an additional bonus room, currently utilized as a conference room, offers endless possibilities as a private home theater, media lounge, or recreation space. With its elegant interiors, exceptional outdoor amenities, and peaceful setting just minutes from the energy and excitement of Annapolis, this remarkable residence offers an extraordinary opportunity to experience luxury living without compromising convenience. Welcome Home!

204 S Villa Ave, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

1193 Hampton Rd, Annapolis
$617,000
4 Beds ⋅ 2 Baths
A must-see on Hampton Road, in the heart of Cape St. Claire! Extensively renovated in 2013 and complemented by numerous recent improvements, this bright and airy 4-bedroom, 2-full-bath home offers a refreshing departure from traditional split-foyer designs. The open-concept main level connects the living room, dining area, and spacious kitchen, creating a welcoming gathering space for everyday living and entertaining. The kitchen features quartz countertops, a large center island with Pottery Barn pendant lighting, stainless steel appliances, and an oyster-style backsplash. A double oven, dishwasher, garbage disposal, and five-stage reverse-osmosis water filtration system were updated in 2024. A generously sized primary bedroom and two additional bedrooms share a remodeled full bathroom with a tub/shower combination. The finished walkout lower level offers flexible living space, including an oversized fourth bedroom, a recreation room with direct access to the covered patio and expansive, level backyard, and a finished laundry room with tiled flooring and additional storage. The fully floored attic provides additional storage space and includes blown-in insulation and shelving. Outdoor living is equally appealing, with a covered deck and patio overlooking the spacious, flat 10,500 sq ft lot. The driveway accommodates up to seven vehicles, while a large storage shed with ramp (10' x 16') and an additional storage area beneath the deck provide ample room for tools, equipment, and seasonal items. The cedar swing set and trampoline convey, adding even more enjoyment to the backyard. Significant updates include a roof replacement in 2022, bedroom and living room windows replaced in 2025, and a new water heater in 2025. The well pump was replaced in 2020 and the pressure tank in 2021. Central HVAC and an owned water-treatment system add everyday comfort and convenience. Maintained as a smoke-free, pet-free household with allergy-conscious living in mind, this home reflects years of continued care and investment. The Hampton Road location offers sidewalk access to both the elementary and high schools, with local shopping and recreation also within walking distance. Residents of Cape St. Claire enjoy private community beaches, marinas, kayak storage, powerboat docks, fishing piers, boat ramps, playgrounds, and a clubhouse available for private rentals. Nearby recreational options include walking trails, sports fields at Cape St. Claire Park, and the Cape St. Claire Swim Club with its competitive swim team. Fairwinds Marina provides additional boating conveniences. Just a short walk away, the community shopping center offers Graul’s Market, a hardware store, casual dining, and a variety of shops. With its distinctive open layout, extensive updates, generous outdoor space, and access to Cape St. Claire’s waterfront amenities, this home offers a wonderful combination of comfort, convenience, and community.

1193 Hampton Rd, Annapolis

Listing courtesy of Redfin Corp. Contact:

1907 Mackiebeth Ct, Annapolis
$1,499,000
5 Beds ⋅ 5 Baths
Unique opportunity to own a brand-new home with builder’s warranty on 1.4 acres in an established Annapolis community. Just 5 minutes from Annapolis shopping. Welcome to 1907 Mackiebeth Court, an exceptional new construction home in the established Twin Hills neighborhood of Annapolis. Offering over 5,000 square feet of finished living space on a private 1.4-acre lot backing to a wooded area, this 5-bedroom, 4.5-bathroom home presents a rare opportunity in the Annapolis market. Built by local builder Howmar Homes, the property showcases craftsmanship, thoughtful design, and premium finishes that go well beyond typical builder-grade construction. The light-filled main level features an open floor plan centered around a gourmet kitchen with quartzite countertops, an oversized island, and premium Samsung & Maytag appliances. The kitchen flows seamlessly into the family room with 10-foot ceilings and a gas fireplace, while the morning room and expansive conservatory provide additional spaces for entertaining and everyday living. Upstairs, the spacious primary suite features a private sitting area, dual walk-in closets, and a luxurious bathroom with a soaking tub, walk-in shower, dual vanities, and separate water closets. Convenient upper-level laundry adds everyday practicality. The finished walkout lower level includes a large recreation room, fifth bedroom, full bathroom, and additional unfinished storage space. Outside, the expansive property offers plenty room to enjoy the outdoors. The approved grading plan includes an optional in-ground pool and patio space, offering exciting opportunities to further enhance the home's outdoor living spaces. Additional features include a side-entry three-car garage and a one-year builder warranty from Howmar Homes. With very few newly constructed homes in the Annapolis area offering this combination of finished square footage, acreage, and elevated craftsmanship, 1907 Mackiebeth Court is a truly unique opportunity. Enjoy the space and privacy of a large property just minutes from downtown Annapolis, waterfront attractions, shopping, and dining.

1907 Mackiebeth Ct, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

700 Mount Alban Dr, Annapolis
$699,000
4 Beds ⋅ 3 Baths
Welcome home to this great four bedroom, two and a half bath Colonial in the amenity abundant Cape St Claire subdivision. The gleaming hardwood floors throughout have just been refinished and are in every room but the basement and baths. So much room to spread out from the family room with a wood burning fireplace and slider to the sunroom, through the kitchen to the formal dining room or the front large living room. The modern kitchen has stainless appliances and sleek countertops. Upstairs find a large primary bedroom with attached full bath, and three other bedrooms share the hall bath. The basement is a clean slate waiting for a vision to finish the large space. Park in the oversized two car garage, or the driveway with space for four more cars. Reverse Osmosis water treatment system installed 2021 and roof replaced 2022.*****Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Minutes from Downtown Annapolis and easy access for commuter routes to Washington, Baltimore, or Ft Meade.****Be sure to check out the interactive floor plan tour****

700 Mount Alban Dr, Annapolis

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

614 Edwards Rd, Annapolis
$514,800
4 Beds ⋅ 2 Baths
Water-Access Community | 4 Bedrooms | 2 Full Baths | Big Backyard | Major Improvements | Garage | Approx 6 Miles to Downtown Annapolis! Enjoy the Best of Annapolis-Area Living in Beechwood on the Burley! Looking for space, convenience, outdoor enjoyment, and a wonderful community setting—all at an attractive price? Welcome to Beechwood on the Burley, a charming water-access community just minutes from Annapolis! This inviting home offers approximately 1,508 square feet of living space, four bedrooms, two full baths, an attached garage, and a generous, level 0.28-acre backyard. With flexible living areas and inviting outdoor spaces, there's room to relax, entertain, work, and play. Inside, you'll find a welcoming open-concept layout, hardwood flooring on the upper level, and a freshly painted interior. The spacious primary bedroom features an en-suite bath, while three additional bedrooms and a full hall bath provide plenty of room for family and guests. The finished lower-level family room offers even more versatility for movie nights, hobbies, a home office, or a playroom. The kitchen features stainless steel appliances, all NEW in September 2026, including a refrigerator with ice maker, range with warming zone and self-cleaning oven, and dishwasher. Enjoy added peace of mind with major recent improvements, including a NEW heat pump and roof in 2023, plus a NEW water heater and sump pump in 2026. The outdoor space is sure to impress! The spacious, level backyard offers room to garden, play, entertain, or simply unwind. The recently stained deck, approximately 37' x 12', is perfect for summer barbecues, outdoor dining, morning coffee, and gatherings with friends and family. The attached garage offers more than covered parking, with a workbench, pegboards, and storage shelving providing excellent space for projects, hobbies, and organization. Ample additional off-street and street parking adds convenience. Enjoy the lifestyle that makes Beechwood on the Burley special! Community amenities include access to a waterfront pier and boat slips, kayak racks, and a playground (availability may be subject to community waitlists). Whether you enjoy boating, kayaking, or simply appreciate being near the water, there's plenty to love about this peaceful neighborhood. The convenient location puts you just a short drive from Sandy Point State Park, local parks, bike paths, marinas, shopping, and restaurants. Historic Annapolis, the U.S. Naval Academy, and Route 50 are also easily accessible, with multiple routes to Annapolis and destinations both east and west. The home is located within the Windsor Farm Elementary attendance area too! More space, meaningful updates, a fantastic backyard, and a water-access community—all at an attractive price south of Route 50! Don't miss this opportunity to enjoy a wonderful combination of comfort, convenience, and outdoor living in a beautiful natural setting. Schedule your showing today! Additional Information: Voluntary Burley Creek Community Association fee is just $50 per year.

614 Edwards Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

996 Headwater Rd, Annapolis
$950,000
4 Beds ⋅ 4 Baths
Best Waterfront Value in Annapolis! Beautifully refreshed Waterfront colonial on a cul-de-sac, now offered with a substantial price improvement. Every inch shines with all-new interior and exterior paint, refinished hardwoods, and all-new carpeting. Main level kitchen has been upgraded with a new GE stainless steel appliance suite, combined with a family room that opens onto a deck with views of the creek, fire circle, playset area, and your own private pier with a boat slip. Main level mud room with laundry, built-in storage, and side entrance. Second level features a primary bedroom with a private balcony, upgraded fixtures in the primary and hall bathrooms, and three additional bedrooms. The fully-finished walkout lower level features granite counters, heated ceramic floors, a built-in electric fireplace, a second kitchen, and a spa bath with a second laundry room—perfect for guests or income potential. Enjoy maximum versatility and serenity minutes from Downtown Annapolis and the Naval Academy! Assumable first mortgage available at 3.25%.

996 Headwater Rd, Annapolis

Listing courtesy of Taylor Properties. Contact:

30 Woodlawn Ave, Annapolis
$599,000
2 Beds ⋅ 1 Baths
Charming Homewood cottage with numerous recent updates! This property is located on a partially secluded lot bordering city-owned, undevelopable land encompassing the headwaters of College Creek. Enjoy a peaceful setting on the back deck with a sense of privacy, all while being conveniently located near downtown Annapolis, shopping, dining, and local amenities. Recent improvements include a newer hot water heater, HVAC system, appliances, windows, newly renovated bathroom, insulation, asphalt driveway, hardscape walkway and retaining wall. A detached finished shed with dedicated electric offers flexible space with the potential to serve as a private home office, studio, or hobby space. This delightful cottage combines classic charm, thoughtful updates, and a convenient Annapolis location! Don't miss this one!

30 Woodlawn Ave, Annapolis

Listing courtesy of Compass. Contact:

130 Great Lake Dr, Annapolis
$650,000
4 Beds ⋅ 3 Baths
SOMETHING SPECIAL IS COMING TO HILLSMERE SHORES! Get ready to fall in love with 130 Great Lake Drive, an exciting new opportunity in one of Annapolis' most sought-after waterfront communities! Offering wonderful versatility and inviting spaces designed for both everyday comfort and effortless entertaining, this home features 2 fireplaces, a fabulous deck perfect for outdoor gatherings, and a separate in-law, nanny, or au pair suite that provides exceptional flexibility for extended family, guests, or multigenerational living. Imagine cozy evenings beside the fire, summer dinners under the stars, and weekends enjoying everything that makes Hillsmere Shores so special—including its beautiful community beach, marina, pool, and vibrant waterfront lifestyle. All just minutes from Historic Downtown Annapolis, shopping, dining, and everything the Chesapeake Bay region has to offer. A home with character, flexibility, and an address you'll love. More details and photographs coming soon. STAY TUNED!

130 Great Lake Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

3134 Anchorage Dr, Annapolis
$899,000
4 Beds ⋅ 3 Baths
Annapolis Renovated Gem A distinctive Annapolis residence where updates, architectural detail, and an enviable waterfront-community setting come together. Welcome to 3134 Anchorage Drive, an extensively updated 4-bedroom, 3-full-bath home offering approximately 3,627 square feet in Annapolis’s desirable Anchorage waterfront community. Situated on a 0.26-acre lot, this distinctive residence features natural stone accents, a fenced backyard, storage shed, attached garage, expansive deck, and covered patio. The 2026 improvements include a new roof, new stainless-steel appliances, new fresh interior paint, new light fixtures throughout, new hardwood flooring in the great room, new lower-level luxury vinyl plank flooring, a fully renovated lower-level bathroom, and basement waterproofing by Charles Pastrana & Sons. Architectural highlights include a dramatic great room with soaring ceilings, three custom arched wood-framed windows with intricate divided-light detailing and decorative fanlights, Pella windows, and sliding-door access to the deck. The welcoming foyer showcases a two-story staircase with custom turned spindles, natural oak handrails, and crafted newel posts. The well-appointed kitchen features Hagerstown custom-made wood cabinetry, granite countertops, a generous pantry, and reverse-osmosis filtration at the kitchen and bar sinks. The spacious Owner’s Suite was an addition to create a larger primary bedroom with a sitting area, custom window moldings, a stained-glass accent, a large walk-in closet, and a spa-inspired en-suite bath with a glass-enclosed shower, whirlpool soaking tub, double granite vanity, and separate water closet. The lower level provides a versatile family room with a traditional cast-iron wood-burning stove and white brick surround, two additional bedrooms, a full bath, recreation room, laundry closet, workshop, utility room, storage, and direct garage access. Additional features include a two-zone air-conditioning system, water-treatment system, generator, and attic storage. Beautifully expanded and renovated, 3134 Anchorage Drive is located in the highly sought-after Anchorage Waterfront community where residents enjoy exceptional amenities with an HOA fee of just $123/month, which includes access to a boat slip, marina, boat ramp, community pool, rack for kayaks and paddle boards and a half basketball court. Don’t miss the chance to own this renovated gem in one of Annapolis’s most coveted neighborhoods.

3134 Anchorage Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1954 Baltimore Annapolis Blvd, Annapolis
$1,150,000
7 Beds ⋅ 4 Baths
Set on a beautiful one acre lot with a U shaped driveway, this expansive 4,500 square foot contemporary rancher offers seven bedrooms, three full baths, generous living spaces, and a layout filled with possibilities. Recently updated by its longtime owners in preparation for its next chapter, the home combines distinctive architectural details with extensive improvements throughout. Step inside to an impressive open floor plan where soaring vaulted ceilings with exposed wood beams immediately draw your eye. Hardwood floors extend through the main living areas, while a dramatic wall of floor to ceiling windows spans the rear of the home, filling the space with natural light and showcasing peaceful wooded views. A two sided fireplace creates a striking focal point between the living and dining areas, adding warmth and character to both spaces. The kitchen offers new appliances along with a separate eat in area and convenient half bath. The main level features four spacious bedrooms, all with ceilings over nine feet. The hall bath includes a soaking tub, while the primary suite offers its own private bath with a walk in shower and new vanity. Step outside from the primary bedroom onto a private balcony overlooking the wooded setting. The finished lower level provides an incredible amount of additional living and entertaining space. An exceptionally large recreation room continues the home's connection to the outdoors with another wall of windows spanning the rear. A bar area opens conveniently to the lower level patio, creating a great setup for entertaining indoors and out. Three additional bedrooms and a full hall bath provide tremendous flexibility for guests, extended family, hobbies, or additional work from home space. The lower level also includes a large cedar closet, additional storage, a laundry and utility room, and a separate bonus room that could serve as an office, gym, hobby room, or additional storage. Recent improvements include fresh interior paint throughout, refinished hardwood floors on the main level, new flooring throughout the lower level, new lighting, new appliances, a new front door and kitchen door, and a new air conditioning system. Located in Ferry Farms, a sought after water privileged community along the Severn River, the property offers the opportunity to enjoy the Annapolis waterfront lifestyle while still having the privacy and space of a full acre. Just across the Severn River from the U.S. Naval Academy and convenient to downtown Annapolis, the location offers a unique combination of water access, natural surroundings, and proximity to everything Annapolis has to offer. With more than 4,500 square feet of living space, seven bedrooms, multiple gathering areas, walls of windows, wooded views, and an acre of property, this is a truly unique home. Thoughtfully refreshed by owners who have loved and cared for it, the home is ready to welcome its next owner while still offering plenty of opportunity to personalize the space and make it your own.

1954 Baltimore Annapolis Blvd, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

126 Stilly Way, Annapolis
$1,160,000
4 Beds ⋅ 5 Baths
Why wait to build when you can move right in? Welcome to 126 Stilly Way, a beautifully finished, nearly new home in Annapolis’ Parkside Preserve. Built in 2024 and offering more than 4,400 square feet of finished living space across three levels, this home combines the appeal of newer construction with the convenience of having the finishing touches already in place. The bright, open main level features a beautifully appointed kitchen with white cabinetry, quartz countertops, stainless steel appliances, gas cooking, double wall ovens, tiled backsplash, and an oversized center island. The kitchen flows seamlessly into the spacious family room, anchored by a gas fireplace with custom built-ins. A separate dining room provides additional space for entertaining. Upstairs, the primary suite features a tray ceiling, walk-in closets, and private bath with dual vanities, soaking tub, and oversized glass-enclosed shower. Three additional bedrooms each with their own walk-in closets and well-appointed baths complete the upper level. The finished lower level adds exceptional flexibility, with an expansive recreation area, wet bar with beverage refrigerator, full bath, and the potential to create a true fifth bedroom while still maintaining plenty of additional living and entertaining space. What truly sets this home apart is how much has already been done. Window treatments are installed, the lower level is finished, the yard is established, and the home is ready to enjoy from day one. Enjoy the benefits of a newer home without waiting on a construction timeline or tackling the many finishing touches that often come after settlement. A covered front porch, HardiePlank and brick exterior, level backyard, and attached two-car garage complete the property. Located just moments from Quiet Waters Park and convenient to Downtown Annapolis, shopping, dining, and major commuter routes, 126 Stilly Way offers the opportunity to enjoy newer construction with the added benefit of a home that is already finished, established, and truly move-in ready.

126 Stilly Way, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

219 Wardour Dr, Annapolis
$3,495,000
5 Beds ⋅ 7 Baths
Located in the coveted Wardour community, this stately home combines timeless architecture with an enviable walkable location near West Annapolis’ shops and restaurants and just minutes from downtown. With stunning curb appeal, spacious 0.55 acre lot, expansive front yard and water views from nearly every room in the home, this property offers a rare combination of privacy and community, where every day feels like a retreat yet conveniences are just minutes away. The main level welcomes with a gracious foyer flanked by formal living and dining rooms, highlighted by custom millwork, crown molding, wainscoting, and hardwood floors. The formal living room features a classic gas fireplace, while the private office with built-ins and the inviting family room with a coffered ceiling provide versatile spaces for work and relaxation. The gourmet kitchen impresses with high-end appliances, a large center island, casual dining area overlooking the backyard, and wet bar adjoining the dining room. A well-designed mudroom off the two-car garage and side entry enhances everyday function. Upstairs, three spacious ensuite bedrooms complement the luxurious primary suite, which offers a serene sitting room with gas fireplace, private balcony, and spa-like bath. The top floor is a flexible open space with full bath, perfect as an office, playroom, studio, or lounge. The lower level is an entertainer’s retreat with a full bar, open gathering space anchored by a wood-burning fireplace, and a room prepped to become a wine cellar. A full bath and additional bedroom complete this versatile level. Conveniently located to access Downtown Annapolis, head over the Bay Bridge to the Eastern shore or jump on Rt. 50 to get back to Washington, DC and just a few short blocks to West Annapolis' charming commercial district's restaurants & shops. Welcome Home!

219 Wardour Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

3124 Starboard Dr, Annapolis
$1,599,000
5 Beds ⋅ 4 Baths
A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and craftsmanship are reflected throughout their exceptional Annapolis home. 3124 Starboard Drive represents their vision of quality, functionality, and enduring design—where no detail was overlooked and every improvement was thoughtfully executed. Known as one of the neighborhood’s exceptional residences, this home offers a level of craftsmanship and attention to detail that is difficult to replicate. From the quality of construction and materials to the thoughtful design choices, the property reflects the discerning standards of a professional who builds and renovates homes for a living. This extraordinary residential real estate transformation is the creation of Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien from Intuitive Design. Together they joined forces and underwent a complete, down-to-the-studs renovation and expansion. They purchased this home in 2015 and over the course of time they turned a 2,000 square foot home into an over 3,700 square feet of luxurious, modern turnkey showpiece with no detail overlooked. This five-bedroom, four-bathroom residence, has an open and elegant floor plan flooded with natural light. The chef kitchen has a stunning 8.9’ x 6.9’ quartz Island countertop offering exceptional workspace and seating for five with striking oversized lantern-style pendant lamps. The Owner’s Suite Spa-inspired primary bath has a custom white double-vanity, luxurious marble countertops, polished brass fixtures, oversized mirrors, elegant glass pendant lighting and heated floors. The expansive walk-in shower is beautifully appointed in veined marble tile with a frameless glass enclosure, multiple shower fixtures and built-in niches, creating a sophisticated, resort-like retreat. The living and family rooms have gas fireplaces and built ins. In addition, the home features a recreation room, fully fenced backyard, a double garage converted into a conditioned and finished Golf simulator room, shed and golf-cart garage. Mechanical systems include a full-house back-up generator, dual zone HVAC systems, tankless water heater, RO water filtration in kitchen and below counter Scotsman Gourmet Ice Maker and water treatment with dual storage tanks, salinator, chlorinator, sediment filter and UV light. This residence was meticulously rebuilt in 2021 - walls, ceilings, floors, fixtures, electrical, and plumbing systems—all removed and replaced with high-end finishes and craftsmanship throughout. The result is a striking blend of contemporary comfort and timeless design. Located in the sought-after waterfront community of Anchorage, this distinctive residence combines sophisticated living with the relaxed character of an established Annapolis neighborhood, offering access to the community’s marina, pool, boat ramp and waterfront amenities.

3124 Starboard Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

1161 Green Holly Dr, Annapolis
$535,000
3 Beds ⋅ 3 Baths
NEW ROOF- 50 year shingle! Welcome to this spacious Colonial in the sought after water privileged community of Cape St. Claire. Step inside to a bright and inviting main level filled with natural light. The spacious living room opens to the updated kitchen featuring a new island with seating for three, new quartz countertops, freshly painted cabinetry, and a cozy breakfast nook overlooking the rear yard. A dining room addition provides plenty of space for gathering and entertaining with direct access to the rear deck and yard. A full bath on this level adds extra convenience. Upstairs, you will find three bedrooms and two full baths. The primary suite features vaulted ceilings, a walk in closet, and a private ensuite bath complete with a soaking tub and separate stall shower. Outside, the property has been freshly landscaped with a new parking pad and fresh grass seed throughout. The rear yard offers plenty of space to enjoy the outdoors, along with a large shed for additional storage. Cape St. Claire offers a sought after waterfront lifestyle just minutes from Annapolis. This established community along the Chesapeake Bay features community several beaches, parks, playgrounds, three marinas, boat ramps, and opportunities for boating, kayaking, fishing, and enjoying life on the water. Known for its strong sense of community, Cape St. Claire hosts neighborhood events throughout the year and offers convenient access to local shopping, dining, schools, and major commuter routes. It is a wonderful setting for buyers looking to enjoy the relaxed Chesapeake Bay lifestyle while remaining close to Annapolis and everything Anne Arundel County has to offer.

1161 Green Holly Dr, Annapolis

Listing courtesy of Cummings & Co. Realtors. Contact:

15 Elliott Rd, Annapolis
$1,275,000
6 Beds ⋅ 6 Baths
$25,000 towards closing for a contract by 10/15. New Construction - Under Roof but still time to pick some finishes! Built by Whitehall Building & Company, this exceptional new home offers luxury finishes, thoughtful design, and quality craftsmanship in one of Annapolis’s most sought-after locations. Tucked away like a private hidden gem, this home places you just a short stroll from the best of Eastport and Downtown Annapolis. Enjoy the waterfront, acclaimed dining, charming boutiques, historic streets, marinas, and the vibrant energy that make Annapolis such a special place to live. With both Eastport and Downtown right outside your door, this is a rare opportunity to experience brand-new luxury in a truly walkable Annapolis location. Visit Whitehall Building & Company for additional information and project details.

15 Elliott Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

2548 Mission Hills Ct, Annapolis
$750,000
3 Beds ⋅ 3 Baths
This immaculate 3 bedroom, ranch-style residence built in 1995 boasts 1,795 sq. ft. of luxurious living space on the main level + a finished basement. Step inside to find an open floor plan adorned with crown moldings and gleaming wood floors creating an inviting atmosphere perfect for entertaining. The gourmet kitchen, complete with an island and table space, is a culinary enthusiast's dream. Host friends and family for Thanksgiving where you can serve large parties in your formal dining room. The main living area is huge, with high ceilings, built-in shelves and a cozy fireplace. Enjoy the private backyard from the enclosed brick patio room. The fully finished, walk out basement gives you even more space for relaxation or hobbies. Heritage Harbour is a 55+ community that is located close to shopping, AAMC, historic Annapolis and major commuter routes ad offers endless amenities, activities and groups to keep you busy having fun, making friends and staying active. Embrace the exclusive amenities that define this community, including an art studio, fitness center, and multiple pools-both indoor and outdoor. Engage in friendly competition on the pickleball courts or enjoy leisurely strolls along the scenic jog/walk paths. With private access to the South River, indulge in water activities like canoeing or kayaking just a mile away. The meticulously maintained grounds and community features, including a clubhouse and library, foster a sense of belonging and camaraderie. Experience the perfect blend of luxury and leisure in this exceptional property, where every day feels like a retreat.

2548 Mission Hills Ct, Annapolis

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

827 Bay Ridge Ave, Annapolis
$869,000
3 Beds ⋅ 3 Baths
Enjoy the convenience and charm of Eastport living at 827 Bay Ridge, just a short walk to local restaurants, shops, marinas, parks, and downtown Annapolis. This updated and well-maintained 3-bedroom, 3-full-bath home offers comfortable, flexible living space. The main level features two bedrooms and two full baths, inviting living areas, hardwood floors, and an updated kitchen with white cabinetry, granite countertops, and stainless steel appliances. Just off the living and dining areas, the screened porch overlooks the private backyard, creating the perfect spot to relax or entertain. The lower level provides additional living space with a third bedroom and full bath, ideal for guests, a private retreat, or a home office. Outdoor features include a welcoming front porch, rear patio, private backyard, and a driveway conveniently located behind the home, along with a storage shed. Whether you’re looking for a full-time residence or a weekend getaway, this turnkey home has everything that makes coastal living so desirable!

827 Bay Ridge Ave, Annapolis

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

424 Halsey Rd, Annapolis
$725,000
4 Beds ⋅ 3 Baths
This spacious split-level home set on over a third of an acre features three main-floor bedrooms, two full baths (one of which is ensuite to the primary bedroom), and hardwood flooring. The vaulted living/dining room opens to a big deck overlooking a fully-fenced back yard. Downstairs, the fourth bedroom can be used as a TV room, office, or home gym. The lower-level includes a spacious family room with wood-burning fireplace, half bath, bonus room, laundry room, and plenty of storage space. The family room opens to the back yard. Numerous property improvements include a newer HVAC (2024), kitchen appliances (2022), replacement windows and sliding doors, and fresh paint throughout. The roof and gutters are less than five years old. Admiral Heights is a popular water-privileged community close to the Navy Marine Corps Stadium and just a mile and a half from downtown Annapolis. The neighborhood consists of more than 600 homes and features community amenities including a pool, a swim club, docks, parks, and kayak/canoe storage on Weems Creek. NOTE: Home is empty - many photos show virtual staging. Also, seller conducted a thorough home inspection in September 2026; a copy of this report is available upon request.

424 Halsey Rd, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

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