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Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.
One of the most popular communities provided by Maryland Sandbox
266
# of Listings
3
Avg # of Bedrooms
$529
Avg. $ / Sq.Ft.
$1,357,478
Med. List Price

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108 Properties Found. Page 4 of 8.

Now priced at $729,900—reduced from $749,900—and including a $5,000 seller credit toward closing costs, this stunning Bridgeport model condo offers unmatched value in the Grandview community. Experience breathtaking views from this stunning Bridgeport model condo in the highly sought-after Grandview community! This beautifully designed home features an open-concept floor plan with gleaming hardwood floors and abundant natural light throughout. The spacious gourmet kitchen is a chef’s dream, complete with granite countertops, stainless steel appliances, and ample cabinetry, perfect for both everyday living and entertaining. The primary suite offers elegant tray ceilings, private access to the deck, and a luxurious ensuite bath with a soaking tub and dual vanities. Step outside to your expansive private deck and take in panoramic views—ideal for morning coffee or evening relaxation. Residents of Grandview enjoy resort-style amenities, including a rooftop pool, bar and lounge, library, meeting room, state-of-the-art fitness center, concierge service, secure entry, and 2 garage parking with an assigned space. Conveniently located within walking distance to shopping, dining, and everyday essentials, this home offers both luxury and lifestyle in one exceptional package. Schedule your private tour today!
#MDAA2141622

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 915

2 Beds

2 Baths

1,616 Sq.Ft.

$729,900

MLS#: MDAA2141622

Stylish Street-Level Condo in the Heart of Annapolis. Welcome to this spacious 1-bedroom, 1.5-bath residence in the highly desirable Acton’s Landing community. Ideally located on the street level for easy access, this condo blends everyday convenience with upscale living. The open-concept design offers a bright, expansive living area and a well-appointed kitchen featuring a center island, breakfast bar, and ample storage—perfect for both weekend escapes and full-time living. A separate den provides flexible space for a home office or a cozy retreat. The primary suite serves as a private sanctuary, complete with a spa-like bath that includes a soaking tub, walk-in shower, and generous closet space. Enjoy the convenience of the building’s parking garage just steps from your door. Residents also have access to a range of amenities, including a fitness center, gathering rooms, library, and more. Just a short walk to the water taxi, park and the shops, restaurants, Naval Academy and the historic charm of downtown Annapolis. Experience the perfect blend of comfort, convenience, and coastal charm in the heart of Annapolis.
#MDAA2142366

ANNAPOLIS

66 FRANKLIN STREET 20

1 Beds

1 Baths

1,342 Sq.Ft.

$725,000

MLS#: MDAA2142366

OPEN Sunday 10 -12 NOOON === WATERFRONT= ONE BEDROOM "C" FLOOR PLAN = EXTRA WIDE CONDO: Four pane sliders in living room and there are 4 glass pane windows in master bedroom == Master has a private exit door to a beach front patio == Front row seats for the Blue Angels flyover and weekly regatta races ... Amenities galore with two community pools / pool house complexes - one directly on the bay == two community sports courts - one by Chase Pond. Onsite Gourmet Cafe - the 'Beacon' overlooking a privately owned 200 slip Marina and just an oyster shell path stroll to the private 1600-foot sandy bayfront beach with a small craft storage area... The front entrance is secured 24/7/365 and the security team walks the premises daily... HOA and CONDO fees are very affordable compared to other areas. Direct entrance walkway already in place from car park for handicap adaptable--- can further level entrance steps to kitchen... Life's a Beach !!
#MDAA2146176

ANNAPOLIS

2020 QUAY VILLAGE COURT T1

1 Beds

1 Baths

1,000 Sq.Ft.

$700,000

MLS#: MDAA2146176

Step into sophisticated comfort in this exceptional third-floor corner residence, a 2024-built condominium offering 1,723 square feet of thoughtfully designed space filled with natural light and showcasing designer finishes, premium upgrades, and meticulous attention to detail throughout. Located within a desirable 55+ active adult community, the open, well-appointed floor plan includes two spacious bedrooms, two full baths, and a private study—perfect for today’s flexible lifestyle. The gourmet kitchen stands out with high-end appliances, upgraded cabinetry, and elegant finishes, ideal for both everyday living and entertaining. Freshly painted and professionally styled, the home features new designer lighting and custom closet systems for added sophistication and functionality. Step outside to a private balcony—perfect for enjoying warm summer days, morning coffee, or evening relaxation. A rare highlight is the combination of two highly sought-after features: a private storage unit, reserved garage parking, an uncommon offering that adds significant value. Enjoy the added benefit of a low condo fee, enhancing both affordability and long-term value. Residents enjoy resort-style amenities, including pickleball courts, scenic walking trails, a golf simulator, dog park, and inviting indoor and outdoor gathering spaces with grilling areas, all ideally located with a quick drive to downtown Annapolis, waterfront dining, shopping, and the Bay Bridge. Impeccably maintained and move-in ready, this residence offers a unique opportunity to own a beautifully upgraded home with exceptional parking and storage in a vibrant, amenity-rich community.
#MDAA2143488

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 311

2 Beds

2 Baths

1,723 Sq.Ft.

$699,999

MLS#: MDAA2143488

Professional photos coming Friday! Welcome to 108 Maple Drive, a beautifully updated rancher in the sought-after waterfront community of Hillsmere Shores. Renovated throughout in 2016, this move-in ready home offers 3 bedrooms, 3 full baths, and the convenience of single-level living in one of Annapolis' most beloved neighborhoods. Inside, you'll find updated finishes, an inviting floor plan, and comfortable living spaces designed for everyday living and entertaining alike. Step outside to enjoy the screened porch overlooking a fully fenced backyard, complete with a large storage shed and plenty of room for pets, play, gardening, or gatherings with family and friends. A spacious driveway provides abundant off-street parking for multiple vehicles, boats, or trailers. Living in Hillsmere Shores means much more than owning a home—it’s a lifestyle. Residents enjoy access to a private marina with South River access, a community pool (additional membership), sandy beach, waterfront pavilions, playgrounds, kayak launches, and boat ramps. The neighborhood is also adjacent to Quiet Waters Park and just minutes from downtown Annapolis, shopping, dining, and commuter routes. Whether you're looking for your first home, your forever home, or the perfect place to enjoy Annapolis waterfront living, 108 Maple Drive offers an incredible opportunity at $699,900.
#MDAA2149008

ANNAPOLIS

108 MAPLE DRIVE

3 Beds

3 Baths

2,140 Sq.Ft.

$699,900

MLS#: MDAA2149008

Bring all offers! Beautiful, well maintained, quality one level living home with basement with water privileges at the end of Lake Ogleton, delivering the ultimate move-in ready experience. Fantastic location on private lane with lots of “New” in 2026 including new roof, skylight with remote shade, kitchen window, heat pump, hot water heater, carpet, sliding glass door, freshly painted, exterior steps to basement, gutters and more. Updated large modern kitchen with vaulted ceiling and skylight, newer stainless-steel appliances, attractive tile backsplash, quartz countertops, generous breakfast/lunch bar opens to the family room with a charming wood burning fireplace. Step into the expansive screened-in porch perfect for relaxing, entertaining and Maryland crab feasts. Elegant wood style flooring throughout. Separate dining room has vaulted ceiling. Large living room with vaulted ceiling could also easily serve as a bonus room, office or playroom. Bedrooms feature brand new carpet. Updated full hall bathroom includes a granite vanity and a large walk-in shower. Master bathroom has designer tile backsplash in tub/shower area with a large built-in shelf. Double sink marble vanity with designer tile border above it. Attractive ceiling fans with lights. Basement has great potential to finish into a recreation room. Water softener system is owned. Well insulated. Spacious garage. Large driveway with ample parking. Public water and sewer hookup available. Situated just minutes from historic downtown Annapolis, shopping, restaurants, water activities, theater, US Naval Academy, marinas, medical facilities, schools and more. Ideal for commuters to Washington DC, Baltimore, Fort Meade, Bay Bridge and beyond. This home checks every box. This is the Annapolis lifestyle at its best — beautifully updated, move in ready, and perfectly situated
#MDAA2145814

ANNAPOLIS

1132 BAY RIDGE ROAD

3 Beds

2 Baths

1,644 Sq.Ft.

$699,000

MLS#: MDAA2145814

Welcome to Primrose Hill, one of Annapolis' most desirable hidden gems, where modern luxury meets the unmatched lifestyle of Maryland's capital city. Perfectly positioned just minutes from Downtown Annapolis, Eastport, City Dock, the United States Naval Academy, waterfront restaurants, marinas, parks, and endless Chesapeake Bay adventures, this stunning four-level residence offers the rare opportunity to enjoy low-maintenance living without sacrificing space, style, or convenience. Flooded with natural light and thoughtfully designed for today's lifestyle, this beautifully updated home features four spacious bedrooms, three full baths, two half baths, and a spectacular top-floor loft retreat complete with skylights and a private bath—ideal as a guest suite, executive office, fitness studio, media room, or private escape. Rich hardwood flooring, designer finishes, and beautifully appointed baths create a sophisticated yet comfortable atmosphere throughout. At the heart of the home, expansive living and entertaining spaces flow effortlessly to an incredible outdoor living area highlighted by a dramatic indoor-outdoor gas fireplace, creating a year-round destination for gathering with friends, hosting game days, enjoying evening cocktails, or simply unwinding after a day on the water. The open design, abundant natural light, and flexible floor plan make this home equally suited for everyday living and entertaining on any scale. Unlike many Annapolis townhomes, this property offers exceptional parking and modern conveniences, including a spacious two-car garage equipped with an electric vehicle charging station, driveway parking for two additional vehicles, nearby guest parking, and convenient overflow parking for visitors. The result is a lock-and-leave lifestyle without compromise. Imagine starting your mornings with a walk through nearby parks, biking into Eastport for brunch on the waterfront, spending afternoons sailing on the Chesapeake Bay, browsing the boutiques and galleries of historic downtown Annapolis, and ending your evenings gathered around the fireplace before retreating to your private sanctuary. Offering four finished levels of beautifully designed living space in one of Annapolis' most convenient and sought-after locations, this is more than a home—it is a lifestyle. Why vacation in Annapolis when you can live here every day?
#MDAA2149462

ANNAPOLIS

103 NORMA ALLEY

4 Beds

3 Baths

2,500 Sq.Ft.

$699,000

MLS#: MDAA2149462

PRICE IMPROVEMENT! MOTIVATED SELLERS!! Experience refined living in this stunning second-floor corner residence, a brand-new 2024-built condominium offering 1,723 square feet of beautifully designed living space filled with natural light. Formerly the community’s model home, this exceptional residence showcases designer finishes, thoughtful upgrades, and meticulous attention to detail throughout. The well-designed floor plan features two spacious bedrooms, two full bathrooms, and a private study—offering the perfect balance of comfort, style, and functionality. The gourmet kitchen is a true centerpiece, featuring high-end appliances, premium cabinetry, and sophisticated finishes, ideal for both everyday living and entertaining. The residence has been professionally decorated and freshly painted, with brand-new designer lighting installed throughout, creating a cohesive and elevated aesthetic. Custom closet organizers add both style and practicality. What truly sets this home apart—and makes it one of the most valuable opportunities in the community—is the rare combination of THREE premium features that are nearly impossible to find together: a private storage unit, a reserved garage parking space, and an additional dedicated parking space with a pre-installed EV charger. These highly sought-after upgrades are extremely limited and represent an estimated value of $47,000+, offering both convenience and long-term investment appeal. Residents enjoy access to an impressive collection of resort-style amenities within this highly sought-after community, including pickleball courts, scenic walking trails, a golf simulator, a dedicated dog park, and expansive indoor and outdoor gathering spaces with grilling areas—perfect for entertaining, relaxing, and connecting with neighbors. Move-in ready and impeccably maintained, this luxury residence presents a rare opportunity to own a former model home with unmatched parking and storage advantages, while enjoying modern design, exceptional amenities, and a vibrant lifestyle in one of the area’s most desirable communities.
#MDAA2138456

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 211

2 Beds

2 Baths

1,723 Sq.Ft.

$698,999

MLS#: MDAA2138456

How many times have you strolled Annapolis' streets and thought, "I wish I lived here!"? 34 Pinkney is your opportunity to be in the center of the good life Annapolis has to offer! This renovated home is the perfect pied-à-terre. Some of the recent updates include New HVAC -2025, New Metal Roof-2020. Cozy living room flows to the dining with fun shiplap walls and built-in seating. The well-planned renovated kitchen has access to the private brick courtyard, just the right size for a lovely gathering. The second floor has two bedrooms, a full bath with a conveniently located washer and dryer. Bonus-Plantation shutters throughout this charming home! The perfect location to enjoy your new Annapolis Life! This one will not last!
#MDAA2145798

ANNAPOLIS

34 PINKNEY STREET

2 Beds

1 Baths

1,040 Sq.Ft.

$695,000

MLS#: MDAA2145798

Welcome to the highly sought-after “Davenport” corner unit in the prestigious GrandView community — perfectly positioned in one of the most desirable locations in the Annapolis Town Center. This exceptional residence is filled with natural light thanks to a stunning wall of windows, offering breathtaking sunset views each evening. Step outside to your private covered corner balcony and enjoy the outdoor. Inside, you’ll find a thoughtfully designed floor plan featuring: 2 bedrooms, 2 baths, den/home office, hardwood floors throughout (no carpet!), newer appliances, granite countertops, 10-foot coffered ceilings and custom window treatments. Storage cage and prime parking! Additional highlights include two assigned garage parking spaces and access to luxury amenities such as concierge services, a fully equipped fitness center, and a rooftop pool. Live just steps from everything the Annapolis Town Center has to offer — including Whole Foods Market, Target, banking, and some of Annapolis’ best restaurants and nightlife. You’re also just minutes from Historic Downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center, and have easy access to Route 50 and I-97 — making commuting a breeze. MUST SEE UNIT! All showings scheduled through ShowingTime.
#MDAA2139904

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 403

2 Beds

2 Baths

1,602 Sq.Ft.

$695,000

MLS#: MDAA2139904

Experience luxury living in this spacious, newly built corner residence overlooking a serene forest retention area. This beautifully designed home includes garage parking and is located in an amenity-rich 55+ community. Enjoy unbeatable convenience just minutes from downtown Annapolis, with easy access to waterfront dining, boutique shopping, Sandy Point State Park, and the iconic Chesapeake Bay Bridge. Inside, the home offers 1,723 square feet of thoughtfully designed living space, featuring: 2 bedrooms plus a versatile den, 2 full bathrooms, a private sitting room off the owner’s suite and interior garage parking with dedicated storage space. Open, light-filled layout ideal for both relaxing and entertaining. This is the perfect place to begin your next chapter in comfort, style, and convenience.
#MDAA2147896

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 301

2 Beds

2 Baths

1,723 Sq.Ft.

$689,900

MLS#: MDAA2147896

Beautifully maintained and filled with natural light, this inviting home offers an open floor plan with vaulted ceilings, hardwood floors, and comfortable living spaces designed for both relaxing and entertaining. The spacious primary suite features a private sitting area and en-suite bath, while the cozy fireplace and rear deck create the perfect setting for everyday living. A fenced backyard backing to trees provides added privacy and a peaceful outdoor retreat. Located in the sought-after water-privileged Bay Highlands community with beaches, marina, boat ramp, playgrounds, and easy access to Downtown Annapolis.
#MDAA2142452

ANNAPOLIS

1180 BAY HIGHLANDS DRIVE

3 Beds

2 Baths

1,758 Sq.Ft.

$685,000

MLS#: MDAA2142452

New on site 3 days ago
ESTATE SALE - Property being sold AS IS. Welcome to 1110 Tyler Avenue. Situated on approximately .51 acres, this loving-maintained Cape Cod shows off its old school charm with an attached garage, 3 bedrooms and 3 full baths. Ready for your updates, the main level offers an en suite primary bedroom, a second bedroom, full bath, and 2 separate living rooms. The lower level features a recreation room, dry bar with refrigerator, laundry room and full bath. The updated kitchen with stainless steel appliances, hardwood floors, light filled living room overlooking the expansive deck, impressive back yard, and updated roof are just a few of its special features. The wow factor is the long, wide driveway that leads to an oversized, detached, 2 car garage with a half bath, an upper-level flex space, and updated roof. Close to Eastport shopping and restaurants, Downtown, and everything Annapolis has to offer. Welcome home!
#MDAA2150162

ANNAPOLIS

1110 TYLER AVENUE

3 Beds

3 Baths

1,388 Sq.Ft.

$685,000

MLS#: MDAA2150162

Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an attached 2 car garage with additional storage, and interior access for everyday convenience. The entry level features an eat-in kitchen with white cabinets and counters, powder room and laundry room with a few steps up to the living room. The thoughtfully designed split-level layout creates a natural separation between the home’s functional spaces and its main entertaining areas, allowing gatherings to flow effortlessly while keeping day-to-day tasks discreetly tucked away. The dramatic living area where soaring ceilings, gas fireplace with custom built-ins, and walls of windows fill the space with natural light while framing the harbor views. Step outside to the expansive full-width waterside deck, the perfect setting for morning coffee, evening cocktails, or simply enjoying the marina activity and views stretching toward the Chesapeake Bay. Upstairs, the spacious primary suite offers a balcony, an ensuite bath with new cabinet and drawer fronts, and a peaceful retreat for relaxing after a long day. A loft-style flex space overlooks the living room below and can easily function as a second bedroom, home office, or additional lounge area, complemented by a full hall bath. Life in Chesapeake Harbour feels like a year-round vacation with an unmatched collection of resort-style amenities, including two waterfront pools, a private sandy beach, exclusive fitness center for a small enclave of residents, tennis and pickleball courts, fishing piers, walking and jogging paths, picnic areas with grills, scenic Chase Pond, and the security of a 24-hour attended gatehouse. The newly opened waterfront marina restaurant adds to the vibrant atmosphere with outdoor dining and live music on weekends. Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, waterfront dining, shopping, and historic attractions, this exceptional residence also offers easy access to Washington, DC, Baltimore, and Baltimore/Washington International Thurgood Marshall Airport. Whether you are searching for a full-time residence or a lock-and-leave waterfront retreat, this home offers the very best of the Annapolis waterfront lifestyle. Welcome Home!
#MDAA2145178

ANNAPOLIS

2002 DAKOTA PLACE 2A

2 Beds

2 Baths

1,915 Sq.Ft.

$650,000

MLS#: MDAA2145178

Hidden Cove has no Age Restrictions. Fully updated and move-in ready, this impressive 5-bedroom, 3.5-bath home offers a finished lower level complete with a bedroom and full bath—ideal for guests, extended living, or a private retreat. The 2022 renovated kitchen is the heart of the home, featuring quartz countertops, soft-close cabinetry, and premium Samsung appliances, seamlessly connecting to the main living and dining areas. All three full bathrooms have been tastefully updated within the past four years, including a spa-inspired primary suite showcasing a soaking tub, rainfall shower, heated towel rack, dual LED vanities, and a cozy electric fireplace heater. Major system upgrades provide peace of mind, including a new electrical panel (2022), Bosch dual-fuel HVAC system (2023), new luxury vinyl plank flooring (2023), all windows replaced, and water heater (2020). Smart home enhancements include a security system, sensors, and hardwired detectors. The finished lower level is designed for both function and entertaining, featuring a dry bar with full refrigerator and cleverly concealed storage. A dedicated home office with Restoration Hardware furnishings adds both style and productivity, while Elfa closet systems throughout maximize organization. Outdoor living is equally impressive with over $30,000 in hardscaping, including an engineered retaining wall, paver patio with gazebo, main-level deck, and a private wooded backdrop. Additional highlights include an upgraded garage with built-in cabinetry, utility sink, and EV wiring. Condo classification offers the benefit of reduced exterior maintenance and sometimes lower insurance costs. Located in the non-age restricted section of Heritage Harbour, residents still have the option to enjoy access to the community’s extensive amenities. Amenities include golf course membership, indoor and outdoor pools, tennis courts, fitness center, clubhouse, boat ramp, water access, and a wide range of social and recreational offerings with a voluntary membership to Heritage Harbour. This home delivers the perfect combination of space, upgrades, and lifestyle.
#MDAA2141470

ANNAPOLIS

2576 HIDDEN COVE ROAD 154

5 Beds

3 Baths

3,326 Sq.Ft.

$650,000

MLS#: MDAA2141470

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Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

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