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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

399

# of Listings

3

Avg # of Bedrooms

$449

Avg. $ / Sq.Ft.

$1,094,724

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

399 Properties Found. Page 3 of 27.

Welcome to 856 St Edmonds Place! Have it all with stunning views from nearly every room, deep water, privacy, and a spacious floorplan for multi generational living! Spectacular custom built waterfront home in the sought after Downs community of Annapolis! Breathtaking views await you from every corner of this updated and well conceived home. Dramatic details throughout highlight the open floorplan and entertaining is a dream! Gourmet Kitchen with high end appliances, light filled formal dining room, soaring ceilings and imposing stone fireplace highlight the gathering room, cozy waterside family room off the kitchen, amazing primary suite with floor to ceiling windows and luxurious bath and oversized closet, two additional bedrooms and a full bath complete the upper level, bright and airy lower level with family room, theater, two additional bedrooms with en suite baths and plenty of storage, enjoy the flexibility of an enormous maintenance free deck and a stunning screened porch, attached two car garage and additional detached one car garage with amazing 1 BR/1Bath updated in law suite/caretaker space, whole house generator, new tram and steps for convenient access to your pier with covered slip, two new boat lifts and jet ski lift nestled perfectly on Brewer Creek with quick access to the Severn River and the Chesapeake Bay! Located close to the community pool and sports courts with an an easy commute to Washington DC, BWI and Baltimore!

ANNAPOLIS

856 ST EDMONDS PLACE

5 Beds

4 Baths

6,412 Sq.Ft.

$3,100,000

MLS#: MDAA2105068

Vacation at Home!
Welcome to 22 East Lake, located in the sought-after waterfront community of Bay Ridge. This 3 bedroom 3.1 bath exceptional home blends refined sophistication with relaxed coastal living, offering the perfect space to both work and play.
Enjoy resort-style amenities right at home with a sparkling waterside pool and spa that set the tone for the ultimate staycation. The incredible chef’s kitchen is fully outfitted with top-of-the-line appliances and thoughtful design, ideal for the culinary enthusiast.
Beautifully renovated throughout, the home features a stunning primary suite, walls of glass in the living room that invite the outdoors in, and a spa-inspired primary bath with a custom wet room, oversized
If you’re looking for a home that feels luxurious, elevated, and just a little bit daring, this one’s for you. And if that's not enough the beautiful apartment with kitchenette and full bath over the fully climate-controlled garage is perfect for teens, in-laws, and overflow guests.

ANNAPOLIS

22 EAST LAKE DRIVE

3 Beds

3 Baths

3,320 Sq.Ft.

$2,975,000

MLS#: MDAA2116350

Exceptionally built custom waterfront home with spectacular panoramic views of Spa Creek. Enjoy the perfect vantage point for watching the Blue Angels performance, the 4th of July fireworks and all the activity up and down the creek. Attention to detail and high-end finishes are the hallmark of this wonderful home with 12 ft ceilings on the main level. Over 5,000 sqft of living space on 3 finished levels, 5 spacious bedrooms and 4 baths. The stunning Primary suite has a private balcony with panoramic views up and down Spa Creek and the luxurious spa-like bath is stunning in its simplistic design. An open floor plan throughout the home encourages indoor/outdoor living and draws you outside to relax on the spacious Ipe deck with modern stainless steel cable railing and elevated views of the water or encourage the party to spill out onto the custom stone patio below and the lush backyard that leads out to the private pier with 40,000lb boat lift, additional lift and kayak dock that will be sure to please any boating enthusiast. A quick 5 minute drive to downtown Annapolis and Eastport and 2 minutes to the Truxon Park pickleball courts or grab a water taxi directly from your dock and head down Spa Creek right into Annapolis for a night out on the town or venture off to some of the Bay's best cruising and fishing areas. Annapolis offers the perfect balance of small-town charm and big world sophistication. Welcome Home!

ANNAPOLIS

145 SPA DRIVE

5 Beds

4 Baths

5,201 Sq.Ft.

$2,950,000

MLS#: MDAA2108534

Welcome to 139 Spa Drive – A Stunning Waterfront Craftsman Home on Spa Creek!

Experience the best of coastal-inspired living at this beautifully designed, single-family home located directly on Spa Creek. This exquisite residence offers three fully finished levels, each with expansive walls of windows that flood the home with natural light and showcase breathtaking water views.

The open-concept layout is ideal for both entertaining and everyday living. A gourmet kitchen sits at the heart of the home, complete with custom shaker cabinetry, quartz countertops, a stylish tile backsplash, premium Bosch appliances, and an oversized center island that offers ample seating and storage. The adjacent Great Room features a cozy gas fireplace and opens to a large waterside deck—perfect for enjoying the serene surroundings year-round.

Upstairs, the luxurious primary suite offers a tranquil escape with its own private balcony overlooking Spa Creek, a second gas fireplace, and a spa-like bathroom featuring a double vanity, freestanding soaking tub, frameless glass walk-in shower, and a linen closet. The expansive, under-finished walk-in closet is a blank canvas offering endless potential to perfectly reflect your personal style and become a dream space. Two additional generously sized bedrooms each have their own beautifully appointed en suite bathrooms, and a convenient second-floor laundry room adds everyday ease.

The lower level offers approximately 1,300 square feet of finished living space, including a bright and spacious walk-out family room plumbed for a future wet bar, a full bath, an egress fourth bedroom, and two storage areas. The recreation space opens to a stone patio and professionally landscaped yard—ideal for hosting or relaxing in style.

Built with lasting quality and exceptional craftsmanship, this home features 2x6 framing, Hardie Plank siding with stone accents, Anderson high-efficiency windows, and a durable standing seam metal roof. Inside, you’ll find 9-foot ceilings throughout, solid wood interior doors, engineered hardwood floors, and detailed architectural millwork. Outdoor features include a bluestone front porch and rear patio, a paver driveway, and professionally designed landscaping. The home is equipped with three heating and cooling zones, a propane tank servicing both fireplaces and the kitchen range, and a full-house sprinkler system with recessed heads.

Whether you’re an avid boater or simply cherish the tranquility of waterfront living, this home delivers a rare combination of elegance, comfort, and direct water access. Enjoy your private, fully outfitted 90-foot slip with a 16-foot width, 54-foot finger pier, and 220-foot platform, and a mean low water depth of 4.5 feet—making this an unparalleled waterfront offering.

ANNAPOLIS

139 SPA DRIVE

4 Beds

4 Baths

4,628 Sq.Ft.

$2,900,000

MLS#: MDAA2115180

Coastal Charm with Iconic Views | 90 River Drive, Bay Ridge!
Experience timeless waterfront living at 90 River Drive in the heart of Bay Ridge, Annapolis. This beautifully appointed 3–4 bedroom, 4-bath home features a detached guest house, ideal for guests, a home office, or a studio space. Enjoy breathtaking views of the Bay Bridge and direct access to one of the area’s most spectacular private beaches. Nestled in a vibrant coastal community known for its sailing, beach walks, and friendly charm, this property offers a rare blend of lifestyle, location, and flexibility.
The highly sought-after Bay Ridge community in Annapolis offers a rare blend of resort-style amenities and vibrant coastal charm. Residents enjoy a scenic community pool and clubhouse overlooking the sparkling waters of the Chesapeake Bay, as well as private community beaches on both the Bay and the River. Boating enthusiasts will appreciate the community marina, complete with a newly renovated clubhouse.

For those who prefer land-based recreation, Bay Ridge features basketball courts, ball fields, pickleball courts, playgrounds, and open green spaces, along with a year-round calendar of community events. Whether you’re walking or biking along miles of waterfront paths, the Bay Ridge lifestyle is truly one-of-a-kind.

Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the perfect balance of small-town charm and big-city access. Commuting is easy with nearby access to Routes 50 and 97, connecting you directly to Baltimore, BWI Airport, Fort Meade/NSA, and Washington, DC. And when it’s time for a getaway, the Eastern Shore and ocean beaches are just a short drive across the Bay Bridge.

ANNAPOLIS

90 RIVER DRIVE

3 Beds

4 Baths

1,830 Sq.Ft.

$2,750,000

MLS#: MDAA2116342

BAY RIDGE WATERFRONT! Great opportunity for a wonderful home with stunning water views of Lake Ogleton in the coveted Bay Ridge community! This 4 bedroom, 4 bath home features vaulted ceilings, screened porch, gourmet Kitchen, spacious bedrooms and private Primary Suite all with beautiful views overlooking Lake Ogleton. The light and bright main level living space is filled with natural light and features an open floor plan joining the kitchen, dining and living space all flowing effortlessly to the expansive waterside screened porch. Spend every night watching the sunset over Lake Ogleton! The 3 bedrooms, 3 baths plus office space on this level provides plenty of room for accommodating family and guests. The spacious Primary bedroom is located on the 3rd floor for added privacy and extraordinary views from the private balcony. The entry level boasts a full bath and the perfect entertaining space with a wet bar, cozy pellet stove, spacious deck, and direct access to the sprawling backyard that flows to the water's edge and to the private deep water dock with 6ft MLW. Enjoy fishing, swimming, kayaking and heading out on the water directly from the fully equipped pier with multiple lifts and slips; perfect for the boating enthusiast! Celebrate the waterfront lifestyle and feel like you are on vacation every day! The sought-after Bay Ridge Community features a community pool with a clubhouse that overlooks the beautiful waters of the Bay, community beaches on both the River and the Bay and a community Marina with a newly renovated clubhouse. Off-the-water activities include enjoying the basketball court, playground, ball fields, common areas and year-round community activities. Walk or ride your bike for miles along the water and enjoy all the benefits of the Bay Ridge lifestyle, there is no other place like it! Located just minutes from downtown Annapolis and Eastport which offer the perfect balance of small-town charm and big world sophistication. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

68 E LAKE DRIVE

4 Beds

4 Baths

3,010 Sq.Ft.

$2,699,000

MLS#: MDAA2102404

Nestled on Chase Pond along the serene shores of the Chesapeake Bay, 2680 Claibourne Court offers an unparalleled waterfront living experience. This meticulously renovated coastal contemporary-style residence boasts 5 bedrooms, 4 full bathrooms, and seamlessly blends luxury with comfort. Set on a generous 2.62-acre waterfront lot, the property features a private pier with boat lifts and a beach, providing direct access to the bay's tranquil waters. The open-concept sun-bathed main level offers a living room featuring a stone fireplace with gas insert, gourmet chefs eat-in kitchen, dining room, sitting room, a generous bedroom with walk-in closet, a full bath, and rear deck the full length of the first floor. Stunning stairs open from the lower level to the crow’s nest adds a wonderful architectural feature. The second level offers a primary suite with private balcony, beautiful bathroom featuring separate vanities, shower, soaking tub, and ample storage. 3 additional bedrooms, 1 full bath, and a large laundry room complete the second level. The 3rd level offers two additional rooms currently used as office and exercise room. The crow’s nest offers 360 degree striking views. The expansive lower level offers a recreation room, wet bar, full bathroom, mud/gardeners’ room, large 2-car garage, and abundance of storage. A flag-stone patio off the rear is great for entertaining. Outdoor amenities include a private pier with boat lifts, a beach area, and lush, landscaped grounds—perfect for boating enthusiasts and nature lovers. The home also features a whole-house sound system and is elevator-ready for future convenience. Located in the highly desirable Annapolis Roads community, this peaceful retreat is just minutes from downtown Annapolis, offering convenient access to shops, restaurants, and cultural attractions—all in a stunning bayfront setting.

ANNAPOLIS

2680 CLAIBOURNE COURT

5 Beds

4 Baths

3,415 Sq.Ft.

$2,695,000

MLS#: MDAA2111674

Exquisite Savannah Style custom-built home in sought after, amenities-rich, Fishing Creek Farm community in Annapolis. This non-riparian waterfront home is nestled between 2 bodies of water providing endless water views from almost every room of the house. Wake up early to watch the wildlife and the sunrise over Cherry Tree Cove from the rear screened porch or enjoy peaceful water views and sunsets over Duvall Creek from the relaxing front porch. Upon entering the home the generous Foyer opens onto the formal Living Room with fireplace and custom built-ins and the spacious Dining Room which flows into the beautiful Gourmet Kitchen filled with high-end appliances and charm. The adjacent spacious Family Room and expansive 3 seasons porch overlooking the lush backyard and sparkling water of Cherry Tree Cove are perfect for entertaining. With 5 bedrooms and 5.5 baths including a private and conveniently located guest suite above the garage, there is plenty of space for a large family and the many guests that are sure to come visit in this stunning setting. The fully finished basement boasts an additional living space, game room, play area, full bath and wet bar. The free-standing Office/Studio area provides endless possibilities. The sought after community of Fishing Creek Farm offers a community pool, tennis courts, marina, beach and much more, all just a quick stroll from this amazing property. Located just minutes from downtown Annapolis and Eastport which offer the perfect balance of small-town charm and big world sophistication. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

1241 CHERRY TREE LANE

5 Beds

5 Baths

6,428 Sq.Ft.

$2,675,000

MLS#: MDAA2115392

Stunning Waterfront New Construction 0n Back Creek in the Eastport area. Don't miss this rare opportunity to build your dream home in one of Annapolis’s most sought-after waterfront communities. Ideally located on a quiet, picturesque corner lot in Eastport, this beautifully designed custom home will offer expansive views of Back Creek and luxury finishes throughout. Enjoy wide plank floors, dramatic walls of glass to showcase the water views, custom built-in kitchen cabinetry, and a chef’s kitchen featuring high end appliances, quartz countertops, oversized island, and a full-height backsplash. Every detail has been thoughtfully selected to blend style, comfort, and function for modern coastal living. This home is conveniently located just close to the heart of Eastport—renowned for its strong sense of community, marinas, walkability, and vibrant dining scene. Enjoy morning strolls to your favorite coffee shop or evenings out at nearby waterfront restaurants. Located in the Parkwood Civic Association (PCA), a voluntary neighborhood group with $100 annual dues that support maintenance of local green spaces—including Hoffman Park and the community docks. PCA membership is also required to apply for a dock slip. Contact the listing agent today or check out Whitehall Building & Co's website to schedule a tour of the model home and start customizing your waterfront residence. With construction soon underway, you could be enjoying life on the water by next boating season.

ANNAPOLIS

703 A GLENDON AVENUE

4 Beds

4 Baths

4,000 Sq.Ft.

$2,650,000

MLS#: MDAA2119986

CASUAL ELEGANCE BEST DESCRIBES THIS COASTAL STYLE HOME IN THE SOUGHT AFTER COMMUNITY OF FISHING CREEK FARM. THIS HOME IS AN ENTERTAINERS DREAM! THIS 5 BEDROOM, 5 BATH HOME HAS IT ALL! EXQUISITE DETAILS THROUGHOUT, RESORT STYLE HEATED POOL WITH WATERFALLS, OUTDOOR SHOWER, OUTDOOR FIREPLACE THAT LEADS TO A GREAT ENTERTAINING AREA UNDER THE DECK OFF THE POOL WITH WET BARS, HIGH TOPS, OUT DOOR TV'S, OUTDOOR KITCHEN/GRILL AND HEATERS BUILT INTO THE CEILING. THIS SUN-DRENCHED HOME HAS CUSTOM MOLDINGS, WALLS OF WINDOWS, FRENCH DOORS AND A FABULOUS SCREENED PORCH THAT LEADS TO A GREAT ENTERTAINING DECK WITH SOME WATERVIEWS AND GREAT SUNSETS. THE MAIN LEVEL IS BEAUTIFUL W/GORMET KITCHEN, HOME OFFICE AND 6TH BEDROOM IF NEEDED. THE PRIMARY BEDROOM IS GORGEOUS WITH A NEW PRIMARY BATH WITH WATERVIEWS FROM THE TUB! THERE IS A GREAT ROOM WITH BUILT IN BUNKS THAT MAKE YOU FEEL LIKE YOU ARE IN NANTUCKET WHERE KIDS CAN HANGOUT, WATCH MOVIES AND HAVE AMAZING SLEEP OVERS! THE LOWER LEVEL IS A GAMEROOM PARADISE WITH A POOL TABLE, DARTS, VIDEO GAMES, FAMILY ROOM WITH ANOTHER BEDROOM AND FULL BATH THAT WOULD BE A GREAT IN-LAW OR AU PAIR SUITE WITH FULL KITCHENETTE. THIS LOWER LEVEL WALKOUT LEVEL LEADS THE THE PATIO OFF THE POOL. THIS IS ONE OF MY FAVORITE HOUSE IN ANNAPOLIS! HOP YOUR GOLF CAR TO DRIVE AROUND THE CORNER TO THE COMMUNITY MARINA, POOL, TENNIS/PICKLEBALL, BEACH. BOAT MOORING CONVEYS AND POSSIBLE JET SKI LIFT. THEO THOMPSON WAS THE AMAZING DESIGNER FOR THIS HOME. OWNERS WILL CONSIDER SELLING FURNISHED. MORE PHOTO'S TO COME! THIS IS ONE OF MY TOP 5 HOUSES i HAVE SOLD-IT IS JUST HAPPY FUN & ENTERTAINING-IT'S SPECIAL!

ANNAPOLIS

3412 HIDDEN RIVER VIEW ROAD

5 Beds

5 Baths

5,671 Sq.Ft.

$2,650,000

MLS#: MDAA2115360

Nestled by the waterfront in a prime lush setting, this property offers a luxurious blend of functional design and artisanal craftsmanship. Enjoy the best of Annapolis waterfront living in this custom home with a private dock and views that inspire. With approximately 2,000 sq. ft. of Timbertek decking, relax either on one of the many main floor outdoor areas or on the master bedroom's private balcony. Inside, the radiant Australian Cypress wood floors set the stage, complementing the soaring ceilings and and welcoming layout; perfect for entertaining. In addition, there are 2 bedrooms, both with ensuite bathrooms (could serve as alternative primary bedroom), and an office on the main level. The kitchen boasts Corian counters, top-tier appliances, and British hand-crafted decorative tiles. Hand-painted touches by renowned Annapolis artist, Cindy Fletcher Holden, grace the kitchen and living spaces. Upstairs you will find the primary suite and another guest bedroom and bath. Add in modern conveniences like a powerful whole-house generator, and tech-ready provisions, and this residence is both a haven of luxury and a masterpiece of design. The mean low water is over 6 feet at the private dock. Incredible views up Lake Ogleton which leads out to the Severn River and Chesapeake Bay respectively. Convenient location to commuting routes, shops and downtown Annapolis. Embrace this harmonious blend of comfort, artistry, and coastal living.

Adjacent lot that is an approx 0.47 acre waterfront parcel with public sewer can be purchased separately for $400,000 or can be combined with 1011 Dulaney for $2,950.000. Engineering has not been done but the lot could be a fabulous accessory dwelling unit (ADU) for this property or an opportunity to maintain the privacy you already have. More details available upon request.

ANNAPOLIS

1011 DULANEY LANE

4 Beds

4 Baths

3,470 Sq.Ft.

$2,600,000

MLS#: MDAA2080722

#MDAA2103110

ANNAPOLIS

2175 CHESAPEAKE HARBOUR DRIVE

4 Beds

4 Baths

2,513 Sq.Ft.

$2,595,000

MLS#: MDAA2103110

This stunning contemporary three-level home on Mill Creek has been completely renovated from top to bottom, seamlessly blending modern design with breathtaking waterfront views. With 375 feet of shoreline, a private deep water pier (7 ft MLW) with boat lift and a sandy beach, this home offers an unparalleled waterfront lifestyle. The meticulous remodel includes but is not limited to new windows, stunning new flooring, upgraded utility systems and updated kitchen and bathrooms, all of which enhanced both form and function throughout the home. The striking exterior features sleek metal-clad siding, accent metal roofing, and expansive windows that flood the interior with natural light while framing panoramic water views. The main level welcomes you with soaring ceilings in the elegant living room, where a dramatic curved wall of windows and a wood-burning fireplace create a warm yet sophisticated ambiance. The open floor plan flows seamlessly from the dining area into the gourmet kitchen, featuring a peninsula and island—both with seating—alongside a casual dining space perfect for everyday meals. A main-level bedroom with windows overlooking the water and a full bath complete this level. Upstairs is dedicated to the primary suite which offers a true retreat with a spa-like ensuite bath, a private rooftop deck, and an open loft-style space ideal for a home office or sitting area. The lower level is designed for relaxation and versatility, with two additional water-view bedrooms, a full bath, and a spacious family room with a wood-burning fireplace and direct access to the backyard and waterfront. A laundry room, tons of storage and a convenient kitchenette make this level perfect for guests or extended stays. Head down to the water’s edge and set out for a day on the water, perfectly located to take advantage of the Chesapeake Bay's best cruising and fishing areas. Attractive destinations such as the Annapolis Harbor, Baltimore's Inner Harbor, St. Michaels, Oxford, and Solomon's Island are only a short cruise away and just minutes from accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

378 FOREST BEACH ROAD

4 Beds

3 Baths

4,122 Sq.Ft.

$2,495,000

MLS#: MDAA2107066

Incredible opportunity to own this once in a lifetime property in the heart of Downtown Annapolis! Wonderful and extensive updates including a new grease trap, new grease lines, new sanitary lines, new counter tops, freshly renovated bathrooms and more! The listing is for the building only but the seller is willing to consider all offers!

ANNAPOLIS

81 MAIN STREET

None Beds

None Baths

N/A

$2,450,000

MLS#: MDAA2105176

Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. See potential plans in the pictures and meet the builder to discuss your dream home or bring your own builder. Don't miss your chance to own the last remaining waterfront lot in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle.

ANNAPOLIS

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$2,390,000

MLS#: MDAA2113706

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