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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
316
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,071,137
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

71 Properties Found. Page 4 of 5.

Coming Soon! Get ready to fall in love with this Annapolis gem Nestled in the sought-after Captain Cove neighborhood on a 1.21-acre wooded lot, this beautifully maintained home is minutes from downtown Annapolis. Unique features include a rooftop deck, expansive back decking, and a bonus treehouse that doubles as a fun space for children or a peaceful retreat for adults—perfect as a she shed or man cave. This is a cozy place to call home, look no further . Don’t miss your chance to own a piece of Annapolis charm. Photos and more details coming soon—stay tuned!
#MDAA2115552

ANNAPOLIS

15 E NAP LANE

5 Beds

3 Baths

6,525 Sq.Ft.

$1,300,700

MLS#: MDAA2115552

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15 right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!!
#MDAA2126556

ANNAPOLIS

1836 CHERRY ROAD

None Beds

None Baths

3.92 acres

$1,300,000

MLS#: MDAA2126556

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!!
#MDAA2126554

ANNAPOLIS

1814 PLEASANT PLAINS ROAD

5 Beds

2 Baths

1,919 Sq.Ft.

$1,300,000

MLS#: MDAA2126554

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek water frontage and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!
#MDAA2124862

ANNAPOLIS

1814 & 1836 PLEASANT PLAINS & CHERRY ROAD

5 Beds

2 Baths

1,919 Sq.Ft.

$1,300,000

MLS#: MDAA2124862

Incredible Opportunity in Bay Ridge! This property sits on an expansive 150-foot-wide lot and has already been remodeled, making it comfortable to live in right away. Move in temporarily while you design your dream home, or work within the existing footprint to create a residence that perfectly suits your lifestyle. Alternatively, take advantage of the generous lot size and premier location to build a brand-new custom home. With tranquil lake views and glimpses of the Chesapeake Bay, the setting is truly special. Bay Ridge is one of Annapolis’s most coveted waterfront neighborhoods, offering unmatched amenities and a strong sense of community. Residents enjoy a private bay front pool and clubhouse, marina, beaches, playgrounds, and endless opportunities for boating, kayaking, and paddle boarding—all just minutes from downtown Annapolis. Known for its welcoming neighborhood spirit and resort-like feel, Bay Ridge offers a lifestyle that is second to none. Whether you envision a light renovation, a full rebuild, or simply enjoying it as-is, this property offers a rare opportunity to make your mark in one of Annapolis’s premier waterfront communities. (Also listed as a house/lot package in residential listings.)
#MDAA2124850

ANNAPOLIS

45 E LAKE DRIVE

None Beds

None Baths

0.45 acres

$1,299,900

MLS#: MDAA2124850

Amazing NEW CONSTRUCTION is now complete! Experience luxury living in this beautifully crafted new home, located in the amenity-rich waterfront community of Arundel on the Bay. Enjoy some partial water views and exceptional design throughout. This quality-built residence features wide-plank hardwood floors, gorgeous, detailed trim work throughout and a thoughtfully designed open-concept layout. The gourmet kitchen boasts contemporary quartz countertops, GE Café appliances including a gas range, microwave drawer, stainless farm sink, center island,and stylish brushed bronze fixtures and lighting! A dedicated office on the main level provides the perfect work-from-home space or 4th bedroom area! The spacious owner's suite offers vaulted ceilings, a custom walk-in closet, and a spa-inspired bath. An additional ensuite bedroom provides comfort and privacy for guests or family. Main garage level has the opportunity for ANOTHER full bath (has rough in) and either another bedroom or large recreational room! Gorgeous TimberTech Decking w/contemporary rails runs entire length of home! Fall in love with everything it has to offer! Be sure to see the pier and playground area a few blocks down the road! Custom builder C.A.Desimone
#MDAA2117330

ANNAPOLIS

3506 ROCKWAY AVENUE

4 Beds

3 Baths

3,576 Sq.Ft.

$1,299,000

MLS#: MDAA2117330

PRICE REDUCED! Move-in ready new construction from acclaimed local builder, Sturbridge Homes. This spectacular home offers over 5,000 square feet of finished space in the heart of Annapolis's Homewood neighborhood, close to all of the entertainment and enjoyment available in our historic town. Located near the new Annapolis Public Library, Maryland Hall, Annapolis Town Center, and the Naval Academy Stadium, this home is situated for you to enjoy the best of in-town life, yet relax in a tree-lined neighborhood environment. This home is excellently upgraded with 9-foot ceilings on all three levels, quartz countertops, ceramic tile, stainless appliances, and hardwood flooring throughout the 1st floor, owner’s suite, and stair/hallways. The primary suite is a luxurious oasis with plenty of space to enjoy, a huge customizable walk-in closet, and a spectacular multi-head walk-in shower. The lower level features a separate entrance, a bedroom and a full bathroom, and a large wet bar with a beverage refrigerator, making it perfect for entertaining guests, caregiving, or multi-generational living. The builder has included many thoughtful touches, like decorative moulding, wood closet and pantry shelving, and a mudroom bench and organizer. The front porch is a perfect spot to savor your morning coffee, and the backyard offers endless possibilities. The home comes with a $15,000 closing cost credit (conditions apply), a $10,000 credit toward closet customization, a package of smart home features, and a 10-year limited warranty. Enjoy the low-maintenance lifestyle of a new construction home for many years to come!
#MDAA2117898

ANNAPOLIS

9 RUSTY RED DR

5 Beds

4 Baths

5,464 Sq.Ft.

$1,299,000

MLS#: MDAA2117898

Opportunities like this don't come along often - this is the only residence of its kind in Shearwater, and it offers a lifestyle unmatched in Annapolis. This 2400 + - spacious 4 - bedroom, 4.5 bath waterfront residence is thoughtfully designed all on one level - no steps, just effortless luxury. Inside, you'll find two inviting fireplaces, multiple living and entertaining areas, and walls of glass that open to the water. Step outside with sweeping views of Spa Creek where every sunset becomes your backdrop. For boaters, this home includes a deeded 35- foot slip, just steps from your door. Whether its a quiet paddle, a sail on the Bay, or a sunset cruise, your waterfront adventure begins right here. Shearwater is one of Annapolis's most coveted gated communities, known for its privacy, amenities, and easy access to downtown. Here, you can enjoy the best of both worlds- resort-style living in a secure enclave, while being minutes away from restaurants, shops, and the charm of Historic Annapolis. This condo is two combined with 2 tax numbers 8B1 and 8 A1, Concrete slab and steel construction. Condo fee includes water & sewer, parking, trash, and snow removal. Enjoy an abundance of nature, blue herons, osprey, and other water fowl. The Shearwater community offers a private, waterfront pool with grill area, pickleball, tennis, racketball, kayak and dinghy rack/storage, a deep water marina and oyster shell walking paths - all within a Gated community. Enjoy a nice walk, bike ride or the water taxi will pick you up at the marina dock and take you downtown. All the fun activities in Eastport are right at your back yard. The Eastport Yacht Club parade of lights boat parade in December makes it final turn right in front of the Shearwater community. Rare opportunity to combine single level living, waterfront access, and the timeless Annapolis Lifestyle.
#MDAA2126908

ANNAPOLIS

8 SPA CREEK LANDING B1/ A1

4 Beds

4 Baths

2,400 Sq.Ft.

$1,295,000

MLS#: MDAA2126908

Enchanting Craftsman-Style Waterfront Retreat in Epping Forest Tucked away in the prestigious gated community of Epping Forest, this beautifully renovated Craftsman-style home offers a rare opportunity to enjoy serene waterfront living with a private deep-water pier on Clements Creek, just off the Severn River. Complete with a 12,000 lb boat lift and a private sandy beach, it’s a dream for boating enthusiasts and nature lovers alike. From this peaceful sanctuary, you’ll have direct access to all of Annapolis’s waterways—and beyond. Expertly positioned on a perfectly elevated 0.39-acre lot, this elegant 4-bedroom, 4-bath residence offers over 3,000 square feet of refined living space spread across three thoughtfully designed levels. Embraced by tranquil wooded surroundings, the home reveals seasonal vistas—lush, leafy treetops in summer, transitioning to sweeping water views in winter, with captivating glimpses throughout the year. A graceful stone stairway with sleek cable railing ascends to the front entrance, framed by lush landscaping and the soothing sounds of nature. This harmonious blend of architecture and setting creates a serene, private retreat—yet it remains just moments from the conveniences of modern living. Inside, the open floor plan and abundant natural light highlight the home’s craftsmanship and thoughtful design. The kitchen, dining area, and living room with fireplace seamlessly connect to a screened-in porch and a spacious deck—ideal for al fresco dining and enjoying the tranquil surroundings. The main level includes a bedroom and full bath, perfect for one-level living. Upstairs, a spacious landing with soaring ceilings leads to two ensuite bedrooms, including the luxurious primary suite with a private balcony, treetop vistas, and a spa-like bath featuring dual vanities and a walk-in tiled shower. The versatile lower level offers a cozy family room with fireplace, an additional bedroom and full bath, a home office or bonus room, generous storage, and a private patio—perfect for guests or multi-generational living. Residents of Epping Forest enjoy an unparalleled lifestyle with access to a waterfront clubhouse and bar, deep-water marina, sandy beach, boat ramp, tennis courts, hiking trails, and a full calendar of community events including fireworks, oyster roasts, holiday festivals, and summer camps. Active social groups like the boat club, volleyball leagues, swim team, and garden club offer something for everyone. Annapolis, known as the "Sailing Capital of America," boasts one of the longest and most vibrant boating seasons on the East Coast—extending well into the fall, when the waterways are framed by dynamic foliage and crisp, golden light. Conveniently located just minutes from Downtown Annapolis, the Bay Bridge, and major routes to Washington, D.C., this home is the perfect blend of relaxation, recreation, and accessibility.
#MDAA2121406

ANNAPOLIS

357 OVERLOOK TRAIL

4 Beds

4 Baths

3,070 Sq.Ft.

$1,250,000

MLS#: MDAA2121406

*****Brand new Culligan Water Softener system Installed***** Exquisite 7,633 Sq. Ft. Stone Front Estate on Over an Acre with Water Access & Resort-Style Amenities Wake up to the peaceful sounds of nature and end your day with breathtaking sunsets from your private balcony in this beautifully renovated 7,633 sq. ft., 6-bedroom, 5.5-bath stone front estate. Set on over an acre in the coveted Saefern neighborhood, this home perfectly blends elegance, comfort, and a one-of-a-kind waterfront lifestyle. The grand foyer greets you with a sparkling chandelier and exquisite tile flooring, flowing into a gourmet kitchen with natural wood cabinetry, stainless steel appliances, a spacious island, and a cozy breakfast area with matching countertops. The open-concept family room invites connection and entertainment, while formal living and dining rooms showcase rich hardwood floors. Upstairs, cathedral ceilings crown the bedrooms, three with private en suites, including the primary suite with a spa-like bath and balcony views of the sunrise and sunset. A conveniently located upstairs laundry room makes everyday living effortless. Refinished hardwoods span the entire upper level. The expansive finished basement offers a wet/dry bar and a versatile bonus room—ideal for a home theater, gym, or even a bowling alley. Outdoor living is just as impressive, with a large deck overlooking a picturesque backyard. The oversized 3-car garage and extended driveway provide parking for up to 11 vehicles. Enjoy exclusive Saefern Saddle & Yacht Club amenities, including marina access with deep and shallow water slips, walking trails, horse stable, dog park, fishing pond, outdoor pool, and tennis and pickleball courts. Brand new roof and all electrical, plumbing, and HVAC work were fully permitted, with final inspections successfully passed for peace of mind. Surrounded by the serenity of nature yet minutes from the Severn River, downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center, and Routes 50 & 97, this home offers the perfect balance of tranquility and convenience.
#MDAA2128028

ANNAPOLIS

522 EPPING FOREST ROAD

6 Beds

5 Baths

7,633 Sq.Ft.

$1,225,000

MLS#: MDAA2128028

None
#MDAA2128006

ANNAPOLIS

32 EAST STREET

3 Beds

2 Baths

2,940 Sq.Ft.

$1,200,000

MLS#: MDAA2128006

Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive water access community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including gardening, relaxing on the rooftop deck, or sitting under the ceiling fans on the large front porch. Each of the five spacious bedrooms offers comfort and style, while four full bathrooms feature premium tile work, modern vanities, and spa-like amenities. All the while, enjoying the water access community amenities that offer boating, fishing, and waterfront recreation just moments from your doorstep. Easy access to local restaurants, shopping, and major roadways.
#MDAA2121748

ANNAPOLIS

767 BON HAVEN DRIVE

5 Beds

4 Baths

3,505 Sq.Ft.

$1,199,999

MLS#: MDAA2121748

Beautifully Appointed Eastport Home. Conveniently located in the heart of Eastport, Annapolis, this newer home offers the perfect blend of style, comfort, and walkability. Set on a premium corner lot, the property features a desirable detached garage and wonderful curb appeal. The main level showcases an open floor plan anchored by a gourmet kitchen with granite countertops, stainless steel appliances, and custom cabinetry with crown molding. A private office provides the perfect space for working from home, while the formal dining room is ideal for hosting dinners. The sitting room across from the office offers an inviting retreat—perfect for curling up with your favorite book or simply unwinding in comfort. A spacious family room with a gas fireplace is the perfect gathering space, complemented by a full bathroom for added convenience. Gleaming wood floors run throughout, tying the spaces together with warmth and elegance, while a wet bar and expansive deck extend the home’s entertaining potential outdoors. Upstairs, the luxurious primary suite boasts a sitting area and spa-like bath, offering a private retreat at the end of the day. Two additional ample-sized bedrooms and another full bathroom provide comfort and flexibility for family or guests, while the conveniently located upper-level laundry makes everyday living a breeze. An unfinished basement with rough in could be finished with a recreation room, bedroom and a full bathroom. Endless possibilities. With easy access to Eastport’s vibrant restaurants and just a short walk to downtown Annapolis, this home is a must-see for those seeking both convenience and elegance.
#MDAA2127072

ANNAPOLIS

412 JEFFERSON STREET

3 Beds

3 Baths

4,006 Sq.Ft.

$1,199,900

MLS#: MDAA2127072

Welcome to this waterfront ranch home in the highly sought-after community of Bon Haven, situated on over an acre of serene land along the beautiful South River. This renovated gem, complete with a new private pier and boat access, offers an idyllic lifestyle for water enthusiasts and nature lovers alike. This property is back on the market due to financing falling through for the buyer! As you arrive, you'll be greeted by an expansive front yard and a spacious driveway leading to the front porch. Step inside to discover the warmth of beautifully renewed hardwood floors that flow seamlessly throughout the main living areas. The living room features a charming wood-burning fireplace with a custom marble mantle, creating a cozy focal point as well as a large picture windows offering lots of natural light! From here, enter the oversized family room, complete with another wood-burning fireplace, custom wood mantle, and direct access to the backyard, water views, and pier. This space also connects to the attached two-car garage. The renovated eat-in kitchen boasts custom cabinetry, granite countertops, and new LVP flooring. Natural light filters through the newly installed Roman shades, adding a touch of elegance to this functional space. Down the hallway, you'll find the private primary suite with an en-suite bathroom and a walk-in closet. Two additional generously sized bedrooms and a large hall bathroom provide ample space for family or guests. The lower level offers a substantial unfinished basement, laundry room, separate room for home gym or office and lots of storage space - all ready for customization to suit your recreational needs. Recent updates include: *Remodeled kitchen *New HVAC system *Water heater and water softening system *Privacy fencing *Fresh paint and updated flooring *Newly built private pier *The property also includes a charming chalet/boat house and a tram, both sold in "as-is" condition. Enjoy endless water activities on the South River, including power boating, canoeing, kayaking, personal watercraft, sailing, waterskiing, swimming, and fishing. All that's left to do is move in and embrace the beauty of waterfront living. Don’t miss your chance to tour this incredible property and experience the charm of all four seasons on the South River!
#MDAA2101278

ANNAPOLIS

2762 BON HAVEN LANE

3 Beds

2 Baths

3,134 Sq.Ft.

$1,199,000

MLS#: MDAA2101278

Walk in and be amazed with a beautiful and luxurious remodeled open floor concept. Open the front door and look to the gorgeous living room with electric fire place that produces up to 5,000 BTU of heat for the comfort on cold and snowy days. Living room flows into your brand new gourmet style kitchen set up for fabulous days of entertaining friends and family. Main floor offers a spectacular primary bedroom with a personal home office and access to a private deck to enjoy the outdoors along with a private laundry room for your convenience not to mention a large room ready to be made into the closet of your dreams, even better a bathroom with a spa like atmosphere , In addition the main floor has an in law suit with a private bathroom and access to a covered deck area. Lets walk to the second floor where you will be amazed with a spectacular second living room/game room/ study area/ etc. make this room as you wish for any entertainment. Three great bedrooms, 2 share a large bath and one with a private in suit bath, all three with walk in closets. All new floors throughout the home along with all new lighting The expansive basement with over 2,700 SQ.FT has an open concept where you can let your imagination take over along with a second home office and full bathroom. This house is conveniently located off Riva rd, just a few minutes from Downtown Annapolis, plenty of near by shopping including Annapolis Mall and a multitude of restaurants. DON’T LET THIS ONE PASS YOU BY !
#MDAA2127360

ANNAPOLIS

301 UNITY LANE

5 Beds

5 Baths

7,616 Sq.Ft.

$1,197,000

MLS#: MDAA2127360

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