One of the most popular communities provided by {{page_data.agentName}}

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
274
# of Listings
3
Avg # of Bedrooms
$510
Avg. $ / Sq.Ft.
$1,357,507
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

274 Properties Found. Page 3 of 19.

Welcome to 202 Wardour Drive! This classic 1940 Dutch Colonial offers timeless character, generous living space, and an unbeatable Annapolis location. Situated on a quarter acre lot with large front yard, the south facing location ensures sunny days ahead! Located in the elegant Wardour community which reflects the naturalistic style of its designer, Frederick Law Olmstead, Jr, with its mature trees, meandering roads and preserved open spaces that foster community connection. Inside, the home features five bedrooms, two bathrooms, gorgeous oak floors (recently refinished in 2026), fireplace, bright sun-porch and large 12x 32 back deck. The south-facing orientation fills the home with natural light, creating a bright and cheerful atmosphere throughout. Recent improvements include freshly painted interior and exterior spaces, a newer roof approximately four years old, new porch benches, and a beautifully installed brick paver sidewalk that enhances the home’s curb appeal. A long driveway and rear detached garage provide ample parking and storage. Residents benefit from access to seven community beach areas and a shaded walking trail traversing the neighborhood, that provide a tranquil retreat for adults and a natural wonderland to explore. Conveniently located within walking distance of the local elementary school, Navy Stadium, Annapolis Street shopping and dining, Historic Downtown Annapolis and offers easy access to Rt. 50 for commuters. With classic architecture, spacious interiors, abundant natural light, and an exceptional in-town location close to everything Annapolis has to offer, this is a rare opportunity to own in one of the area’s most beloved neighborhoods. Schedule your private tour today!
#MDAA2144980

ANNAPOLIS

202 WARDOUR DRIVE

5 Beds

2 Baths

2,100 Sq.Ft.

$2,765,000

MLS#: MDAA2144980

Perched above the Severn River in the gated waterfront community of Epping Forest, this exceptional property captures sweeping water views and effortless indoor/outdoor living just minutes from downtown Annapolis. Thoughtfully designed with an open floor plan and walls of windows, the home is filled with natural light, high ceilings, custom millwork and seamless sightlines to the Severn river from nearly every vantage point. Expansive ipe decks with sleek cable railing extend the living space outdoors, creating the perfect setting for sunset entertaining or quiet mornings overlooking the water. The primary suite is a true retreat, complete with a private balcony overlooking the Severn; an idyllic perch for enjoying elevated river views and summer breezes. On the lower level, a covered flagstone patio offers an additional outdoor haven, ideal for relaxed evenings, gathering with friends or stepping directly out toward the waterfront. Inside, beautifully appointed gathering spaces flow easily from the gourmet kitchen to the dining and living areas, offering both comfortable everyday living and gracious entertaining. Three spacious bedrooms, three full baths and two half baths are thoughtfully distributed across four finished levels, providing flexibility for guests, work from home needs or additional recreation space. The private pier with deep water and two lifts, including a dedicated jet ski lift, invites endless days on the Severn, with quick access to Annapolis waterways and beyond. Ideally positioned close to Epping Forest’s renowned amenities, residents enjoy a clubhouse with waterside dining, marina, sandy beach, boat ramp, tennis courts, walking trails and a vibrant calendar of social events. An additional 0.115-acre parcel on Sherwood Trail (Tax ID: 224010114205) conveys with the sale and offers convenient supplemental parking, providing easy access for the many guests who will be sure to come visit. A rare opportunity to embrace panoramic river views, exceptional community amenities and the quintessential Annapolitan waterfront lifestyle. Epping Forest is a Special Tax District ($3,059.47 annually) with binding Rules and Regulations. Welcome Home!
#MDAA2137986

ANNAPOLIS

349 SHERWOOD TRAIL

3 Beds

3 Baths

3,185 Sq.Ft.

$2,550,000

MLS#: MDAA2137986

READY TO BUILD NOW!! Introducing an exceptional opportunity to build your dream home with a local custom home builder on a rare 2.19-acre homesite in the highly sought-after water-privileged community of Winchester on the Severn—a neighborhood where everyday living feels like a vacation. This thoughtfully designed custom home will offer over 6,700 square feet of finished living space, featuring 6 bedrooms, 6 full baths, and 1 half bath, along with a 3-car garage, blending timeless craftsmanship with modern luxury and functionality. The main level is designed with both comfort and entertainment in mind, showcasing an open-concept floor plan anchored by a gourmet kitchen featuring high-end appliances, an expansive workspace, and seamless flow into gathering spaces. A beautifully appointed butler’s pantry includes a built-in ice maker and is complemented by a walk-in pantry, demonstrating the careful attention to detail found throughout the home. A rare main-level bedroom with en suite bath, along with a dedicated private office, provides exceptional flexibility for guests, multi-generational living, or work-from-home convenience. Upstairs, you’ll find four generously sized bedrooms, each offering its own walk-in closet and own en suite bathroom —a rare and highly desirable feature. The primary suite serves as a luxurious retreat, complete with separate his-and-hers walk-in closets and a spa-inspired bathroom featuring a soaking tub and oversized walk-in shower. The finished lower level is designed for entertainment and relaxation, featuring a spacious recreation room, a dedicated theater room, and an optional bar area with its own pantry and possible wine storage room. An additional en suite bedroom on this level makes the space ideal for extended guests, in-laws, or a live-in nanny. Set on an exceptionally rare 2.19-acre homesite, the property offers endless possibilities for outdoor living, including space approved for a future pool, pickleball court, or custom outdoor entertainment retreat of your choice —creating the ultimate private backyard oasis. Life in Winchester on the Severn offers an unmatched lifestyle. Simply hop on your golf cart and head to one of the finest community beaches on the Severn River, where residents enjoy a playground, pavilion, sandy beach, swimming pier, kayak and paddleboard storage and launch, boat ramp, and breathtaking sunsets over the water. This is an extremely rare opportunity to create a custom residence in one of the area’s most desirable water-privileged communities—where luxury, space, and lifestyle come together seamlessly.
#MDAA2142274

ANNAPOLIS

1603 WINCHESTER ROAD

6 Beds

6 Baths

6,709 Sq.Ft.

$2,500,000

MLS#: MDAA2142274

A magazine-worthy Historic District renovation, completed in 2026. Designed by well-known Annapolis architect Jay Schwarz and Clara Rose Interior Design, this home features a brand-new kitchen, wet bar, and fully reconfigured third floor with every detail thoughtfully considered. Water access at the end of the block, Acton's Cove waterfront park around the corner, all of downtown Annapolis within easy walking distance, and easy parking on Market Street round out a lifestyle that's hard to beat. The kitchen features custom designed cabinetry with Taj Mahal quartzite countertops, ceramic tile backsplash, and unlacquered brass hardware. New lighting from Serena & Lily, Williams Sonoma, and Pooky. All new GE Monogram appliances include a refrigerator, panel-ready dishwasher, six-burner induction range, convection wall oven, and a five-in-one oven that steams, dehydrates, microwaves, convects, and broils. A full pantry with navy cabinetry offers generous storage, a separate freezer, and ice maker. The custom designed bar includes brass railings, reeded glass cabinets, a dedicated sink, and storage for plates, linens, and beverages. Brand-new HVAC. A full-width screened-in porch spans the entire front of the home. Ten-foot ceilings on the first two floors and period-true character carry throughout. A classic front office with wood paneling and wood ceiling leads to the main living spaces, including a formal family room with fireplace, gracious dining room, and a second casual family room. Seasonal water views can be enjoyed from multiple areas. The eat-in kitchen flows directly to a hardscaped rear patio with gazebo. Upstairs, the primary suite offers winter water views, dual closets with organizers, and a renovated bathroom. The second bedroom has an en-suite bath, and the second level also includes the laundry room. The third floor has been completely reimagined with three new rooms that make clever use of the eaves, each with built-in shelving and closets, along with a new full bath featuring black-and-white penny tile mosaic floors and double-stripe wall tile carried to the face of the tub, plus a custom vanity with quartz countertops. A brand-new carpet runner leads up to the third floor, with new carpet throughout the bedrooms. Don't miss this truly exceptional Annapolis home!
#MDAA2143042

ANNAPOLIS

83 MARKET STREET

5 Beds

4 Baths

3,178 Sq.Ft.

$2,450,000

MLS#: MDAA2143042

Picturesque Craftsman-style waterfront cottage in Epping Forest! Mornings begin with coffee on the porch as the water glistens across Saltworks Creek and stretches out to the Severn River, while evenings are spent gathered by the firepit, watching boats drift by under painted skies. Welcome to effortless waterfront living in the private, gated community of Epping Forest where every day feels like a getaway and every detail is designed for ease. This completely renovated property offers the perfect balance of charm, comfort, and low-maintenance living, making it an ideal full-time residence or lock-and-go retreat. New owner’s thoughtfully completed the whole house renovation in the last year, with additional second floor Restoration Hardware full bath, creating beautiful 2nd upper level bedroom suite, updated kitchen and appliances, new first floor flooring, custom designed kitchen pantry and primary bedroom closet by Chesapeake Closets, raised lower level ceiling to 10’, fresh paint inside and out, all decks and staircase to water polyurethaned, significant landscaping and hardscaping of entire property with expanded driveway to 3-4 cars, new Ring security system and Leaf Gutter system, and more! Previous owner recent improvements in last 1 to 2 years include, new second floor dormer, covered balcony, windows and flooring, new primary bedroom full bath and lower level full bath with Restoration Hardware, new 1st floor gas fireplace and mantel, new roof, new pressure treated stairs to water, new deep water 50’ floating dock with water and power. The home is move-in ready and designed to maximize both lifestyle and convenience. Inside, tall ceilings and walls of windows invite natural light to pour in while framing the surrounding landscape and wide, open water views. The open floor plan creates an easy flow between the gourmet kitchen, dining area, and living room with fireplace, all seamlessly extending to the waterside covered porch, an inviting space for al fresco dining, morning breezes, or unwinding after a day on the water. Upstairs, two ensuite bedrooms provide private retreats, including a serene primary suite with its own balcony overlooking the water, perfect for capturing sunsets and summer breezes. The lower level offers additional flexibility with a family room, guest bedroom, and full bath, ensuring plenty of space for visiting family and friends. Outdoors, the boating lifestyle takes center stage. The recently built deep-water floating dock with a 50-foot slip, complemented by a dedicated mooring ball, creates an exceptional setup for effortless days on the water with quick access to the Severn River, Annapolis Harbor, and the Chesapeake Bay beyond. Epping Forest enhances the experience with a vibrant, amenity-rich setting, offering a clubhouse with waterfront dining, deep-water marina, sandy beach, boat ramp, tennis courts, and scenic walking trails, along with a full calendar of social events and clubs. All just minutes from downtown Annapolis and convenient commuter routes, this is a rare opportunity to enjoy a truly turnkey waterfront lifestyle in one of the area’s most cherished communities. Epping Forest is a Special Tax District ($2,934.96/yr.) with binding Rules & Regulations. Welcome Home!
#MDAA2139878

ANNAPOLIS

327 RIVERVIEW TRAIL

3 Beds

3 Baths

1,831 Sq.Ft.

$2,349,000

MLS#: MDAA2139878

Welcome to an exceptional four level townhome in the coveted Village of Chesapeake Harbour in Annapolis, where every floor captures sweeping views of the Severn River and the iconic Chesapeake Bay Bridge. An elevator services all levels, offering both convenience and comfort while enhancing the ease of everyday living. Multiple balconies and decks invite you to step outside and take in sunrise over the water and evening lights shimmering across the Bay. The main level showcases a generously sized kitchen with crisp white cabinetry, abundant storage, and a spacious center work area that anchors the space beautifully. The combined living and dining room is positioned to highlight the breathtaking backdrop and features its own fireplace, adding warmth and ambiance to the dramatic waterfront setting. On the third level, the primary suite offers stunning water views, a private bath with a relaxing soaking tub, and a fireplace that creates a true retreat atmosphere. An additional bedroom with soaring ceiling and wonderful natural light, along with a hall bath featuring a tub shower combination, complete this level. The fourth floor provides exceptional flexibility as a third bedroom, guest retreat, or additional living space, all enhanced by balcony access and panoramic views. The lower level functions beautifully as a welcoming family room with a cozy fireplace, ideal for relaxed evenings at home. From here, step directly out to the community boardwalk and pier, making waterfront walks and time by the water part of everyday life. Residents enjoy beautifully maintained common grounds, a community center, pools, tennis courts, and water privileges that define the Chesapeake Harbour lifestyle.
#MDAA2131678

ANNAPOLIS

2215 CHESAPEAKE HARBOUR DRIVE E

3 Beds

3 Baths

3,086 Sq.Ft.

$2,300,000

MLS#: MDAA2131678

A rare offering in gated Epping Forest! This mid-century modern waterfront sanctuary rises above Saltworks Creek on a quiet protected cove—where timeless design meets an ethereal, peaceful connection to the water and outside. Originally built in 1978, the almost 3600 sq. ft residence recently underwent a comprehensive renovation inside and out while honoring Mid-century authenticity and maintaining an effortless flow and contemporary preference. From the street side, the home presents a timeless silhouette with a recent 70K Elevator with ramp that serves as a secondary entrance servicing 2 out of the 3 levels. Waterside, the home is the ultimate expression of blurring the line between nature and interior with floor to ceiling glass walls, 8' sliding glass doors and unobstructed views from the deck. This home wasn't designed to look at the water but rather live with it. A massive stone central fireplace is the heart of the living area creating a cozy architectural retreat. Tasteful moderization but true to its mid-century roots, every element of the home has been considered preserving the architechural integrity while offering the comfort and convenience expected today. More than a home, this is a rare opportunity to own a piece of design history- reimagined for modern waterfront living. See documents for list of 925K spent on restoration since purchase including brand new private pier. Epping Forest is a Gated Waterfront Community on the Severn River with a community beach, waterfront clubhouse with restaurant and bar, tennis/pickleball and marina (new marina is currently under construction) Strong neighborhood connections where neighbors treat each other like family and fun happens weekly! Year around community events codify friendships, 4th of July Fireworks, Oyster & Bull Roast, Boat Club, Summer Volleyball League, community chapel, yoga & summer camps. Come experience the best Chesapeake Bay Maritime Annapolitan Lifestyle around! Epping Forest Inc is a special benefit tax district with bylaws and binding rules and regulations with Non-Riparian Waterfront. Special financing via Pentagon Federal Credit Jumbo 7/6 ARM available to low as 5.50%.
#MDAA2136126

ANNAPOLIS

1739 VINEYARD TRAIL

4 Beds

3 Baths

2,890 Sq.Ft.

$2,200,000

MLS#: MDAA2136126

Perfectly positioned in the heart of downtown Annapolis, this distinguished historic residence offers a rare opportunity to own a piece of the city’s architectural legacy while enjoying the convenience of two coveted off-street parking spaces. Overlooking the beautifully preserved grounds of St. John’s College, the home captures timeless views that enhance its already exceptional setting. Steeped in history, the property reflects an evolution of craftsmanship spanning centuries, with the original portion dating to the mid 1800s, an expansion in the late 1800s, and a thoughtfully integrated addition in 1921. Sold fully furnished, the interiors are curated with elegant period pieces that complement the home’s character and provide a seamless, move-in-ready experience. Enjoy peace of mind with the updated electrical and plumbing in 1990 , new hot water heater in January of 2024, new shake shingle roof in April 2026 and 2 new heat pumps in March 2025 Inside, classic architectural details unfold across the main level, where two gracious parlors—each anchored by a fireplace—offer inviting spaces for both intimate gatherings and relaxed everyday living. A welcoming entry hall with an open staircase sets the tone, leading to a charming dining room with its own fireplace and a convenient pass-through to the kitchen, blending historic ambiance with functional flow. The upper levels provide flexibility and space, with four bedrooms and two full baths on the second floor, while an additional bedroom occupies the top level—ideal for guests, a private retreat, or creative workspace. Below, the basement offers practical utility space and storage. Just moments from the shops, restaurants, and waterfront attractions of downtown, as well as the United States Naval Academy, this residence invites you to fully immerse yourself in the vibrant Annapolis lifestyle. From morning walks along tree-lined streets to evenings enjoying the energy of the harbor, this is a home where history, location, and livability converge in a truly special way. Welcome Home!
#MDAA2143146

ANNAPOLIS

250 PRINCE GEORGE STREET

5 Beds

2 Baths

2,888 Sq.Ft.

$2,150,000

MLS#: MDAA2143146

For sale , this is a huge opportunity 2 ASSETS FOR SALE , 1991-1993 West Street: 3000 sf retail building Lot Size.Discover an exceptional investment opportunity with this portfolio of two retail assets located at 1991 and 1993 West Street, Annapolis, MD. - Property Overview: - 1991 West St: - Lot Size: 8,000 sq. ft. - Zoning: BCE (Business Corridor Enhancement district) - Features a retail building with high visibility and heavy traffic, ideal for attracting customers. - The current tenant is willing to continue leasing or vacate if necessary, providing flexibility for potential buyers. - 1993 West St: - Lot Size: 4,800 sq. ft. - This property is currently condemned, with value primarily in the land itself, offering a unique redevelopment opportunity. Location Highlights: - Situated in a bustling area with high foot traffic and direct proximity to Annapolis’ historic downtown, this location promises excellent visibility and accessibility for any retail business. Important Note: - Please do not visit the property without a scheduled appointment to ensure a smooth viewing experience. Take advantage of this rare chance to invest in prime real estate in a thriving area. Contact us for more details or to schedule a viewing!
#MDAA2128872

ANNAPOLIS

1991-1993 WEST STREET

None Beds

None Baths

3,000 Sq.Ft.

$2,099,000

MLS#: MDAA2128872

Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.
#MDAA2144868

ANNAPOLIS

146 DUKE OF GLOUCESTER STREET

4 Beds

3 Baths

3,042 Sq.Ft.

$1,999,999

MLS#: MDAA2144868

Nestled along the banks of Watergate Harbor with direct access to the South River, in the prestigious Watergate neighborhood of Annapolis, 3712 Gateshead Drive offers the ultimate waterfront lifestyle with waterviews from every room in the home. When you enter the home you are greeted with the marble flooring in the foyer which transitions beautifully to the gleaming hardwood flooring throughout the main and upper level. As you enter the Living Room, natural light spills into the Bay Window while the wood burning fireplace is the focal point of the room. Next you enter the gorgeous waterfront Living Room with a private deck overlooking the Harbor plus views of the South River. The heart of the home is a gourmet kitchen adorned with sleek upgraded countertops and elegant glass-front cabinets. Recent updates in the kitchen include new GE Profile cooktop in 2024, new GE Profile oven and microwave in 2025 and new Kenmore Elite refrigerator in 2020. The open floor plan of kitchen provides a large island, kitchen table space and direct access to the Family Room. The Family Room offers the second wood burning fireplace on the main level and sliders to your waterfront deck. Journey upstairs when you will find 3 large guest rooms as well as the primary. The first bedroom will be the envy of your guests with a deck overlooking the South River and multiple closets. The other two bedrooms offer hardwood flooring and waterviews of the South River. The primary suite is a true sanctuary with tons of windows to take in the views. The en suite bath features a granite double bowl vanity, separate shower and soaking tub designed to "soak in" the views. As mentioned, the home features a walkout basement which is exceedingly rare in waterfront homes and provides tons of natural light. The expansive rec room in the basement features a cozy wood burning fireplace and is perfect for entertaining or relaxing after a day on the bay. Walk outside to the backyard which is made for entertaining. The large composite deck leads to the path which takes you to the waterfront firepit. This stunning home boasts a private 46 foot pier with a new 10,000 lb boat lift and a floating pier for those looking for idyllic days spent on the water. And for all the gardeners out there, not only is it the second largest lot in the community it is definitely one of the prettiest with professional landscaping throughout. from Homestead Gardens. You won't know what to do with all of the storage this home offers from the pull down attic storage over the oversized two car garage to the huge storage room just outside of the basement walk out. Complete peace of mind with dual zone heat pumps complete with a propane booster. In addition to the private pier, the community of Watergate offers a community marina, dry moorings, basketball courts, and a sandy beach with fire pit, pavilion and playground. The community offers something for everyone with neighborhood events throughout the year! This is more than a home- it's a gateway to a life of sophistication, comfort, and endless waterfront adventures.
#MDAA2140862

ANNAPOLIS

3712 GATESHEAD DRIVE

4 Beds

2 Baths

3,620 Sq.Ft.

$1,999,900

MLS#: MDAA2140862

A rare opportunity for a well located worship facility on 23 acres in Cape St. Claire with exceptional frontage on Rt 50. This large complex with extensive acreage allows a congregation an unusual and great opportunity to grow or fund itself. Existing complex can be restored and used with a great opportunity for later expansion for a larger facility on the additional acreage. Selling addition acres for subdivision may be possible. Available preliminary engineering supports subdivision possibilities. This facility's main room is big enough for 175 and building boasts over 4600 total sq ft, includes a kitchen with serving bar, study, multipurpose room, foyer and reception desk, offices, and classrooms. Noteworthy architectural features include palladium windows, exposed brick, beamed ceilings and a custom staircase. The main building will require less updating and the parsonage, once used as offices, will require significant renovation. Property sold as-is, where-is. Zoning is residential and supports some commercial uses. See attached zoning table for R1 uses. All uses will require certificate of use and occupancy.
#MDAA2123582

ANNAPOLIS

1016-1024 E COLLEGE PARKWAY

None Beds

None Baths

4,473 Sq.Ft.

$1,995,000

MLS#: MDAA2123582

23-acre parcel zoned primarily R-1, with some O-S. Preliminary engineering work indicates the property can be subdivided and coul support multiple residential lots. The concept drawing attached.
#MDAA2123584

ANNAPOLIS

1016 E COLLEGE PARKWAY

None Beds

None Baths

23.33 acres

$1,995,000

MLS#: MDAA2123584

Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been extensively remodeled, offering a perfect blend of classic charm and contemporary elegance. The home is set on a generously sized lot, providing abundant green space, with new sod and landscaping coming soon. Premium exterior finishes include an inviting front porch, James Hardi siding and Anderson 400 windows. Inside, the home features a interior sprinkler system, two fireplaces, and all new plumbing and electrical systems. As you step inside, the open and versatile floor plan begins with a multi-use room to the left ideal for an office or sitting area- while a spacious area to the right offers flexibility for living and dining. The layout then flows seamlessly into the kitchen and into a comfortable family room, creating an ideal setup for both everyday living and entertaining. Hardwood floors, high ceilings, and impressive millwork carry throughout. Upstairs, the second floor hosts all three large bedrooms, including the luxurious master’s suite. The master’s suite features a spa-like bath complete with a dual vanity, frameless glass shower, and soaking tub. A conveniently located washer and dryer are also on this level. A large, fully finished basement provides ample storage, especially in the sizable utility area, offering flexible space for a home gym, recreation, or more. Notably, the home features a double staircase one in the front portion of the home and another in the rear, leading directly into the kitchen and family room adding a unique and functional design element. Additional upgrades include all new plumbing and electrical systems. A generous rear deck is perfect for entertaining, and there are three off street parking spaces, plus the potential for a future garage with an accessory dwelling unit (ADU) above and or pool. All of this is just steps from restaurants, shopping, yacht clubs and everything Eastport and downtown Annapolis have to offer. Days on market reflect the extensive permitting period to begin the remodel and addition. ** Approx. 3950 finished sq. ft. Tax records are incorrect. **
#MDAA2131396

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,990,000

MLS#: MDAA2131396

The Henry Brown House, Circa 1860, is a distinguished residence once associated with Charles Hammond and Richard Harwood, with earlier ties to William Paca. Ideally positioned on prestigious King George Street in the heart of Historic Downtown Annapolis, this exceptional home offers a rare blend of heritage and modern luxury. Amazing view overlooking Ogle Hall. The home has been thoughtfully updated with a new roof, gutters, siding, and beautifully redesigned kitchen and bathrooms. Every detail has been carefully considered, from freshly painted interiors and updated doors and hardware to the stunning heart of pine floors that anchor the home in warmth and character. The residence offers four spacious bedrooms and three full bathrooms two with heated floors, complemented by a second-floor den and convenient second-floor laundry. Two fireplaces add inviting ambiance, while the third floor features a charming coffee bar with beverage cooler. The lower level includes an additional refrigerator/freezer for added functionality and a workbench for home projects. Comfort is ensured year-round with three sources of heat, a gas boiler for radiant heat and two additional HVAC systems. A termite and full home inspection was completed in May of 2026, offering peace of mind. The professional landscaped grounds are enhanced with irrigation and elegant lighting, creating a picturesque outdoor setting. Located just steps from boutiques, fine dining, City Dock, and marinas-with direct access to the U.S. Naval Academy. This home places you at the center of Annapolis living. Convenient to Rt 50 and Rt 97 provide easy access to Washington, DC and Baltimore. A truly rare offering where historic significance meets refined modern living.
#MDAA2143686

ANNAPOLIS

254 KING GEORGE STREET

4 Beds

3 Baths

2,877 Sq.Ft.

$1,950,000

MLS#: MDAA2143686

1 2 3 4 5 ... 19
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 $$

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

I agree to receive email communication and understand I can unsubscribe at any time.

I agree to be contacted by Maryland Sandbox via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

I agree to receive communications and understand I can unsubscribe at any time.

I agree to be contacted by Maryland Sandbox via call, email, and text for real estate services. To opt out, you can reply 'stop' at any time or reply 'help' for assistance. You can also click the unsubscribe link in the emails. Message and data rates may apply. Message frequency may vary. Privacy Policy

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service