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

Browse Annapolis Real Estate Listings

74 Properties Found. Page 2 of 5.

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

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for 6+ vehicles. Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully fully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area. No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers and more. The result is a turnkey home where historic character meets modern sophistication & luxury. The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat.  schedule your showing today.
#MDAA2144086

ANNAPOLIS

192 DUKE OF GLOUCESTER

6 Beds

4 Baths

3,415 Sq.Ft.

$1,950,000

MLS#: MDAA2144086

New on site 1 day ago
Tucked along the protected waters of Ramsgate Harbor with direct access through the canal to the South River and the Chesapeake Bay beyond, this exceptional waterfront retreat captures the essence of relaxed coastal living. Set on beautifully landscaped grounds with approximately 100 feet of waterfrontage, the property is designed to embrace the outdoors at every turn, from the heated saltwater pool and expansive waterside entertaining areas to the private pier ready for boating adventures and sunset cruises.

The main level is thoughtfully arranged for both everyday comfort and effortless entertaining. A well-appointed galley kitchen with high-end appliances flows seamlessly into the adjacent family room with fireplace, while the expansive living and dining areas open directly to the covered waterside deck, creating a seamless indoor-outdoor connection overlooking the pool and tranquil harbor views. Whether hosting summer gatherings or enjoying a quiet morning coffee with the breeze off the water, the setting is both inviting and unforgettable.

The upper level offers four bedrooms and two full baths, including a spacious waterfront primary suite with vaulted ceilings, a beautifully appointed ensuite bath, and calming water views that create a true private retreat. The walkout lower level adds exceptional flexibility with two additional bedrooms, a full bath, laundry room, and a recreation room with doors leading directly to the covered patio and pool area. A cozy fireplace beneath the covered patio creates the perfect year-round gathering space after a day on the boat or evenings spent poolside. 

Completing the property is a three-car garage, circular driveway, and lush mature landscaping that enhances the privacy and natural beauty of this waterfront setting. The amenities-rich Watergate community offers a marina, pavilion, and playground just moments away, adding to the exceptional lifestyle this property provides. Ideally situated off of the South River allowing for quick cruises to waterfront destinations like Mike’s Crab House, Historic Annapolis Harbor, the Chesapeake Bay, and countless waterfront restaurants and destinations beyond. Welcome Home!
#MDAA2145168

ANNAPOLIS

3706 THOMAS POINT ROAD

6 Beds

3 Baths

3,211 Sq.Ft.

$1,950,000

MLS#: MDAA2145168

On the market for the first time in over 33 years, this exceptional waterfront home on protected Watergate Harbor is a rare opportunity to own a piece of Annapolis's most coveted water lifestyle. With 200+ feet of private waterfront and seconds-away access to the South River, this is the property you've been waiting for.

Step outside to your private 41' pier —  with 2 slips, one with an 15,000lb boat lift and floating dock — and enjoy manicured lawns that sweep gently to the water's edge. Whether you're launching a boat at sunrise or hosting summer gatherings on the grass, the outdoor experience here is simply unmatched.

Inside, over 3,400 finished square feet above grade offers a warm, gracious floor plan designed for both everyday living and effortless entertaining. The heart of the home is a spacious, updated kitchen and family room with high ceilings, and French doors that open directly to the waterside decks. The formal dining and living rooms add classic elegance, while the show-stopping sun room — lined with walls of windows overlooking the harbor and South River — is a space unlike any other, anchored by a pass-through fireplace shared with the living room.

Upstairs, three bedrooms and two full baths await. The primary suite is a true retreat, featuring vaulted ceilings, a spa-inspired bath, a walk-in closet, and a private balcony perfectly positioned to catch the South River's legendary sunsets. A convenient upper-level laundry room rounds out the second floor.

The lower level offers an abundance of unfinished storage space plus a full bath with shower — ideal for rinsing off after a day on the water. An oversized two-car side-load garage completes the picture.

The exterior of house was professionally painted within the last year; and the waterside deck is also new. Lovely landscaping complements the home. 

Beyond your own backyard, the Watergate community enriches daily life with a marina, pavilion, small beach, tot lot, basketball court, and a full calendar of neighborhood social events throughout the year.

NO CONTINGENT CONTRACTS PLEASE
#MDAA2144030

ANNAPOLIS

3718 RAMSGATE DRIVE

3 Beds

3 Baths

3,417 Sq.Ft.

$1,945,000

MLS#: MDAA2144030

This brand new, fully renovated 16-bedroom, 6-bathroom residence in Annapolis offers an exceptional opportunity for assisted living or specialized care operations. Thoughtfully redesigned and fully permitted with the county for use as an assisted living facility, the property combines modern upgrades with full regulatory compliance. The spacious layout features three separate living areas, providing flexibility for resident comfort, programming, or private quarters. A full kitchen serves the home, complemented by two additional kitchenettes for added convenience and efficiency. Designed with accessibility and safety as top priorities, the entire home is ADA compliant and equipped with two separate ramp entrances for easy access. Safety features include illuminated exit signage, a fire sprinkler system throughout, and pre-wiring for security cameras to ensure peace of mind. This turnkey, code-compliant property is ideal for operators seeking a move-in-ready assisted living home built to meet today’s safety, accessibility, and comfort standards. Conveniently located minutes from Sandy Point State Park. Additionally the home is close by Luminis Anne Arundel Hospital.
#MDAA2137670

ANNAPOLIS

1349 YORKTOWN ROAD

16 Beds

6 Baths

5,719 Sq.Ft.

$1,900,000

MLS#: MDAA2137670

Last available opportunity for a buildable Waterfront lot on Lake Ogleton in the coveted community of Bay Ridge in Annapolis!  This .22 acre lot has been in the same family for the past 58 years and is coming to market for the first time. With 57 feet of waterfrontage on the sparkling shores of Lake Ogleton, the possibilities are endless for building the waterfront home of your dreams! This property is priced to sell quickly, at $361,000 below the tax assessed value!  Contact your architect and take the first step toward bringing your vision of the ideal Annapolis lifestyle on the water! The sought-after Bay Ridge Community features a plethora of amenities, including 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, pickleball courts, 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.
#MDAA2137314

ANNAPOLIS

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$1,895,000

MLS#: MDAA2137314

Rare Builder Opportunity – Prime Minor Subdivision in Annapolis, MD (Anne Arundel County)
Exceptional opportunity for builders and investors to acquire a newly divided minor subdivision totaling over 2 acres in highly desirable Annapolis, MD. These spacious,  4 buildable lots offer the perfect setting to create luxury custom homes in a sought-after location.
Ideally situated just a couple of miles from the Historic District, this property provides convenient access to Annapolis’ vibrant shops, restaurants, coffee houses, and everyday amenities—offering future homeowners both privacy and proximity.
The largest lot, Lot 1 includes an existing home that has been significantly upgraded in 2023, featuring:
* New HVAC system
* Updated electrical and plumbing
* New roofing
* Refinished hardwood floors
* Lower level ready for expansion
The existing home on this property is currently tenant-occupied on a month-to-month lease, providing flexibility for future plans (continued income, future expansion, etc).
This property represents a rare chance to secure buildable land in Annapolis, with nearly two years of permitting already completed. Engineering and permit work have been professionally handled by Messick Engineering, positioning the project for a smooth transition for development at settlement.
Important Notes:
* Do Not Enter Property without authorization
* Tenant Occupied – Appointments Required
For sincere inquiries, please contact Equity Property Investments. 
Thank you for your interest.
#MDAA2139760

ANNAPOLIS

927 OLD ANNAPOLIS NECK ROAD

None Beds

None Baths

2.07 acres

$1,800,000

MLS#: MDAA2139760

A rare and spectacular 3,400 sq. ft. penthouse offering at the GrandView in Annapolis Towne Centre. Bathed in natural light from expansive windows, and enhanced by dramatic 11-foot ceilings, this residence offers an exceptional sense of space and sophistication. Rich hickory hardwood floors, granite countertops, and a striking fireplace anchor the beautifully appointed interiors, while dual balconies provide inviting outdoor retreats. A charming den and dedicated office space add both flexibility and function.
Residents enjoy a full complement of amenities, including assigned garage parking, concierge service, a fitness center, and a rooftop pool with thoughtfully designed entertaining spaces. Walking to Whole Foods, shops, restaurants and services. Welcome to Annapolis Towne Centre living at its finest!
#MDAA2143720

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1105

3 Beds

3 Baths

3,368 Sq.Ft.

$1,800,000

MLS#: MDAA2143720

WELCOME TO THIS BEAUTIFULLY DESIGNED 5/6 BEDROOM, 4 FULL BATH BRICK BEAUTY IN THE HIGHLY SOUGHT AFTER WATER-PRIVILEGED COMMUNITY OF FISHING CREEK FARM! 

FROM THE MOMENT YOU ENTER, THE HOME FEELS BOTH ELEVATED AND INVITING WITH WELL-APPOINTED SPACES, NATURAL FLOW, AND QUALITY FINISHES THROUGHOUT. THE MAIN LEVEL OFFERS A TWO STORY FOYER AND A HOME OFFICE (OR MAIN LEVEL BEDROOM) WITH PLANTATION SHUTTERS AND DIRECT ACCESS TO A TASTEFULLY RENOVATED FULL BATH.  THE FORMAL DINING ROOM PROVIDES THE PERFECT SPACE FOR ENTERTAINING AND GATHERINGS.

THE RENOVATED GOURMET KITCHEN SERVES AS THE HEART OF THE HOME, FEATURING A QUARTZITE ISLAND, SOAPSTONE COUNTERS, GE MONOGRAM APPLIANCES, GAS COOKTOP, WARMING DRAWER, BOSCH DISHWASHER, WINE COOLER, REVERSE OSMOSIS SYSTEM, WALK-IN PANTRY, AND A  WINE BAR PERFECT FOR ENTERTAINING.

LIVING SPACES ARE BOTH COMFORTABLE AND REFINED, INCLUDING A COFFERED CEILING FAMILY ROOM WITH PROPANE FIREPLACE, A FORMAL LIVING ROOM WITH A SECOND  GAS FIREPLACE, AND A  SPACIOUS  LIGHT-FILLED SUNROOM WITH DIRECT ACCESS TO THE SCREENED-IN PORCH. THE BREAKFAST ROOM FEATURES  A NEWER EXTERIOR DOOR, AND THE MUDROOM ADDED IN 2020 OFFERS EVERYDAY FUNCTIONALITY.

UPSTAIRS, YOU WILL FIND FOUR BEDROOMS WITH NEW CARPET THROUGHOUT.  THE PRIMARY SUITE OFFERS A TRUE RETREAT WITH A FULLY RENOVATED PRIMARY BATH AND SEASONAL  WATER VIEWS. THE HALL BATH IS EQUALLY IMPRESSIVE WITH QUARTZITE FINISHES, PORCELAIN TILE FLOORS, SKYLIGHT,  A LARGE SOAKING TUB, AND A CEDAR-LINED CLOSET.

THE WALK OUT LOWER LEVEL IS FULLY FINISHED WITH NEW CARPET, A FULL BATH, BUILT-IN SPEAKERS, AND FLEXIBLE SPACE IDEAL FOR ENTERTAINING, GUESTS, OR A HOME GYM.

THE EXTERIOR COMPLEMENTS THE INTERIOR BEAUTIFULLY WITH PAINTED BRICK AND FRESHLY PAINTED CEDAR SIDING ALONG THE REAR. OUTDOOR LIVING IS EXCEPTIONAL WITH AN EXPANSIVE AZEK DECK AND SCREENED PORCH DESIGNED FOR ENTERTAINING AND RELAXING, OVERLOOKING THE PRIVATE FENCED BACKYARD BACKING TO TREES.  ADDITIONAL FEATURES INCLUDE A WOOD-BURNING FIRE PIT, UNDERGROUND SPRINKLER SYSTEM, AND INSULATED STORAGE UNDER THE DECK.  RECENT UPGRADES INCLUDE A NEW WELL PUMP AND WATER TREATMENT SYSTEM.

THIS IS  A RARE OPPORTUNITY TO OWN A TURNKEY HOME IN ONE OF ANNAPOLIS’ MOST DESIRABLE WATER ACCESS COMMUNITIES, OFFERING A MARINA, WATERSIDE POOL & CLUBHOUSE, TENNIS/PICKLEBALL COURT, BEACH AND MORE!   ALL JUST MINUTES TO DOWNTOWN ANNAPOLIS WITH A CONVENIENT COMMUTE TO DC, NORTHERN VA AND BALTIMORE.  COME AND ENJOY THE LAND OF PLEASANT LIVING!
#MDAA2140530

ANNAPOLIS

1207 THOMAS POINT COURT

5 Beds

4 Baths

4,589 Sq.Ft.

$1,750,000

MLS#: MDAA2140530

Rarely offered ground level residential condominium located at the intersection of Murray Hill and the city's Historic District. Secure garage parking for 2 cars, plus driveway parking for an additional vehicle w/private entry.  Originally developed by John Pilli & constructed by Gate One custom builders, this exquisite residence was built with luxury high-end finishes including Legno Bastone wide-plank hardwood flooring, Caesarstone counter-tops, Omega cabinetry, Thermador appliances & beautiful designer selected plumbing and lighting fixtures. Recently re-built by Lynbrook of Annapolis with numerous, thoughtful additions including fireplace, soaking tub, multiple built-ins, extra closets and sliding doors for privacy.  Featuring 9.5' ceilings, expansive windows, & enormous outdoor patio with off-street parking & EV charger.  and interior space of 2269 sq feet. Amenities include elevator, rooftop terrace w/views of Spa Creek and city skyline, secured covered parking, gas cooking and water usage.  Located in a premier and quiet section of downtown Annapolis yet an easy walk to Main St shops, restaurants & the West St Arts District. Luxury lock & leave at its finest!
#MDAA2143604

ANNAPOLIS

51 FRANKLIN STREET

2 Beds

2 Baths

2,269 Sq.Ft.

$1,750,000

MLS#: MDAA2143604

An exceptional opportunity awaits in coveted West Annapolis—a rare 0.61-acre offering with endless potential. Whether you envision a thoughtful renovation or a custom new build, this expansive lot provides the perfect canvas to create your dream residence in one of the area’s most sought-after neighborhoods. Approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural designs by Custom Designs Unlimited convey with the property (city approvals secured; permits not yet pulled), offering a valuable head start toward bringing your vision to life.

The generously sized lot and current AS-IS cottage provides an abundance of outdoor space, inviting a plethora of outdoor gatherings, summer barbecues, and relaxed evenings enjoying the vibrant West Annapolis lifestyle. Just beyond your doorstep, stroll to acclaimed restaurants, local pubs, charming boutiques, and convenient street-end water access. Ideally situated near Downtown Annapolis, Navy Stadium events, and the Naval Academy, the location also provides effortless commuter access to Route 50 and the Bay Bridge for Eastern Shore escapes or travel to Washington, D.C.

A truly special setting offered AS-IS, ready for its next chapter. Welcome Home!
#MDAA2136908

ANNAPOLIS

4 SHILEY STREET

None Beds

None Baths

0.61 acres

$1,700,000

MLS#: MDAA2136908

An exceptional opportunity awaits in coveted West Annapolis—a rare 0.61-acre offering with endless potential. Whether you envision a thoughtful renovation or a custom new build, this expansive lot provides the perfect canvas to create your dream residence in one of the area’s most sought-after neighborhoods. Approved civil engineering plans by Drum, Loyka & Associates, LLC and architectural designs by Custom Designs Unlimited convey with the property (city approvals secured; permits not yet pulled), offering a valuable head start toward bringing your vision to life.

The generously sized lot and current AS-IS cottage provides an abundance of outdoor space, inviting a plethora of outdoor gatherings, summer barbecues, and relaxed evenings enjoying the vibrant West Annapolis lifestyle. Just beyond your doorstep, stroll to acclaimed restaurants, local pubs, charming boutiques, and convenient street-end water access. Ideally situated near Downtown Annapolis, Navy Stadium events, and the Naval Academy, the location also provides effortless commuter access to Route 50 and the Bay Bridge for Eastern Shore escapes or travel to Washington, D.C.

A truly special setting offered AS-IS, ready for its next chapter. Welcome Home!
#MDAA2137186

ANNAPOLIS

4 SHILEY STREET

4 Beds

2 Baths

1,557 Sq.Ft.

$1,700,000

MLS#: MDAA2137186

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