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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

166

# of Listings

2

Avg # of Bedrooms

$499

Avg. $ / Sq.Ft.

$959,198

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$1M - $3M

32 Properties Found. Page 1 of 3.

#MDAA2131890

ANNAPOLIS

703 GLENDON AVENUE

5 Beds

4 Baths

4,116 Sq.Ft.

$2,950,000

MLS#: MDAA2131890

#MDAA2123548

ANNAPOLIS

778 BON HAVEN DRIVE

6 Beds

4 Baths

5,094 Sq.Ft.

$2,800,000

MLS#: MDAA2123548

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 4 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

4 Beds

5 Baths

6,428 Sq.Ft.

$2,675,000

MLS#: MDAA2115392

Price Reduction! Seller says to bring all offers! Built by Captain Beriah Maybury in 1772 and known as the Kings' Arms Tavern, this Historically designated property is a MUST SEE! This Five-Bay wide brick Single Family Home sits on top of a high scored stone foundation. 9.5 foot ceilings illuminated by nearly floor to ceiling windows showcase a lovely Library with built-In Bookcases and a wood burning Fireplace; a Two Room Parlor, also with a wood burning Fireplace; an addition erected possibly as early as the 1830's includes a large Dining Room with high domed ceiling, a kitchen and a small porch. The upstairs 4 Bedrooms, 3 with their own wood burning Fireplace, wood floors, 2 full Baths and laundry provide plenty of room! The partially finished basement, most recently used as a woodworking shop, has a separate street entrance and could possibly be reimagined as additional living space. The long, gated driveway leads to 2 garage spaces and parking for an additional 6 cars and a charming English garden and patio area. Furnace chimney recently relined. This home is being sold AS IS, but has great bones. Bring your own TLC. Call Listing Agent with questions.

ANNAPOLIS

41 CORNHILL STREET

4 Beds

2 Baths

4,404 Sq.Ft.

$2,100,000

MLS#: MDAA2109384

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!

ANNAPOLIS

1991-1993 WEST STREET

None Beds

None Baths

3,000 Sq.Ft.

$2,099,000

MLS#: MDAA2128872

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.

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.

ANNAPOLIS

1016 E COLLEGE PARKWAY

None Beds

None Baths

23.33 acres

$1,995,000

MLS#: MDAA2123584

Elegant charm meets modern convenience in this one-of-a-kind residence located in the heart of Murray Hill. Offering the very best of the downtown lifestyle, this remarkable property boasts a chef’s kitchen with custom cabinetry, granite counters, and high-end appliances and soaring ceilings. The stunning Living room with gas fireplace and light filled dining area flows seamlessly to the picturesque gardens in the front yard to the elegant fountain in the back. Elevator service to all levels provides ease, while the spacious primary retreat encompassing the entire top floor includes a sitting room/office, private covered porch, and breathtaking views of Spa Creek and the iconic Annapolis skyline.

Unmatched in both location and amenities, this residence includes a rare downtown garage, plenty of parking, multiple guest suites for friends and family, and elegant details throughout—from granite foyer floors to a library and breakfast room filled with light and curated finishes. Whether entertaining in style or enjoying a quiet evening watching the boats glide by, this home represents the finest package in the city: an extraordinary blend of history, luxury, and walkable convenience just steps from everything downtown Annapolis has to offer. Welcome Home!

ANNAPOLIS

2 SOUTHGATE AVENUE 10

3 Beds

2 Baths

3,884 Sq.Ft.

$1,975,000

MLS#: MDAA2129932

An exclusive and rare opportunity could be yours! Welcome to 51 Franklin, consisting of 9 high-end boutique units, developed by John Pilli & constructed by Gate One custom builders in 2020. Located at the intersection of Murray Hill and the city's Historic District, this exquisite condo provides high-end finishes including Legno-Bastone wide-plank hardwood flooring, Caesarstone waterfall counters, Omega cabinetry, Thermador & Wolf appliances, and beautiful designer plumbing and lighting fixtures. California Closets in all bedrooms, pantry and coat closet. Airy ten foot ceilings. Amenities include elevator, rooftop terrace w/luxurious views, secured covered garage parking with 2 assigned spots per unit, extra storage unit 3 steps from condo entry, gas cooking and water usage. Easy walking to Main St, the West St Arts District, and all points Downtown Annapolis...a true lock and leave experience for the next fortunate Owner! SEE VIDEO 'TOURS' FOR IN DEPTH INFO ABOUT THIS SMALL, EXTRAORDINARY HIGH END CONDO BUILDING DESIGNED BY THE ARCHITECTS OF FOURTH STREET DESIGN, AND BUILT BY JOHN PILLI AND GATE ONE BUILDERS

ANNAPOLIS

51 FRANKLIN STREET

2 Beds

2 Baths

2,269 Sq.Ft.

$1,695,000

MLS#: MDAA2127792

FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views with this rare opportunity to own an exquisite penthouse at the GrandView in Annapolis Town Center. Perched atop the prestigious 12th floor, this sprawling residence stands as one of the most coveted penthouses, offering panoramic views that stretch for miles, complemented by two expansive balconies that provide front-row seats to the vibrant holiday events and outdoor venues of the Town Center.

Step inside to discover a world of refined elegance, where light cascades through oversized windows, illuminating the dramatic 11-foot ceilings that stretch overhead, creating an atmosphere of open, airy sophistication. This penthouse boasts an expansive layout, featuring three private ensuite bedrooms, each a serene retreat of comfort and luxury. A large den offers flexibility for your lifestyle, whether as a home office, media room, or additional guest space, ensuring this home meets your every need. Newly installed 2-Zone HVAC system, new tankless water heater, and new washer and dryer.

The heart of this home is the open floor plan, seamlessly connecting living spaces with Brazilian cherry hardwood and ceramic tile floors underfoot, exuding warmth and timeless elegance. The gourmet kitchen is a chef's dream, outfitted with high-end appliances, sumptuous granite countertops, and a massive kitchen island, making it perfect for hosting gatherings or savoring quiet moments over coffee.

GrandView isn’t just a residence; it’s a community that offers a true sense of belonging. Residents enjoy exclusive access to a rooftop sky lounge and pool, an outdoor kitchen, a state-of-the-art fitness center, and a club/party room, all designed to foster a lifestyle not just of luxury, but of wellness and social connectivity. The addition of a professionally managed concierge staff ensures every day is lived with ease, convenience, and security.

Situated in the heart of Annapolis, GrandView places you just a stroll away from the finest dining, Whole Foods, Target, Life Time Fitness Club, banking, and boutique shopping. Historic downtown Annapolis, the US Naval Academy, Anne Arundel Medical Center, and Annapolis Mall are mere minutes away, making this a dream location for commuters with quick access to Route 50 and 97.

Seize this unmatched opportunity to indulge in refined urban living at its most sophisticated. Schedule your showing today and take the first step into a life filled with luxury, comfort, and breathtaking beauty in this unparalleled penthouse residence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1210

3 Beds

3 Baths

3,520 Sq.Ft.

$1,695,000

MLS#: MDAA2127736

Discover a rare deep-water retreat on peaceful Burley Creek, an inviting waterfront home where contemporary architecture, warm natural textures, and the serenity of nature come together in a way that instantly feels like a getaway. With soaring vaulted ceilings, natural wood accents, dramatic stacked-stone fireplaces, and sunlight spilling in from every angle, the home offers a cozy, ski-chalet ambiance, only here, the views are of still water, quiet mornings, and the deep blue of 10’ mean low water.

Tucked into a lovely setting yet just minutes from downtown Annapolis, this refreshed three-bedroom, three-bath contemporary offers one bedroom on each level, creating ideal separation and flexibility for guests, multi-generational living, or weekend retreats. The interior has been thoughtfully updated throughout, including fresh paint on every level and new LVP flooring that adds a soft, modern touch while enhancing the warm architectural lines of the home. Expansive windows and sliding doors draw in natural light and frame sweeping views of the creek, bringing the outdoors in and making every room feel connected to the water.

The main level is the heart of the home, where the dramatic stone fireplace rises to meet the vaulted ceiling and creates a gathering space that feels both elevated and deeply comfortable. The dining area and living room flow seamlessly onto the outdoor decks, offering multiple places to enjoy morning coffee, read a book, or simply breathe in the calm that surrounds the property. The kitchen and breakfast area provide direct access to the outdoors and enjoy tile flooring that complements the clean, modern updates found throughout the rest of the home.

Each floor offers its own bedroom and full bath. The lower level is bright and welcoming with a renovated full bathroom and a walkout directly to the waterfront lawn, ideal for guests, a studio, or a home office. The main level bedroom sits near a beautifully updated full bath featuring new flooring, vanity, and lighting. The upper-level primary suite feels like a private retreat of its own. A spacious walk-in closet provides ample storage, while the ensuite bath, complete with an elevated soaking tub that feels like something out of Old Hollywood adds a touch of whimsy and charm. The open dual-vanity area and tucked-away water closet function beautifully while keeping the suite’s retreat-like feel intact.

Outside, the property shines with multiple decks, quiet sitting areas, and a gently sloping lawn leading to the water’s edge. The private dock, with an impressive 10' MLW, can accommodate up to five boats, an exceptional feature rarely found in Annapolis at any price point. Electric and potable water at the dock, with 30 AMP hook up. Boaters will appreciate both the depth and flexibility, with the potential to rent one or more slips for added income if desired.

Whether you're hosting waterfront gatherings, relaxing by one of the two stunning stacked-stone fireplaces, or unwinding on one of the many peaceful outdoor spaces, this home offers a lifestyle that balances luxury, comfort, and natural beauty. Warm, inviting, architecturally unique, and designed to embrace the water from every angle, this property offers a one-of-a-kind opportunity to enjoy deep-water living in a setting that feels like a year-round retreat.

A truly exceptional Annapolis offering where luxury design, cozy chalet ambiance, and premier boating features meet in perfect harmony.

ANNAPOLIS

1836 BURLEY LANE

3 Beds

3 Baths

2,016 Sq.Ft.

$1,695,000

MLS#: MDAA2132644

Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This exceptional 4-bedroom, 4-bathroom home is perfectly situated on the shores offering unique views of the Chesapeake Bay and Oyster Creek from nearly every room. Step inside to discover the open design, highlighting a gourmet kitchen designed for both beauty and function, featuring granite countertops, stainless steel appliances, and breakfast bar. The open-concept living and dining areas flow easily out to the multi-level waterfront decking, ideal for entertaining or simply enjoying the peaceful surroundings. The luxury primary suite is a true sanctuary, complete with a private waterfront deck, spa-like bathroom featuring a walk-in shower, soaking tub, and a generous walk-in closet. The third-level living space includes a full bath and offers endless possibilities—perfect as a media room, guest suite, or home office with elevated views.
Outside, a private pier with a 20,000 lb boat lift invites you to explore the water with ease. Whether you're boating, fishing, or just soaking in the serene creekfront setting, this property offers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own a slice of waterfront paradise on Oyster Creek. Property is in a Special Tax District. - $2,274.75 annually.

ANNAPOLIS

3300 SHORE DRIVE

4 Beds

4 Baths

2,798 Sq.Ft.

$1,650,000

MLS#: MDAA2116986

PHOTOS TO BE UPDATED THROUGHOUT BUILDING PROCESS!! This is a rare opportunity to own a newly built, beautifully designed home on a large lot in an established neighborhood-with nature at your doorstep and everything Annapolis has to offer just minutes away. This home is estimated to be completed in March, 2026. With a stunning Colonial architectural style, this beautiful home offers 5-bedrooms and 4.5-baths and sits on the last available lot in the Twin Hills neighborhood which is 1.4 acres and borders lush trees and a preservation area. It offers a rare blend of privacy, openness and a connection to nature. Whether you are hosting friends or enjoying a quiet night in, the thoughtful layout makes everyday living feel seamless and relaxed.

As you step inside, you are greeted by an inviting open floor plan with an abundance of light throughout that seamlessly connects the open-concept gourmet kitchen to the family room, creating an ideal space for both entertaining and everyday living. The kitchen features stainless steel appliances, including double wall ovens, cooktop and built-in microwave, complemented by a spacious island and quartz countertops. The Morning Room (Breakfast Room) and Conservatory offers light filled retreats year round. You will also find five generously sized bedrooms, each designed with comfort in mind. The primary suite is a true retreat, with a spacious sitting room and dual walk-in closets in addition to a luxurious en-suite bathroom featuring a soaking tub, walk-in shower, and dual vanities as well as dual water closets! The family room features 10’ ceilings and a relaxing gas fireplace to keep you warm in the cooler nights! The full basement, with an outside entrance, provides extra entertaining spaces with a extensive recreation room, true fifth bedroom and full bath as well as an unfinished area which leaves endless possibilities for customization, whether you envision a home theater, gym, or additional living space. The bedroom floor laundry adds a touch of practicality to daily routines, while the cozy family room off the kitchen serves as the heart of the home, perfect for relaxation and connection. The side-entry garage accommodates three vehicles and a generous amount of storage space, ensuring convenience and ease of access.

This residence is not just a home; it's a lifestyle choice that embodies luxury, comfort, and modern living. Experience the perfect blend of sophistication and warmth in this remarkable new construction home, where every detail has been thoughtfully curated for your enjoyment. All of this with an Annapolis address (and a close proximity to the water and fine restaurants Annapolis has to offer) to add to the joy you will feel from choosing this as your next home. Howmar Homes is a local builder dedicated to treating every house as if it were his own. With no shortcuts taken, each home reflects true care and craftsmanship you can see and feel in every detail. An optional inground pool has already been approved and has been cited on property for future or present consideration. If you act quickly, you can still select final finishings. Don’t miss your chance! Schedule your showing today!

ANNAPOLIS

1907 MACKIEBETH COURT

5 Beds

4 Baths

5,437 Sq.Ft.

$1,575,000

MLS#: MDAA2125858

Incredible Opportunity in the Heart of Eastport!

Beautifully remodeled Victorian located on the Eastport Peninsula. Features include a welcoming front porch, wood floors, and a chef’s kitchen with Viking appliances, a 6-burner stove, and vented hood. Windows and roof were replaced in 2025; roof includes new gutter guards. Energy-efficient appliances, including a gas on-demand water heater, have earned this home an Energy Star Certificate from BGE.

Flexible heating and cooling options with radiator heat and five mini-split units providing a total of 48,000 BTUs for heating and cooling. Skylights feature solar shades, and the fully encapsulated crawl space enhances year-round comfort and efficiency.

Upper level offers two bedrooms, each with a full bath, plus a full-size washer and dryer.

Enjoy a private, fully fenced backyard (new fence 2020) with mature native trees and landscaping—perfect for relaxing or entertaining. The detached accessory structure offers endless possibilities: office, studio, hobby room, or gym. And don't forget.....there is an off street driveway !!

This property is move-in ready—just bring your personal touch!

ANNAPOLIS

120 CHESAPEAKE AVENUE

2 Beds

2 Baths

2,130 Sq.Ft.

$1,449,000

MLS#: MDAA2130442

Don’t miss this stunning new construction in the highly desirable Homewood neighborhood of Annapolis. Perfectly situated within walking distance to downtown, this thoughtfully designed luxury residence offers the ideal blend of sophistication, comfort, and convenience. Step inside to soaring 9-foot ceilings on every level and a light-filled open floor plan. The gourmet kitchen is a chef’s dream, featuring 42-inch custom cabinetry, quartz countertops with coordinating backsplash, stainless steel appliances, and an oversized island that flows seamlessly into the dining area and spacious family room with a cozy gas fireplace. Sliding doors extend the living space to a private deck, creating the perfect setting for entertaining. A stylish powder room and functional mudroom with laundry space complete the main level. Upstairs, the expansive primary suite offers a large walk-in closet and a spa-inspired bath with double vanity, soaking tub, and glass-enclosed shower. Two additional bedrooms and a well-appointed guest bath provide both comfort and practicality. The finished lower level offers even more living space with a generous recreation room, a fourth bedroom, and a full bath—ideal for guests or extended family. Set on a charming tree-lined street, this home captures the unique character of Homewood with the benefits of modern construction. Residents enjoy a vibrant, walkable community with abundant green spaces and easy access to major routes, while remaining just steps from the energy of downtown Annapolis. This home offers the rare opportunity to experience the best of luxury living in one of the city’s most coveted neighborhoods.

ANNAPOLIS

1207 MCGUCKIAN STREET

4 Beds

3 Baths

3,150 Sq.Ft.

$1,395,000

MLS#: MDAA2127608

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