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

208

# of Listings

3

Avg # of Bedrooms

$513

Avg. $ / Sq.Ft.

$1,087,200

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$1M - $3M

46 Properties Found. Page 1 of 4.

#MDAA2123548

ANNAPOLIS

778 BON HAVEN DRIVE

6 Beds

4 Baths

5,094 Sq.Ft.

$2,800,000

MLS#: MDAA2123548

#MDAA2137670

ANNAPOLIS

1349 YORKTOWN ROAD

16 Beds

6 Baths

5,719 Sq.Ft.

$2,799,000

MLS#: MDAA2137670

**Open House - Sunday, March 29th, 11-1 pm** Welcome to 856 St Edmonds Place! Newly positioned $700k below recent appraisal! Have it all with stunning views from nearly every room, deep water, privacy, and a spacious floorplan for multi generational living! Spectacular custom built waterfront home in the sought after Downs community of Annapolis! Breathtaking views await you from every corner of this updated and well conceived home. Dramatic details throughout highlight the open floorplan and entertaining is a dream! Gourmet Kitchen with high end appliances, light filled formal dining room, soaring ceilings and imposing stone fireplace highlight the gathering room, cozy waterside family room off the kitchen, amazing primary suite with floor to ceiling windows, views to die for and luxurious bath and oversized closet, two additional bedrooms and a full bath complete the upper level, bright and airy lower level with family room, theater, two additional bedrooms with en suite baths, great views and plenty of storage, enjoy the flexibility of an enormous maintenance free deck and a stunning screened porch, attached two car garage and additional detached one car garage with an amazing 1 BR/1Bath updated in law suite/caretaker space, whole house generator, new tram and steps for convenient access to your pier with covered slip, two new boat lifts and jet ski lift nestled perfectly on Brewer Creek with quick access to the Severn River and the Chesapeake Bay! Located close to the community pool and sports courts with an an easy commute to Washington DC, BWI and Baltimore!

ANNAPOLIS

856 ST EDMONDS PLACE

5 Beds

4 Baths

6,412 Sq.Ft.

$2,795,000

MLS#: MDAA2136468

#MDAA2131890

ANNAPOLIS

703 GLENDON AVENUE

5 Beds

4 Baths

4,116 Sq.Ft.

$2,750,000

MLS#: MDAA2131890

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!

ANNAPOLIS

349 SHERWOOD TRAIL

3 Beds

3 Baths

3,185 Sq.Ft.

$2,550,000

MLS#: MDAA2137986

New on site 1 day ago

Welcome to 22 E Lake Drive! This exceptional waterfront residence offers striking architectural elements with expansive, light-filled interiors and seamless indoor-outdoor living along the Chesapeake Bay.
The main level open floor plan is designed for effortless flow and everyday living. The living room anchors the space, featuring a floor-to-ceiling stone fireplace and a wall of bi-fold glass doors that fully open to the pool and waterfront, creating a seamless extension of the home’s living and entertaining areas. Rich hardwood flooring, recessed lighting, and designer fixtures enhance the space throughout. A long, gallery-style entry hall offers a formal sense of arrival and includes a discreet powder room. The gourmet kitchen is both functional and elevated, featuring a large central island, custom cherry cabinetry, dark granite countertops, and a slate-tiled floor. High-end appliances include a gas range, double wall ovens, and a wine refrigerator. The slightly elevated, split-level design provides a clear vantage point over the dining and living areas while maintaining a defined culinary workspace.
The home’s multi-level layout offers intentional separation of its four bedrooms for optimal privacy. The first upper level includes two well-sized bedrooms, a shared hall bath, and the expansive primary suite.
The primary suite is a true sanctuary, defined by soaring wood-beam ceilings, a dramatic gabled roofline, and a wall of glass doors that open to a private balcony overlooking the water. A sliding barn door leads to the spa-inspired bath, wrapped in oversized charcoal slate tile and featuring an expansive wet room with multiple body jets and rainfall shower, a deep soaking tub positioned beneath a wall of windows, and a sleek floating dual vanity. The primary suite’s private balcony, finished with sleek cable railings, provides an elevated vantage point overlooking the pool, lawn, and panoramic water views. Above the suite, a unique loft space offers a quiet, sun-drenched retreat ideal for a home office, lounge, or library. Overlooking the bedroom below and framed by vaulted ceilings and a wide gable window, this elevated space captures sweeping waterfront views while maintaining a sense of privacy.
A detached carriage-style garage includes a fully independent above-garage suite, offering exceptional versatility. This space features over 500 square feet of open living area with A-frame ceilings and large windows, a full bathroom, a modern kitchenette with quartz countertops and high-gloss cabinetry, and a dedicated laundry area. With its own private access, it is ideal for guests, an au pair suite, home office, or creative studio.
The exterior is designed as a private waterfront retreat. A custom-shaped in-ground pool and elevated spa serve as the focal point of the backyard, surrounded by expansive decking for lounging and entertaining. A level, manicured lawn extends to the shoreline.
Enjoy direct access to the Chesapeake Bay via a shared pier, perfect for boating, crabbing, or taking in the sunset. Unforgettable sunsets, a premier Bay Ridge Annapolis location, a short walk to the community beach, and quick access to Route 50 and Downtown—this is waterfront living at its finest. Schedule your private tour today!

ANNAPOLIS

22 E LAKE DRIVE

3 Beds

2 Baths

2,338 Sq.Ft.

$2,550,000

MLS#: MDAA2139914

New on site 2 days ago

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 beautifully updated property offers the perfect balance of charm, comfort, and low-maintenance living, making it an ideal full-time residence or lock-and-go retreat. Thoughtfully improved in the last 2 years with a new roof, all full bathrooms remodeled with Restoration Hardware, new flooring on all 3 levels, fresh paint inside and out, raised ceiling in lower level, updated kitchen, floating dock, redesigned upper level with additional bathroom and a spacious balcony, just to name a few. 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!

ANNAPOLIS

327 RIVERVIEW TRAIL

3 Beds

3 Baths

1,831 Sq.Ft.

$2,495,000

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.

ANNAPOLIS

2215 CHESAPEAKE HARBOUR DRIVE E

3 Beds

3 Baths

3,086 Sq.Ft.

$2,300,000

MLS#: MDAA2131678

#MDAA2134136

ANNAPOLIS

2175 CHESAPEAKE HARBOUR DRIVE

4 Beds

4 Baths

2,513 Sq.Ft.

$2,295,000

MLS#: MDAA2134136

Embrace the ease of true coastal living in this beautifully appointed home, ideally situated just a short stroll from the waterfront and the bustling center of Downtown Annapolis. Blending classic seaside charm with refined finishes, this meticulously curated home features stunning interiors, where every detail reflects superior craftsmanship and thoughtful design. Rich hardwood flooring, custom moldings, and plantation shutters in the living room establish a sophisticated ambiance throughout. The formal living room, anchored by a gas fireplace, offers an inviting yet polished setting for both intimate evenings and gracious entertaining. At the heart of the home, the gourmet kitchen is impeccably appointed with professional-grade Thermador appliances, an expansive Silestone center island, and a custom-designed polished nickel pot rack by Ann Morris—a striking statement of artistry and function. Step out to the covered patio overlooking the thoughtfully designed gardens, creating a seamless transition between refined interiors and serene outdoor living. The primary suite is a sanctuary of comfort and privacy, featuring two substantial walk-in closets, a spa-inspired bath and a private balcony. A separate den on the primary suite level with its own balcony provides space for a study or a quiet reading room. The third level features two additional ensuite bedrooms both with vaulted ceilings, one offers a private balcony and the other a French balcony - both bathed in natural light and architectural character. Completing this exceptional offering is a detached two-car garage with unfinished storage above and the added exclusivity of private gated parking. The large unfinished lower level is perfect for extra storage! Perfectly positioned within walking distance to Downtown Annapolis’ acclaimed restaurants, boutiques, and cultural attractions, this home presents a rare opportunity to experience coastal living with grace, sophistication, and enduring style.

ANNAPOLIS

400 CHESAPEAKE AVENUE 2-101

3 Beds

3 Baths

2,566 Sq.Ft.

$2,150,000

MLS#: MDAA2137608

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

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 modern 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 four 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 above. 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.

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,990,000

MLS#: MDAA2131396

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.

ANNAPOLIS

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$1,895,000

MLS#: MDAA2137314

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