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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

353

# of Listings

3

Avg # of Bedrooms

$481

Avg. $ / Sq.Ft.

$1,099,099

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

353 Properties Found. Page 8 of 24.

Waterfront Living in Epping Forest with Stunning Views!

Nestled in the exclusive, gated community of Epping Forest, this beautifully maintained 2-bedroom, 2.5-bath home offers serene water views and a relaxed yet sophisticated lifestyle. Designed for effortless living, the open floor plan features 10-foot ceilings, gleaming hardwood floors, and a cozy fireplace in the Great Room. The expansive gourmet kitchen flows seamlessly into the all-season sunroom, complete with dedicated HVAC and stunning water vistas. A convenient half bath and laundry room complete the main level.

Upstairs, the grand owner’s suite boasts an oversized walk-in closet, a spa-like bathroom, and a private deck overlooking the water—perfect for morning coffee or evening sunsets. A spacious guest bedroom (or ideal office/den) with a charming full bath completes the upper level.

Outside, a fully fenced yard provides a secure space for furry friends to play freely. Off-street parking is plentiful, a rare and highly sought-after feature in this private enclave.

Epping Forest is more than a neighborhood—it’s a lifestyle. This vibrant waterfront community offers a marina with direct Severn River access, a private beach, clubhouse with a restaurant, boat club, fishing tournaments, tennis, volleyball, basketball, and year-round social events like oyster roasts, dock parties, summer camps, and holiday celebrations, including spectacular July 4th fireworks.

Located just minutes from major highways, shopping, and Historic Downtown Annapolis, this is a rare opportunity to experience the best of waterfront living. Come discover the charm of Epping Forest and make it your home!

ANNAPOLIS

336 SEVERN ROAD

2 Beds

2 Baths

1,708 Sq.Ft.

$975,000

MLS#: MDAA2110674

Stunning contemporary home in Winchester on the Severn featuring abundant windows that provide private treetop views. Situated at one of the highest elevations, the property is surrounded by parkland and overlooks wooded areas. Enjoy multi-level decks, stone patios, and custom hardscaping, complete with a private putting green and hot tub. The community offers a voluntary association fee of $260 per year for access to amenities, including a private beach, dock, canoeing, playground, covered picnic pavilion and 2 areas with boat slips (extra fee) The Chase Creek Swim Club is also nearby (extra fee). A true gem!

ANNAPOLIS

1534 CIRCLE DRIVE

5 Beds

3 Baths

2,316 Sq.Ft.

$975,000

MLS#: MDAA2116724

Welcome to 1141 Mainsail Drive, a renovated Classic Colonial style home located in the sought-after Waterfront Community of Anchorage. This 4-bedroom, 2.5-bathroom property has undergone over $200,000 in renovations over the past 20 years while preserving its classic colonial charm. This beautiful corner lot has a newly repaved driveway, a 2-car garage and is only a block away from the amenities which include a 49-slip marina, a boat ramp, an outdoor pool, racks for kayak and paddle boards and a half basketball court.
Many improvements have been done throughout the home including a total refurbishing of the hardwood floors (main level and upper level), fresh paint, upgraded kitchen with marble countertops and stainless-steel appliances, gas line, renovated bathrooms, replacement of windows, roof, siding, gutters, finished basement and water proofing (French drain), laundry room with 2021 washer and dryer, furnace, water heater, well pump, sump pump, sewer line and more.
The tall symmetrical windows in the main level invite light into this classic colonial style layout with a newly painted double-sided masonry wood burning fireplace and an open-layout kitchen. The main level includes a foyer, powder room, family room, living room, dining room and kitchen. The eat-in-kitchen flows seamlessly into “the heart of the home”, the casual dining area and family room, creating an open and inviting space for everyday living. The French doors from the casual dining area lead to a rear brick patio for outdoor entertainment. The 2-car garage is attached to the home with direct entrance into the main level. The upper level features 4-bedrooms, 2-upgraded bathrooms and a den/home office nook. The lower level is a fully finished basement with space for a recreation room, home office and/or fitness area. Also, there is a renovated Laundry / Utility Room with an additional storage space.
Do not miss this opportunity to purchase a renovated colonial in Anchorage as they are a rare find and especially at this price point. Anchorage is a small community (106-homes), with no cut through streets, and mature landscaping. This .34-acres property is 3.5-miles from downtown historic Annapolis, 1-mile from the 340-acre Quiet Waters Park, 35-miles from Washington D.C. and 32-miles from Baltimore.

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

2,176 Sq.Ft.

$970,000

MLS#: MDAA2108692

OPEN HOUSE THIS SATURDAY JUNE 7th 11-1
Welcome to 712 Pearson Point Place—The best lot location in Kingsport! This beautifully maintained property is ideally situated in a sought-after pool and dock community with scenic walking paths. Featuring five spacious bedrooms, four and one half bathrooms, fully finished basement, and a stylish, functional layout, this home offers both comfort and elegance. Enjoy light-filled living spaces, a well-appointed/updated kitchen, and inviting outdoor area perfect for relaxing or entertaining. With top-tier community amenities just steps away, this is Kingsport living at its finest!

ANNAPOLIS

712 PEARSON POINT PLACE

5 Beds

4 Baths

5,184 Sq.Ft.

$970,000

MLS#: MDAA2113996

Price Reduction to this former model home in Kingsport! Step into an inviting two story foyer that sets the tone for the entire residence! This home offers a blend of elegance and functionality. Many updates have been done by current homeowners. A three story, three-sided brick home on a corner lot that emanates timeless elegance. This home has two inviting front porches for relaxation. Entering the two story foyer with marble floor, you will see framed mirrors, and a Juliet balcony. A formal living room, hardwood floors, and one of three gas fireplaces. A bay window for your grand piano, or to sit with morning coffee. The dining room, includes a mirrored wall, and hardwood floors. A half bath with marble tile floor is off the living room. An open concept kitchen, family room, laundry room and pantry are situated towards the back of the home. The kitchen is an entertainer's dream with a large two level granite island with cooktop, hardwood floors, and a double wall oven for your holiday baking! A walk-in pantry with ample shelving. The family room has floor to ceiling windows, hardwood floors, and the second gas fireplace situated next to built in glass shelves. The family room looks out on a private enclosed fenced back yard with a two level gray slate patio to enjoy the gardens.
On the second level, you will find a split hallway with hardwood floors. The primary bedroom, includes an attached bathroom which was updated in March 2022; a soaking tub with jets and a walk-in shower with dual shower heads, dual sink vanities, quartz counter tops. The primary bedroom, has a ten foot tray ceiling, ceiling fan, recessed lighting, wainscoting, two walk-in closets, and a sitting area for relaxing. There are three other bedrooms on the upper level, the largest of the three features a private porch, hardwood floors, private bath with tub/shower, and ceramic tile floor. Perfect for visitors. Another bedroom features built-in bookshelves. The last of the four bedrooms overlooks the upstairs porch.
The lower level is fully finished. A family room with built in counter w/cabinets, wainscoting, an egress window. Another room serves as a bonus room or flex room that could be used as a fifth bedroom, and is currently used as a gym, with a wall of mirrors, built-in counter with shelving and drawers. There is also a home office that is a homeowners dream, with built in bookcases, shelving to store your books, and the third gas fireplace. Another room currently used for storage, can be used for hobbies, or to store your wine. A full bathroom is also located on the lower level. Crown molding throughout enhances the character of this home.
Two new Air Conditioner Units- August 2017 and July 2019. Duct cleaning - March 2024, New Roof-Oct.-2019, Hardwood floors on main floor and stairs were refinished-May 2024. Kitchen counter to match kitchen island granite w/new sink April 2025. Sound surround throughout the house to include the outdoor patio. Central Vac, Sprinkler System, 75 Gallon Hot Water Tank- February 2022, Hot/cold water faucet in the garage, Security system.
A community pool, two tot lots, walking trails, water access to Church Creek, dock, kayak launch, and kayak storage.
Convenient to Rt.50/97 to D.C., Baltimore, Bay Bridge and beaches. 3.2 miles to Naval Academy, and historic downtown Annapolis.

ANNAPOLIS

709 PILOT HOUSE DRIVE

4 Beds

4 Baths

4,494 Sq.Ft.

$959,900

MLS#: MDAA2111234

New on site 1 day ago

**Professional photos coming soon** Showings start Friday June 6th

Welcome to 918 Preserve Drive in the very desirable community of Chesapeake Preserve. This large traditional colonial has exceptional curb appeal with its New England style stone front and welcoming front porch. The home offers a traditional floor plan with generous rooms on all levels. The center hall foyer has a vaulted ceiling and great light, and leads to a large living room and dining room. The eat-in kitchen has been updated with painted cabinetry and quartz countertops, and opens to a generous family room with a stone gas fireplace. Large windows provide natural light throughout the home. A home office and laundry room are also located on the main level. Upstairs you'll find an expansive primary suite with a sitting area, walk in closets, and a primary bathroom with both a walk-in shower and soaking tub. There are three additional bedrooms and a full bathroom on the second level. New carpet was about to be installed by the current owners, who are offering a credit to the next homeowner so that they may choose the carpet/flooring of their choice.
The finished basement with a full bathroom offers many options as additional recreation space. The current owners added new carpet to the entire basement, and have these areas currently arranged as a workout room, family recreation room and an additional bedroom.
Recent improvements to the home include: all new door hardware throughout, new light fixtures on main level, interior paint, fresh paint and new hardware to kitchen cabinets, new quartz countertops, Nest thermostats, new window treatments to the upstairs bedrooms, new carpet in the basement and a new sump. The sellers are offering a $12,000 credit to buyers for new carpet selections in the rest of the home.

The home has a lovely fenced rear yard abutting an expansive green space that is part of a county easement providing clear views of fields and woods. This well maintained area acts as an extension of the yard with room to play, walk dogs, and access wooded trails. Chesapeake Preserve is a quiet residential community with shared common areas, and backs to a Corcoran Environmental Study Area, a state owned woodland preserve managed by DNR adjacent to Sandy Point State Park.

ANNAPOLIS

918 PRESERVE DRIVE

5 Beds

3 Baths

4,388 Sq.Ft.

$959,000

MLS#: MDAA2116752

🏡 1367 Cedar Avenue – Modern Comfort Meets Coastal Charm

Set on a beautifully landscaped corner lot just two blocks from Fishing Creek, this 5-bedroom, 3.5-bath updated craftsman colonial in Arundel on the Bay is the kind of home that instantly makes you feel at ease. Think breezy porch mornings, backyard cookouts, and friendly neighborhood waves—it’s Annapolis living at its best.

The welcoming slate front porch leads you into a light-filled main level with an open-concept layout that’s perfect for entertaining or simply enjoying everyday life. The expanded gourmet kitchen is the heart of the home, featuring quartz countertops, stainless appliances, a big island/breakfast bar, Restoration Hardware lighting, and custom soft-close cabinetry. Off the foyer, a cozy window seat invites you to curl up with a book or a coffee. The main-level office (or 5th bedroom!) faces the front and includes custom built-in cabinetry—ideal for guests, work-from-home days, or creative projects.

Upstairs, you’ll find four generous bedrooms with custom-designed closets, plus a newly added Kohler walk-in Jacuzzi tub in the hall bath—perfect for relaxing soaks or added accessibility.

Downstairs, the fully finished lower level adds even more flexibility with a spacious rec room, full bath, laundry, workshop, and a large storage room—everything you need, right where you need it.

Step outside and the fun continues! The fenced backyard was designed for gathering and play, featuring a custom HardiePlank deck with a built-in grill, storage bar, and room to lounge or entertain. There’s a Wi-Fi-controlled irrigation system, a professionally manicured lawn, and an expanded stamped concrete driveway. The oversized garage includes smart built-in storage, and the 20kW whole-home generator ensures you’re never left in the dark.

This smart home also includes a Nest thermostat, video doorbell, dual-zone HVAC, and automatic lighting—because convenience is a luxury too.

Living in Arundel on the Bay means more than just enjoying the beach and pier (though they’re pretty great). With a boat ramp, kayak racks, playground, basketball court, and community events like paddleboard yoga, movie nights, and summer beach parties, this neighborhood is as fun and welcoming as they come.

ANNAPOLIS

1367 CEDAR AVENUE

5 Beds

3 Baths

3,036 Sq.Ft.

$949,000

MLS#: MDAA2116610

Living in Shearwater is truly a dream, offering the perfect blend of leisure, recreation, and waterfront serenity. This exclusive gated community boasts top-tier amenities, including a deep water marina, dinghy floating dock, kayak launch, pickleball, tennis, racquetball courts, and a stunning waterfront pool. Conveniently located, it's an easy, nice walk, bike ride, or water taxi trip to downtown. For outdoor enthusiasts, kayaking right from your doorstep adds to the unparalleled lifestyle. This beautifully appointed waterfront terrace condominium provides the convenience of one-level living with 1855 sq. ft. of thoughtfully crafted space, ensuring comfort and southwest exposure. The Kitchen includes a handsome kitchen bar, perfect for entertaining friends or enjoying a glass of wine while cooking up your favorite meal. The sleek, modern design is complemented by high-end induction cooking, offering precision and efficiency for the discerning home Chef. Well-appointed walk-in pantry. A sliding glass door in the kitchen leads to an ample alfresco area ideal for entertaining and grilling. The generous living room invites relaxation with a cozy wood-burning fireplace. Cozy nook with window seat . The roomy laundry room provides additional storage. Private office nook off the Primary suite, perfect nook for working from home, managing daily tasks, tucked away for privacy yet conveniently accessible. Observe blue herons, egrets, ducks, and bald eagles from your garden terrace. There are boat slips available depending on size and water depth. The cost of $62 per foot of overall boat length per year. Most slips are 15-18 wide. Depth ranges 6-8 ft MLW. Power and water included. The marina includes 34 slips owned by the Shearwater Association, as well as 28 slips that are deeded to Condominium Owners. Other facilities owned by the Association include 13 spaces for dinghies and 42 spaces for kayaks. Electricity and water are available to all users of the marina facilities at no charge. Dinghies $195 per year - Kayaks $100 per year. LCE slip owners may also rent their slips to other condominium owners or tenants. Contact the Dockmaster for all information regarding resident and guest slip availability. Spa Creek is one of the most sought-after waterways in all of Annapolis, taking you to downtown Ego Alley. Perfect spot to watch the Parade of Lights in December, a tradition in Annapolis. And best of all, it's nestled along the waterfront, offering peaceful mornings and golden hour views and the kind of lifestyle that turns every day into a getaway.

ANNAPOLIS

3 SPA CREEK LANDING A

2 Beds

2 Baths

1,855 Sq.Ft.

$948,000

MLS#: MDAA2112968

• Eclectic downtown location with 8 on-site parking spaces
• Unit has a reception/bullpen area, 5 offices, a kitchen that seats 4, copy/fax room and 2 restrooms (one with shower)
• Upgraded finishes and systems throughout
• Close proximity to Maryland State House, Circuit Court, State Office Buildings, United States Naval Academy, Annapolis City Dock, and St. John’s College
• Walking distance to Rams Head Bar & Grill, El Toro Bravo, Level, Tsunami, and various retail shops and services
• Taxes for the unit are $10,040 annually
• MX zoning, permitting uses of office, retail, restaurants, galleries, and laboratories.

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

N/A

$940,000

MLS#: MDAA2110468

An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. Built by a member of the renowned Willard family, whose craftsmanship helped shape the Chesapeake Bay deadrise fishing boat, this property carries a rich history and offers a rare chance to create something truly special. The home itself features hardwood floors, beamed ceilings, and a screened-in porch - all positioned to capture the scenic surroundings. With a little thinning of the underbrush, you’ll have stunning water views from most rooms! Looking for even more potential? The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department requirements, with the final piece being a public water extension along the existing house frontage. The subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the legwork to get it to this point will convey.
This is more than just a home—it’s a unique opportunity to craft your dream estate in a prime Annapolis location. Don’t miss out—schedule your showing today to explore the possibilities!

PLEASE NOTE: The home does have a moisture issue, and the HVAC system is not currently functioning. Call agent for more info. Documentation for the subdivision efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The home is being sold strictly as-is, where is. Any inspections for buyer's information only.

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2116058

**PRICE IMPROVED** An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. Built by a member of the renowned Willard family, whose craftsmanship helped shape the Chesapeake Bay deadrise fishing boat, this property carries a rich history and offers a rare chance to create something truly special. The home itself features hardwood floors, beamed ceilings, and a screened-in porch - all positioned to capture the scenic surroundings. With a little thinning of the underbrush, you’ll have stunning water views from most rooms! Looking for even more potential? The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department requirements, with the final piece being a public water extension along the existing house frontage. The subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the legwork to get it to this point will convey.
This is more than just a home—it’s a unique opportunity to craft your dream estate in a prime Annapolis location. Don’t miss out—schedule your showing today to explore the possibilities!

PLEASE NOTE: The home does have a moisture issue, and the HVAC system is not currently functioning. Call agent for more info. Documentation for the subdivision efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The home is being sold strictly as-is, where is. Any inspections for buyer's information only.

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2103336

#MDAA2114818

ANNAPOLIS

735 GLENWOOD STREET

3 Beds

2 Baths

2,634 Sq.Ft.

$895,000

MLS#: MDAA2114818

#MDAA2109972

ANNAPOLIS

710 CRISFIELD WAY

4 Beds

4 Baths

4,612 Sq.Ft.

$885,000

MLS#: MDAA2109972

Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community: Welcome to 3117 Port Way, a beautifully updated home nestled in the highly desirable Anchorage Waterfront community of Annapolis. This spacious 5-bedroom, 3-bathroom residence offers approximately 2,400 square feet of open-concept living space on a 0.34-acre lot, complete with a partially fenced backyard and invisible fence, ideal for pets or added privacy. This move-in-ready property combines modern comfort, thoughtful upgrades, and premium waterfront community living—an absolute gem in Annapolis!

Step inside to discover a bright and airy layout enhanced by large windows that invite abundant natural light and offer tranquil views of the mature landscape. The modern kitchen is a chef’s delight, featuring quartz countertops, a gas range, white cabinetry, skylights, and stainless-steel appliances. Additional highlights include a 1-car garage, generous living and dining areas, and thoughtful updates throughout.

The primary bedroom features its own en-suite bathroom, providing a private retreat within the home where you fall asleep hearing the horns of ships anchored on the Chesapeake Bay. The family room offers a cozy ambiance with a wood-burning fireplace and a rough-in for gas conversion, flanked by custom wall built-ins—perfect for displaying books, décor, or media. Throughout the upstairs bedrooms, primary bath, and lower-level bedrooms, you’ll find professionally installed solid wooden doors, adding a refined and durable touch. A laundry chute conveniently located in the hallway bathroom leads to a well-equipped laundry room with ample storage space and an adjacent separate utility room for added organization.

The main level boasts gleaming hardwood floors, seamlessly connecting the living, dining, and kitchen areas in a cohesive open-plan layout. Comfort meets efficiency with a high-efficiency cooling system and hydronic gas heating for year-round comfort. Additional upgrades include a water treatment system with softener, a whole-house central vacuum system, and a gas generator.
A new roof was installed in April 2025, adding value and durability, while the spacious backyard provides the perfect setting for entertaining, relaxing, or enjoying outdoor activities.

Located in the highly sought-after Anchorage Waterfront community, residents enjoy exceptional amenities with an HOA fee of just $118/month, which includes access to a boat slip, marina, boat ramp, community pool, rack for kayaks and paddle boards and a half basketball court. Don’t miss the chance to own this hidden gem in one of Annapolis’s most coveted neighborhoods.

ANNAPOLIS

3117 PORT WAY

5 Beds

3 Baths

2,288 Sq.Ft.

$875,000

MLS#: MDAA2116652

Located just across from the Annapolis Library and minutes from the heart of downtown, this 1940s home blends preserved historic charm with prime land potential. Set on a large, flat lot, it offers original refinished pine floors, arched entryways, solid wood doors, and built-in features that speak to a level of craftsmanship rarely found today.

The main level includes two bedrooms and a full bath, a sun-filled living room with built-ins and a wood-burning fireplace, and a separate sunroom ideal for quiet mornings or flexible living space. Upstairs, three additional bedrooms and another full bath provide space for family, guests, or a home office setup.

A walk-up attic—recently insulated—offers the option to finish for added living space or use as-is for ample storage. The unfinished basement presents even more flexibility. Outside, a large, detached two-car garage sits at the rear of the lot, offering convenience and potential for future workshop or studio space.

The home has been freshly painted throughout and updated with modern lighting fixtures. Electrical systems have been fully updated, including GFCI protection and grounded outlets—bringing peace of mind without sacrificing the home's character.

This property caters to a range of possibilities. Ideal for those drawn to historic architecture and character-filled spaces, it’s also a strong contender as a land offering in an enviable location. Whether you’re envisioning a personal renovation, restoring and expanding on its original bones, or considering the lot for future development, the location—walkable to downtown and steps from the library—makes this a rare opportunity.

ANNAPOLIS

1411 WEST STREET

None Beds

None Baths

0.49 acres

$875,000

MLS#: MDAA2112956

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