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

266

# of Listings

3

Avg # of Bedrooms

$529

Avg. $ / Sq.Ft.

$1,357,478

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

108 Properties Found. Page 2 of 8.

Open House SUNDAY 11/31 11AM-1PM. Please join us!Adorable bungalow coming soon in sought-after West Annapolis! Super fun, walkable location—catch Navy Midshipmen football games or stroll to Chessie’s Wharf, Positano’s, Bean Rush Cafe , Always Ice Cream Company & more! Just a short distance to Downtown Annapolis for waterfront dining, shopping, and historic charm. Easy one-level living with a great fenced-in yard and a large detached garage. Professional interior photos coming soon—stay tuned!

ANNAPOLIS

607 MELVIN AVENUE

2 Beds

2 Baths

1,102 Sq.Ft.

$899,000

MLS#: MDAA2136076

New Construction in Cape St. Claire. Home construction has now started. Delivery date will be end of August or beginning of September. Days on the market began when lot was purchased. Please look at the documents section of the listing to see all standard features included with this home and all floor plans and site plan. Pictures shown in this listing are of the home now framed and a previous completed home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire during the construction of that home. This same floor plan will be constructed on this site. Please contact listing agent with any questions.

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$896,000

MLS#: MDAA2130056

Some addresses just make life better. This one is tucked back in Beechwood on the Burley — a sought-after water-privileged community in St. Margarets, with private access to Burley Creek for kayaking, canoeing, and boating, plus a community pier, dock slips, and picnic area steps from your door. Downtown Annapolis is less than 2 miles away, yet the setting feels genuinely private, sheltered under a canopy of mature trees on a generous 0.7-acre lot.
The house itself offers a rare combination: five bedrooms a, an open kitchen-to-family-room layout, a potential main-level bedroom and full bath ideal for guests or multigenerational living, a kitchen island, and built-in Bose surround sound with TV that conveys. A dedicated main-floor den gives you the flexibility to work from home without sacrificing living space. The two-car attached garage with four additional driveway spaces means there is always room for boats, bikes, kayaks, and company.
Launch your boat from the private community ramp with quick access to Burley Creek and the Severn River, enjoy the community pier and waterfront playground, and experience the Annapolis lifestyle at its finest with easy access to restaurants, shopping, and marinas by both boat and car.
Whether you are upsizing into a home that finally fits the whole family, seeking a place to launch a kayak on a Tuesday morning before work, or looking for a Chesapeake Bay-area property that gives you space without sacrificing proximity to Annapolis, this home delivers on all counts.
Come see it before summer is in full swing!

ANNAPOLIS

1848 CHERRY ROAD

6 Beds

3 Baths

3,150 Sq.Ft.

$895,000

MLS#: MDAA2144280

Welcome to Kingsport—where timeless elegance meets waterfront living. Nestled within this coveted, water-privileged community, this exceptional 5-bedroom, 4.5-bath residence offers a seamless blend of sophistication, comfort, and everyday luxury.
A grand entry welcomes you with rich hardwoods and graceful architectural details, leading to a formal oval dining room, refined living room, and a private main-level office—perfect for today’s lifestyle. The heart of the home is a beautifully appointed gourmet kitchen, featuring a custom center island with cooktop, dual wall ovens, gleaming granite countertops, and extensive cabinetry. The space flows effortlessly into a dramatic family room, highlighted by soaring vaulted ceilings, plantation shutters, and a warm gas fireplace.
Upstairs, the primary suite is a true retreat, offering a spa-inspired bath and dual walk-in closets. An elegant en-suite bedroom and two additional bedrooms with a shared bath complete the upper level, offering both comfort and privacy.
The fully finished lower level is designed for entertaining and relaxation, featuring a spacious recreation room with a wet bar, a private guest suite, a playroom, and abundant storage.

Outdoors, a fully fenced backyard invites quiet moments and gatherings alike, with a paver patio, raised garden beds, and serene wooded views backing to scenic walking paths.

Residents of Kingsport enjoy an exceptional lifestyle with resort-style amenities including a community pool, playgrounds, hiking and biking trails, kayak launch and storage, and a picturesque pier on Crab Creek—ideal for sunset views, fishing, or peaceful afternoons by the water.

Perfectly positioned just minutes from downtown Annapolis and convenient to major commuter routes, this home offers the rare opportunity to live beautifully in one of the area’s most desirable communities.

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

3,586 Sq.Ft.

$865,000

MLS#: MDAA2143706

Quintessential Eastport charm in this sought-after Lower Eastport location. A welcoming front porch invites you to enjoy the vibrant local lifestyle. Inside, the light-filled layout features a spacious kitchen with a breakfast bar, a dedicated dining area, a convenient mudroom side entrance, half bath, & first-floor laundry. The upper level offers two generously sized bedrooms and a full bath. Relax on the large, private screened-in back porch overlooking a huge, level backyard perfect for entertaining. A standout feature is the over-sized detached shed/barn equipped with mini split (Heat and AC), ideal for a workshop, home office, or studio. This move-in-ready home is steps away from marinas, street-end waterfront parks, shopping, dining, and downtown Annapolis.

ANNAPOLIS

418 CHESAPEAKE AVENUE

2 Beds

1 Baths

1,128 Sq.Ft.

$850,000

MLS#: MDAA2147534

Our Adams model with a 2' extenstion will be built at this beautiful location near Duvall Creek. Home is priced at the base house only - act fast to choose the options and additions to make this home your own. Photos are of the model with optional In-Law Suite.
Contact Listing Agent to schedule appointment.

ANNAPOLIS

3268 KITTY DUVALL DRIVE

4 Beds

2 Baths

2,474 Sq.Ft.

$849,990

MLS#: MDAA2147542

Welcome to 1848 Carriage Road, a timeless gem that is beautifully situated in the highly sought-after Lindamoor community. Just a short stroll from the community beach and only a few streets from both neighborhood docks, this home offers the perfect blend of water accessibility, convenience, and undeniable charm.

Step inside to discover a warm and inviting main level filled with large windows and natural light. The spacious living room flows seamlessly into the dining area and kitchen, creating an ideal layout. Designed for easy living, the home functions like a rancher, with three generous sized, sun-filled bedrooms, two bathrooms and everything you need on the main level. The kitchen opens onto a deck overlooking a spacious, wooded backyard — perfect for gardening, entertaining, pets, or play.

The fully finished walk-out lower level significantly expands the living space and offers exceptional flexibility. With direct access from the garage and a large sliding door to the backyard, this level features a spacious family room, a separate sitting area perfect for a media room or home office, a large fourth bedroom, and a full bathroom. Abundant storage and versatile spaces provide endless possibilities for guests, fitness, recreation, or work-from-home needs.

Ideally located just minutes from historic downtown Annapolis, you'll enjoy easy access to waterfront restaurants, boutique shopping, marinas, and year-round cultural events, along with convenient commuting routes to both Washington, D.C. and Baltimore.

Offered at an attractive price and ready for its next owners, this is a rare opportunity to enjoy the lifestyle and amenities that make Lindamoor one of Annapolis’ desirable waterfront communities.

Don't miss your chance to make this charming property your new home.

ANNAPOLIS

1848 CARRIAGE DRIVE

4 Beds

3 Baths

2,622 Sq.Ft.

$849,000

MLS#: MDAA2148380

Experience the very best of downtown Annapolis living at Acton's Landing. Ideally located just a block from the waterfront and within easy walking distance of City Dock, Main Street, the Naval Academy, restaurants, shops, and marinas, this sought-after community offers an exceptional opportunity to enjoy a truly walkable Annapolis lifestyle.
Acton's Landing is known for its distinctive residences, where no two floor plans are exactly alike. Residents enjoy secure entry, elevators, a fitness center, library, beautifully maintained common spaces, and inviting outdoor gathering areas. The building has also undergone significant recent improvements, including a full interior refresh and exterior rehabilitation.
This light-filled residence offers over 1,400 square feet of comfortable one-level living. Large windows fill the home with natural light, while the open floor plan creates inviting spaces for both everyday living and entertaining. The updated kitchen features peninsula seating and opens seamlessly to the dining and living areas. Two private balconies provide additional outdoor living space.
The thoughtfully designed floor plan includes two spacious bedroom suites, each with its own updated bathroom and generous closet space, along with a dedicated home office and an additional half bath for guests. The living area includes a custom built-in entertainment center and a 55-inch Samsung (2024) television. Recent owner improvements include fresh interior paint, a new HVAC system, new hot water heater, new dishwasher, and an under-sink water filtration system, allowing the next owner to move in and immediately enjoy the home. Whether you're enjoying waterfront strolls, dining al fresco, summer concerts, or the shops and restaurants that make Annapolis such a special place to live, Acton's Landing places it all just outside your door.

ANNAPOLIS

66 FRANKLIN STREET 412

2 Beds

2 Baths

1,479 Sq.Ft.

$849,000

MLS#: MDAA2149170

New on site 1 day ago

An exceptional opportunity to embrace the coveted Eastport lifestyle while planning and permitting your future dream home. Situated on a generously sized lot in one of Annapolis' most desirable waterfront communities, this property offers the rare chance to move in, enjoy, and thoughtfully design your long-term vision.

The existing home is a contributing structure within the Eastport Overlay District, helping preserve the neighborhood's distinctive character and charm while offering potential for substantial expansion. Buyers are encouraged to conduct their own due diligence regarding future improvements, additions, and permitting requirements. The home features solid bones, off-street parking, and endless possibilities for customization.

Perfectly positioned just moments from Safe Harbor Marina, Annapolis Yacht Club, Eastport Yacht Club, Lewnes' Steakhouse, waterfront dining, shopping, and downtown Annapolis. Start enjoying everything Eastport has to offer this summer and create a legacy property in one of the Chesapeake Bay's most sought-after locations.

*The second photo is an AI concept*

ANNAPOLIS

513 FIFTH STREET

2 Beds

1 Baths

892 Sq.Ft.

$845,000

MLS#: MDAA2148872

Charming water-privileged split-foyer residence in the desirable Beale Manor community, offering 3,145 finished square feet of thoughtfully designed living space. Recent updates include a roof replacement, a newer water heater, fresh interior paint, and beautifully refinished flooring throughout the main level, enhancing both style and peace of mind. // The traditional layout begins with a formal living room featuring large picture windows that draw in abundant natural light and flows seamlessly into the formal dining room, creating an inviting setting for gatherings. The updated eat-in kitchen is both stylish and functional, showcasing crisp white cabinetry with sleek bar pulls, a peninsula breakfast bar, black appliances including double ovens, a built-in workstation, and a bright breakfast area with sliding door access to the screened porch. Just off the kitchen, the welcoming family room is highlighted by a white-washed brick fireplace and filled with natural light, while a convenient powder room and laundry area complete the main level. // The upper level features four generously sized bedrooms, including a spacious owner’s suite with a comfortable sitting area, dual closets—one a walk-in with a custom organization system—and a private ensuite bath with a soaking tub and separate shower. A centrally located full bathroom with an extended vanity serves the additional bedrooms. The walk-out finished lower level provides exceptional versatility, offering a large recreation space, a full bathroom, a bar area with a rough-in for a sink, and a fifth bedroom ideal for a home office, gym, or guest space. // Outdoor living is equally appealing, with a screened porch overlooking the backyard, an open-air deck that steps down to a patio, and a spacious, flat, fully fenced yard backing to trees for added privacy. // Residents of Beale Manor enjoy a wealth of community amenities, including a scenic waterfront pool, a basketball court, and a whimsical pollinator garden, fostering a vibrant, connected lifestyle.

ANNAPOLIS

3135 ANCHORAGE DRIVE

5 Beds

3 Baths

3,145 Sq.Ft.

$830,000

MLS#: MDAA2134882

Welcome home to this one of a kind three bedroom, two and a half bath rancher on a double lot in sought after Cape St Claire. One level living at it's finest, with a huge sunroom with vaulted ceiling on one wing, and the bedrooms on the other wing of this sprawling rancher. This property has been lovingly maintained by the owners, with the addition of the sunroom, powder room, laundry room, and part of the garage in more recent years. The 600 square foot light filled sunroom is the focal point of the house now, with wonderful built in bookshelves and entertainment center. The original family room has a wood burning fireplace, and makes a cozy den or office. Stainless appliances and table space in the kitchen with French doors leading to the stone patio out back. The living room and dining room have ample space for gatherings. In the bedroom wing of the house find the primary bedroom with an attached full bath and two more ample bedrooms share the hall full bath. Recent updates include; in 2020 - Fast Care Floor System installed in garage & driveway resurfaced, in 2023 a new roof, in 2025 new well pump, updated electric to code, one new air conditioner, new stainless steel liner in fireplace , & new oil tank, and in 2026 - new faucets in kitchen and master bath****** Cape St Claire amenities include, beaches, fishing/crabbing pier, boat ramp, playgrounds, marina, & more. Broadneck School District. Close to shops and restaurants. Mins from Downtown Annapolis, and easy access for commuter routes to Washington, Baltimore, and close to Ft Meade. Great location, minutes from downtown Annapolis, and good commuter location with quick access to Rt 50 & I-97 close to Washington or Baltimore

ANNAPOLIS

1047 LITTLE MAGOTHY VIEW

3 Beds

2 Baths

2,892 Sq.Ft.

$825,000

MLS#: MDAA2146800

#MDAA2149354

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 205

3 Beds

3 Baths

1,729 Sq.Ft.

$825,000

MLS#: MDAA2149354

Open House Sunday 12-2 Welcome to Winchester On The Severn. One of Annapolis's most established waterfront community's. This home provides mature landscaping with a canopy of lovely trees and bushes both in the front and rear yard. Covered front porch! You will be pleased to enter a spacious foyer. Main level bedroom with a full bath to the left. A few steps up to the open floor plan with spacious living room that feeds into the dining room. Be prepared to enjoy the screened porch off the dining room. A wonderful spot to relax and enjoy the back yard. The eat in kitchen is filled with light! Comfortable family room is complimented with a wood burning fireplace. And you can also walk out from the family room to the back yard! The basement is dry and has a new 2025 heat pump. The 3 additional bedrooms have fresh paint. The larger bedroom is en-suite. Ready to know about the neighborhood? Amenities include private beach on the Severn River, marina, boat ramp, multiple piers, dog beach, beach pavilion, and the Chase Creek swim club. Nearby is the B&A trail. You may not want to leave the home but if you do it is a short ride to Annapolis and all major routes. Welcome. Enjoy

ANNAPOLIS

1518 WINCHESTER ROAD

4 Beds

3 Baths

2,249 Sq.Ft.

$825,000

MLS#: MDAA2147986

The sellers are offering $10,000.00 towards purchaser closing costs!
Enjoy the water privileged lifestyle of the Annapolis Roads community on Lake Ogleton, Annapolis. This distinctive home offers an abundance of custom features, indoor and outdoor living spaces, great views, architectural details, and access to some of Annapolis' most sought-after waterfront amenities. From the beautiful screened porch / family room, to the covered deck, ivy covered brick walled patio, and sun room, there are many special areas to relax or entertain. The property backs up to the Lake Ogleton tidal wetlands, with all the associated wildlife!
The large number of windows and double doors provide natural light and amazing air flow throughout. The sunroom is a standout feature, showcasing hand-hewn beams, custom cabinetry, and a wall of New England-style windows that fill the space with natural light, and, of course, fresh air.
Custom lighting throughout the home highlights the crown moulding, built-in shelving, cabinetry, and workspaces. The spacious primary suite features an ensuite bath with a jetted tub, walk-in closet, and an additional shoe closet. A second jetted tub is located in the upper-level hall bath.
Extensive landscaping surrounds the property, creating multiple inviting outdoor spaces.
Major systems and appliances recently updated include the furnace (3 years), dishwasher, two air conditioning units( approximately 9 years), washer and dryer. Updated windows.
Residents enjoy access to Annapolis Roads' exceptional amenities, including a boat ramp, private beach, bayfront pavilion, bayside picnic area, playground, fire pit, community pier, kayak/SUP storage, extensive hiking trails, and a variety of neighborhood events throughout the year.
Drop your boat in and visit the Annapolis Historic District by water; something very
few neighborhoods offer.
A unique opportunity to enjoy the waterfront lifestyle, charm, character, and community spirit that make Annapolis Roads such a special place to call home.

ANNAPOLIS

2644 QUEEN ANNE CIRCLE

3 Beds

3 Baths

3,000 Sq.Ft.

$820,000

MLS#: MDAA2146714

Nestled in the charming Boucher Place community, this exquisite end-of-row townhouse offers a perfect blend of coastal and traditional architectural styles, creating a warm and inviting atmosphere. Built in 2013, this residence boasts 1,800 square feet of thoughtfully designed living space, ideal for those seeking comfort and elegance. The kitchen is a chef's dream, featuring upgraded countertops, a spacious island, and high-end stainless steel appliances, including a gas range and built-in microwave. The combination of hardwood on the main level, throughout adds a touch of sophistication, while plush carpeting in the bedrooms ensures a cozy retreat. The home features three generously sized bedrooms, each designed with comfort in mind. The primary suite is a true sanctuary, complete with a walk-in closet and a luxurious en-suite bathroom featuring a tub shower. Enjoy the warmth of the gas fireplace in the family room, creating a perfect ambiance for relaxation. Thoughtful details such as ceiling fans and window treatments enhance the home's comfort and style. Step outside to your private outdoor oasis, where a roof top balcony, deck, and patio await, perfect for enjoying morning coffee or evening gatherings. The beautifully landscaped courtyard view adds to the serene atmosphere, making it an ideal spot to unwind. This property also includes a detached two-car garage with rear entry, ensuring convenience and ample storage. The paved driveway and well-maintained sidewalks enhance the overall appeal of the home. As part of the Boucher Place community, residents benefit from included association services such as lawn maintenance, snow removal, and insurance, allowing for a low-maintenance lifestyle. Experience the perfect blend of luxury and comfort in this stunning townhouse, where every detail has been carefully curated to create a welcoming home. Embrace the exclusive lifestyle that awaits you in this beautiful property. New Roof in 2024 and new hardwoods in 2025.

ANNAPOLIS

19 BOUCHER PLACE

3 Beds

3 Baths

1,800 Sq.Ft.

$819,000

MLS#: MDAA2142690

1 2 3 4 ... 8

Buyers resources

7 Reasons to Work with a Realtor

7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

First Name

Last Name

Email

Phone

MLS Property Number

Your message

What is 3 + 4 ?

Reason for contacting?

Buying a home

Selling a home

Other

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

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

Update Your Temporary Password

Accessibility Menu

Personalize your search

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

or enter email address

Email address (Must be valid)

Already have an account ? Login here

Continue your home search

Email address

First name First Name

Last name Last Name

Phone number (Optional)

Password

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

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

Already have an account ? Login here

We use cookies

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

Privacy Policy Terms of Service