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
264
# of Listings
3
Avg # of Bedrooms
$418
Avg. $ / Sq.Ft.
$854,290
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

264 Properties Found. Page 5 of 18.

A Rare Exceptional Retreat in Winchester Estates — Annapolis, MD Welcome to an extraordinary custom-built residence where timeless elegance meets unparalleled serenity. Set on a magnificently landscaped, park-like acre, this 5-bedroom, 4-bath estate offers a level of privacy and tranquility seldom found so close to the heart of downtown Annapolis. Nestled within the prestigious Winchester Estates, this property grants private water-access creating a lifestyle that blends luxury living with the best Annapolis has to offer. Inside, unique design and exceptional craftsmanship define every space. The chef’s kitchen, outfitted for the culinary enthusiast, anchors the main level and opens seamlessly to a grand, light-filled living area—an ideal setting for refined entertaining or intimate gatherings. Expansive windows invite the lush landscape indoors, enhancing the home’s natural harmony and sense of calm. The elegant lower level offers a rare level of versatility, featuring a full private suite with its own bedroom, bathroom, kitchen, dining room, and living room—perfect for multigenerational living, distinguished guest accommodations, or an au pair residence. Outside, the estate’s grounds unfold like a private sanctuary. Mature trees, newly developing gardens, and verdant open spaces create an atmosphere of effortless peace—a truly restorative environment just minutes from world-class dining, boutique shopping, and the historic charm of Annapolis. Highlights Include: * Custom-built architecture on a serene 1+ acre park-like lot * Extensive cutting-edge electronic pet fence system * Exclusive neighborhood water-access privileges * Right next door to the beautiful Baltimore Annapolis Trail Park * Gourmet chef’s kitchen with Blue Star 8 Burner Stove and expansive entertaining areas * Full private lower-level suite with separate living quarters * A Total of Five spacious bedrooms and four well-appointed bathrooms * Two upper level bedrooms have self-contained climate control * Exceptional privacy in one of Annapolis’ most coveted communities * Full Premium Warranty Offered This is more than a home—it is a private retreat offering refined luxury, natural beauty, and an unmatched Annapolis lifestyle.
#MDAA2130382

ANNAPOLIS

1635 WINCHESTER ROAD

5 Beds

4 Baths

3,660 Sq.Ft.

$1,139,400

MLS#: MDAA2130382

Walk in and be amazed with a beautiful and luxurious remodeled open floor concept. Open the front door and look to the gorgeous living room with electric fire place that produces up to 5,000 BTU of heat for the comfort on cold and snowy days. Living room flows into your brand new gourmet style kitchen set up for fabulous days of entertaining friends and family. Main floor offers a spectacular primary bedroom with a personal home office and access to a private deck to enjoy the outdoors along with a private laundry room for your convenience not to mention a large room ready to be made into the closet of your dreams, even better a bathroom with a spa like atmosphere , In addition the main floor has an in law suit with a private bathroom and access to a covered deck area. Lets walk to the second floor where you will be amazed with a spectacular second living room/game room/ study area/ etc. make this room as you wish for any entertainment. Three great bedrooms, 2 share a large bath and one with a private in suit bath, all three with walk in closets. All new floors throughout the home along with all new lighting The expansive basement with over 2,700 SQ.FT has an open concept where you can let your imagination take over along with a second home office and full bathroom. This house is conveniently located off Riva rd, just a few minutes from Downtown Annapolis, plenty of near by shopping including Annapolis Mall and a multitude of restaurants. DON’T LET THIS ONE PASS YOU BY !
#MDAA2127360

ANNAPOLIS

301 UNITY LANE

5 Beds

5 Baths

7,616 Sq.Ft.

$1,127,000

MLS#: MDAA2127360

Price Reduction: Motivated Seller BRING ALL OFFERS! Get ready to fall in love with this Annapolis gem Nestled in the sought-after Captain Cove neighborhood on a 1.21-acre wooded lot, this beautifully maintained home is minutes from downtown Annapolis. Unique features include a rooftop deck, expansive back decking, and a bonus treehouse that doubles as a fun space for children or a peaceful retreat for adults—perfect as a she shed or man cave. This is a cozy place to call home, look no further . Don’t miss your chance to own a piece of Annapolis charm. Professional photos to follow!
#MDAA2115552

ANNAPOLIS

15 E NAP LANE

5 Beds

3 Baths

5,465 Sq.Ft.

$1,100,000

MLS#: MDAA2115552

Development opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.). Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Assemblage possible with adjacent buildings at 2 & 4 Annapolis Street grossing rent from 6 retail & 2 residential tenants totaling $20,700/Mo.
#MDAA2127368

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

2,064 Sq.Ft.

$975,000

MLS#: MDAA2127368

Time to Make a Lifestyle Change – Stunning & Fabulous at The GrandView! Welcome to The Flagship, a unique and highly sought-after corner unit in the premier GrandView community. Perfectly positioned for the best location, views, and luxury, this residence offers an unmatched lifestyle in the heart of Annapolis Town Center. Step inside and be captivated by the wall of windows that flood the space with natural light and showcase panoramic views of Annapolis Town Center’s vibrant activity. Enjoy morning coffee or evening cocktails from your private, covered corner balcony. This 2-bedroom, 2-bath home is beautifully appointed with granite countertops, 10-foot coffered ceilings, hardwood floors, and custom window treatments. Recent upgrades include: New HVAC system, New stainless steel appliances, New bedroom carpeting, Updated lighting and black hardware through out. Additional features include an assigned storage unit and two reserved garage parking spaces. Residents of The GrandView enjoy luxury amenities such as: Concierge services, Fitness center, and Rooftop pool with stunning city views. Live the walkable lifestyle! Stroll to Whole Foods Market, Target, fine dining, cafés, banking, and boutique shopping—all just steps from your door. You’re minutes from Historic Downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center, and with easy access to Route 50 and I-97 for effortless commuting. This is truly a must-see residence—a perfect blend of comfort, convenience, and modern elegance in one of Annapolis’ most desirable addresses.
#MDAA2127946

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1004

2 Beds

2 Baths

1,794 Sq.Ft.

$975,000

MLS#: MDAA2127946

Redevelopment opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.) Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Possible assemblage with adjacent 2 buildings at 2-4 Annapolis Street...gross rents totaling $20,700/Mo. from 6 retail & 2 residential tenants. Total land area for 2, 4 & 10 Annapolis Street is approximately 37,500 sq. ft. (0.86 acres).
#MDAA2127370

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

0.34 acres

$975,000

MLS#: MDAA2127370

This stunning home is move-in ready and boasts high-end upgrades throughout. It features a first-floor owner's suite, plus three additional bedrooms on the second level, along with two full bathrooms and a spacious loft. The gourmet kitchen is a chef’s dream, complete with custom cabinetry and an open-concept design. The impressive two-story family room with soaring ceilings creates a dramatic focal point, while the finished basement rec room, featuring a wet bar with a refrigerator and sink, is perfect for entertaining. Experience luxury living at its finest—schedule your tour today! Photos for illustration purposes only. Agent must attend first visit.
#MDAA2125928

ANNAPOLIS

106 STILLY WAY

4 Beds

4 Baths

4,594 Sq.Ft.

$974,990

MLS#: MDAA2125928

Nestled in the serene Dellwood community, this contemporary gem offers an exclusive lifestyle defined by luxury and comfort. Perfect location leaves you minutes from downtown Annapolis, Luminus Health Hospital as well as all the charm Annapolis proper (Parole) has to offer. Step inside to discover an inviting open floor plan adorned with rich hardwood and ceramic tile flooring, seamlessly blending elegance with warmth. The heart of the home features a country-style kitchen equipped with stainless steel appliances, including a six-burner stove and double ovens, perfect for culinary enthusiasts. Main level bedroom if needed with full bath attached. Currently being used as the office. Unwind in the spacious living area, complete with a cozy wood stove or wood burning fireplace and built-in sound system, or retreat to the inviting screened in porch to take in the natural setting of this large corner lot. Enjoy outdoor living with multiple decks and porches, a personal lap pool, ideal for exercise or relaxation. The property also includes water access to the Severn River with boat slip included if that fits your needs , enhancing your lifestyle with boating and fishing opportunities. With an attached garage and additional storage, this home is designed for effortless living.
#MDAA2131896

ANNAPOLIS

1800 SEVERN GROVE ROAD

3 Beds

3 Baths

2,281 Sq.Ft.

$967,000

MLS#: MDAA2131896

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry. Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion. Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs, while the detached three-car garage offers access to an unfinished upper-level space that provides additional room to tailor to personal needs. A back deck extends off the main level, with a second deck accessible from the unfinished space above the three-car garage. Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.
#MDAA2131620

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$949,900

MLS#: MDAA2131620

• 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.
#MDAA2110468

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

1,971 Sq.Ft.

$940,000

MLS#: MDAA2110468

Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a half bathrooms. You’ll fall in love the moment you walk in! Highlights include a large eat-in kitchen that opens to the family room, perfect for gatherings, plus a mudroom with ample storage. There’s even a cozy area off the kitchen ideal for a home office or homework station. The oversized owner’s suite boasts a custom walk-in closet and a spacious bathroom for the ultimate retreat. The fully finished basement includes a full bathroom, and the three-car garage provides plenty of space for vehicles and storage. All of this sits on a flat lot in a quiet cul-de-sac, offering both privacy and convenience.
#MDAA2127206

ANNAPOLIS

1909 ELEANOR COURT

5 Beds

3 Baths

4,790 Sq.Ft.

$935,000

MLS#: MDAA2127206

Welcome to your dream home in the St Margaret's Landing! This exquisite 5-bedroom, 4.5-bathroom residence offers three expansive levels of living. Originally a Ryland home model, this property features two primary suites—one on the main level and another on the upper level—ideal for multi-generational living or hosting guests. Inside, you'll find custom closets, elegant plantation shutters, and gleaming hardwood floors throughout. Modern lighting fixtures add a touch of sophistication to every room. The gourmet kitchen, with its inviting island, is perfect for casual breakfasts or entertaining guests, while the fully screened deck offers a serene spot for morning coffee or evening happy hours as you watch the sunset. Enjoy the privacy of a tree-lined backyard, providing a peaceful retreat. Cozy up by the fireplace in the inviting family room or host memorable holiday dinners in the formal dining room. The versatile lower level is designed for entertainment and relaxation, featuring a movie area, workout space, and room for game nights, complete with two bars, a pool table, and a full bathroom. This meticulously maintained home is a rare find in one of the area's most sought-after neighborhoods. Don’t miss the opportunity to make it yours!
#MDAA2132320

ANNAPOLIS

1612 TRAWLER LANE

5 Beds

4 Baths

4,386 Sq.Ft.

$929,000

MLS#: MDAA2132320

This is an estate sale and being sold "As Is." A rancher that has been in this family for years, it does require updating--the value of this property is in the land and located in Pendennis Mount as many individuals would love to build a larger home in this community or rehab an existing home. This property is located in the well-desired subdivision of Pendennis Mount with properties selling for up to $9M on the water.. This property in not located in the "city" of Anapolis so no city property tax assessed. There is a private community access to the waters of the Severn River that has a pier and boat slips.... If one wants to join the Boat Club, one can join--agent is verifying fees and will update this info. There is also a public county park, Jonas Green Park, just outside of Pendennis Mount (next to the Naval Academy Bridge off Rt. 450) that offers a sandy beach for cartop boat launching, 288-foot fishing pier, picnic tables and restrooms for public use, but no swimming--(per their website). One can access downtown Annapolis, the Naval Academy within minutes. Easy access to Rtes 2, 50 and I-97. Easy driving to DC, Baltimore, or the Eastern Shore.
#MDAA2130856

ANNAPOLIS

16 BRICE ROAD

3 Beds

1 Baths

1,936 Sq.Ft.

$900,000

MLS#: MDAA2130856

The perfect blend of 1950s charm and modern Annapolis living, situated steps from the water and an easy walk or bike ride across the Naval Academy Bridge to West Annapolis and the historic downtown area. This classic Pendennis Mount ranch-style home, built in 1959, has been beautifully updated. Step inside to find the home's original character with hardwood floors, now opened up into a generous main living and dining area. The real showstopper is the expansive rear kitchen addition featuring vaulted ceilings, huge windows overlooking the backyard, and a chef's setup: granite countertops, stainless steel appliances, a gas cooktop, and a large walk-in pantry. The main level hosts 3 bedrooms and a full bath, while the finished lower level provides excellent flexibility with a large den, 2 additional bedrooms, a kitchenette, and bonus room with french doors that open to a patio—perfect for a guest suite or entertaining space. You’ll also appreciate the two-car attached garage with extra storage space for a workshop or whatever your needs may be. The driveway was freshly paved last year. Situated on a spacious, fully fenced 0.34-acre lot with mature trees, this property offers rare privacy and two patios. Enjoy the quiet, safe streets of the highly desirable Pendennis Mount community featuring a newly renovated community playground. You are minutes away from Jonas Green Park. Commuting is convenient with swift access to routes toward Baltimore and Washington D.C.
#MDAA2131196

ANNAPOLIS

1913 DULANEY PLACE

5 Beds

2 Baths

2,969 Sq.Ft.

$899,999

MLS#: MDAA2131196

This is the one you've been waiting for! First open house scheduled for Sunday, November 23, 2025 from 2-4pm. Come visit this well maintained, 5 bedroom, 3 and 1/2 bath gorgeous home located on 1.43 acres in the sought after community of The Ridges! This lovely home is situated in a wooded wonderland while still being close to all that Annapolis has to offer! As you enter, you'll immediately note the beauty and warmth of the gleaming hardwood floors throughout the main level. The floor plan provides for a spacious formal dining room and separate living room which has a charming bay window that overlooks the backyard. You'll next discover the bright and inviting kitchen with plenty of room for preparing a gourmet meal! The center island is a great place for hanging out, while the breakfast table area is fantastic for casual dining. Your attention is then drawn to the huge family room with soaring ceilings and a lovely wood burning fireplace that's perfect for those cozy winter nights. Sliding glass doors are to your left, and what a treat they reveal! An amazing screened in porch awaits you and is sure to be a favorite spot for enjoying the pleasures of the outdoor world. Back inside, a bonus room presents options to be a guest room, office, or library- you choose! Rounding out the main level is a cute half bath for convenience. Ascending the stairs, you'll turn to the left to enter your spacious primary bedroom suite! Vaulted ceilings with hardwood floors will impress you upon entering this room. You'll next be drawn into the spectacular primary bath, remodeled just weeks ago! Featuring a show stopping soaking tub, double sink vanity, new LVP flooring, paint, toilet, and lighting - this room wows! Back into the hallway, you'll find three additional bedrooms with a full hall bath to service them. Going further, you'll enter an oversized loft that overlooks the family room making it a great space for a TV room, playroom, or another option for an office! Next, you'll head back downstairs to explore the lower level. You'll first enter an enormous recreation room with endless options for use! Make it a game room with space for a pool table, bar, or movie theatre. You'll also find a 5th bedroom with an ensuite full bath on this level, as well as two large storage rooms for seasonal items. An attached two car garage with space for shelving, along with parking pads for additional guests, rounds out all this house has to offer. 2025 updates include refreshing the deck and screened in porch, as well as remodeling the primary bathroom. Roof replaced 2015, water heater 2017, Goodman HVAC unit 2017, well pump replaced 2018, kitchen remodeled 2018, driveway replaced 2019. Minutes to restaurants, shopping, and downtown Annapolis, this is a perfect location for all your needs. *All inforamtion deemed reliable but should be independantly verified for accuracy.
#MDAA2128064

ANNAPOLIS

621 WOOD LOT TRAIL ROAD

5 Beds

3 Baths

3,970 Sq.Ft.

$894,900

MLS#: MDAA2128064

1 ... 3 4 5 6 7 ... 18
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 $$

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

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

Already have an account ? Login here

Continue your home search

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