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
316
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,071,137
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

316 Properties Found. Page 7 of 22.

RARE FIND -- Lock & Leave! Private setting in Sailor's Quay in heart of Eastport -- tucked away off main street with lovely plantings in front and a shaded back patio surrounded by trees -- perfect retreat and/or entertaining in style! Brick front porch entry, Hardie-plank exterior, open floor-plan with four levels of flexible space. Custom touches throughout including plantation shutters, wall coverings, crown molding and wainscotting. Main level has hardwood floors, walls of windows for light -- living room with gas fireplace, dining room, powder room and kitchen with atrium door out to a fenced rear yard with circular paver patio and half-wall for extra seating and electric awning....secluded and magical! There is a pretty stone pathway amongst hydrangeas that leads to the front of the house. Upstairs is the primary suite with adjoining bath situated at rear of house and two additional bedrooms with full bath on hallway. Also on the hallway is a large laundry closet currently used for clothing but with washer/dryer hookups intact On the third floor there is a large room (30 x20) which serves as family room and 4th bedroom. The lower level is partially finished into rooms with insulation and an egress window -- workshop with upgraded electricity, storage, utility, office and a half-bath with plumbing to add shower. Additional laundry with washer and dryer is in place here. Two-zoned gas HVAC, 75-gal HWH, garden lighting and sprinkler system on timers. Sailor's Quay community has additional parking off-street on Stevens Alley as an added bonus to their HOA lawn / tree maintenance and snow removal. Location makes this a wonderful prospect for Commissioning Week rental, etc. This is an opportunity to live in-town close to shops, restaurants and all that City Dock / DTA has to offer. Pop over to Vin 909 or Easport Kitchen, Adams Grille, Diehl's Produce, etc in Eastport Shopping Center. So many services nearby to make life easy and spontaneous!
#MDAA2119148

ANNAPOLIS

10 SAILORS WAY

4 Beds

2 Baths

2,843 Sq.Ft.

$1,125,000

MLS#: MDAA2119148

This expansive two-story home showcases a gracious design with abundant room to grow and entertain. Off the foyer is a formal dining room that complements the casual nook and breakfast room, plus a gourmet kitchen and a Great Room with a charming fireplace. On the second floor is a loft surrounded by three secondary bedrooms and a luxurious owner’s suite with a spa-style bathroom. A lower-level recreation room presents endless possibilities. Home is on smart rent lock for your viewing pleasure.
#MDAA2118098

ANNAPOLIS

120 STILLY WAY

6 Beds

5 Baths

4,934 Sq.Ft.

$1,097,990

MLS#: MDAA2118098

This historic and inviting Colonial home, built in 1786, is uniquely charming with large, elegant living spaces. Full of sophistication, it is also exceptionally comfortable and livable. Built as a tavern that Thomas Jefferson famously visited, 39 Cornhill is considered one of the best surviving homes of its kind in America with a remarkable amount of original material. This meticulously maintained residence invites you to experience the best of life in Annapolis as it has been enjoyed for centuries. Unwind in the sunny living room with original wide-plank pine floors and custom cabinets. Enjoy an intimate dinner or host large parties in the pleasant dining room space. Gaze out the bright and airy kitchen’s large windows at the private courtyard outside. Oversized custom cabinets, generous storage, plenty of counter space and room for dining are all part of this exceptional kitchen. The laundry room and a powder room are conveniently located off the kitchen. Another kitchen door leads directly to the pleasant outdoor courtyard, perfect for relaxing or entertaining. The home’s elegant front door opens to a wide entrance hall, the elegant living and dining rooms and the original staircase with impressive architectural detail. A large coat closet provides plenty of storage. On the second level, the serene primary bedroom includes exceptionally roomy closets. Three additional bedrooms are comfortable spaces for guests and/or home offices, ensuring flexibility to suit your lifestyle. The attic features a huge storage area and the basement is newly improved. In this historic home, the charm of downtown Annapolis surrounds you and calls you to be part of its rich history and vibrant lifestyle. BONUS-Rented parking and garage just outside the back gate through the deeded access to the alley.
#MDAA2127644

ANNAPOLIS

39 CORNHILL STREET

3 Beds

1 Baths

1,946 Sq.Ft.

$1,095,000

MLS#: MDAA2127644

English Tudor featuring a stone front patio for nature lovers and bird watchers. Surrounded by large trees for tons of shade and a 45 foot rear deck for large gatherings and rear lawn for play areas. Almost 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. Spacious kitchen with two sliders to rear deck, solid cherry cabinets, quartz island with smooth cooktop with built-in exhaust fan, stainless steel appliances. The great room has cathedral ceilings, wood beams and wide plank redwood siding, wood burning fireplace and slider to rear deck. First floor guest room features wood flooring and access to walk-in shower. Laundry room with loads of built-in shelving, commercial grade Maytag washer, Maytag dryer. Upstairs features high end neutral carpet, 3 bedroom, 2 full baths and generous closet space. Lower level has clubroom, full bath, office/5th BR potential (needs larger window for egress) and large storage room. The community has water privileges with fishing pier and canoe storage and sidewalks for dog walking or strolling the neighborhood. Convenient location for commuting to Baltimore or D.C. and 20 minutes to BWI Airport. Six miles to Downtown Annapolis for great shopping and restaurants.
#MDAA2117832

ANNAPOLIS

553 CHOPTANK COVE COURT

5 Beds

4 Baths

4,438 Sq.Ft.

$1,077,000

MLS#: MDAA2117832

Development opportunity in an established boutique shopping & business district. Value is in the land (17,000 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.
#MDAA2127368

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

2,064 Sq.Ft.

$1,050,000

MLS#: MDAA2127368

Development opportunity in an established boutique shopping & business district. Value is in the land (17,000 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.
#MDAA2127370

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

0.39 acres

$1,050,000

MLS#: MDAA2127370

New on site 1 day ago
Timeless Style. Modern Comfort. Coveted Location. Welcome to 5 Arlie Drive, a beautifully updated five-bedroom, three-and-a-half-bath home tucked away at the end of a quiet cul-de-sac in Pendennis Mount—one of Annapolis’ most desirable and well-established communities. Built in 1998, this property stands out as a rare example of a newer home that offers the character of Annapolis living with the comfort and functionality of modern construction. Step inside to over 3,500 square feet of finished living space, where light-filled rooms and thoughtful updates blend everyday luxury with effortless livability. The remodeled kitchen features quartz countertops, stainless steel appliances, a gas range, and elegant finishes that make cooking and entertaining a joy. The main level flows naturally to a 3/4-season enclosed porch, creating a seamless indoor-outdoor living experience perfect for morning coffee, dining, or unwinding at the end of the day. Upstairs, the spacious primary suite features a large walk-in closet and a serene en-suite bath. The finished walkout lower level adds versatility with a legal bedroom, modern full bath, and access to the stone paver patio and private backyard retreat—ideal for gatherings! Recent updates include a kitchen renovation, powder room remodel (2019), fresh paint throughout (2024), lighting upgrades, and a built-in generator supporting key systems such as HVAC, kitchen, living room, master suite, and water heater. Located just minutes from Downtown Annapolis, the U.S. Naval Academy, West Annapolis shops and cafés, the Severn Inn, and major commuter routes, this home delivers the best of Chesapeake Bay living within the top-rated Broadneck School District.
#MDAA2129580

ANNAPOLIS

5 ARLIE DRIVE

5 Beds

3 Baths

3,502 Sq.Ft.

$999,999

MLS#: MDAA2129580

Welcome to this beautifully maintained residence in the amenity-rich community of Kingsport in Annapolis. Tucked into a picturesque neighborhood known for its scenic walking paths, swimming pool, tot lots, community pier, kayak storage, tranquil ponds with fountains, and lush landscaping, this home offers an exceptional lifestyle both inside and out. Lovingly cared for by its original owners, this gem is now ready for its next chapter. From the moment you arrive, you'll be captivated by the charming front porch and the professionally landscaped yard, supported by an extensive irrigation system. Step inside to discover soaring ceilings, gleaming hardwood floors, and elegant moldings that highlight the home's architectural character. The main level is thoughtfully designed for both everyday living and entertaining, featuring formal living and dining rooms, a spacious kitchen with ample cabinetry and workspace, a dedicated office, a convenient laundry room, and a bright sunroom overlooking the peaceful backyard. Upstairs, you will find four generously sized bedrooms, including an impressive primary suite with tray ceilings, panoramic windows, and dual walk-in closets. The en suite bath is a true retreat, offering both space and style. The fully finished lower level is a true standout, offering endless flexibility with a game room, music room, fitness area, workshop/storage space, and a full bath. The addition of a full egress walkout provides direct access to the beautifully designed paver patio and backyard—ideal for outdoor enjoyment. Ideally located just minutes from shopping, downtown Annapolis, the U.S. Naval Academy, and offering easy access to Washington, D.C., and Baltimore, this home combines lifestyle, location, and luxury. Don’t miss the opportunity to make it yours.
#MDAA2122894

ANNAPOLIS

702 PEARSON POINT PLACE

4 Beds

3 Baths

6,321 Sq.Ft.

$989,500

MLS#: MDAA2122894

Experience luxury and light in this rare 3-bedroom, 2.5-bath condo in the highly sought-after Park Place community. This corner unit boasts incredible 180° views and is filled with natural light from expansive windows throughout. With three deeded garage parking spaces located right next to each other—an unparalleled convenience in downtown Annapolis—you’ll never have to worry about parking again. Inside, a spacious open-concept layout welcomes you with upgraded appliances, generous storage, and a stylish design that makes everyday living and entertaining effortless. The sun-drenched living and dining areas flow into a modern kitchen, ideal for both casual meals and special gatherings. The serene primary suite features an en-suite bath and a peaceful ambiance, while two additional bedrooms offer the perfect setup for guests, a home office, or both. Park Place offers a true lock-and-leave lifestyle with 24/7 front desk staff, beautifully maintained grounds, a pool, fitness center, party room, and a private outdoor patio with grills and a dog park. And for added convenience, a private shuttle picks up right from the courtyard and takes you anywhere in downtown Annapolis. Perfectly positioned to enjoy the best of in-town living, this home combines elegance, ease, and vibrant community energy. Welcome to Park Place—your next chapter starts here.
#MDAA2112582

ANNAPOLIS

5 PARK PLACE 428

3 Beds

2 Baths

1,822 Sq.Ft.

$985,000

MLS#: MDAA2112582

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.

$984,990

MLS#: MDAA2125928

Fantastic brick front Cape Cod, quality built by KOCH Homes! First time offered for sale! This lovely 1/2+ acre property backs to Quiet Water’s Park with Harness Creek water access. Enjoy three finished levels! Step into a welcoming two-story foyer and a soaring two-story family room with a propane gas fireplace that opens to the spacious kitchen with eating area and large center island! A very large laundry room/mud room with additional storage is conveniently located off both the garage and kitchen. The large first floor owner suite features a walk-in closet, spacious owner bath, and a separate office/sitting room with additional closet space and an atrium door leading to the deck! Separate living room and dining room with hardwood floors! Hardwood floors extend throughout the first level! Upstairs offers three generous sized bedrooms and a large full bath! The lower level provides an enormous finished recreational room and plenty of unfinished space for all your storage needs. With a little cosmetic updating this home will be your dream!
#MDAA2111626

ANNAPOLIS

795 HARNESS CREEK VIEW DRIVE

4 Beds

2 Baths

4,549 Sq.Ft.

$975,000

MLS#: MDAA2111626

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

OFFER DEADLINE WEDNESDAY AT 10PM OCTOBER 22nd. Welcome to this stunning California-style elevated rancher nestled on a 1.11-acre professionally landscaped lot in the highly desirable Downs on the Severn. Offering a perfect blend of luxury, comfort, and thoughtful upgrades, this home is a peaceful retreat surrounded by nature. This special, well cared for home features 3 Bedrooms and 4 Bathrooms. There is also an additional half bath in the entrance of the home. All bedrooms are located on the main level of the home. Come see this Luxurious, Modern ,Primary Suite with two expansive walk-in closets and a beautifully updated ensuite bath. The two additional main-level bedrooms share a fully renovated hall bath.. There are recently installed Birdseye Maple hardwood floors that flow seamlessly throughout the entire home, adding warmth and elegance. Interior Upgrades & Layout feature a Gourmet Kitchen Renovation with custom cabinetry, granite countertops, stainless steel appliances, and open-concept flow to the dining and family rooms. This home is perfect for entertaining all year round. Bright and airy layout enhanced by 4 new skylights, bringing natural light into the heart of the home. As you walk to the back you are greeted by a Sunroom/Screened Porch with a cozy gas fireplace, perfect for year-round enjoyment! In the summertime open up all the full length windows and doors to enjoy outdoor living inside! There is a side facing, 2 car garage with plenty of room. You will absolutely feel like you are on vacation when you venture up the private, landscaped driveway. There is always plenty of room for parking on this private lot. Mature and newly enhanced landscaping will make you feel as if you are in Homestead Gardens! There is also 7 Sprinkler Zones on the property for easy care. The Downs On Severn features 2 marinas, a community pool with swim team, tennis courts with pickle ball, clubhouse with year round socials, and tot lot with little library. The new Clements Creek floating dock Marina with community tables with fire pits where just put in 2024 . There are all boat size slips and we would check what is currently available. There are also boat lifts available for an extra fee. You will feel like you are always on vacation at 1676 Saint Albans Square! Come make an appointment to view this home today as this home will not be on the market very long on the market!
#MDAA2128692

ANNAPOLIS

1676 SAINT ALBANS SQUARE

3 Beds

3 Baths

3,959 Sq.Ft.

$969,000

MLS#: MDAA2128692

Nestled into the tree tops off a private drive in highly sought after Winchester on the Severn, this mid century raised rancher will check all your boxes. From the moment you pull up the private drive to the home, you are immediately at ease. Step out of the car to the sounds of birds and the rustle of the trees. You will feel as though you have escaped it all, yet you are right in the heart of Winchester, a quick drive from Historic Downtown Annapolis and a stones throw to the famed B&A trail. As you enter the front walk, you will be immediately struck by the quality of craftsmanship and materials on the exterior of the home. Once inside, the rich wood beams, wood trim and floors strike a dramatic combination with the soaring ceilings. The abundant windows and doors leading out to the sunroom will ensure that the beauty of the natural surroundings take center stage. The chef's kitchen is equipped with granite countertops, a deep sink, lovely picture window over the sink, double wall ovens and high end fixtures. The sunroom serves as an additional dining space and relaxing sitting room with full views of the surroundings. You will feel as though you have escaped to a mountain retreat! The main level offers a full hall bath and three comfortable bedrooms including an owner's suite with ensuite bath and double closets. The fully finished lower level is a lovely living space on its own with a cozy den, office and flexible bonus space that could be a 4th bedroom with its own ensuite bath. The lower sunroom is the perfect spot to partake in your morning yoga and meander out to the hot tub for a leisurely soak. Entertaining is a breeze with the expansive, multi-level decks and putting green for fun. After a day on the water, use the outdoor shower to rinse away the salt and sand. Winchester offers two beaches (one is referred to as Dog Beach for obvious reasons) and two marinas. The beauty of a water access community on the Severn River is easy access into Annapolis by boat without going out into the choppy Bay. You can hop on a small tender and dock in town at the dinghy dock for dinner any time you please. Walk or bike up the B&A trail for coffee, ice cream or grab must haves at the gourmet cheese shop. Brunch at the Severn Inn overlooking the River or pop over to Garten Beer Garden for a lovely supper with friends. This is not merely a beautiful home, this is a highly sought after lifestyle.
#MDAA2128442

ANNAPOLIS

1534 CIRCLE DRIVE

4 Beds

3 Baths

3,470 Sq.Ft.

$965,000

MLS#: MDAA2128442

Stunning Updated Colonial in a Water-Privileged Community! This beautifully renovated four-bedroom, two-and-a-half bath home features a custom kitchen with all-new cabinetry, Calcutta Quartz countertops, and sleek stainless-steel appliances, including dual ovens with a gas cooktop. The inviting family room is equipped with built-in surround sound speakers, perfect for entertaining. The luxurious primary suite offers a spa-like experience with a large shower featuring dual shower heads, a soaking tub, a custom border-lit mirror, and a towel warming bar for those chilly days. Convenience is key with a second-floor laundry closet. Step outside from the family room onto a spacious Trex deck that overlooks a large backyard. The property includes an attached two-car garage and a fantastic 30x50 detached two-story toy barn garage, complete with a car lift 10' doors and 13' ceilings and the potential to finish the upstairs space into a perfect in-law or teen apartment. This home also boasts a new roof, a freshly paved driveway, and all-new plumbing and insulation. Enjoy the perks of a water-privileged community with access to a sandy beach and a community dock. This home and Detached garage sits on a double lot with separate gravel road on backside for easy access for boats, RV's storage. This home truly has it all!
#MDAA2111664

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

3,078 Sq.Ft.

$950,000

MLS#: MDAA2111664

1 ... 5 6 7 8 9 ... 22
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