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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
318
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,069,668
Med. List Price

Browse Annapolis Real Estate Listings

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$250,000 - $500,000

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$3M - $5M

Over $5M

72 Properties Found. Page 5 of 5.

There’s a timeless allure to this cheerful yellow home on Green Street. Built in the 1870s as part of Annapolis’s historic core, it retains the character of its era with original hardwood floors, a classic Queen Anne façade with its distinctive mansard roof, and a welcoming front porch, while also offering the comfort of thoughtful modern updates. Inside, history meets convenience. Three gas fireplaces anchor the living spaces, and the kitchen blends rustic character with modern function: clapboard cupboards with wrought-iron hinges, exposed beams, a Dacor gas range, and sea-green granite counters. French doors open onto an expansive deck, making outdoor dining effortless. Upstairs, the second-floor bathroom is a retreat in itself, expansive, spa-like, and designed for daily indulgence. The top-floor suite has been transformed into a private escape in 2023, while a powder room on the main level adds charm and practicality. The metal roof lining was also replaced in 2023, a thoughtful update that complements these renovations. The setting completes the picture. Just 475 feet from the base of Main Street, you’re steps from shopping, dining, and the waterfront. Yet the backyard feels worlds away, with a brick path leading to a private courtyard surrounded by greenery. From the rear bedroom balcony, you can enjoy serene treetop views with your morning coffee. 168 Green Street is more than a house; it’s a rare opportunity to own a piece of Annapolis history that lives beautifully in the present. Sq footage per photographer's floor plan
#MDAA2128222

ANNAPOLIS

168 GREEN STREET

3 Beds

2 Baths

1,922 Sq.Ft.

$1,195,000

MLS#: MDAA2128222

Experience the Essence of Annapolis Charm at 179 Green Street Nestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, this location offers the very best of city living in one of the city's most coveted neighborhoods. Inside on the main level, you'll find wide-board pine floors, a thoughtfully updated kitchen with new cabinetry and appliances, and inviting front and side porches perfect for morning coffee or evening relaxation. Rarely found in downtown Annapolis, two oversized off parking spaces add incredible convenience. Upstairs, the home features two spacious bedrooms and a versatile third room—ideal for a home office, den, or oversized walk-in closet. The newly fenced backyard offers a private oasis for entertaining, dining al fresco, or simply enjoying the outdoors. Living at 179 Green Street means immersing yourself in a lifestyle rich with history and culture. Stroll cobblestone streets to award-winning restaurants, art galleries, and the iconic City Dock. Enjoy sailing, community events, and the vibrant energy of downtown—right outside your door. Don’t miss your chance to own a piece of Annapolis charm. Schedule your private tour today.
#MDAA2111662

ANNAPOLIS

179 GREEN STREET

2 Beds

1 Baths

2,304 Sq.Ft.

$1,175,000

MLS#: MDAA2111662

Perfectly situated just minutes from the heart of Downtown Annapolis, yet tucked away for privacy, this 4 br, 3.5 bath NEW CONSTRUCTION coastal inspired home with a 2 car garage and optional detached guest cottage by Whitehall Building & Company offers the best of both worlds—convenience and tranquility. With over 3,400 square feet of finely crafted living space across three levels, every detail has been thoughtfully designed to deliver both comfort and sophistication. Step inside and be greeted by soaring 10-foot ceilings, expansive wide-plank flooring, and an open-concept layout ideal for both everyday living and elegant entertaining. The chef’s kitchen is the centerpiece of the home, featuring a grand center island, quartz countertops with matching backsplash, premium stainless steel appliances, and abundant storage. Flowing seamlessly into the breakfast area and spacious family room, this home is designed for hosting unforgettable gatherings. A versatile flex room offers the perfect space for a formal dining room, private home office, or cozy reading retreat. Additional main-level highlights include a custom mudroom, walk-in pantry, and stylish powder room. The upper level is a true sanctuary, boasting a luxurious primary suite with a generous walk-in closet and spa-inspired bath complete with dual vanities, a frameless glass shower, and a freestanding soaking tub. Two additional bedrooms share a beautifully appointed guest bath, while a convenient second-floor laundry room adds ease to daily living. The lower level provides endless possibilities, including a spacious recreation room, full bath and optional 5th bedroom—perfect for overnight guests or extended family. For those seeking even more flexibility, an optional detached guest house is available, offering a private one-bedroom suite with full bath, living room, and kitchenette—an ideal space for visitors, multigenerational living, or an au pair. All of this in an enviable location just minutes from the U.S. Naval Academy, fine dining, boutique shopping, waterfront attractions, and major commuter routes. Don’t miss the opportunity to personalize your finishes and create the luxury home of your dreams in the heart of Annapolis. Permits are almost fully approved and delivery of your new home is only 8 months away.
#MDAA2123968

ANNAPOLIS

13 ELLIOTT ROAD

4 Beds

3 Baths

3,292 Sq.Ft.

$1,175,000

MLS#: MDAA2123968

Incredible West Annapolis home that has been renovated from top to bottom with high end finishes,, and reconfigured interior that includes a primary bedroom on the main level. Lovely fenced yard, new roof, new everything! Main Level Master Suit with walk in closets! Buyer agents warmly welcome and appreciated!
#MDAA2125152

ANNAPOLIS

1 TUCKER STREET

3 Beds

2 Baths

2,571 Sq.Ft.

$1,175,000

MLS#: MDAA2125152

Motivated Sellers! Come take advantage of this incredible opportunity! Discover a classic brick residence in Murray Hill— Lovingly maintained and beautifully detailed, this timeless home features solid plaster walls, hardwood floors, 8½‑foot ceilings, and graceful archways. The updated kitchen flows seamlessly into a versatile layout that can easily accommodate a first‑floor primary suite—currently styled as a family room with an office and adjoining full bath. Charming, intimate evenings come alive in the inviting living room, centered around a wood‑burning fireplace with an elegant mantel and built‑in bookcases. Step onto the tiled, screened porch for a tranquil retreat, and appreciate the practicality of a mudroom just off the kitchen. The spacious walk‑up attic offers abundant storage or future creative possibilities, while the large basement—complete with a separate entrance and workshop space—provides even more room to grow. Roof is 13 years old and HVAC units are less than 4 years old. Located just steps from Maryland Hall for the Performing Arts, home to the annual Annapolis Film Festival, the Annapols Symphony, art classes and live music. And only three blocks away, Amos Garrett Park awaits—perfect for launching your kayak or paddleboard or taking the boat taxi to City Dock! A rare opportunity to own a character‑filled home in one of Annapolis’s most beloved neighborhoods. Don’t miss it!
#MDAA2121372

ANNAPOLIS

637 CHASE STREET

3 Beds

2 Baths

4,333 Sq.Ft.

$1,148,000

MLS#: MDAA2121372

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

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.
#MDAA2125028

ANNAPOLIS

5 ARLIE DRIVE

5 Beds

3 Baths

3,502 Sq.Ft.

$1,074,900

MLS#: MDAA2125028

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

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