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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
310
# of Listings
3
Avg # of Bedrooms
$440
Avg. $ / Sq.Ft.
$996,943
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

310 Properties Found. Page 6 of 21.

Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive water access community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including gardening, relaxing on the rooftop deck, or sitting under the ceiling fans on the large front porch. Each of the five spacious bedrooms offers comfort and style, while four full bathrooms feature premium tile work, modern vanities, and spa-like amenities. All the while, enjoying the water access community amenities that offer boating, fishing, and waterfront recreation just moments from your doorstep. Easy access to local restaurants, shopping, and major roadways.
#MDAA2121748

ANNAPOLIS

767 BON HAVEN DRIVE

5 Beds

4 Baths

3,505 Sq.Ft.

$1,195,000

MLS#: MDAA2121748

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

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.

$1,150,000

MLS#: MDAA2128222

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

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

6,525 Sq.Ft.

$1,100,000

MLS#: MDAA2115552

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

This home is nestled in a lush garden setting, so close to dining, shopping and all that downtown Eastport and Annapolis have to offer yet this home feels tucked in to its own private space. This home has been lovingly cared for by the original owner. The private back stone patio with circular stone wall and yard are a perfect place for enjoying a cup of coffee or tea to start your morning and is a great space for entertaining. There is a retractable awning to cover the patio when needed and landscape lighting comes on each evening (on timer) creating ambiance and there is an irrigation system also on a timer for easy living. Entering into the front of the home from the beautiful covered brick porch, the open floor plan of the main level welcomes you past an elegant formal dining area with wainscoting to the heart of the home, the kitchen and great room with gas fireplace. The great room opens out to the back garden and patio. The one car garage has interior access to the great room. A half bath is also included on the main level. Proceeding upstairs, to the bedroom level, there is a primary bedroom with en-suite bath and walk-in closet overlooking the treed back yard. Two additional light filled bedrooms, full hall bath, a walk in closet that has a washer and dryer hook up in it and 2 additional closets for more storage complete this second level. There is a third level that can be utilized many different ways, it is currently a family room (approximately 20 x 30) and also functions as a guest bedroom with a day bed ensconced in a window nook. In addition to these uses, it could also function as a home office, a gym, a 4th bedroom, playroom or more! The basement features a small office area, laundry room, half bath that has a shower rough in for future expansion, utility/storage room, workshop and an egress window. The workshop areas have been insulated and include electric and HVAC to make it easy to finish out the space for more living space. The home features natural gas heat with two separate zones, zoned central air conditioning, new gas 75 gallon water heater and interior sprinkler fire suppression system. Two laundry locations in the home, bedroom level and basement. Garden lighting and irrigation systems on timers. As a part of the 15 home development known as Sailor's Quay the HOA for Sailor's Quay features lawn maintenance, common area maintenance, snow removal and additional parking on Steven's Alley, which is just a house away from #10, See last photo.
#MDAA2129930

ANNAPOLIS

10 SAILORS WAY

3 Beds

2 Baths

3,043 Sq.Ft.

$1,050,000

MLS#: MDAA2129930

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.

$1,050,000

MLS#: MDAA2127368

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

$1,050,000

MLS#: MDAA2127370

Your gorgeous new Annapolis home awaits! Located on more than an acre of meticulously landscaped grounds in a quiet cul-de-sac, this elegant brick colonial features classic design with modern updates and a serene environment. The main level flows seamlessly for everyday living and entertaining. A stunning, newly renovated kitchen shines with white cabinetry, a large center island, stainless steel appliances, and gas cooking, opening to the breakfast area and family room with a cozy gas fireplace. Formal living and dining rooms are perfect for hosting gatherings. French doors lead to a flexible main level bedroom with an adjacent half bath that also works perfectly as a home office. Upstairs, the spacious primary bedroom includes an ensuite bathroom and two walk-in closets. One of the closets is fabulously oversized and could easily be converted into a sitting room or additional home office/library. Three additional bedrooms share a well-appointed hall bath. The fully finished lower level is perfect for play, fitness, or movie nights, with a new half bath and a walkout to the backyard. Outdoor living is a dream! Relax or entertain on the deck overlooking a wooded, private yard with lush planting beds. There's room to roam in the fully fenced backyard! Notable improvements and comforts make this beautiful home truly move-in ready. Recent updates include a new roof, a new HVAC system, a renovated kitchen with new appliances, an 80-gallon water heater, a whole-home Generac generator, an automatic lawn sprinkler system, and a water softener with a constant pressure system. Natural gas powers the fireplace and range, eliminating the need to manage tanks. A garage-style shed provides excellent storage. 1868 Lynnfield Drive is situated in a prime Annapolis location, just minutes from shopping, restaurants, the historic downtown area, and the newly updated Eisenhower golf course. Conveniently located, you'll have an easy commute to Baltimore, DC, or Ft. Meade/NSA as well as BWI Airport. Find a new home for your boat at one of the many Annapolis marinas and yacht clubs! Space, updates, and a peaceful setting on a tree-lined cul-de-sac — this one checks all the boxes. Welcome home!
#MDAA2128974

ANNAPOLIS

1868 LYNNFIELD DRIVE

5 Beds

2 Baths

4,274 Sq.Ft.

$1,050,000

MLS#: MDAA2128974

Ready for Quick Move-in! 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.

$999,990

MLS#: MDAA2118098

Opportunities like this don't come along often - this is the only residence of its kind in Shearwater, and it offers a lifestyle unmatched in Annapolis. This 2400 + - spacious 4 - bedroom, 4.5 bath waterfront residence is thoughtfully designed all on one level - no steps, just effortless luxury. Inside, you'll find two inviting fireplaces, multiple living and entertaining areas, and walls of glass that open to the water. Step outside with sweeping views of Spa Creek where every sunset becomes your backdrop. For boaters, this home includes a deeded 35- foot slip, just steps from your door. Whether its a quiet paddle, a sail on the Bay, or a sunset cruise, your waterfront adventure begins right here. Shearwater is one of Annapolis's most coveted gated communities, known for its privacy, amenities, and easy access to downtown. Here, you can enjoy the best of both worlds- resort-style living in a secure enclave, while being minutes away from restaurants, shops, and the charm of Historic Annapolis. This condo is two combined with 2 tax numbers 8B1 and 8 A1, Concrete slab and steel construction. Condo fee includes water & sewer, parking, trash, and snow removal. Enjoy an abundance of nature, blue herons, osprey, and other water fowl. The Shearwater community offers a private, waterfront pool with grill area, pickleball, tennis, racketball, kayak and dinghy rack/storage, a deep water marina and oyster shell walking paths - all within a Gated community. Enjoy a nice walk, bike ride or the water taxi will pick you up at the marina dock and take you downtown. All the fun activities in Eastport are right at your back yard. The Eastport Yacht Club parade of lights boat parade in December makes it final turn right in front of the Shearwater community. Rare opportunity to combine single level living, waterfront access, and the timeless Annapolis Lifestyle.
#MDAA2126908

ANNAPOLIS

8 SPA CREEK LANDING B1/ A1

4 Beds

4 Baths

2,400 Sq.Ft.

$999,500

MLS#: MDAA2126908

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

5,124 Sq.Ft.

$975,000

MLS#: MDAA2127206

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