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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
208
# of Listings
3
Avg # of Bedrooms
$513
Avg. $ / Sq.Ft.
$1,087,200
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

80 Properties Found. Page 1 of 6.

Welcome to the heart of downtown Annapolis at 179 Green Street. This charming home blends timeless character with modern comfort, this is just a block from Main Street and City Dock, few block from the Naval Academy, State Capitol building, boutique shopping, and Annapolis Elementary School. Located in one of the city’s most desirable neighborhoods, it offers exceptional walkability and vibrant city living. Move in ready with a new roof, new updated kitchen, new full bathroom on main floor, new plumbing, new electrical, new basement ceiling, new fenced in yard, The main level features inviting front and enclosed side porches—perfect for morning coffee or unwinding with a glass of wine in the evening. Inside, wide-board pine floors lead to an updated L-shaped kitchen with bright white cabinetry, stainless steel appliances, and a convenient stackable washer and dryer nearby. The living room showcases rich wood wainscoting, detailed wood trim, custom built-in bookcases, and a rustic fireplace accent, creating a warm and cozy atmosphere. A dedicated dining room completes the main level, ideal for everyday living and entertaining. Upstairs, the home offers two spacious bedrooms and there is an extra versatile space featuring an exposed beam ceiling, curved built-in arch shelving, and custom cabinetry—ideal for a home office, or a den. A large bathroom showcases a Victorian-style Van Buren clawfoot tub, new LVP flooring adding timeless historic character. Outdoors, the fenced backyard provides a private retreat for entertaining or relaxing. The property also includes two oversized off-street parking spaces, offering exceptional convenience. Step into a lifestyle steeped in history and culture. Wander charming cobblestone streets to acclaimed dining, embrace sailing and local events, and enjoy the dynamic rhythm of downtown living just beyond your doorstep. This is a rare opportunity to own a true piece of Annapolis charm—schedule your private showing today. Fireplace non operational.
#MDAA2135874

ANNAPOLIS

179 GREEN STREET

2 Beds

2 Baths

1,656 Sq.Ft.

$999,999

MLS#: MDAA2135874

*** A must-see opportunity in the desirable Eastport Peninsula! This unique property features two attached dwellings in one, offering exceptional flexibility and income potential. The original dwelling, once a charming church, has been thoughtfully converted into a 2-bedroom, 1.5-bath home with an open-concept main level full of character and charm. The second dwelling, located at the rear, is a cozy cottage complete with 1 bedroom, loft, and kitchen —perfect for rental income, guests, or extended family. A truly special property with endless possibilities—don’t miss it!
#MDAA2131796

ANNAPOLIS

200 CHESAPEAKE AVENUE

2 Beds

1 Baths

2,942 Sq.Ft.

$999,900

MLS#: MDAA2131796

Welcome to Eastport Estates at Griscom Square, a brand-new construction community of just 11 luxury single-family homes, located within one mile of downtown Eastport! Each residence showcases high-end finishes, spacious open-concept layouts, 9-foot ceilings, 4-5 Bedrooms, gourmet kitchen, modern baths, 2-car garages with private parking, and quality craftsmanship throughout, creating a truly well-built home. Inspired by its coastal setting, each home incorporates light-filled spaces and design elements that reflect Eastport’s nautical character. Enjoy effortless access to Eastport’s vibrant waterfront dining, live music, local marinas, yacht clubs, and scenic sunset views - or bike to or take the water taxi to City Dock, downtown Annapolis, and the United States Naval Academy. Luxury, lifestyle, and location - together in one place. This is a rare opportunity to build your own home this close to town. Lot and model options available!
#MDAA2134724

ANNAPOLIS

105 GRISCOM SQUARE WAY

4 Beds

3 Baths

2,850 Sq.Ft.

$995,000

MLS#: MDAA2134724

Located just moments from the shoreline, 509 Chesapeake Ave presents a rare opportunity to secure a 4-bedroom, 2-bath single-family home in one of Annapolis’s most desirable waterfront-adjacent areas. Whether you’re an investor searching for your next project or a homeowner ready to create your dream coastal retreat, this property offers incredible potential. The home features a spacious layout with four bedrooms and two full baths, providing a solid foundation for renovation and value-add improvements. With the right vision, this property could be transformed into a stunning primary residence, vacation home, or resale opportunity. Positioned just steps from the water, enjoy the lifestyle perks of boating, dining, and all that Annapolis waterfront living has to offer. The location alone makes this a standout opportunity—properties this close to the water with this much upside are hard to find. Ideal for buyers looking to renovate, customize, and build equity in a prime location. Bring your contractor, your vision, and unlock the full potential of this Annapolis gem.
#MDAA2140184

ANNAPOLIS

509 CHESAPEAKE AVENUE

4 Beds

2 Baths

1,800 Sq.Ft.

$975,000

MLS#: MDAA2140184

New on site today
46 Lafayette Ave is a Murray Hill classic, a beautifully updated Craftsman four-square where original heart-of-pine floors and a charming covered front porch meet a stunning gourmet kitchen. The open floor plan flows naturally from the marble-topped island into dining and living spaces, making it effortless for everyday living and entertaining alike. Cooks will love the stainless appliances, high-end cabinetry, and subway tile backsplash. Thoughtful details throughout, custom plantation shutters, upgraded lighting, and a first-floor laundry room make the home as functional as it is beautiful. Three finished levels offer four bedrooms plus a sitting area and home office, while the private backyard patio is perfect for al fresco dining. A full unfinished basement adds ample storage. Updates since 2018 include a new roof, HVAC, and exterior work. Steps from Lafayette Waterfront Park and West Street's shops and restaurants, this is Murray Hill living at its best.
#MDAA2140284

ANNAPOLIS

46 LAFAYETTE AVENUE

4 Beds

1 Baths

1,800 Sq.Ft.

$975,000

MLS#: MDAA2140284

To be built! Two outstanding plans ready for new owner to make their choice and selections! Builder is ready to go! Plans and permits in hand and building can start right away! Extraordinary opportunity to tailor a home to fit your lifestyle and needs. Excellent open floor plans. Great flexible spaces with floor plans to meet your needs. Options include a main level primary suite, larger 2nd floor primary or extra baths. Construction to perm loans are easier and better than you think. A truly rare chance to build a home with water views in the exclusive water-privileged neighborhood of Beacon Hill. Construction to perm loans are easier and better than you think and can be adapted to fit your financial situation. Contact the listing agent for details. Beacon Hill was originally a community of only forty houses, with twenty lots directly on the Bay and the other twenty with water views. 1546 Shipsview is undoubtedly the best of the ‘ water view’ lots. Directly across the street from 1546 is one of the community's two public water access points. It is the perfect spot to wade into the Bay or sit with a morning coffee and watch the sunrise. 1546 is a rare gem in a highly sought-after community. DO NOT DELAY, or you will miss the opportunity to build in this very special neighborhood. Easy access/commuter routes to the Chesapeake Bay Bridge, the Eastern Shore , Washington and Baltimore.
#MDAA2136356

ANNAPOLIS

1546 SHIPSVIEW ROAD

4 Beds

3 Baths

2,449 Sq.Ft.

$969,000

MLS#: MDAA2136356

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

New on site 1 day ago
Welcome to this exceptional Kingsport 4 BR, 5 BA home with over 4600+ SF of beautifully designed finished living space tailored for both everyday comfort and unforgettable entertaining. Thoughtfully enhanced by its original owners, the home features over $150K in state of the art, commercial grade electronics, seamlessly integrating lighting, whole-home audio, and premium theatre systems throughout. The state of the art whole house Savant control system includes an 11 zone whole house audio and 7 zone video matrix switching system that integrates scene control with audio, video, lighting, thermostats, and cameras. The house also includes a commercial grade network system complete with wireless access points on each level. The lower level is a true showpiece boasting a stunning Rec Room anchored by a custom 8' bar complete with granite countertops, sink, beverage refrigerator, ice maker and draught cocktail system, along with generous bar seating - perfect for hosting gatherings of any size. Brand new carpeting throughout the lower level. Movie nights reach a whole new level in the impressive 17' x 18' soundproofed 4K Home Theatre Room, with luxury stadium seating and top-tier screen & projector technology with 7.2.4 Dolby Atmos sound for an immersive cinematic experience. The main level features inviting two story foyer, home office with built ins, formal Living and Dining Rooms and stunning cherry Kitchen with granite and stainless appliances, double ovens, gas cooking in center island and large pantry. The dramatic 2 story Family Room is a true centerpiece of the home highlighted by soaring floor to ceiling windows that flood the space with natural light and a second home theater system complete with in-wall speakers and Frame TV. Recently updated with plush new carpeting, the room also features a cozy gas fireplace and elegant custom built-in cabinetry creating the perfect balance of warmth and sophistication. Upstairs, the hallway showcases rich hardwood flooring, leading to an exquisite Primary Suite and beautifully renovated Owners Bath that offers a spa-like experience with large walk in travertine shower featuring shower head, a rain shower and body sprays, soaking tub and dual walk in closets. All additional Bedrooms on the upper level are comfortably appointed with carpeting. This home features a fully insulated 2 car garage and newly installed insulated garage doors. Outdoors the rear paver patio provides a serene and inviting setting for entertaining, complete with a fully fenced yard, a striking water feature and 13' awning, perfect for relaxing or hosting guests in comfort. Ideally located in the sought-after Kingsport community, this home is just minutes from Downtown Annapolis, offering convenient highway access along with exceptional neighborhood amenities including beautiful outdoor pool, walking trails, tot lots and water access on Crab Creek with pier and kayak launch. Kingsport is just minutes to easy access to Rt. 50/97, Washington DC, Fort Meade, and Baltimore.
#MDAA2139820

ANNAPOLIS

707 PILOT HOUSE DRIVE

4 Beds

4 Baths

4,797 Sq.Ft.

$945,000

MLS#: MDAA2139820

New on site today
Tucked away in the woods on a quiet cul-de-sac, this stunning single-family home sits on a private and picturesque .77-acre lot, offering the perfect blend of tranquility and modern comfort. With 4 spacious bedrooms and 3.5 bathrooms, this home features a bright, open floor plan designed for both everyday living and entertaining. The Spacious kitchen with windows on 2 sides and stainless appliances, flows seamlessly into the main living areas, while abundant natural light fills the home, creating a warm and inviting atmosphere throughout. The expansive primary suite is a true retreat, featuring a vaulted ceiling and a spa-like bathroom complete with skylights that bring in beautiful natural light. Step outside to enjoy the peaceful surroundings from the large screened-in porch just off the living room, or host gatherings on the oversized deck overlooking the wooded backyard. Additional highlights include a 2-car garage and thoughtful updates throughout. Major system upgrades provide peace of mind, including a new lifetime warranty architectural shingle roof and gutters (2023), new hot water heater (2023), and HVAC system replaced in 2018. The home was also freshly repainted in 2022, making it truly move-in ready. This is a rare opportunity to own a beautifully updated home in a serene, private setting—while still being conveniently located to everything you need.
#MDAA2140616

ANNAPOLIS

1070 FOXCROFT RUN RUN

4 Beds

3 Baths

3,286 Sq.Ft.

$939,999

MLS#: MDAA2140616

Perfectly positioned in Eastport, Annapolis, just moments from downtown, this brand-new home places you in the heart of it all: boat shows, waterfront dinners, parades, morning coffee walks, and sunset strolls along the harbor. Leave the car behind and lean into the Annapolis lifestyle. Inside, the home blends modern design with thoughtful flexibility. With 5 bedrooms and 3 full baths, including two bedrooms on the main level, you have options, guest space, multigenerational living, or the ideal home office. Upstairs, the primary suite offers a private retreat with a walk-in shower, double-sink vanity, and elevated finishes. Two additional bedrooms share a well-appointed hall bath with a tub. Gold accents throughout the kitchen and bathrooms add warmth and character, while oak-toned flooring and windows on every side allow natural light to pour throughout the home. The kitchen is the centerpiece, expansive island, generous prep space, and seamless access to the backyard through sliding glass doors, with an additional rear entry for convenience. There is even potential for a deck installation prior to closing, offering flexibility for the next owner. Outdoor living is just as intentional. A rare front yard in Eastport is framed by a half fence and gate, while the fully fenced backyard creates a private setting for cookouts, gatherings, or quiet evenings at home. A welcoming front porch completes the picture. This is not just a new build. It is an opportunity to live fully connected to everything Annapolis has to offer, with the comfort of a rare brand-new construction.
#MDAA2136542

ANNAPOLIS

148 JEFFERSON STREET

5 Beds

3 Baths

2,330 Sq.Ft.

$925,000

MLS#: MDAA2136542

Prime West Annapolis Opportunity | B-1 Zoning | 13 Annapolis Street. Positioned in the heart of high-demand West Annapolis, 13 Annapolis Street presents an exceptionally rare opportunity to acquire a property with B-1 zoning flexibility in one of Annapolis’ most dynamic commercial districts. This is the kind of location where vision, creativity, and smart planning can translate into long-term value. B-1 zoning opens the door to a variety of potential uses such as boutique retail, professional offices, wellness studios, salons, galleries, cafés, creative workspaces, or thoughtfully designed mixed-use concepts (buyer to verify specific uses with the City). Whether you’re an entrepreneur looking to establish a flagship presence, a business owner seeking visibility, or an investor with a redevelopment vision, this property offers the versatility to bring those plans to life. Adding to its appeal is a feature rarely found in West Annapolis: a private driveway with abundant off-street parking, a significant advantage for clients, customers, or tenants and a true differentiator in this walkable corridor. Surrounded by beloved local restaurants, shops, and everyday conveniences, the property benefits from strong foot traffic, excellent visibility, and the vibrant energy that defines West Annapolis. Opportunities with this combination of location, zoning, and parking simply do not come along often.
#MDAA2135402

ANNAPOLIS

13 ANNAPOLIS STREET

None Beds

None Baths

2,240 Sq.Ft.

$925,000

MLS#: MDAA2135402

New on site 2 days ago
Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for buyers seeking lifestyle, investment potential, or business use in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached home, not a rowhome or townhouse, providing enhanced privacy, natural light, and a more versatile footprint. The extensive renovation includes a brand new roof, all new electrical and plumbing systems, a new high-efficiency mini-split HVAC system, redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. The outdoor spaces have been completely upgraded with a new deck, new brick patio pavers, new fencing, and ambient lighting that creates a warm and inviting atmosphere for evening entertaining. Inside, the home features a bright two-story entry foyer and a professionally curated interior design that blends modern comfort with intentional functionality. With three bedrooms and two full bathrooms, the layout is flexible enough to support full-time living, guest accommodations, workspace needs, or commercial adaptation. The main-level primary suite opens directly to a private brick patio, while the second bedroom features access to a rear deck overlooking the fully fenced yard. These indoor-outdoor connections are rarely found in Downtown Annapolis and significantly enhance livability. The kitchen has been completely reimagined with new cabinetry, countertops, and appliances, designed to support both daily living and entertaining. The open dining area comfortably accommodates gatherings, reinforcing the home’s versatility. Adding even more value, this property is being sold fully furnished. Every piece has been professionally selected, allowing the next owner to move in immediately, operate as a short-term rental, or transition into a commercial or mixed-use setup with minimal effort. Historically, this property has served multiple purposes, including a furniture store, office space, and duplex residence, highlighting the true flexibility and long-term value of its mixed-use zoning designation. Step outside into a fully fenced private yard featuring a brick patio, outdoor dining area, lounge seating, and ambient lighting, creating a unique urban retreat just steps from the energy of Downtown Annapolis. Located just moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, this property offers unmatched walkability and access. With convenient proximity to Baltimore, Washington D.C., and BWI Airport, it is equally appealing for commuters, investors, and second-home buyers. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.
#MDAA2140068

ANNAPOLIS

220 WEST STREET

3 Beds

2 Baths

1,540 Sq.Ft.

$924,900

MLS#: MDAA2140068

Modern accents meet classic Georgian design in a downtown Annapolis private enclave of customized homes. Monthly neighborhood get togethers, progressive dinners, holiday celebrations and lovingly curated green spaces for outdoor living. Self managed HOA includes yard care and snow removal for lock and leave convenience. If you’re looking for rolling acres with grass to cut weeds to pull beds to mulch and snow to shovel this is not the home for you. If you desire almost 4000 sq feet with a small carbon footprint energy efficient with Georgian timeless beauty turn key lock and leave where weekends are your own then this is the one for you. Add a close knit community of only 30 homes with holiday and social gatherings to attend (or not) walking biking distance to Historic Annapolis and Eastport and short DC Baltimore commute. Two ensuites, office space, flex space and huge storage rooms. Private outdoor paved patio and 2 car garage with additional 2 driveway spaces along with extra guest parking, rare for in town Annapolis living. Hardwoods on upper and lower levels with carpeted bonus room in fully finished basement offering its own full bath. Brick front and Hardiplank siding. Gym, hiking trails, sports and pickle ball courts, and boat/ kayak/paddle launch across the street. Urban vibe with suburban feel, premier coastal living, Restaurants shopping and conveniences within biking and walking distance. Summer nights at Dining Under the Stars on West Street. Morning walks to the historic waterfront of City Dock Kayaking on Spa Creek just across the street. Happy hours in Downtown Annapolis. Water taxi or bike ride to Eastport for dinner. Navy game days coming soon! With nearby marinas for boating, waterfront parks, and recreation centers within walking distance everything you need to live and love Annapolis. Primrose Hill is coastal living among an exceptional collection of homes where every day feels like a retreat in your luxury primary residence or weekend sanctuary. Beautiful private neighborhood areas for dog walking. Residents enjoy picnics and relaxing outdoors in amazing community areas. Iconic Craftmark design with model upgrades throughout create a luxury home with all the modern touches for easy living. Newly built to age gracefully with modern accents set against classic design. Finished Lower level with family room, full bathroom, office, storage and additional room for wellness space, spa, music room or other flexible lifestyle area.
#MDAA2138534

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

3,978 Sq.Ft.

$924,900

MLS#: MDAA2138534

Experience the best of Annapolis living in this beautifully cared-for Kingsport home, offering a perfect blend of comfort, style, and thoughtful upgrades. Built by Basheer & Edgemoore, this 4 bedroom, 4.5 bath residence welcomes you with a bright two-story foyer and an inviting layout designed for both everyday living and effortless entertaining. Hardwood floors, plantation shutters. recessed lighting, and detailed trim work enhance the main level. The formal dining room is ideal for gatherings, while the spacious eat-in kitchen features a center island with cooktop, double wall ovens, granite countertops, pantry and stainless steel appliances. The kitchen opens directly into the impressive two-story family room, complete with a gas fireplace and a dramatic wall of windows that fill the room with natural light. A private office, powder room, laundry with utility sink and built-ins and access to the upgraded 2-car garage complete the main level. Upstairs, the generous primary suite offers two walk-in closets with built-ins, a sitting room and a spa-like bath with soaking tub and separate shower. A second bedroom includes an en-suite bath, while the other two bedrooms share a Jack-and-Jill bathroom. The lower level includes a full bath, recreation room, abundance storage and an egress window - ideal for adding a fifth bedroom. Plenty of space for gym equipment, workshop and still have plenty of storage space. The backyard is fenced in and has private patio area with lovely landscaping. No need for a grasscutter in the back. Kingsport amenities include walking/biking trails, water access with kayak dock, two playgrounds and a community pool with hot tub. Nice public areas for sitting, picnics and dog walking . Convenient to downtown Annapolis, Naval Academy, shopping, dining , marinas and major commuter routes.
#MDAA2139344

ANNAPOLIS

706 DRAKE WAY

4 Beds

4 Baths

4,571 Sq.Ft.

$905,000

MLS#: MDAA2139344

GREAT OPPORTUNITY! Huge building offers two levels with office on main level and office on upper level, both units are vacant and ready to run your business as you rent the other unit out or combine both. Close to Annapolis Mall, Route 50 and much more!
#MDAA2135848

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

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