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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
163
# of Listings
3
Avg # of Bedrooms
$492
Avg. $ / Sq.Ft.
$944,708
Med. List Price

Browse Annapolis Real Estate Listings

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66 Properties Found. Page 1 of 5.

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.

$1,000,000

MLS#: MDAA2135402

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, added half bathroom, 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

1 Baths

1,656 Sq.Ft.

$999,999

MLS#: MDAA2135874

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

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.

$950,000

MLS#: MDAA2136542

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 3 days ago
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.
#MDAA2137020

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1004

2 Beds

2 Baths

1,794 Sq.Ft.

$949,000

MLS#: MDAA2137020

Tucked away at the end of a quiet, secluded street off No Cherry Grove (one of the prettiest streets in sought after Homewood) is the home you have been waiting for! This exceptional 4 BR, 2.5 BA, 3 level Contemporary offers rare privacy while remaining within walking distance to West Street Library, shops and restaurants and nearby Downtown Annapolis. Built in 1980, the home features a highly desirable main level Primary Suite complemented by elegant formal Living and Dining Rooms, a spacious Family Room, 2 fireplaces and custom built-ins. The remodeled granite Kitchen offers stainless appliances, solid wood cabinetry and leads to adjacent Family Room which opens seamlessly to beautiful outdoor living with decking and patio, perfect for entertaining or just enjoying the peaceful setting. Finished Lower Level adds lots of square footage. Set on a private, fully fenced lot, this home truly delivers PRIVACY, PRIVACY, PRIVACY- a rare find so close to the heart of Annapolis proper. Additional highlights include an oversized two car garage, circular driveway and generous storage throughout all three levels. Offered fully furnished, this property has an impressive rental history, serving as a corporate rental for over 10 years, consistently commanding $6500/mo. This makes it an outstanding opportunity for investors or buyers seeking short term rental or executive rental potential, as well as a turnkey primary or second home. A unique blend of seclusion, walkability and proven income, thisHomewood gem is truly one of a kind.
#MDAA2134282

ANNAPOLIS

1403 COREY LANE

4 Beds

2 Baths

1,960 Sq.Ft.

$925,000

MLS#: MDAA2134282

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

Open House this Saturday Feb 7th from 2-4PM! Rare double-lot opportunity in water-privileged Annapolis Roads! This beautifully updated home at 1009 Old Bay Ridge Rd conveys with the adjoining parcel at 1011 Old Bay Ridge Rd for a combined 0.55 acres. Enjoy exceptional outdoor space, extensive hardscaping, ample parking, golf-putting green, and a large detached barn-style garage/outbuilding ideal for parking, boat storage, hobbies/workshop, or storage. The renovated main level offers two family rooms, dining room, updated kitchen, and a bright sunroom. Upstairs includes a primary bedroom with full bath access, plus three additional bedrooms and two more full baths. Finished lower level featuring additional living space, workspace, & storage. Annapolis Roads amenities include a private beach, boat ramp, kayak storage, playground, pavilion, firepit, and waterfront overlook with Chesapeake Bay views. This home is conveniently located within a short distance to downtown Annapolis, the United States Naval Academy, amazing restaurants, shopping, and plenty of fun activities. A unique chance to own a spacious property in one of Annapolis’s most desirable communities! Hurry to this one, it won't last long!
#MDAA2132254

ANNAPOLIS

1009 OLD BAY RIDGE ROAD

4 Beds

3 Baths

2,845 Sq.Ft.

$899,000

MLS#: MDAA2132254

New Construction in Cape St. Claire. Home construction will start in February. Days on the market began when lot was purchased. Sales price would be reduced to $872,000 if buyer gets a construction perm loan to purchase home before the actual construction begins. Please look at the documents section of the listing to see all standard features included with this home and all floor plans and site plan. Pictures shown in this listing are of a previous home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire during the construction of that home. This same floor plan will be constructed on this site. Please contact listing agent with any questions. Home is scheduled to be completed by July/August of 2026.
#MDAA2130056

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$894,000

MLS#: MDAA2130056

Set within the sought-after, water privileged community of Annapolis Cove. This stately brick residence offers timeless style and serene connection to nature. Tucked away on the headwaters of Blackwater creek, the home enjoys private backyard framed by peaceful water views and lush natural surroundings. Morning light glimmers across the creek as blue herons and native birds glide by, ever-changing backdrop. the setting is quiet and restorative-ideal for those appreciate privacy, beauty, and a calming presence on Black Water Creek. Nestled in mature trees and screened by nature. Traditional 4/5 bedroom home features lots of welcoming spaces for all. Designed for both connection and relaxation. Four bedrooms, three full baths and a half bath on the main floor. Full Lower walk out level features gas fireplace stove for those cozy nites around the recreation room and bedroom and bath. A rare retreat. Annapolis Cove is a scenic waterfront community in Annapolis. It has a beautiful private marina on Lake Ogleton that opens to the Chesapeake Bay, just south of the mouth of the Severn River. The Cove has a waterfront park,recreational area with picnic tables, basketball court and a toddler playground overlooking the marina. Annapolis Cove Residents are able to join the Bay Ridge Pool and Swim team Each Summer. Bay Ridge pool is a private members only pool which is for Bay Ridge and Annapolis Cove Community Members. Annapolis Cove is a 10 minute drive from the Annapolis Historic district and less than five minutes from Quiet Waters Park.
#MDAA2132662

ANNAPOLIS

3233 CHRISLAND DRIVE

5 Beds

3 Baths

2,518 Sq.Ft.

$849,900

MLS#: MDAA2132662

Truly one of a kind, this exceptional 1-bedroom, 2 full-bath residence in sought-after Acton’s Landing, has been completely transformed by its current owners, who have spared no expense in creating a refined, turnkey home of remarkable quality and scale. With over 1,800 square feet, 9'+ ceilings, an open floor plan, and a dedicated office/den that has potential as a guest space or second bedroom, this residence offers flexibility, sophistication and comfort in equal measure. Uniquely positioned within the building, the home enjoys access to a second-floor lounge overlooking the interior courtyard—an amenity exclusive to this level. The sellers were told by fellow residents that this home boasts one of the largest kitchens in the building, and it shows. Anchored by an impressive 8'5" x 3'10" waterfall island with Calacatta® Venezia polished quartz, the kitchen is outfitted with premium GE® Monogram and Profile appliances, a striking imported Quelline® glazed ceramic backsplash from Spain, a pantry with wood shelving, wine cooler, and an abundance of cabinet and counter space—making it equally suited for entertaining and everyday living. Throughout the residence, new Mirage® Red Oak Nordic hardwood flooring with a Cashmere finish creates a cohesive, elegant aesthetic. A bank of windows in the sunroom fills the home with natural light. The expansive primary suite is a private retreat, featuring French doors, a walk-in closet plus an additional double-door closet, and a spa-inspired bath with a soaking tub, separate frameless glass shower, quartz double vanity, and high-end finishes throughout. A separate laundry room with full-size washer and dryer and built-in shelving completes the layout. This offering includes a dedicated garage parking space and private storage unit, with guest parking available in the garage. The building itself has undergone significant recent improvements, including a full interior refresh in 2025 and ongoing exterior rehabilitation, ensuring both beauty and peace of mind for years to come. Located in the heart of Annapolis with a Walk Score of 92, Acton’s Landing places you just two blocks from the waterfront, Water Taxi, City Dock, St. John’s College, the Naval Academy, and an abundance of shops, dining, and cultural attractions. Of particular note, Acton’s Landing is no longer subject to age restrictions This is a rare opportunity to own a meticulously reimagined residence where luxury, location, and livability converge.
#MDAA2134636

ANNAPOLIS

66 FRANKLIN STREET 214

1 Beds

2 Baths

1,821 Sq.Ft.

$840,000

MLS#: MDAA2134636

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a one-of-a-kind, almost 1-acre homesite, in the sought-after Annapolis area. Our exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor and upper hallways, granite or quartz countertops in the kitchen, upgraded cabinets with soft close doors, drawers and crown molding, ceramic-clad baths and laundry room floor, stainless appliances including refrigerator, a washer and dryer package, stone accents on the exterior, a portico porch, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails and black iron balusters, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion by adding optional finished spaces in the basement including a rec room, bedroom, den / media room and a full bathroom at an additional cost. Come home and enjoy the Chesapeake lifestyle in the heart of Annapolis? This property is located just minutes to Oyster Creek, Fishing Creek and historic Annapolis with plenty of access to shopping and dining choices. You will enjoy a convenient commute to Baltimore and Washington DC. This is a rare opportunity for new construction on a large lot in this sought after area. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features available. Prices, terms, conditions, and availability are subject to change without prior written notice. Other Models Are Available.
#MDAA2129594

ANNAPOLIS

3123 ARUNDEL ON THE BAY ROAD - TAFT MODEL

4 Beds

2 Baths

2,580 Sq.Ft.

$799,990

MLS#: MDAA2129594

Experience upscale urban living in this stunning 3rd-floor Everest model at Grandview, ideally located on the retail boulevard side of Annapolis Town Center. This residence offers a true city feel with unbeatable walkability to premier shopping and dining. The open-concept living and dining area features bamboo flooring, a dramatic tray ceiling, and floor-to-ceiling glass doors leading to a private balcony filled with natural light. Elegant French doors open to a versatile bonus room, ideal as a home office or third bedroom. The kitchen is designed for both entertaining and everyday living, showcasing stone and granite countertops, a professional-grade double oven, and a peninsula breakfast bar. A spacious laundry room and additional storage cage add convenience. Two luxury bedroom suites each feature custom closet organizers. The primary suite includes a spa-inspired bath with a soaking tub and walk-in shower, while the second suite offers a double-sink vanity and walk-in shower—perfect for guests or flexible living. Enjoy resort-style amenities including concierge services, fitness center, and a rooftop pool with social lounges, plus two assigned garage parking spaces. Walk to Whole Foods, Target, and top restaurants like True Food Kitchen and Cooper’s Hawk. Minutes from Historic Downtown Annapolis, Anne Arundel Medical Center, Annapolis Mall, with easy access to Route 50 and I-97. A must-see for those seeking a luxury, maintenance-free lifestyle.
#MDAA2135756

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 309

2 Beds

2 Baths

1,681 Sq.Ft.

$770,000

MLS#: MDAA2135756

Nestled in the serene enclave of Rolling Knolls, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, set against a backdrop of lush trees and tranquil woods. Spanning an impressive 0.85 acres, the property is a private retreat, perfectly situated at the end of a peaceful cul-de-sac, ensuring both seclusion and a sense of community. Step inside to discover an inviting open floor plan that seamlessly connects the living spaces, ideal for both entertaining and everyday living. Fully Remodeled 2025. Including but not limited to a Brand new roof,Kitchen, Flooring, Appliances,Siding,Windows, bathrooms, and much much more! The well-appointed kitchen flows effortlessly into the dining area, creating a perfect setting for gatherings with loved ones. The layout is thoughtfully designed, featuring an entry-level bedroom that offers convenience and flexibility, while the formal dining room adds a touch of sophistication for special occasions. Retreat to the luxurious primary bath. Additional bathroom features include a stall shower and a tub-shower combination, ensuring comfort and convenience for all. The fully finished basement presents endless possibilities, whether it be a home gym, entertainment area, or additional living space. With ample storage and a dedicated laundry area, this home is designed for modern living. Outside, the expansive lot is a nature lover's dream, with mature trees providing shade and privacy. The peaceful surroundings create a serene escape, perfect for enjoying morning coffee or evening sunsets. The oversized attached garage and private paved driveway offer ample parking and easy access. This property is not just a home; it's a lifestyle. Experience the tranquility of wooded views and the luxury of spacious living in a community that values privacy and nature. Embrace the opportunity to make this exceptional residence your own, where every detail has been crafted for comfort and elegance.
#MDAA2131464

ANNAPOLIS

524 RIDGE ROAD

4 Beds

3 Baths

2,944 Sq.Ft.

$750,000

MLS#: MDAA2131464

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