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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

375

# of Listings

3

Avg # of Bedrooms

$480

Avg. $ / Sq.Ft.

$1,091,863

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

375 Properties Found. Page 7 of 25.

#MDAA2097228

ANNAPOLIS

301 UNITY LANE

5 Beds

5 Baths

7,616 Sq.Ft.

$1,219,000

MLS#: MDAA2097228

Step into a piece of Annapolis history with the Philip Clayton House, a cherished landmark dating back to 1834. Perfectly situated within walking distance to the City Dock, U.S. Naval Academy, and the vibrant shops and restaurants of Downtown Annapolis, this residence blends timeless character with everyday convenience. Over nearly two centuries, the home has undergone thoughtful renovations and expansions, preserving its historic charm while enhancing livability. You'll be captivated by the heart of pine floors,
many original moldings, and multiple fireplaces that reflect its storied past. The spacious family room addition seamlessly opens to a private patio and fenced backyard—ideal for outdoor entertaining or peaceful relaxation. Inside, the home features 4 generously sized bedrooms and 2.5 bathrooms, offering comfortable accommodations for residents and guests alike. The large kitchen, complete with a central island, serves as a natural gathering space—perfect for family meals or entertaining. Currently operating as a successful VRBO, this property offers both residential appeal and investment potential.

Don’t miss your chance to own a piece of Annapolis history!

ANNAPOLIS

160 GREEN STREET

4 Beds

2 Baths

2,322 Sq.Ft.

$1,200,000

MLS#: MDAA2113866

#MDAA2094906

ANNAPOLIS

3536 SARATOGA AVENUE

4 Beds

3 Baths

2,368 Sq.Ft.

$1,196,000

MLS#: MDAA2094906

#MDAA2108738

ANNAPOLIS

827 JANICE DRIVE

4 Beds

4 Baths

4,000 Sq.Ft.

$1,195,000

MLS#: MDAA2108738

Live the Annapolis lifestyle just close enough to enjoy in-town living, but tucked away in a quiet little enclave avoiding all the noise and parking challenges in town. The current homeowner refers to Primrose Hill as a "serene little gem'. Walk to coffee shops and dining hot spots, launch the boat or hop on the water taxi right up the street. This distinguished Georgian-style home offers the best of both worlds—peaceful, private living with unparalleled access to the city's most desirable amenities. The HOA cares for the lawn and snow removal, just lock and leave and head out of town stress free! Originally the model home for the community, every inch of this residence reflects elevated design and attention to detail a discerning buyer would expect. The timeless Georgian brick front exudes classic charm, while the interior reveals a sophisticated, modern aesthetic. A sleek, designer kitchen with upgraded appliances flows effortlessly into an open-concept main living area—ideal for entertaining or relaxed everyday living. The inviting family room is anchored by custom built-ins and a gas fireplace, adding warmth and architectural interest. This 5-bedroom, 4.5-bath home is designed for comfort and style. The upper level features four spacious bedrooms, including a luxurious owner’s suite with cathedral ceilings, an expansive walk-in closet, and a spa-inspired bathroom retreat. Bedroom two boasts its own private ensuite, offering flexibility for guests or multigenerational living. A conveniently located upstairs laundry enhances everyday functionality. The fully finished lower level includes a generous recreation room and a versatile bonus room—perfect for a home gym, office, or guest bedroom. A rare two-car garage with additional driveway parking adds convenience, especially valuable in this in-town location. Residents enjoy exclusive access to nearby amenities such as the Pip Moyer Recreation Center with tennis and pickleball courts, fitness classes and a swim club. The park like setting and intentional green spaces serve as the perfect backdrop for weekly neighborhood wine nights and social gatherings throughout the year fostering a welcoming and connected sense of community.
This location provides a quick commute to DC and Baltimore. CHECK OUT THE VIRTUAL TOUR;

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

3,978 Sq.Ft.

$1,195,000

MLS#: MDAA2113794

Welcome to Unit 508 at Severn 100—a rarely offered, elegant 1,173-square-foot, 2-bedroom, 2-bath residence offering front-row seats to the most vibrant views of The Annapolis Harbor, Spa Creek and The US Naval Academy. Located in the heart of Eastport, this luxurious condo blends upscale finishes with unmatched water views. Step inside to rich mahogany floors, a beautiful spacious kitchen with upscale KitchenAid stainless steel appliances and granite counter tops. Two renovated Spa-inspired marble baths, one with an air jet soaking tub and one with a large walk- in shower are designed with comfort and style in mind. Both have heated floors. Thoughtfully redesigned walls adding pocket doors creating more closet space. Walls of glass, frame ever-changing scenes of the bustling harbor—sailboats gliding by, sunsets painting the sky, and moonsets reflecting off the water. At night, the twinkling lights of downtown Annapolis create a magical, starlit backdrop. It truly is a real life movie playing out in front of you 24/7. Enjoy the ease of secure building access, a dedicated garage parking spot on the main level, and elevator service right to your door. Just outside, Eastport’s vibrant maritime district, restaurants, and marinas are all within walking distance—bringing the best of Annapolis to your doorstep.
Whether you’re watching the bustling harbor or soaking in the golden glow of a waterfront sunset, Unit 508 offers a lifestyle that’s as dynamic as it is peaceful. There’s never a dull moment on the harbor—come experience it for yourself.

ANNAPOLIS

100 SEVERN AVENUE 508

2 Beds

2 Baths

1,173 Sq.Ft.

$1,195,000

MLS#: MDAA2111360

Lot 115 has officially stepped out on its own after being unmerged from 703 Glendon Avenue (although they could be bought together), and it's ready for someone to build something special. With just over a quarter-acre and Nestled in the heart of Eastport, this 11,362 sq ft lot offers the perfect blend of quiet privacy and connection to one of Annapolis’s most beloved neighborhoods.

Set along the tranquil waters of Back Creek, this property offers peaceful water views, free from boat traffic and city noise—just enough to remind you why you chose the maritime life.. It’s tucked just far enough off the main path that it feels like a bit of a secret, yet you’re still minutes from downtown Annapolis.

Eastport is known for its strong sense of community, walkability, and a laid-back spirit best summed up by its motto: “Fun With a Purpose.” You’ll find that energy in the local restaurants and watering holes—Vin909, Lewnes Steakhouse, Davis’ Pub, Boatyard Bar & Grill, Chart House, Black Wall Hitch and more—all just a short stroll or bike ride away.

Whether you're thinking modern retreat or classic coastal cottage, Lot 115 is a quiet corner of Eastport waiting for its next chapter. Come check it out!

According to the President of the Park Wood Association: The Parkwood Civic Association (PCA) is a voluntary group (not an HOA) with $100 annual dues used to maintain community areas like Parkwood & Short Street Park, Hoffman Park, and the docks, as well as fund a fall picnic. PCA membership is required to apply for a dock slip. Applicants must own the boat, registered to their Parkwood address. A waitlist, based on boat size, is managed by the dock master. Slip fees are additional—about $800 for large and $550 for small slips.

For a clearer visual understanding of Lot 115 please review the Existing Lot Coverage Summary pdf in the document section of this listing. You will also find some other helpful resources and information to help you along the way!

ANNAPOLIS

LT 115 703 GLENDON AVENUE

None Beds

None Baths

0.26 acres

$1,175,000

MLS#: MDAA2109892

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.

ANNAPOLIS

179 GREEN STREET

2 Beds

1 Baths

1,656 Sq.Ft.

$1,175,000

MLS#: MDAA2111662

New on site 2 days ago

Where to Begin?
Where timeless style meets smart functionality, this stunning one-level gem in Murray Hill is more than just a home. Bathed in natural light with soaring vaulted ceilings, this meticulously renovated architectural treasure offers a surprising sense of openness and calm. Every inch has been thoughtfully designed to create a private, peaceful oasis just steps from the heart of Annapolis.

Inside, custom details steal the show. The living room showcases beamed vaulted ceilings with smart home lighting, and a sleek gas fireplace topped with custom artwork lifting to reveal a hidden flat screen television. The gourmet kitchen with gas cooking has top of the line appliances and thoughtfully organized custom cabinetry. The primary bedroom offers an en-suite bathroom with a beautifully tiled walk in shower, and a walk-in closet. In the second bedroom, currently used as charming library, a wall of built-in bookshelves conceals a queen-sized Murphy bed ready to welcome your overnight guests in style. A yet another surprise is the hidden hydraulic lift door, reminiscent of a yacht’s below deck entrance, leading to a dry, spacious basement perfect for storage or a future wine cellar.

Tucked away on the quiet lower block of Southgate Avenue, this home enjoys the rare combination of tranquility and walkability. You’ll enjoy water access and picturesque Spa Creek views from the floating dock at the end of the street. Stroll up the street and within minutes you’re immersed in the vibrant energy, shops, and dining of downtown Annapolis.

In the beloved historic neighborhood of Murray Hill, there is nothing more unique . This is more than a home—it’s a hidden treasure waiting to be discovered.

ANNAPOLIS

16 SOUTHGATE AVENUE

2 Beds

2 Baths

1,109 Sq.Ft.

$1,151,000

MLS#: MDAA2114034

Sellers are offering $25,000 to go towards siding replacement. This beautiful property offers three levels of spacious, comfortable living in the neighborhood of Epping Forest. Walking through the front door, vaulted ceilings and natural light greet you in the dining/living room area off the kitchen. A main level bedroom suite offers convenience and a second suite upstairs boasts extra privacy. The Severn River can be seen through the trees off the double level deck which is accessed through the dining room, primary suite, or basement common room. On the bottom level, two bedrooms share a full bath and a common living space. Sliding doors add more natural light and additional exits to the lower deck. The private neighborhood beach and clubhouse offer peak enjoyment in the summer months! The club house offers family and golf cart friendly community for all ages! Ample storage, parking, and living space make this home unique in the gated community!

HVAC replaced in October of 2020
Both decks replaced in December of 2020
Water treatment system replaced in February of 2022
Roof replaced in November of 2023

Buyer must review and acknowledge Epping Forest Constitution and Bylaws. See Documents.

ANNAPOLIS

319 EPPING WAY

4 Beds

3 Baths

2,372 Sq.Ft.

$1,150,000

MLS#: MDAA2095698

Live the Eastport Dream – Luxury, Water Access & Walkability at 827 Janice Drive. Step into a rare opportunity to own a custom-built showpiece in Eastport’s best-kept secret—Green Acres. Welcome to 827 Janice Drive, where elevated design meets the unbeatable Annapolis lifestyle. This 4,000+ square foot home, meticulously constructed by Cedar Square Homes, is more than just beautiful—it's move-in ready, thoughtfully curated, and built to impress at every turn. From the moment you arrive, the home makes a statement—grand entry, sunlit spaces, and a floor plan that flows effortlessly. At the heart is a chef’s kitchen that doesn’t hold back: massive quartz island, premium stainless appliances, 42-inch custom cabinetry, and designer lighting. Whether you're hosting a crowd or enjoying a quiet morning coffee, this kitchen delivers.
The main level also includes a gas fireplace in the family room, private office, and expansive entertaining spaces. Upstairs, escape to a luxurious primary suite with spa-like bath, featuring a freestanding soaking tub, oversized glass shower, and serene finishes. Three additional bedrooms and two more designer baths complete the upper level, offering room for everyone. Downstairs? It’s the ultimate flex space: a fully finished basement with rec room, den, and full bath—perfect for guests, workouts, media nights, or whatever your lifestyle demands. But what truly sets this home apart is location and community. Green Acres is an enclave of tranquility in the heart of Eastport, with tree-lined streets, friendly neighbors, and private water access to Back Creek including a residents-only pier with kayak and paddleboard storage. Launch into adventure from your own neighborhood. Walk or bike to Downtown Annapolis, the marina, restaurants, and the iconic Eastport charm. It’s all just minutes away. This isn’t just another luxury home—it’s a once-in-a-generation lifestyle opportunity. And it’s ready for you, right now. New, never lived in, and ready for immediate occupancy. Showings are easy—schedule yours today and experience why 827 Janice Drive stands in a league of its own.

ANNAPOLIS

827 JANICE DRIVE

4 Beds

4 Baths

4,000 Sq.Ft.

$1,150,000

MLS#: MDAA2114928

This stunning log home on 2.48 scenic acres offers the perfect blend of rustic elegance and thoughtful upgrades. Surrounded by lush landscaping, the property provides treetop views and a glimpse of the water during the winter months. The impressive two-story living room showcases a dramatic wood-burning fireplace and flows effortlessly into the dining area and the gourmet kitchen, which features granite countertops, a breakfast bar, ample cabinet space, and all major appliances.

Three generously sized bedrooms are located on the main level, each with gleaming hardwood floors. The primary suite includes a ceiling fan, walk-in closet, a spa-like bathroom with a soaking tub and separate shower, and private access to the deck.

Upstairs, a sunlit loft with oversized skylights offers flexible space for a home office, family room, or den and includes a full bathroom. The finished basement adds even more living space, with a spacious recreation room featuring wall-to-wall carpeting and recessed lighting, a fourth bedroom, a laundry area, and plenty of storage.

Outdoor living is just as inviting, with a large rear deck that backs to wooded privacy and a welcoming front paver walkway and deck. The driveway provides ample parking, and the home is just a short walk from community beach access.

Ideally located near major highways and downtown Annapolis, this home offers tranquil surroundings with convenient access to shopping, dining, and everyday necessities.

ANNAPOLIS

2977 SOUTHAVEN DRIVE

4 Beds

4 Baths

3,200 Sq.Ft.

$1,100,000

MLS#: MDAA2113476

Immerse yourself in the epitome of sophisticated living at GrandView, where luxury meets meticulous craftsmanship in this impeccably renovated condo at the heart of the Annapolis Town Center. This residence has been transformed with an unwavering commitment to detail, creating a haven of transitional design elegance.

As you enter, the home welcomes you with a seamless open-concept design, illuminated by an abundance of natural light pouring through expansive wall-to-wall windows. The gourmet kitchen, adorned with stainless steel Thermador appliances and marble countertops with full height marble backsplash, offers a perfect blend of functionality and style. A cozy breakfast nook and bright white cabinetry add a touch of warmth to the culinary space.

Step outside onto the spacious covered corner balcony, where you can bask in the ambiance of Town Center activities, creating the perfect backdrop for outdoor relaxation and entertaining.

Discover tranquility in the two generously-sized bedrooms, each thoughtfully outfitted with custom designed closet storage solutions. The primary owner's suite is a sanctuary of luxury, featuring a dressing room, a spa-like bathroom and curved elevation of tinted windows for added privacy and style.

This residence boasts a myriad of updates, including custom electronic window treatments, exquisite marble flooring/countertops and shower walls, built-in closet organizers, premium trim throughout, and all new and custom cabinetry throughout, all new plumbing fixtures and kitchen appliances. With 10’ 6” high ceilings enhancing the sense of space, every detail has been carefully curated to elevate your living experience.

GrandView offers a true sense of community, providing residents with access to a rooftop sky lounge, rooftop pool, outdoor kitchen, state-of-the-art fitness center, and a club/party room. The professionally managed concierge staff ensures convenience and security.

Conveniently located, GrandView is just a stroll away from Annapolis' finest restaurants, Whole Foods, Target, Life Time Fitness Club, banking, and local shops. Minutes from Historic downtown Annapolis, the US Naval Academy, Anne Arundel Medical Center, and Annapolis Mall, this residence is a commuter's dream with easy access to Route 50 and 97.

Don't miss the opportunity to experience refined urban living at its finest. Schedule a showing today and embark on a new chapter of sophisticated living in this captivating residence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 504

2 Beds

2 Baths

1,945 Sq.Ft.

$1,099,500

MLS#: MDAA2101336

New on site 1 day ago

Rare Opportunity in Exclusive Bay Ridge!
Welcome to your dream home in the sought-after Bay Ridge Community. This beautifully maintained, move-in-ready 3-bedroom, 1.5-bath home offers an open and airy floor plan designed for both comfort and entertainment. Step into the updated kitchen, featuring stainless steel appliances, tall modern cabinetry with abundant storage, granite countertops, and an eat-in area perfect for morning coffee. The separate formal dining room is ideal for hosting dinners and holiday gatherings. Unwind in the spacious living room, complete with an electric fireplace and a sliding glass door with integrated blinds that opens onto an exceptionally large patio — the perfect setting for summer barbecues, celebrations, and quiet evenings under the stars. A versatile bonus room: create a serene home office, cozy reading nook, or personal yoga retreat. The convenient mudroom includes additional storage, washer/dryer, a half bath, and direct access to the patio. The master bedroom features a walk-in closet, while the updated full bathroom boasts ceramic tile, a modern vanity, and a shower. The outdoor living space is a true highlight — host unforgettable parties, graduations, and get-togethers on your sprawling patio with a large outdoor kitchen. After a day of sun and sand at the private beach, rinse off in your convenient outdoor bathhouse before stepping inside. As a Bay Ridge resident, you’ll enjoy access to an incredible suite of amenities, including a community pool, marina with boat slip opportunities, private beach, park, and more — all just minutes from downtown, dining, and shopping. Don’t miss your chance to call this stunning home in one of the area’s most coveted waterfront communities your own. ALL CONTRACTS ARE DUE BY 5 PM ON SUNDAY, JUNE 8.

ANNAPOLIS

13 WAINWRIGHT AVENUE

3 Beds

1 Baths

1,620 Sq.Ft.

$1,090,000

MLS#: MDAA2114074

Recently updated colonial with all new custom kitchen cabinets, stainless appliances, dual oven w/gas cooktop. Family room with built in surround sound speakers-bring your own equipment. Primary suite with custom bath large shower with dual heads, nice soakiing tub, border-lighted mirror and a towel warming bar. Laundry closet on 2nd floor. Parrtial unfinished basement with utilities plus space for a possible movie/man cave. Attached oversized 2 car garage with extra storage area. 3 car-plus garage 10' doors 13' ceilings, car lift-great for those do-it-yourself folks, tons of space above to finish for rooms-in-law/teenage apartment!
House sits on a double lot space for a pool? Plenty of room for boats, RV's or other toys? Access to back of lot by a gravel driveway

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$1,050,000

MLS#: MDAA2111664

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