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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

359

# of Listings

3

Avg # of Bedrooms

$479

Avg. $ / Sq.Ft.

$1,097,034

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

359 Properties Found. Page 7 of 24.

#MDAA2108738

ANNAPOLIS

827 JANICE DRIVE

4 Beds

4 Baths

4,000 Sq.Ft.

$1,195,000

MLS#: MDAA2108738

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

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.

$1,175,000

MLS#: MDAA2114928

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

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

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

This stunning home, available for delivery in April, boasts high-end upgrades throughout. It features a first-floor owner's suite, plus three additional bedrooms on the second level, along with two full bathrooms and a spacious loft. The gourmet kitchen is a chef’s dream, complete with custom cabinetry and an open-concept design. The impressive two-story family room with soaring ceilings creates a dramatic focal point, while the finished basement rec room, featuring a wet bar with a refrigerator and sink, is perfect for entertaining. Experience luxury living at its finest—schedule your tour today! Photos for illustration purposes only. Agent must attend first visit.

ANNAPOLIS

106 STILLY WAY

4 Beds

4 Baths

4,594 Sq.Ft.

$1,047,590

MLS#: MDAA2103810

New Construction - Move In Ready March 2025! Please go to Model home to tour!

Welcome to the Lynnfield model at Parkside Preserve, where luxury meets tranquility in this stunning new construction adjacent to the serene Quiet Waters Park. With over 5,017 finished square footage this meticulously designed living space across four levels, featuring 5-bedrooms, 5.5-bathrooms, 4th level loft, and finished lower level with a a true walk-out basement is a perfect fit for modern living.

Step inside and be captivated by the elegance of the owner’s suite, featuring a tray ceiling and a spacious walk-in closet. Enjoy the comfort of 9' ceilings throughout, including in the finished basement, and cozy up by the gas fireplace in the expansive living area. The exterior impresses with a blend of brick and HardiePlank, complemented by a welcoming front porch and a front-entry garage.

The heart of the home—the kitchen—is a chef’s dream. It boasts two 36' wall ovens (one with an air fryer), a 30' gas cooktop, a stainless steel hood, and a built-in microwave. The staggered white maple cabinetry, complete with under-cabinet lighting and display glass door cabinets, pairs beautifully with the iced white quartz countertops and tiled backsplash.

All full bathrooms feature maple cabinetry, quartz countertops, and oversized ceramic tile for a touch of luxury. The finished basement is an entertainer’s paradise with an enormous rec. room, a wet bar, and the fourth full bath.

This is more than just a home—it’s a lifestyle. Don’t miss the opportunity to be the first to live in this spectacular residence at Parkside Preserve.

Photos are for illustration purposes only.

ANNAPOLIS

110 STILLY WAY

5 Beds

5 Baths

5,017 Sq.Ft.

$1,039,990

MLS#: MDAA2098972

Welcome to 711 Genessee Street – where modern luxury meets the heart of Annapolis charm. Located in the coveted West Annapolis School District, this newer construction stunner (built in 2021) offers the perfect blend of upscale finishes, smart design, and unbeatable location—all within walking distance to shops, dining, and everything you love about Annapolis living.
Step inside to find a main level designed for both everyday comfort and effortless entertaining. The open-concept layout is grounded by wide plank wood flooring, enhanced by custom moldings, and anchored by a cozy gas fireplace. The chef’s kitchen is a standout feature, boasting 42” custom cabinetry, quartz countertops, a top-of-the-line appliance package, and a gas cooktop—perfect for everything from weekday meals to weekend gatherings. Custom oak stairs and railings tie the space together with warmth and character.
Upstairs, retreat to your primary suite complete with cathedral ceilings and a spa-like ambiance. The upper level continues the upscale feel with 9-foot ceilings and custom tray ceilings, creating a spacious, airy vibe throughout the bedrooms and baths.
The fully finished lower level adds even more versatility, featuring a large recreation room, an additional bedroom, a full bath, and plenty of storage space—ideal for guests, hobbies, or a second living area.
Outside, enjoy a welcoming front porch that invites morning coffee and neighborhood chats, while the rear paver patio offers the perfect spot for outdoor dining or summer soirées. The fully fenced-in backyard is a private escape, ready for pets, play, or peaceful lounging.
Don't miss your chance to own this thoughtfully upgraded, move-in ready gem in one of Annapolis' most desirable neighborhoods. 711 Genessee Street is more than a home—it’s a lifestyle upgrade.

ANNAPOLIS

711 GENESSEE STREET

4 Beds

3 Baths

3,148 Sq.Ft.

$999,900

MLS#: MDAA2108296

Welcome to 1141 Mainsail Drive, a renovated Classic Colonial style home located in the sought-after Waterfront Community of Anchorage. This 4-bedroom, 2.5-bathroom property has undergone over $200,000 in renovations over the past 20 years while preserving its classic colonial charm. This beautiful corner lot has a newly repaved driveway, a 2-car garage and is only a block away from the amenities which include a 49-slip marina, a boat ramp, an outdoor pool, racks for kayak and paddle boards and a half basketball court.
Many improvements have been done throughout the home including a total refurbishing of the hardwood floors (main level and upper level), fresh paint, upgraded kitchen with marble countertops and stainless-steel appliances, gas line, renovated bathrooms, replacement of windows, roof, siding, gutters, finished basement and water proofing (French drain), laundry room with 2021 washer and dryer, furnace, water heater, well pump, sump pump, sewer line and more.
The tall symmetrical windows in the main level invite light into this classic colonial style layout with a newly painted double-sided masonry wood burning fireplace and an open-layout kitchen. The main level includes a foyer, powder room, family room, living room, dining room and kitchen. The eat-in-kitchen flows seamlessly into “the heart of the home”, the casual dining area and family room, creating an open and inviting space for everyday living. The French doors from the casual dining area lead to a rear brick patio for outdoor entertainment. The 2-car garage is attached to the home with direct entrance into the main level. The upper level features 4-bedrooms, 2-upgraded bathrooms and a den/home office nook. The lower level is a fully finished basement with space for a recreation room, home office and/or fitness area. Also, there is a renovated Laundry / Utility Room with an additional storage space.
Do not miss this opportunity to purchase a renovated colonial in Anchorage as they are a rare find and especially at this price point. Anchorage is a small community (106-homes), with no cut through streets, and mature landscaping. This .34-acres property is 3.5-miles from downtown historic Annapolis, 1-mile from the 340-acre Quiet Waters Park, 35-miles from Washington D.C. and 32-miles from Baltimore.

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

2,176 Sq.Ft.

$985,000

MLS#: MDAA2108692

***Be at the forefront of the Neighborhood Property Expansions and Enjoy the Future Appreciation of
this stunning five-bedroom, three full and one-half bath colonial is located in the Mulberry Hill community. Situated on a large corner lot, this home boasts a covered front porch, rear deck and attached three-car garage. Inside, you will find beautiful hardwood floors, recessed lighting, crown molding and fresh paint throughout. The main level features a formal living room, separate dining room and step-down family room with a gas fireplace and mantel. The spacious, table-space kitchen boasts granite countertops, center island, stainless steel appliances and a bay-window breakfast nook. Upstairs, the primary suite offers a luxurious retreat with hardwood floors, a private bath and a bonus room. Three additional bedrooms with new carpet and an updated full hall bath complete the upper level. The finished, walk-up lower level offers a versatile recreation room, a flexible fifth bedroom, perfect for use as a home office, den or guest room and a full bathroom. Located in a quiet setting, just minutes from the Naval Academy and the Naval Academy Golf Course, yet close to everything that Annapolis has to offer, this home is truly a dream come true!

ANNAPOLIS

1825 JOHNSON ROAD

5 Beds

3 Baths

3,028 Sq.Ft.

$985,000

MLS#: MDAA2098830

Welcome to this DESIGNER SHOWCASE including a custom painted entry that draws you in the moment you open the door. Owner worked with a reputable interior designer to select all finishes to include designer light fixtures, gorgeous real hardwood floors, custom designed bathrooms, and so many interesting trim details. Transitional timeless design with a coast twist. ONE OF A KIND and RARE GEM! END UNIT. Not one detail has been overlooked! And a beautiful gated waterfront and water-privileged community. BE PREPARED to be wowed when you open the front door with a top of the line renovation over $350,000. NOTICE ALL OF THE BEAUTIFUL ARCHED DOORWAYS!New Bosch HVAC, and tankless hot water heater. All the vents were professionally cleaned after renovation. This is an opportunity that doesn't come along too often to move right into a turn-key TOTALLY RENOVATED & AND REDESIGNED BY AMAZING LOCAL DESIGNER !! gorgeously designed home in the exclusive community of Chesapeake Harbour. No expense has been spared to make this custom first-class from floor to ceiling. Totally redesigned and totally renovated with all permits. Custom window treatments throughout and designer light fixtures. Custom gourmet kitchen with quartz counters, stainless steel appliances, an abundance of drawer storage, perfect bar/pass through and much more! Three bedrooms and three full bathrooms. Each space offers light and invites you to relax and be happy you don't have to redo anything. Two-car garage with storage room and storage installed in ceiling of garage. Two gas fireplaces. Beautiful custom shiplap in living room and master bedroom. Multiple decks and from the top deck off master, owner loves to relax and watch the boats and bay bridge. His and her custom closets. And talk about the community, Community beach and pier and two pools, one heated and one waterfront looking out at the Bay. Tennis and pickleball courts for your fun and exercise. Don't worry about getting your steps in with all the waterfront walking paths, If you don't feel like cooking, walk on over to The Beacon with dockside seating . This is a gated community with 24/7 security and guard gate. You can have it all with the best of coastal living in this vibrant and secure community. The pictures really don't do it justice. WAS TEMP OFF THE MARKET NOVEMBER TO NOW!

ANNAPOLIS

7015 CHESAPEAKE HARBOUR DRIVE 23B

3 Beds

3 Baths

2,041 Sq.Ft.

$985,000

MLS#: MDAA2073518

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Buyers resources

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7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

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SELLERS RESOURCES

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