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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

300

# of Listings

3

Avg # of Bedrooms

$467

Avg. $ / Sq.Ft.

$1,062,130

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

109 Properties Found. Page 1 of 8.

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.

$999,900

MLS#: MDAA2103810

Welcome to this exceptional former model home in the prestigious Monticello enclave—ideally located just moments from Annapolis’ finest dining, shopping, and commuter routes. This residence showcases endless upgrades and over 6,700 square feet of refined living across three spacious levels, blending timeless elegance with cutting-edge comfort.
A dramatic two-story foyer with striking black-and-white marble flooring and designer lighting sets the tone upon entry. The formal dining room offers a sophisticated setting for entertaining and opens seamlessly to an outdoor deck, perfect for al fresco gatherings. The gourmet eat-in kitchen is a culinary dream, featuring high-end appliances, quartz countertops with a waterfall edge, and an open flow into the family and breakfast rooms—designed for effortless living.
The main level includes an ensuite bedroom, ideal for guests or multigenerational living, as well as integrated smart features like electronic door locks, a whole-house sound system, and destination control thermostats.
Upstairs, retreat to a luxurious Primary Suite complete with a private sitting area with fireplace, balcony, and an enviable walk-in closet with built-in storage. The spa-inspired bath offers a jetted soaking tub, new steam shower, dual vanities, and curated designer finishes. Three additional spacious bedrooms include an en-suite and a Jack-and-Jill bath—perfect for family or guests.
The fully finished walk-out lower level is built for entertainment and flexibility, featuring a wet bar, recreation area, theater, and a private bonus suite for guests, hobbies, or office space.
Additional features include an irrigation system, smart home technology, a 2-car garage, and access to Monticello's private amenities including a community pool and dog park—all in a tree-lined, beautifully maintained neighborhood.

ANNAPOLIS

2000 MONTICELLO DRIVE

6 Beds

6 Baths

6,612 Sq.Ft.

$999,000

MLS#: MDAA2116636

Welcome to this beautifully maintained residence in the amenity-rich community of Kingsport in Annapolis. Tucked into a picturesque neighborhood known for its scenic walking paths, swimming pool, tot lots, community pier, kayak storage, tranquil ponds with fountains, and lush landscaping, this home offers an exceptional lifestyle both inside and out.
Lovingly cared for by its original owners, this gem is now ready for its next chapter. From the moment you arrive, you'll be captivated by the charming front porch and the professionally landscaped yard, supported by an extensive irrigation system. Step inside to discover soaring ceilings, gleaming hardwood floors, and elegant moldings that highlight the home's architectural character.

The main level is thoughtfully designed for both everyday living and entertaining, featuring formal living and dining rooms, a spacious kitchen with ample cabinetry and workspace, a dedicated office, a convenient laundry room, and a bright sunroom overlooking the peaceful backyard.

Upstairs, you will find four generously sized bedrooms, including an impressive primary suite with tray ceilings, panoramic windows, and dual walk-in closets. The en suite bath is a true retreat, offering both space and style.

The fully finished lower level is a true standout, offering endless flexibility with a game room, music room, fitness area, workshop/storage space, and a full bath. The addition of a full egress walkout provides direct access to the beautifully designed paver patio and backyard—ideal for outdoor enjoyment.

Ideally located just minutes from shopping, downtown Annapolis, the U.S. Naval Academy, and offering easy access to Washington, D.C., and Baltimore, this home combines lifestyle, location, and luxury. Don’t miss the opportunity to make it yours.

ANNAPOLIS

702 PEARSON POINT PLACE

4 Beds

3 Baths

6,321 Sq.Ft.

$989,500

MLS#: MDAA2122894

Stunning contemporary in Winchester on the Severn featuring abundant windows that provide lovely views. Enjoy multi-level decks, patios, and custom hardscaping, complete with a private putting green and hot tub. Main level includes foyer, large sunroom, living room with stone fireplace - dining room combination, kitchen with granite countertops, main bedroom with adjoining full bath, 2 additional bedrooms and full bath in hall. The lower level includes another sunroom with exit to the rear yard, recreation room, study, and another very spacious room (potential 4th bedroom) with super bath and side exit. A real beauty! (Total Sq ft is likely larger than shown in tax record. An appraiser recently measured total sq ft at 3,548)

The Winchester on the Severn community offers a voluntary association fee of $260 per year for access to amenities, including a private beach, dock, canoeing, playground, and covered picnic pavilion . The community also has 2 different areas with boat slips that when available can be rented for an additional fee. The Chase Creek Swim Club is also nearby and joinable for an additional fee.

ANNAPOLIS

1534 CIRCLE DRIVE

4 Beds

3 Baths

2,876 Sq.Ft.

$975,000

MLS#: MDAA2116724

Stunning Updated Colonial in a Water-Privileged Community! This beautifully renovated four-bedroom, two-and-a-half bath home features a custom kitchen with all-new cabinetry, Calcutta Quartz countertops, and sleek stainless-steel appliances, including dual ovens with a gas cooktop. The inviting family room is equipped with built-in surround sound speakers, perfect for entertaining. The luxurious primary suite offers a spa-like experience with a large shower featuring dual shower heads, a soaking tub, a custom border-lit mirror, and a towel warming bar for those chilly days. Convenience is key with a second-floor laundry closet. Step outside from the family room onto a spacious Trex deck that overlooks a large backyard. The property includes an attached two-car garage and a fantastic 30x50 detached two-story toy barn garage, complete with a car lift 10' doors and 13' ceilings and the potential to finish the upstairs space into a perfect in-law or teen apartment. This home also boasts a new roof, a freshly paved driveway, and all-new plumbing and insulation. Enjoy the perks of a water-privileged community with access to a sandy beach and a community dock. This home and Detached garage sits on a double lot with separate gravel road on backside for easy access for boats, RV's storage. This home truly has it all!

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

3,078 Sq.Ft.

$950,000

MLS#: MDAA2111664

Welcome to your dream home in the exclusive Windfern Forest community—a private, water-privileged enclave of executive homes offering both tranquility and recreation. Nestled on a spacious .54-acre cul-de-sac lot, this well-maintained home offers approximately 5,100 square feet of living space. Inside, you’ll find four generously sized bedrooms and 3.5 bathrooms, including a luxurious primary bedroom suite that features an attached sitting room. The main level showcases hardwood floors adding warmth and sophistication, along with custom window treatments, cozy family room with fireplace, and a bright sunroom. A dedicated library/den/office with custom built-ins provides a productive and stylish workspace. The elegant formal dining room with its beautiful molding sets the stage for memorable entertaining. Enjoy the versatility of the lower-level recreation room plus bonus room and full bath—ideal for a guest suite, a home gym, or media space. You’ll also appreciate the abundant storage in the unfinished portion of the basement. Enjoy professionally landscaped grounds and access to kayaking, paddleboarding, and boat slips. Access to boat slips is available on a first-come, first-served basis. Conveniently located near shopping centers, restaurants, and major commuter routes, offering convenience without sacrificing peace and quiet. This home blends comfort, elegance, and lifestyle—making it a rare opportunity in a highly desirable setting.

ANNAPOLIS

534 POST OAK ROAD

4 Beds

3 Baths

5,040 Sq.Ft.

$950,000

MLS#: MDAA2114686

Welcome to 1141 Mainsail Drive, a beautifully updated colonial nestled on a desirable corner lot in Anchorage, one of Annapolis’ most coveted waterfront communities. This move-in-ready 4-bedroom, 2.5-bathroom home blends timeless colonial charm with thoughtful modern upgrades. Just one block from the community’s 49-slip marina, boat ramp, kayak and paddleboard racks, outdoor pool, and half basketball court, this property offers an exceptional lifestyle both inside and out.

Inside, you’ll find a traditional yet open layout floor plan with refinished hardwood floors on both the main and upper levels and tall windows that fill the home with natural light. The main level features a welcoming foyer, formal living and dining rooms, a powder room, and a family room with a freshly painted double-sided masonry wood-burning fireplace. The renovated eat-in kitchen boasts marble countertops, stainless steel appliances, and a gas line, seamlessly flowing into the casual dining area and family room—ideal for everyday living and entertaining. French doors lead to a charming brick patio, perfect for outdoor gatherings.

Upstairs, the primary suite with an en-suite bathroom and three (3) additional bedrooms are complemented by another bathroom and a versatile den/home office nook. The fully finished renovated basement, completed in July 2025, adds valuable living space with high-performance waterproof Pergo flooring, a recreation room, home gym or office area, and a renovated laundry/utility room with 2021 washer and dryer and ample storage.

Extensive updates include: roof, siding, gutters, and windows, new driveway and French drain system, new sump pump with backup battery system (July 2025), upgraded furnace, water heater, well pump, and sewer line.

The attached two-car garage provides convenient interior access, and the .34-acre lot features mature landscaping and a sense of privacy rare in Annapolis.

With only 106 homes, Anchorage is a close-knit, non-through-traffic community surrounded by wooded serenity and located just 3.5 miles to historic downtown Annapolis, 1 mile to Quiet Waters Park, and within 35 miles of D.C. and Baltimore.

Don’t miss this rare opportunity to own a thoughtfully renovated colonial in this hidden gem of a waterfront neighborhood—homes here rarely come to market at this price point.

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

3,264 Sq.Ft.

$949,000

MLS#: MDAA2108692

• Eclectic downtown location with 8 on-site parking spaces
• Unit has a reception/bullpen area, 5 offices, a kitchen that seats 4, copy/fax room and 2 restrooms (one with shower)
• Upgraded finishes and systems throughout
• Close proximity to Maryland State House, Circuit Court, State Office Buildings, United States Naval Academy, Annapolis City Dock, and St. John’s College
• Walking distance to Rams Head Bar & Grill, El Toro Bravo, Level, Tsunami, and various retail shops and services
• Taxes for the unit are $10,040 annually
• MX zoning, permitting uses of office, retail, restaurants, galleries, and laboratories.

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

1,971 Sq.Ft.

$940,000

MLS#: MDAA2110468

An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. Built by a member of the renowned Willard family, whose craftsmanship helped shape the Chesapeake Bay deadrise fishing boat, this property carries a rich history and offers a rare chance to create something truly special. The home itself features hardwood floors, beamed ceilings, and a screened-in porch - all positioned to capture the scenic surroundings. With a little thinning of the underbrush, you’ll have stunning water views from most rooms! Looking for even more potential? The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department requirements, with the final piece being a public water extension along the existing house frontage. The subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the legwork to get it to this point will convey.
This is more than just a home—it’s a unique opportunity to craft your dream estate in a prime Annapolis location. Don’t miss out—schedule your showing today to explore the possibilities!

PLEASE NOTE: Documentation for the subdivision efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The home is being sold strictly as-is, where is. Any inspections for buyer's information only.

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2116058

This stunning log home on 2.48 scenic acres (with the potential to subdivide) 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.

$925,000

MLS#: MDAA2113476

Stunning 5BR/4.5BA Luxury Home
Grand residence featuring hardwood foyer, formal oval dining room, living room, and main-level office. Gourmet kitchen with island cooktop, dual wall ovens, granite counters, and abundant cabinetry opens to the family room with vaulted ceilings, plantation shutters, and gas fireplace. The upper level includes a primary suite with spa bath and dual walk-in closets, en-suite second bedroom, plus two additional bedrooms with shared bath. The finished lower level offers a rec room with a wet bar, guest suite, and storage. Fully fenced yard with paver patio and raised garden bed. Property backs up to woods and walking paths. Close proximity to all commuter routes and minutes from downtown Annapolis

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

5,151 Sq.Ft.

$899,000

MLS#: MDAA2120506

#MDAA2121868

ANNAPOLIS

1601 RIDOUT ROAD

4 Beds

2 Baths

3,774 Sq.Ft.

$895,000

MLS#: MDAA2121868

Admiral Heights Beauty! 309 McDonough Rd features modern upgrades in a layout design for everyday living. With major systems updated and stylish finishes throughout, this is a home you can move right into and enjoy for years to come.
The kitchen, updated in 2021, features butcher block counters, crisp white cabinetry, and modern appliances. Hardwood floors flow through the main and upper levels, while the family room and lower level offer the comfort and durability of luxury vinyl plank flooring (2025). Both the primary bath (2023) and hall bath (2025) shine with recent renovations, and the refreshed basement (2024) adds inviting bonus space. Key system upgrades include the roof and windows/doors (2017), siding (2020), HVAC (2016), and an electric car charger (2023) for convenient at-home charging. Step outside and enjoy peaceful summer evenings beneath the pergola on your private patio. The fully fenced backyard (2020) is a true retreat, with native plantings, an herb garden, and four storage sheds—ideal for gardening, hobbies, or extra storage. A two-car carport, side gravel pad, and driveway provide ample off-street parking. This location offers the best in Annapolis living—neighborhood waterfront parks and community docks for kayaking or canoeing, plus the option to join the Admiral Heights Swim Club or a private boat club. Just minutes from downtown Annapolis and City Dock, with quick access to US 50/301 and MD 2, you’ll enjoy an easy commute to D.C. or Baltimore while coming home to the quiet charm of a well-established neighborhood.

ANNAPOLIS

309 MCDONOUGH ROAD

4 Beds

2 Baths

3,040 Sq.Ft.

$890,000

MLS#: MDAA2122618

MAJOR PRICE IMPROVEMENT!!!
Welcome home to this gorgeous 4-bedroom, 3-bath home in the sought-after North River Forest neighborhood. Situated on over an acre, this property features a bright, open floor plan with two first-floor bedrooms and a full bath, plus a spacious family room with soaring ceilings, skylights, and beautiful hardwood floors. The home as been pointed up and painted, has a water filtration system and softener and a radon mitigation system.

The eat-in chef’s kitchen is a dream—complete with a gas cooktop, double ovens, island, quartz countertops, and a huge pantry that’s practically its own room. Perfect for hosting and everyday living!

Upstairs, the expansive primary suite includes room for a sitting area and a luxurious private bath with a soaking tub and walk-in shower. A charming loft area overlooks the family room below, adding even more versatility to the layout.

The lower level features a fourth bedroom, a full bath, a laundry room, and a flexible rec room or bonus space to use however you need.

The exterior is clad in high-end Hardie Plank fiber cement siding—a hallmark of quality construction - as well as a new roof. Outdoor living is just as impressive with a large Trex deck, partially covered and partially open. In the summer, you can cool off or get in a workout in the 15-foot swim spa, and in winter, enjoy the peaceful views of the South River. Backing to community open space, the property offers a rare sense of privacy and tranquility.

All this, just minutes from shopping, restaurants, and commuter routes. This is a truly special opportunity you won’t want to miss.

ANNAPOLIS

2020 JOHN HANSON OVERLOOK

4 Beds

3 Baths

4,592 Sq.Ft.

$875,000

MLS#: MDAA2103690

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful almost half acre lot with walkout basement condition in the well-established neighborhood of Rolling Knolls, in Annapolis. *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. 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, granite or quartz countertops in the kitchen, upgraded cabinets with soft close doors and drawers, ceramic-clad baths and laundry room floor, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, 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 including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. This location is a convenient commute to Baltimore and Washington DC and just minutes to historic Annapolis, Maryland. This is a rare opportunity for new construction in the Annapolis area. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features that are available. Prices, terms, conditions, and availability are subject to change without prior written notice. Other plans are available for this lot, including a rancher plan.

ANNAPOLIS

2175 GLENCREST CIRCLE - TAFT MODEL

4 Beds

2 Baths

3,480 Sq.Ft.

$849,990

MLS#: MDAA2123152

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