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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
320
# of Listings
3
Avg # of Bedrooms
$464
Avg. $ / Sq.Ft.
$1,069,545
Med. List Price

Browse Annapolis Real Estate Listings

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320 Properties Found. Page 16 of 22.

Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly sought-after Whispering Woods community. Step inside to find a recently renovated kitchen with modern finishes perfect for both everyday living and entertaining. The open space layout offers comfortable living space filled with natural light, while the upper level provides three spacious bedrooms, including a relaxing primary suite with its own bathroom. Out back you'll discover your own private retreat - a peaceful backyard with a pond and flourishing floral garden, creating the perfect setting for quiet mornings or evening gatherings. With plenty of street parking and a serene community atmosphere, this home blends comfort, convenience, and charm. All Appliances under 2 years old. The refrigerator is brand new, along with sliding glass doors. Great community for walking and biking. Great location, a true commuter’s delight - close to Annapolis, Naval Academy, Baltimore, Washington DC, Fort Meade, Chesapeake Bay Bridge, BWI Airport, and Close to major roads such as Route 50, Route 2, I-97, and more. Only minutes to downtown Annapolis, Shopping, Walking & Bike Trails, Restaurants, Social Activities, Sandy Point, Chesapeake Bay, and more. The Loan is Assumable on this home !!
#MDAA2126896

ANNAPOLIS

1116 RIVERBOAT COURT

3 Beds

2 Baths

1,310 Sq.Ft.

$384,000

MLS#: MDAA2126896

This 3 bed / 2 bath condo has everything you need a cozy fireplace, spacious layout, and no stairs! The primary suite is your retreat, while two extra bedrooms give you space for family, guests, or even a home office. Plus, you’ll love the community pool when the weather warms up.
#MDAA2126636

ANNAPOLIS

2026 GOV THOMAS BLADEN WAY 102

3 Beds

2 Baths

1,317 Sq.Ft.

$379,999

MLS#: MDAA2126636

New on site 1 day ago
Professional Photos Coming Soon !
#MDAA2128786

ANNAPOLIS

2704 SUMMERVIEW WAY 103

2 Beds

2 Baths

1,285 Sq.Ft.

$379,990

MLS#: MDAA2128786

Discover easy, low maintenance living in this updated two bedroom, two bath condo nestled among the treetops of sought after Heritage Harbour, one of Annapolis’s premier 55+ communities. The home features fresh paint and new flooring throughout the main living areas, plus a remodeled kitchen with modern countertops, sleek cabinetry, and newer appliances. Major system updates include a replaced HVAC, water heater, washer, and dryer, so you can move right in and enjoy peace of mind. Relax on your private balcony surrounded by nature, or take advantage of convenient building amenities including an elevator, game room, and indoor/outdoor pools. Heritage Harbour residents enjoy resort-style amenities: a community lodge with a fitness room, billiards room, library, and gathering spaces; golf, tennis, pickleball, water access, boat storage, an additional community pool, and nearby shops and restaurants. Minutes from Downtown Annapolis and the Chesapeake Bay, this location offers comfort, convenience, and community all in one.
#MDAA2122918

ANNAPOLIS

930 ASTERN WAY 405

2 Beds

2 Baths

1,464 Sq.Ft.

$379,900

MLS#: MDAA2122918

Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and unmatched amenities. This 2-bedroom, 2-bath condo is priced to sell and provides a wonderful opportunity to make it your own. Inside, the unit offers a bright and spacious layout filled with natural light. The living room and both bedrooms open onto a private balcony with serene views of trees and woods—the perfect spot for morning coffee or evening relaxation. The condo needs a bit of TLC, but it has great bones and is priced accordingly. Features of Unit #203: Open floor plan with excellent natural light Balcony access from both bedrooms and living room Convenient parking space in the secured garage Large private storage unit located right in front of your parking space Easy in-and-out access within the garage Community Amenities at Heritage Harbour: 9-hole golf course & pro shop Indoor & outdoor swimming pools Fitness center with aerobics & exercise classes Tennis courts, pickleball, and bocce ball Community lodge with auditorium, dining room, billiards, and library Walking and biking trails throughout the neighborhood Dock & waterfront access on the South River Kayak/canoe racks and launch areas Woodworking shop & craft rooms On-site security & professional management Social clubs, classes, and community events year-round This is a chance to enjoy all the benefits of Heritage Harbour’s lifestyle at a fantastic value. With a little updating, this condo could be the perfect home for your next chapter. Don’t miss out—schedule your showing today!
#MDAA2121676

ANNAPOLIS

803 COXSWAIN WAY 203

2 Beds

2 Baths

1,190 Sq.Ft.

$379,900

MLS#: MDAA2121676

Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring throughout, presenting a promising canvas for renovation. Strategically located, this property is in close proximity to essential amenities and community .Public transportation is conveniently accessible with the Riva Road & Forest Drive bus station less than 700 meters away, enhancing the location. Additional features include a rear deck perfect for relaxation or casual gatherings, a useful rear shed for extra storage, and a generous off-street parking area that can accommodate up to 12 vehicles. Despite being sold as-is, with no repairs from the seller, the property's inherent potential and dual-use capability as both a residential and commercial space make it a lucrative deal. Capitalize on the chance to customize this space into a thriving business venture or a mixed-use development that promises both rental income and renovation possibilities. Dive into this project and shape it into your vision of success! Property is being sold AS-IS, Seller will make no repairs. All offers must have $1000 deposit and proof of deposit. Buyer responsible for all due diligence on condition of home. So much potential! Make this your today!!
#MDAA2127802

ANNAPOLIS

40 OAK COURT

2 Beds

2 Baths

1,061 Sq.Ft.

$376,000

MLS#: MDAA2127802

Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two bedrooms/offices, two full bathrooms, and robust hardwood flooring throughout, presenting a promising canvas for renovation. Strategically located, this property is in close proximity to essential amenities and community features. Public transportation is conveniently accessible with the Riva Road & Forest Drive bus station less than 700 meters away, enhancing the location's connectivity. Additional features include a rear deck perfect for relaxation or casual gatherings, a useful rear shed for extra storage, and a generous off-street parking area that can accommodate up to 12 vehicles. Despite being sold as-is, with no repairs from the seller, the property's inherent potential and dual-use capability as both a residential and commercial space make it a lucrative deal. Capitalize on the chance to customize this space into a thriving business venture or a mixed-use development that promises both rental income and renovation possibilities. Dive into this project and shape it into your vision of success! Property is being sold AS-IS, Seller will make no repairs. All offers must have $1000 deposit and proof of deposit. So much potential! Make this your today!!
#MDAA2127800

ANNAPOLIS

40 OAK COURT

None Beds

None Baths

1,061 Sq.Ft.

$376,000

MLS#: MDAA2127800

New on site today
Welcome to one of the best locations in Painters Hill! This move-in-ready 3-bedroom, 2.5-bath townhouse offers the perfect blend of comfort, convenience, and community. Inside, this charming two-level home features fresh paint throughout and a spacious, open-concept main floor ideal for entertaining. The updated kitchen, renovated eight years ago, boasts quartz countertops, a double oven, and classic wooden blinds. The adjoining living and dining areas showcase new laminate flooring and a cozy wood-burning fireplace, opening to a sunny, oversized fenced deck—your own private outdoor oasis with a storage shed and peaceful views of open space and nearby single-family homes in The Landings. Upstairs, you’ll find new carpeting and a large primary bedroom with an en-suite bath. Two additional bedrooms share a second full bath, and laundry is conveniently located on the bedroom level. Additional updates include an architectural roof installed in 2018, a new hot water heater in 2025 and parking easily available in front of the home. Enjoy the active lifestyle with neighborhood amenities including a swimming pool and tennis courts—just steps from your front door! Located a few blocks from the Pip Moyer Recreation Center and close to Truxton Park—with walking trails and water access to Spa Creek—this home offers the perfect combination of style, space, and location. Don’t miss it!
#MDAA2128718

ANNAPOLIS

8 ROCKWELL COURT

3 Beds

2 Baths

1,450 Sq.Ft.

$375,000

MLS#: MDAA2128718

Welcome to your next home! Located in Annapolis, this townhouse at 93 Clay St offers spacious living with its four bedrooms and three bathrooms. Designed in the stylish End Unit Attach/Row House architecture, this residence provides a blend of modern comforts and classic appeal. Inside, you're greeted with a seamless flow of carpet and laminate floors, providing a cozy yet elegant atmosphere throughout the home. The central air conditioning ensures year-round comfort, complemented by efficient electric heating. This home is perfectly equipped for modern living, featuring a convenient in-unit washer and dryer, making laundry days a breeze. The layout promotes both privacy and open living, ideal for entertaining guests or enjoying quiet family evenings. Each bedroom offers ample space, ensuring everyone has their own retreat. The bathrooms are designed with functionality in mind, providing a perfect start to your day or a relaxing end. 93 Clay St is ready to welcome you home. Don't miss the opportunity to make this delightful townhouse your own!
#MDAA2117410

ANNAPOLIS

93 CLAY STREET

4 Beds

2 Baths

2,022 Sq.Ft.

$375,000

MLS#: MDAA2117410

Welcome to 122 Roselawn Road, a beautifully renovated single-family home in the heart of Annapolis, MD. This 2-bedroom, 1-bathroom gem offers the perfect blend of modern upgrades and timeless charm. Step inside to discover fresh finishes and an open layout, making this home warm and inviting. Enjoy cooking in the gourmet kitchen featuring stainless steel appliances, ample cabinet space, and sleek countertops. The cozy living spaces are perfect for relaxing or entertaining guests. The large fenced backyard for outdoor gatherings, or creating your dream garden. Prime location situated in a peaceful neighborhood, yet close to shopping, dining, and everything Annapolis has to offer. This home is ready for you to move in and start creating memories Schedule your showing today and make 122 Roselawn Road your new address!..
#MDAA2098698

ANNAPOLIS

122 ROSELAWN ROAD

2 Beds

1 Baths

700 Sq.Ft.

$360,000

MLS#: MDAA2098698

Price Reduced!!! Welcome to your new home! This beautifully maintained property offers an open-concept floor plan filled with natural light and updates throughout! The heart of the home features a well-appointed kitchen with quality cabinetry and stainless steel appliances and an adorable eat-in breakfast nook. Recent updates include newer flooring, fresh paint, and an upgraded bathroom, making this home completely move-in ready. Enjoy morning coffee or evening unwinding on your walk-out deck. The community is unmatched in convenience and amenities. Perfectly located near major commuting routes, downtown Annapolis, Annapolis Mall, and Town Centre, you’ll have shopping, dining, and entertainment at your fingertips. Located in the highly regarded West Annapolis Elementary School District. Enjoy resort-style living with access to a swimming pool, fitness center, tennis courts, and scenic walking paths, all right outside your door. This home has been meticulously cared for and offers the perfect combination of comfort, style, and location. Don’t miss the opportunity to make it yours!
#MDAA2124784

ANNAPOLIS

2026 GOV THOMAS BLADEN WAY 203

2 Beds

1 Baths

1,006 Sq.Ft.

$358,000

MLS#: MDAA2124784

**NEW PRICE** Welcome to your Annapolis retreat—Unit #211 is a bright and breezy 2-bedroom, 2-bath condo with a den, offering the largest floor plan in the community with over 1,150 sq ft. Located in the vibrant and active 55+ community of Heritage Harbor, this home is just steps from the South River and offers an exceptional blend of comfort, style, and resort-style amenities. Inside, you'll find an open layout with brand NEW wide-plank LVP flooring throughout, creating a seamless flow from the spacious living and dining areas to a private balcony perfect for relaxing. The den offers additional living space and has brand new French doors to extra privacy. The updated kitchen features white shaker cabinets, carrara-look countertops, and stainless steel appliances. The primary suite offers a walk-in closet, access to the private balcony, and a beautifully renovated en-suite bath. A full-sized NEW washer and dryer are included in-unit for added convenience, plus one assigned parking space also conveys with the unit. Other updates include fresh paint throughout including walls, ceiling, and trim. The building has recently installed a new elevator and carpet throughout the hallway. Residents of Heritage Harbor enjoy access to a wealth of amenities including pools, tennis and pickleball courts, a 9-hole golf course, kayak launch, boat slips on the South River, a clubhouse with dining, and even RV and boat storage on-site. Whether you're enjoying a quiet morning on the water or an active afternoon on the courts, Unit #211 offers the perfect balance of relaxation and recreation in a picturesque Annapolis setting.
#MDAA2117406

ANNAPOLIS

2900 SHIPMASTER WAY 211

2 Beds

2 Baths

1,154 Sq.Ft.

$349,900

MLS#: MDAA2117406

Step into this beautifully renovated Annapolis charmer — completely updated from the ground up in 2018! Every detail has been thoughtfully designed for comfort and style, from the **custom kitchen with quartz countertops and stainless steel appliances** to the **gleaming hardwood floors** and **spa-inspired bath**. The home features **newer roof and windows**, efficient systems, and modern finishes throughout, offering a true move-in-ready experience. Outside, enjoy a **large fenced yard**, **above-ground pool**, and **screened-in rear porch** — perfect for entertaining or relaxing all year long. Located within walking distance to **shopping, restaurants, and downtown Annapolis**, this home delivers unbeatable convenience and charm. Why rent when you can own this thoughtfully renovated gem for less?
#MDAA2127172

ANNAPOLIS

27 DORSEY AVENUE

2 Beds

1 Baths

672 Sq.Ft.

$349,900

MLS#: MDAA2127172

Welcome to your new home in Whispering Woods! This charming duplex offers practical living with off-street parking and a two-car driveway. The main level has an open-concept living room, kitchen, and dining area, complete with a half bath and shared laundry. Enjoy direct access to a ground-level deck, a spacious fenced yard, and a storage shed. Upstairs you’ll find the master bedroom with a walk-in closet, a second bedroom with ample storage, and a full bathroom. The home features elegant engineered wood flooring, with tile in wet areas. Enjoy recent, extensive upgrades in this home. Highlights include a new Kenmore washer/dryer and fully renovated bathroom with new tub, tile, flooring, vanity and toilet. Completed in 2022. Exterior improvements feature a 2023 French Drain, and concrete driveway with retaining wall, and a ground-level deck. Partial new fence placed in 2025. For those of whom commute for work or play. You'll find the location of this home is conveniently located. With easy access to RT 50, I-97, and I-95, making commutes to Annapolis, Washington D.C., and Baltimore effortless.
#MDAA2127724

ANNAPOLIS

1553 STAR PINE DRIVE

2 Beds

1 Baths

1,060 Sq.Ft.

$346,000

MLS#: MDAA2127724

One level living at it's best! Spacious Windgate condo showcases private main building door with intercom system, 2 Master Bedrooms with walk-in closets, laundry off kitchen, cozy gas fireplace in Living Room with access to private patio. New fridge, washer & dryer in '24 and brand new paint and flooring throughout! Conveniently located to major commuter routes, dining, shopping & more!
#MDAA2128112

ANNAPOLIS

2000 PHILLIPS TERRACE 4

2 Beds

2 Baths

1,113 Sq.Ft.

$335,000

MLS#: MDAA2128112

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