Annapolis Overlook Real Estate

Annapolis Overlook Real Estate

Welcome to Annapolis Overlook, a picturesque subdivision nestled in the heart of Annapolis, Maryland. This charming community offers an ideal blend of suburban tranquility and vibrant city life, making it a perfect haven for families, professionals, and retirees alike.

Annapolis Overlook is strategically located just minutes away from the historic downtown area of Annapolis, where you can explore a rich tapestry of culture, dining, and waterfront activities. The area is renowned for its stunning views of the Chesapeake Bay, providing residents with a daily dose of natural beauty. Whether you enjoy sailing, fishing, or simply taking leisurely strolls along the water, Annapolis Overlook places you right in the midst of it all.

The subdivision boasts beautifully designed homes that reflect modern elegance while maintaining a warm, inviting atmosphere. Spacious layouts, manicured lawns, and friendly neighbors create a sense of community that is hard to resist. Families will appreciate the top-rated schools nearby, ensuring that children receive a quality education in a nurturing environment.

For those who love the outdoors, Annapolis Overlook is surrounded by parks and recreational areas, perfect for hiking, biking, or picnicking. The proximity to major highways and the Annapolis Bypass makes commuting to nearby cities and attractions a breeze.

Discover the charm and convenience of Annapolis Overlook, where your dream home awaits in a community that truly feels like a retreat. Experience the perfect blend of comfort, convenience, and coastal living—your new life begins here!

Newest Listings in Annapolis Overlook

$335,000
3 Beds ⋅ 3 Baths ⋅ MDAA2156932 MLS ⋅ Annapolis Overlook BLDG.
Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table space, making it a cozy spot for casual meals. The home features three spacious bedrooms, including a primary suite that encompasses the entire third floor, with a luxurious walk-in closet and an en-suite bathroom. Additional highlights include a laundry room, a second-floor bathroom, updated lighting, ceiling fans for added comfort, and plush carpeting that enhances the inviting atmosphere throughout. The stainless steel refrigerator and gas range, washer, dryer, carpet, and heat pump have all been updated within the past 5 years. The home has a brand-new storm door and bay window at the front of the house). Homeowners and investors will appreciate the low-maintenance lifestyle this property offers, with an association fee that includes lawn maintenance and snow removal. The community amenities include outdoor common grounds, a refreshing pool, and a fitness center. Parking is hassle-free with two parking permits included -one parking place is assigned and located directly in front of the townhome. An additional car can be parked (with permit), in the "Permit Required" spaces. The community's prime location (close proximity to Quiet Waters Park, Downtown Annapolis, the US Naval Academy, and shopping) ensures easy access to local amenities and attractions. Whether you're looking to buy or invest, this Annapolis Overlook property is a fantastic opportunity. With its blend of modern features, community amenities, and strategic location, it stands ready to deliver both comfort and value for years to come. Don't miss your chance to purchase this delightful home!

40 Ironstone Ct Unit #B, Annapolis
$299,900
2 Beds ⋅ 2 Baths ⋅ MDAA2156796 MLS
Discover this charming 2-bedroom, 2-bathroom unit in the desirable Annapolis Overlook community. Spanning 1,229 sq. ft. , this well-maintained garden-style apartment offers a blend of comfort and modern living. The open floor plan seamlessly connects the dining and living areas, enhanced by recessed lighting and a cozy wood-burning fireplace, perfect for relaxation. The kitchen is equipped with upgraded countertops and essential appliances, including a built-in microwave, dishwasher, and self-cleaning electric oven. Enjoy the convenience of a stacked washer and dryer within the unit, making laundry days a breeze. The primary suite features a spacious walk-in closet and an en-suite bathroom, providing a private retreat. Step outside to your private deck, ideal for morning coffee or evening gatherings. The community amenities include a refreshing outdoor pool, exercise room, and playground, catering to an active lifestyle. With assigned parking and maintenance services included in the association fee, convenience is at your fingertips. This property is not only a home but a lifestyle, offering a perfect balance of tranquility and accessibility. Experience the best of community living in a well-appointed space that meets all your needs. Schedule a tour today! Furniture can be sold with the unit as well for a turn-key option if the buyer(s) are looking for that. Please inquire!

20 Greystone Ct Unit #I, Annapolis
$300,000
2 Beds ⋅ 2 Baths ⋅ MDAA2155524 MLS
Welcome home to this fantastic two bedroom, two bath condo. Located on the ground level with a view of grassy area, trees, and the community pool. Open concept for the living and dining room area, with a bump out used currently as an exercise area, but it can be anything your heart desires. The modern kitchen is updated with silestone countertops, stainless appliances and the range is brand new. The living room has a slider which leads to a nice patio the grassy common area and pool beyond. The primary bedroom has a wonderfully tiled full bath, and the second bedroom shares the second bath with the common area. A brand new washer and dryer are inside the unit. Amenities include the community pool and fitness center. Great location, minutes from downtown Annapolis, or commuter routes to Washington, Ft Meade, or Baltimore. Be sure to check out the virtual floor plan tour!

10 Hearthstone Ct Unit #B, Annapolis
$450,000
4 Beds ⋅ 2 Baths ⋅ MDAA2154182 MLS
Fully Renovated Rancher in a Highly Desired Neighborhood! Welcome to this beautifully renovated rancher, featuring 4 bedrooms, 2 full bathrooms, and a fully finished basement. The main level offers beautiful hardwood floors and a completely updated kitchen featuring 42-inch cabinets, quartz countertops, a separate island, and stainless steel appliances. The spacious finished basement provides a large family room, a fourth bedroom, and a full bathroom—perfect for guests, a home office, or additional living space. Enjoy the private backyard and new deck, ideal for outdoor entertaining and relaxing. Located on a quiet street in a highly sought-after neighborhood, the home is conveniently close to major routes, shopping, and everyday amenities. All required permits have been obtained for the renovations. Recent updates include: New siding; New roof; New windows; New gas furnace; New central A/C; New hot water heater; New sump pump; New deck; Fully renovated kitchen; Finished basement with bedroom and full bathroom. Nothing to do but move in and enjoy!

105 Rosecrest Dr, Annapolis
$315,000
2 Beds ⋅ 2 Baths ⋅ MDAA2152754 MLS
Tucked on a quiet court in The Landings, this move-in-ready 2-bedroom, 1.5-bath Annapolis townhome pairs easy living with rare, wooded privacy. It's about a 5-minute stroll to Truxtun Park for tennis, ball fields, trails, boat ramp and pool along Spa Creek, with Historic Downtown Annapolis, City Dock and the U.S. Naval Academy about 10 minutes away and Quiet Waters Park a short drive south. Inside, a bright white kitchen offers a butcher-block island, generous cabinetry, recessed lighting and a sunny window over the sink, flowing to a hardwood-floored living and dining area with a sliding door to the patio. Upstairs, two bedrooms showcase vaulted wood-plank ceilings, ceiling fans and ample closets. Out back, a covered paver patio, fully fenced yard and lush shade gardens create a private outdoor escape. Built in 1980 with community pool and tennis and quick access to Bay Ridge Ave, Forest Dr and Rt 50. Commute times are as follows (estimated): Minutes from the water in the Annapolis Neck/Eastport area of Anne Arundel County. About a 5-minute stroll to Truxtun Park for tennis, ball fields, trails, boat ramp, pool and Spa Creek access; roughly 10 minutes to Historic Downtown Annapolis, City Dock and the U.S. Naval Academy; about 7 minutes to Anne Arundel Medical Center; shopping within 1.3 miles; Quiet Waters Park and the Chesapeake Bay a short drive; fast Route 50, Bay Ridge Ave and Forest Dr access to Annapolis, Baltimore and D.C. Schedule a tour today!

11 Winslow Ct, Annapolis
$280,000
2 Beds ⋅ 2 Baths ⋅ MDAA2152518 MLS
Welcome to 50-G Sandstone Court, nestled in the desirable Annapolis Overlook community, where comfort, convenience, and easy living come together. This beautifully maintained 2-bedroom, 2-bath condominium is truly move-in ready and offers a bright, welcoming atmosphere you'll be proud to call home. Step inside to discover a spacious, open-concept living area that creates the perfect setting for relaxing after a long day or gathering with family and friends. Natural light fills the space, while sliding glass doors lead to a private deck overlooking peaceful green space—an ideal spot to enjoy your morning coffee, unwind with a good book, or simply take in the outdoors. The thoughtfully designed kitchen features generous counter space, making meal preparation both convenient and enjoyable. Just off the kitchen, the adjoining dining area provides the perfect setting for everyday meals or entertaining guests. The tranquil primary suite is filled with natural light and offers serene views of the landscaped green space behind the building. An en-suite bath with a tub/shower combination provides both comfort and privacy. The second bedroom is generously sized with wall-to-wall carpeting and a spacious closet, making it ideal for guests, a home office, or additional living space. A second full bathroom with a tub/shower combination is conveniently located nearby. Whether you're a first-time homebuyer, looking to downsize, or seeking a low-maintenance lifestyle, this home offers the perfect combination of space, functionality, and location. Situated just minutes from Historic Downtown Annapolis, you'll enjoy easy access to charming boutiques, waterfront dining, marinas, entertainment, and the U.S. Naval Academy. Major commuter routes, shopping centers, parks, and everyday conveniences are all within close reach, making travel to Baltimore, Washington, D.C., and surrounding areas a breeze. Don't miss the opportunity to own this inviting home in a wonderful community—50-G Sandstone Court is ready to welcome you home.

50 Sandstone Ct, Annapolis
$335,000
3 Beds ⋅ 3 Baths ⋅ MDAA2145606 MLS
IGNORE DAYS ON MARKET BUYER FAILED TO PERFORM**FHA APPROVED!** This is **NOT a condominium**—it's a townhome with the convenience of condo-style exterior maintenance. The HOA takes care of **the roof, siding, gutters, shutters, pressure washing, and other exterior maintenance**, giving you more time to enjoy homeownership and less time worrying about upkeep. Can we say, BONUS?! Welcome to 10A Ironstone Court, one of the best values in Annapolis. Offering 3 bedrooms, 2.5 bathrooms, and a spacious, functional layout, this home presents an incredible opportunity to own in a highly desirable location while adding your own personal touches. The standout feature is the entire top-level primary suite, a private retreat complete with a cozy fireplace, soaking tub, separate shower, walk-in closet, and the convenience of bedroom-level laundry. The home has been priced with future updates in mind, giving the next owner the opportunity to refresh the paint and flooring to match their own style while building instant equity. With solid bones, generous living space, and an attractive price point, this is the perfect opportunity for buyers who recognize value. Enjoy community amenities including a **pool and clubhouse**, all while being just minutes from Historic Downtown Annapolis, the U.S. Naval Academy, waterfront dining, shopping, parks, and major commuter routes to Washington, DC and Baltimore. Finding a 3-bedroom townhome in Annapolis at this price point is becoming increasingly rare, especially one that is **FHA approved** and offers the peace of mind of comprehensive exterior maintenance through the HOA. Whether you're a first-time buyer, downsizing, or investing in your future, this home offers exceptional value and endless potential. Schedule your private showing today!

10 Ironstone Ct, Annapolis
$275,000
2 Beds ⋅ 2 Baths ⋅ MDAA2142750 MLS
PRICE REDUCED FOR QUICK SALE! Back on the market with new photos! Welcome to this beautifully updated terrace-level condo offering the perfect blend of comfort and style. This 2-bedroom unit features fresh paint, brand-new carpet, and an upgraded kitchen complete with new countertops and stainless steel appliances. Enjoy easy single-level living with a spacious, open-concept layout that flows seamlessly to a private setting with peaceful forest views—ideal for relaxing or entertaining. Community amenities include an outdoor pool, fitness center, and clubhouse. Two reserved parking spaces convey. Now vacant, move-in ready, and one of the best updated values in the community—don't miss it! Now offered at a new, improved price, this move-in ready home is one of the best updated values in the community—don't miss it!

10 Sandstone Ct Unit #K, Annapolis
$329,000
3 Beds ⋅ 3 Baths ⋅ MDAA2140034 MLS
Beautifully maintained 3-level townhome in the desirable Annapolis Overlook community in Annapolis! This spacious home offers approximately 1,680 sq ft with 3 bedrooms, 2.5 baths, and a functional layout designed for comfortable living. The main level features a bright living area, separate dining space, and an updated kitchen with ample cabinet storage and room for entertaining. Upstairs you’ll find generously sized bedrooms including a primary suite with private bath and great closet space. Enjoy low-maintenance living in a well-established community conveniently located near downtown Annapolis, the Naval Academy, shopping, restaurants, and major commuter routes. The 21403 area is known for its coastal lifestyle, outdoor recreation, and close proximity to the Chesapeake Bay.  Perfect for first-time buyers, investors, or anyone looking for easy living in a prime Annapolis location!

40 Ironstone Ct Unit #J, Annapolis
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