Annapolis Overlook Real Estate

Annapolis Overlook Real Estate

Welcome to Annapolis Overlook, a hidden gem nestled in the heart of Annapolis, Maryland. This picturesque subdivision offers an idyllic blend of suburban tranquility and urban convenience, making it the perfect place to call home. With its beautifully designed homes, lush green spaces, and friendly community atmosphere, Annapolis Overlook is ideal for families, professionals, and retirees alike.

Situated in Anne Arundel County, Annapolis Overlook boasts easy access to major highways and public transportation, allowing residents to explore all that Maryland has to offer. Just minutes away, you’ll find the vibrant downtown area of Annapolis, renowned for its historic charm, waterfront dining, and boutique shopping. Enjoy leisurely strolls along the scenic Chesapeake Bay or immerse yourself in the rich maritime history that this capital city has to offer.

The subdivision is characterized by its well-maintained streets and a variety of architectural styles, ensuring that there is something for everyone. Residents can take advantage of the community's amenities, including walking trails, parks, and recreational facilities, promoting an active and engaging lifestyle. With a strong sense of community, neighbors frequently gather for events, fostering friendships and a welcoming atmosphere.

Families will appreciate the proximity to highly-rated schools and educational institutions, providing excellent opportunities for children. Whether you’re looking for a cozy starter home or a spacious family residence, Annapolis Overlook offers a diverse selection of properties to suit your needs.

Discover the charm of Annapolis Overlook, where modern living meets the beauty of nature, and make this vibrant community your new home.

Newest Listings in Annapolis Overlook

$315,000
2 Beds ⋅ 2 Baths
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

Listing courtesy of Kelly and Co Realty, LLC. Contact: 4434919387
$280,000
2 Beds ⋅ 2 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact: khylah.settle@cbmove.com
$485,000
4 Beds ⋅ 2 Baths
Fully renovated rancher with all required permits in highly desired neighborhood. Completely updated kitchen with 42" cabinets, quartz countertop, separate island and stainless steel appliances. Main level hardwood floor. Fully finished basement with 4th bedroom and full bathroom, plus huge family room. New siding. New roof. New windows. New gas furnace. New central AC. New HWH. New sump pump. New deck. Private back yard. House located on quiet street, close to major routs and shopping.

105 Rosecrest Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$335,000
3 Beds ⋅ 3 Baths
**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

Listing courtesy of EXP Realty, LLC. Contact: 8333357433
$285,000
2 Beds ⋅ 2 Baths
Price Reduced! 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

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102724800
$334,000
3 Beds ⋅ 3 Baths
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

Listing courtesy of Keller Williams Flagship. Contact:

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