Annapolis Overlook Real Estate

Annapolis Overlook Real Estate

Welcome to Annapolis Overlook, a charming subdivision nestled in the heart of Anne Arundel County, Maryland. This picturesque community offers a unique blend of suburban tranquility and vibrant city life, making it the perfect place to call home.

Annapolis Overlook is strategically located just minutes away from the historic downtown Annapolis, renowned for its rich maritime heritage, boutique shopping, and an array of dining options that cater to every palate. Residents enjoy the convenience of having the Chesapeake Bay at their doorstep, providing endless opportunities for boating, fishing, and enjoying scenic waterfront views.

The subdivision itself boasts beautifully designed homes that reflect a range of architectural styles, ensuring there’s something for everyone. Tree-lined streets and well-maintained parks enhance the community's appeal, offering residents a serene environment to relax and unwind. Families will appreciate the highly-rated schools in the area, making it an ideal choice for those with children.

Annapolis Overlook is also conveniently located near major highways, making commuting to Baltimore, Washington D.C., and beyond a breeze. The community is rich in recreational opportunities, with nearby golf courses, hiking trails, and parks that invite outdoor enthusiasts to explore the natural beauty of Maryland.

Whether you're looking for a peaceful retreat or a vibrant community, Annapolis Overlook offers the perfect balance. Experience the charm of this delightful subdivision and discover why it’s one of the most sought-after neighborhoods in Annapolis. Your dream home awaits!

Newest Listings in Annapolis Overlook

2 Beds ⋅ 2 Baths

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

Listing courtesy of Compass. Contact: (410) 429-7425

2 Beds ⋅ 2 Baths

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

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

4 Beds ⋅ 2 Baths

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

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

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

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

2 Beds ⋅ 2 Baths

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

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102724800

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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