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

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

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

3 Beds ⋅ 3 Baths

FHA APPROVED This is NOT a condo! Welcome to 10A Ironstone Ct, the BEST-PRICED 3-bedroom, 2.5-bathroom move-in-ready townhome in Annapolis. This beautifully maintained, spacious home offers the perfect blend of comfort, convenience, and the highly sought-after Annapolis lifestyle. The highlight is the stunning top-level primary suite, a private retreat complete with a cozy fireplace, soaking tub, separate shower, and walk-in closet. For everyday ease, the laundry room is conveniently located right on the bedroom level. Enjoy fantastic community amenities including a pool and clubhouse, all while being just minutes from Downtown Annapolis, waterfront dining, boutique shopping, entertainment, and major commuter routes. Competitively priced and ready for its next owner, schedule your tour today! PS HOA covers ALL exterior maintenance (roof, siding, gutters, shutters, etc)

10 Ironstone Ct, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8333357433

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

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:

3 Beds ⋅ 2 Baths

Spring has arrived, and this beautifully updated 3-bedroom, 2-bath condo offers the perfect opportunity to enjoy the best of the Annapolis lifestyle. Located on the 3rd floor, this light-filled home combines modern upgrades, comfort, and unbeatable access to outdoor recreation and waterfront attractions. Inside, the open-concept living, dining, and kitchen area creates a warm and inviting flow, complete with a cozy fireplace—perfect for relaxing after a day on the water or exploring the city. The renovated kitchen (2022) features granite countertops, farmhouse sink, stainless steel appliances, and contemporary cabinetry designed for both everyday living and entertaining. Brand-new windows (2021) fill the home with natural light. The spacious primary suite includes a private en-suite bath and direct access to a walkout patio overlooking the community pool—an ideal spot for morning coffee, evening sunsets, or enjoying the spring breeze. Generous closet space throughout and updated bathroom finishes add to the home’s appeal. For buyers who love the outdoors, this location is exceptional. Just minutes away, enjoy scenic walking and biking trails, waterfront views, picnic areas, dog-friendly spaces, and seasonal outdoor activities at Quiet Waters Park, a local favorite with over 300 acres of trails and water access. You’re also moments from Historic Downtown Annapolis, Spa Creek, Back Creek marinas, waterfront dining, kayaking, sailing, and Chesapeake Bay attractions, making it easy to enjoy the coastal lifestyle that makes Annapolis so desirable. Community amenities include a swimming pool and convenient pet stations for easy living. Whether you're looking for a primary residence, a low-maintenance coastal retreat, or a home close to parks and the waterfront, this condo offers outstanding value and location. Now is the perfect time to make your move—schedule your private showing today and experience spring in Annapolis at its best.

10 Sandstone Ct, Annapolis

Listing courtesy of Smart Realty, LLC. Contact: 3012525515

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