Annapolis Overlook Real Estate

Annapolis Overlook Real Estate

Welcome to Annapolis Overlook, a hidden gem nestled within the historic charm of Annapolis, Maryland. This picturesque subdivision offers a unique blend of suburban tranquility and vibrant city life, making it an ideal choice for families, professionals, and retirees alike.

Annapolis Overlook boasts beautifully designed homes, each reflecting modern elegance and comfort. With a variety of architectural styles, residents can find the perfect fit for their lifestyle. The community is characterized by its lush green spaces, tree-lined streets, and friendly neighbors, fostering a warm and welcoming atmosphere.

Located just minutes from the heart of Annapolis, residents can easily explore the city's rich maritime history, renowned dining options, and eclectic shopping districts. Whether you're strolling along the scenic waterfront or enjoying a leisurely afternoon at the historic State House, Annapolis is brimming with cultural experiences waiting to be discovered.

Nature enthusiasts will appreciate the proximity to several parks and recreational areas, including the stunning Broadneck Park and the serene Sandy Point State Park, perfect for hiking, biking, and enjoying the great outdoors. Families will also benefit from the highly-rated Anne Arundel County schools, ensuring quality education for children of all ages.

Annapolis Overlook is not just a place to live; it's a lifestyle. With its ideal location, beautiful homes, and strong sense of community, this subdivision is a perfect choice for those looking to embrace the best of Maryland living. Come discover the charm and convenience of Annapolis Overlook—your dream home awaits!

Newest Listings in Annapolis Overlook

2 Beds ⋅ 2 Baths

Welcome home to this beautiful 2-bedroom, 2-bath home—the largest model in Annapolis Overlook! This bright spacious residence features an open concept layout, high ceilings, crown molding, abundant natural light, and a cozy two-sided wood-burning fireplace. The show stopping remodeled kitchen is designed for cooking and entertaining, featuring a stunning 6 foot quartz island, open shelving, ample cabinetry and storage, and generous workspace. It flows seamlessly into the oversized dining and living areas, creating the perfect gathering space. The primary suite offers high ceilings, plush carpeting, a walk-in closet with a professional organizer, and an en suite bath with a soaking tub. The second bedroom is filled with natural light and includes its own full en suite bath. Enjoy peaceful wooded views from your private balcony, plus an in-home washer and dryer and ample storage throughout. Community amenities include a pool, fitness center, two assigned parking spaces, exterior maintenance, lawn care, trash, and snow removal. Conveniently located just minutes from Downtown Annapolis, Quiet Waters Park, shopping, and major commuter routes. This is a must see property! Schedule your tour today!

30 Hearthstone Ct Unit #G, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

3 Beds ⋅ 3 Baths

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

Listing courtesy of RE/MAX One. Contact: 4437718009

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 Unit #G, 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:

Start Your Search

Kathleen McMahan

For Kathleen McMahan, real estate has always been about more than buying and selling homes. It’s about people, relationships, and helping clients feel confident during some of the biggest transitions of their lives. With more than a decade of experience in Maryland and Washington, D.C. real estate, Kathleen has built her business around a simple philosophy: stay positive, work hard, communicate honestly, and treat every client’s move as if it were her own. Positivity has long been Kathleen’s “north star,” both personally and professionally. When her oldest son spent time in the NICU, she focused on learning everything she could from his nurses so she would feel prepared when it was finally time to bring him home. That experience reinforced something she carries into her work today: even during stressful and uncertain moments, knowledge, preparation, and the right perspective can make all the difference. That mindset has helped Kathleen build a successful real estate career based largely on relationships, referrals, and clients who return to her as their lives and real estate needs evolve. Now, as the agent behind McMahan Homes at Real Broker, she brings the experience of more than a decade in the industry together with the personal attention and flexibility of an independent real estate business. Originally from New Jersey, Kathleen came to Maryland to attend Salisbury University. Her studies in sociology and marketing helped spark a lasting curiosity about people—what motivates them, what matters to them, and what makes a place truly feel like home. Today, that curiosity is one of her greatest strengths as an agent. Kathleen takes the time to understand not just what her clients are looking for on paper, but what they want their lives to look like. Whether she’s preparing a home for the market, negotiating on behalf of a seller, helping a buyer find the right community, or simply answering the questions that come up along the way, her goal is to make the process feel informed, personal, and manageable. Kathleen lives in Maryland with her husband and two sons. When she isn’t working, you’ll most likely find her spending time with her family, dreaming about her next trip to the Florida Keys, or planning her next home project.

Learn More