Annapolis Roads Homes for Sale

Annapolis Roads Homes for Sale

Welcome to Annapolis Roads, a hidden gem nestled in the heart of Annapolis, Maryland. This charming waterfront subdivision offers the perfect blend of tranquility and community spirit, making it an ideal place for families, retirees, and anyone looking to embrace the coastal lifestyle.

Annapolis Roads is known for its picturesque streets lined with beautiful, well-maintained homes, each showcasing unique architectural styles that reflect the character of the area. The community is primarily comprised of single-family homes, many of which boast stunning views of the water and easy access to local parks and recreational areas. With homes for sale that range from cozy cottages to spacious residences, there’s something for everyone in this delightful neighborhood.

Living in Annapolis Roads means enjoying the best of both worlds: a serene environment surrounded by nature, yet just a short drive from the vibrant downtown Annapolis. Residents can take advantage of the nearby marinas, where boating and fishing enthusiasts can launch their vessels and explore the scenic Chesapeake Bay. The community also offers convenient access to local shops, restaurants, and cultural attractions, ensuring that you’ll never run out of things to do.

Whether you’re looking for a place to call home or an investment opportunity, Annapolis Roads has an array of homes for sale that cater to diverse tastes and budgets. Discover the charm and warmth of this enchanting community, and let Annapolis Roads be the backdrop for your next chapter. Embrace a lifestyle filled with coastal beauty, community camaraderie, and endless possibilities!

Newest Annapolis Roads Homes for Sale

4 Beds ⋅ 4 Baths

Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself!

2691 Claibourne Rd, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

4 Beds ⋅ 5 Baths

GREAT PRICE. Space, flexibility and the Annapolis water-oriented lifestyle come together at 1007 Harbor Drive, offering 3722 finished square feet, four bedrooms, three full and two half baths, a two car garage and a finished lower level - all in the sought-after Annapolis Roads community. The versatile floor plan provides room to spread out, work from home, entertain and accommodate guests, while the finished lower level adds a recreation room, kitchenette, full bath, bonus room and private entrance. Outdoor living is equally impressive. Enjoy the screened porch, deck, 10-person hot tub and newly built fire pit with custom paver patio overlooking the level, fenced backyard. An extra-wide driveway provides parking for additional vehicles, a boat or RV, while the two-car garage offers extensive storage with a floored attic, shelving and cabinets. Inside, hardwood and luxury vinyl plank flooring, fresh paint, new upstairs carpet and recessed lighting complement a spacious main level with a wood-burning fireplace, dedicated living room/home office, dining space, kitchen with granite countertops and island, and a bright breakfast area with vaulted ceiling and skylights. Upstairs are four bedrooms, including a generous primary suite with sitting/dressing area, walk-in closet and its own laundry, plus an updated hall bath with double vanity. Major improvements include a two-zone HVAC system and most windows replaced in 2024, roof approximately 2020, refrigerator 2025, cooktop 2023 and dishwasher 2022. A Choice home warranty through 2030 conveys to the buyer. And then there's the lifestyle. Annapolis Roads residents enjoy access to a sandy community beach, boat ramp, waterfront park, playground, picnic area and pavilion along the Chesapeake Bay—all just minutes from Downtown Annapolis, Quiet Waters Park, shopping, dining and major commuter routes. No HOA.

1007 Harbor Dr, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

7 Beds ⋅ 9 Baths

A truly iconic Annapolis offering, this extraordinarily rare waterfront estate is gracefully set on 7.5 remarkably private acres, showcasing what may be the most breathtaking panoramic views in all of Annapolis. With endless, horizon-stretching vistas that evoke the feel of an oceanfront retreat, the Chesapeake Bay unfolds before you with the Bay Bridge creating a dramatic backdrop in the distance, while Annapolis’ beloved summer sailboat races become part of your everyday scenery. A setting of this magnitude—offering serenity, privacy, and commanding water views—is simply irreplaceable. Encompassing more than 9,000 square feet, this grand residence was thoughtfully designed to maximize its extraordinary setting, with jaw-dropping water views greeting you the moment you step through the front door and drawing your eye through the soaring two-story family room straight to the Chesapeake beyond. The architectural footprint and flow are exceptional, creating the perfect canvas for a visionary buyer to elevate this estate into a world-class showpiece. The main level is anchored by an expansive waterfront primary retreat, a sanctuary unto itself featuring dual walk-in closets, a spa-inspired bath with a jetted soaking tub, oversized skylit shower, separate vanities, a bidet, and a private spiral staircase leading directly to the lower-level fitness and hot tub retreat. Two additional generously sized en suite bedrooms with walk-in closets are also conveniently located on the main level, along with a richly appointed study/library, elegant formal dining room, spacious kitchen with island and breakfast area, plus an additional family gathering space designed for effortless everyday living and entertaining. Upstairs, two exceptional en suite bedrooms each offer walk-in closets, fireplaces, private waterfront balconies, and spectacular elevated views that feel suspended above the Bay. The walkout lower level is equally impressive, designed for entertaining and multigenerational flexibility, featuring expansive recreation spaces opening directly to the waterfront patio, plus a fully self-contained in-law or au pair apartment complete with its own kitchen, family room, full bath, separate entrance, and—of course—those same extraordinary views. What sets this offering even further apart is the remarkable future potential already in motion. With public sewer and an extraordinary 7.5-acre footprint, the possibilities are nearly limitless. Seller-approved county plans—transferable to the next owner—dramatically accelerate the vision, including plans for shoreline improvements, tree clearing to further expand views, bank reshaping, revetment enhancements, a new tram and stair access to the pier, a widened driveway with a new entrance feature, a detached guest house with its own private entrance from Lyons Dr, a pickleball court, a gazebo, and additional grounds enhancements. This is more than a home—it is one of Annapolis’ most extraordinary legacy properties, offering a once-in-a-generation opportunity to create an unparalleled waterfront masterpiece.

2562 Carrollton Rd, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

6 Beds ⋅ 4 Baths

Waterfront Views - Annapolis Roads Community! AMAZING BRAND NEW WATER VIEW HOME in a desirable Annapolis, MD location! This stunning 6 bedroom, 4 full bathroom residence offers multigenerational living plus all the amenities of Annapolis Roads . Ask about the lock and leave lifestyle. Situated in the sought-after Annapolis Roads community, the home occupies a premium 20,125 sq ft corner lot and features a 2-car side load garage. Included two year lawn maintenance 9-foot ceilings and LVP hardwood floors throughout Gourmet kitchen with stainless steel appliances, 42-inch white maple cabinets, large island and quartz countertops A spacious great room centers around an inviting fireplace Formal dining room, living room Main level 6th bedroom/den/office option, full bathroom Conveniently located laundry room near the garage entrance 6 bedrooms and 4 full bathrooms Expansive primary suite with a bonus room perfect for an office, gym, or reading room Luxurious primary bathroom showcasing a quartz double bowl vanity, ceramic tile throughout, soaking tub and a large glass shower A secondary suite bedroom and bath are located down the hall Three additional bedrooms and a full bathroom complete this level For future expansion, the home includes a 1,717 sq ft unfinished basement ready for customization. Act now to own this home.

2644 Claibourne Rd, 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