Annapolis Roads Homes for Sale

Annapolis Roads Homes for Sale

Welcome to Annapolis Roads, a charming waterfront subdivision nestled in the heart of Annapolis, Maryland. This picturesque community offers an idyllic blend of serene living and vibrant local culture, making it an ideal choice for those seeking a peaceful retreat without sacrificing convenience.

Annapolis Roads boasts a unique blend of architectural styles, from cozy cottages to elegant waterfront estates, ensuring there’s a perfect home for every taste. Many properties in this sought-after neighborhood feature stunning views of the Chesapeake Bay, providing residents with a front-row seat to breathtaking sunsets and the gentle sounds of nature. With homes for sale that cater to a variety of budgets and preferences, prospective buyers will find an array of options, whether you’re looking for a charming weekend getaway or a permanent residence.

The community is not only defined by its beautiful homes but also by its friendly atmosphere and engaging lifestyle. Residents enjoy easy access to a private beach, perfect for swimming, sunbathing, and enjoying water sports. With nearby parks, walking trails, and recreational facilities, outdoor enthusiasts will find plenty to explore.

Annapolis Roads is conveniently located just minutes from downtown Annapolis, where you can indulge in fine dining, boutique shopping, and cultural experiences. The rich history of this area is palpable, with landmarks and events that celebrate its maritime heritage.

If you’re ready to embrace a lifestyle of tranquility and charm, discover the homes for sale in Annapolis Roads today and take the first step toward your dream home in this enchanting community!

Newest Annapolis Roads Homes for Sale

$825,000
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
$800,000
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
$6,500,000
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:

$1,294,880
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, 3 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. Special features include Special financing 2/1/buydown at 4.5 % 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 3 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