Annapolis Roads Real Estate

Annapolis Roads Real Estate

Welcome to Annapolis Roads, an enchanting waterfront subdivision nestled in the heart of Annapolis, Maryland. This charming community is a hidden gem located within Anne Arundel County, offering residents a unique blend of serene living and vibrant local culture.

Annapolis Roads is renowned for its picturesque views and access to the Chesapeake Bay, making it a haven for boating enthusiasts and nature lovers alike. With its tree-lined streets and beautifully maintained homes, the neighborhood exudes a welcoming atmosphere that fosters a strong sense of community. Residents enjoy the convenience of nearby parks, walking trails, and private beach access, perfect for summer picnics or evening strolls by the water.

The subdivision is also ideally situated just minutes away from downtown Annapolis, where you can immerse yourself in the rich history and charm of Maryland’s capital. Explore the local boutiques, indulge in fresh seafood at waterfront restaurants, or take a leisurely sail on the bay. The area boasts excellent schools, making it a fantastic choice for families looking to settle down in a nurturing environment.

Whether you're seeking a permanent residence or a seasonal retreat, Annapolis Roads offers a unique lifestyle that celebrates the beauty of coastal living. With its close-knit community vibe and proximity to the best of Annapolis, this subdivision is not just a place to live; it’s a place to thrive. Come discover the magic of Annapolis Roads—where your dream home awaits!

Newest Listings in Annapolis Roads

4 Beds ⋅ 5 Baths

This beautifully updated Colonial offers the perfect blend of comfort, space, and functionality. Featuring four bedrooms, three full and two half baths, this home is designed for both everyday living and effortless entertaining. Relax on the inviting covered front porch, unwind on the screened porch, soak in the 10-person hot tub, or gather around the newly built fire pit with its custom paver patio in the level, fenced backyard. Inside, you'll find hardwood floors, luxury vinyl plank flooring, new carpet upstairs, recessed lighting throughout, and a warm family room with a wood-burning fireplace. The thoughtfully designed floor plan includes a mudroom and the convenience of two laundry areas, including one in the primary suite. The finished lower level, with its private entrance, offers exceptional flexibility with a large recreation room, kitchenette, full bath, and bonus room—ideal for guests, multigenerational living, a home office, or hobby space. Recent updates include most windows and a two-zone HVAC system installed in 2024. Storage is plentiful with a spacious crawl space beneath the addition and a two-car garage featuring a floored attic, shelving, cabinets, pegboard, and pull-down stairs. An extra-wide driveway provides plenty of room for an RV, boat, or additional vehicles. Located in the water-oriented community of Annapolis Roads, residents enjoy community water access, a sandy beach, boat ramp, picnic area, and playground, all just minutes from Downtown Annapolis, Route 50, shopping, and dining. Harbor Drive is a private road maintained by the Annapolis Roads Property Owners Association (ARPOA). No HOA. Home warranty with Choice good through 2030 conveys to buyer.

1007 Harbor Dr, Annapolis

Listing courtesy of CENTURY 21 New Millennium. Contact: 4102669005

4 Beds ⋅ 4 Baths

Nestled in the highly sought-after Annapolis Roads community, this spacious Colonial offers the perfect blend of comfort, privacy, and coastal living. Featuring 4 bedrooms and 3.5 baths, this well-appointed home showcases hardwood floors, a beautifully updated kitchen with granite countertops, a formal living room, dining room, and convenient main-level laundry. The upper level boasts a spacious primary suite with a vaulted ceiling, an oversized walk-in closet, and a private en-suite bath. Three additional generously sized bedrooms and a full hall bath complete the second floor. The finished lower level provides a versatile family room, a full bath, and abundant storage space—ideal for entertaining, guests, or a home office. Step outside to your own private sanctuary. The expansive sunroom overlooks a peaceful wooded backdrop, creating the perfect setting to relax, enjoy your morning coffee, and watch the birds year-round. A custom built 10' x 8' 10' tall matching shed with electricity completes the beautiful backyard. Additional highlights include a two-car garage and ample driveway parking. For added comfort, the heat pump was replaced in 2025, which switches to propane when the temperature drops below 40F. There's added assurance of a 17kw whole-house generator that runs on propane. This Siemens System with a Generac generator kicks in automatically when the power has been out for five minutes and runs the entire house. There are three 100 gallon propane tanks that can run the generator for a week. The water softener system is less than four years old. Residents of Annapolis Roads enjoy exceptional community amenities, including a private beach, boat ramp, fishing pier, bayfront pavilion, bayside picnic area, playground, fire pit, community pier, kayak storage, extensive hiking trails, and a variety of neighborhood events throughout the year. Located just minutes from downtown Annapolis, shopping, dining, and major commuter routes.

2691 Claibourne Rd, Annapolis

Listing courtesy of Redfin Corp. Contact: 3016586186

3 Beds ⋅ 4 Baths

Enjoy the water access lifestyle of the Annapolis Roads community on Lake Ogleton, Annapolis. This distinctive home offers an abundance of custom features, indoor and outdoor living spaces, seasonal filtered views of the water, architectural details, and access to some of Annapolis' most sought-after waterfront amenities. From the beautiful screened porch / family room, to the covered deck, ivy covered brick walled patio, and sun room, there are many special areas to relax or entertain. The property backs up to the Lake Ogleton tidal wetlands, with all the associated wildlife! The large number of windows and double doors provide natural light and amazing flow flow throughout. The sunroom is a standout feature, showcasing hand-hewn beams, custom cabinetry, and a wall of New England-style windows that fill the space with natural light, and, of course, fresh air. Entertaining is a delight with the smooth flow between rooms. Custom lighting throughout the home highlights the crown moulding, built-in shelving, cabinetry, and workspaces. The spacious primary suite features an ensuite bath with a jetted tub, walk-in closet, and an additional shoe closet. A second jetted tub is located in the upper-level hall bath. Extensive landscaping surrounds the property, creating multiple inviting outdoor spaces. The rear yard slopes to the wetland, and is a blank slate, ready for a gardener. Major systems and appliances recently updated include the furnace (3 years), dishwasher, two air conditioning units( approximately 9 years), washer and dryer. Updated windows. Residents enjoy access to Annapolis Roads' exceptional amenities, including a boat ramp, private beach, bayfront pavilion, bayside picnic area, playground, fire pit, community pier, kayak/SUP storage, extensive hiking trails, and a variety of neighborhood events throughout the year. Drop your boat in and visit the Annapolis Historic District by water; something very few neighborhoods offer. A unique opportunity to enjoy the waterfront lifestyle, charm, character, and community spirit that make Annapolis Roads such a special place to call home.

2644 Queen Anne Cir, Annapolis

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

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, 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:

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