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4 Beds
5 Baths
2,513SqFt
Active
Experience exceptional Chesapeake Bay waterfront living in this stunning four-level townhome offering unobstructed Bay views from nearly every room. Ideally located in Chesapeake Beach, this home provides convenient access to Annapolis, Washington, D.C., and the surrounding Metro area while embracing the relaxed lifestyle of Maryland's waterfront communities. Enjoy all that Chesapeake Beach and neighboring North Beach have to offer, including award-winning restaurants, seasonal events, a scenic boardwalk perfect for walking, running, charming local shops, and friendly coastal living. This is the only BAYFRONT home currently available in the highly desirable Windward Key community. Wake up to breathtaking sunrises, launch your kayak directly from your yard, hunt for shark teeth along the shoreline, and enjoy the sights of passing sailboats, fishing vessels, and cruise ships—all from the comfort of home. Inside, an open-concept floor plan showcases beautiful Brazilian Koa hardwood flooring throughout the main living areas. The spacious kitchen features abundant cabinetry, elegant marble countertops, and a premium Bluestar gas range fueled by a dedicated propane tank. The adjoining dining area flows seamlessly into the light-filled living room, where a wall of windows and two sets of sliding glass doors open to a large waterfront deck—perfect for entertaining or simply relaxing while taking in the ever-changing Bay views. The upper level features a spacious waterfront primary suite with a private balcony, ideal for enjoying morning coffee while watching the sunrise over the Bay. The luxurious primary bath offers a beautifully tiled walk-in shower. Two additional bedrooms and a full bath complete this level. The top floor provides a private retreat currently used as an office but easily serving as a fourth bedroom or guest suite. Complete with a full bath and its own private deck, this space offers incredible flexibility and privacy. The finished lower level expands the home's versatility with space for a recreation room, gym, studio, office, or additional bedroom, along with a full bath and laundry room featuring exterior access. A covered waterfront patio provides easy access to the community pool and outdoor amenities. Windward Key residents enjoy exclusive access to a private beach, pickleball court, community pool, and marina, where boat slips may be purchased separately. HOA services include lawn maintenance and trash removal, allowing for truly low-maintenance waterfront living. (length of footage is approx.) Additional upgrades and features include: • New Trex decking and railings throughout • Built-in bookshelves that convey with the home • Main-level deck grill connected to the propane system • Attached garage with space for one vehicle plus extensive storage • More than 3,000 square feet of living space • Four levels of outdoor living areas designed to maximize the waterfront lifestyle Opportunities to own a true Bayfront home in Windward Key are rare. Combining spectacular views, generous living space, exceptional amenities, and an affordable price point, this home offers the very best of Chesapeake Bay living.
Property Details | ||
|---|---|---|
| Price | $885,000 | |
| Bedrooms | 4 | |
| Full Baths | 4 | |
| Half Baths | 1 | |
| Total Baths | 5 | |
| Property Style | Transitional,Other | |
| Lot Size Area Units | Square Feet | |
| Acres | 0.04 | |
| Property Type | Residential | |
| Sub type | Townhouse | |
| MLS Sub type | Interior Row/Townhouse | |
| Stories | 4 | |
| Features | Bathroom - Walk-In Shower,Breakfast Area,Built-Ins,Carpet,Ceiling Fan(s),Combination Dining/Living,Dining Area,Floor Plan - Open,Kitchen - Table Space,Pantry,Primary Bath(s),Primary Bedroom - Bay Front,Skylight(s),Upgraded Countertops,Walk-in Closet(s),Wood Floors | |
| Exterior Features | BBQ Grill,Private Beach,Awning(s),Sidewalks | |
| Year Built | 1988 | |
| Fireplaces | 1 | |
| Subdivision | WINDWARD KEY | |
| View | Bay,Panoramic,Scenic Vista,Water | |
| Waterfront | Chesapeake Bay | |
| Heating | Heat Pump(s) | |
| Foundation | Slab | |
| Accessibility | Other | |
| Lot Description | Adjoins - Open Space,Premium,Other | |
| Parking Description | Paved Driveway,Paved Parking,Private | |
| Garage spaces | 1 | |
| Association Name | SENTRY MANAGEMENT | |
| Association Fee | 410 | |
| Association Amenities | Beach,Pickleball Courts,Pool - Outdoor | |
Geographic Data | ||
| Directions | Bayside Rd. turn into Windward Key. Immediate left, 8183 on your right | |
| County | CALVERT | |
| Latitude | 38.69383 | |
| Longitude | -76.53316 | |
Address Information | ||
| Address | 8183 WINDWARD KEY DR, CHESAPEAKE BEACH, MD 20732 | |
| Postal Code | 20732 | |
| City | CHESAPEAKE BEACH | |
| State | MD | |
| Country | United States | |
Listing Information | ||
| Listing Office | Deep Roots Real Estate | |
| Listing Office Email | broker.deeprootsre@gmail.com | |
| Listing Agent | Sally Showalter | |
| Special listing conditions | Standard | |
| Ownership | Fee Simple | |
School Information | ||
| District | CALVERT COUNTY PUBLIC SCHOOLS | |
| Elementary School | BEACH | |
| Middle School | WINDY HILL | |
| High School | NORTHERN | |
MLS Information | ||
| Days on market | 1 | |
| MLS Status | Active | |
| Listing Date | Jun 25, 2026 | |
| Listing Last Modified | Jun 25, 2026 | |
| Tax ID | 0503119378 | |
| Tax Year | 2025 | |
| Tax Annual Amount | 6810 | |
| MLS # | MDCA2027960 | |
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Last updated: 2026-06-25T17:30:26.993096Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.