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8183 WINDWARD KEY DR, CHESAPEAKE BEACH, MD 20732

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: 2026-06-25T20:30:28.468436Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.