8183 Windward Key Dr, Chesapeake Beach, MD 20732
Local realty services provided by:Better Homes and Gardens Real Estate Community Realty
8183 Windward Key Dr,Chesapeake Beach, MD 20732
$885,000
- 4 Beds
- 5 Baths
- 2,513 sq. ft.
- Townhouse
- Pending
Listed by: sally l. d. showalter
Office: deep roots real estate
MLS#:MDCA2027960
Source:BRIGHTMLS
Price summary
- Price:$885,000
- Price per sq. ft.:$352.17
- Monthly HOA dues:$410
About this home
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....
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Home facts
- Year built:1988
- Listing ID #:MDCA2027960
- Added:6 day(s) ago
- Updated:June 30, 2026 at 09:08 AM
Rooms and interior
- Bedrooms:4
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Dining Description:Combination Dining/Living, Dining Area
- Bathrooms Description:Primary Bath(s)
- Kitchen Description:Breakfast Area, Built-In Microwave, Built-Ins, Carpet, Dishwasher, Disposal, Extra Refrigerator/Freezer, Icemaker, Kitchen - Table Space, Pantry, Range Hood, Refrigerator, Six Burner Stove, Stainless Steel Appliances, Upgraded Countertops
- Bedroom Description:Carpet, Primary Bedroom - Bay Front, Walk In Closet(s)
- Living area:2,513 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C, Heat Pump(s)
- Heating:Electric, Heat Pump(s)
Structure and exterior
- Year built:1988
- Building area:2,513 sq. ft.
- Lot area:0.04 Acres
- Lot Features:Adjoins - Open Space, Bayfront, Premium
- Architectural Style:Transitional
- Construction Materials:Frame
- Exterior Features:Awning(s), BBQ Grill, Private Beach, Sidewalks
- Foundation Description:Slab
- Levels:4 Story
Schools
- High school:NORTHERN
- Middle school:WINDY HILL
- Elementary school:BEACH
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$885,000
- Price per sq. ft.:$352.17
- Tax amount:$6,810 (2025)
Features and amenities
- Laundry features:Dryer, Washer
- Amenities:Built-Ins, Carpet, Ceiling Fan(s), Primary Bedroom - Bay Front, Skylight(s)
Parking
- Parking description:Attached Garage, Garage - Front Entry, Inside Access, Parking Lot, Paved Driveway, Paved Parking, Private
- Garage:Yes
- Garage spaces:1
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