8183 Windward Key Dr

Chesapeake Beach, MD 20732
  • $885,000

    Price
  • 4

    Bed
  • 5

    Bath
  • 2,513

    SqFt

About the Listing DEEP1 - 49547

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.

Listing Highlights

Status Active With Contingency
Days on Site 7
Property Type Townhome
MLS ® MDCA2027960
Year Built 1988
Total Square Footage 2,513
Lot/Acreage 0.04
County Calvert
Neighborhood Windward Key
HOA Dues 410/Monthly
Elementary School Beach
Middle School Windy Hill
High School Northern

Interior Details

  • Bedrooms: 4
  • Bathrooms: 4 Full / 1 Half
  • Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Extra Refrigerator/Freezer, Icemaker, Range Hood, Refrigerator, Six Burner Stove, Stainless Steel Appliances, Washer
  • Air Cond: Heat Pump(s),Central A/C,Ceiling Fan(s)
  • Heating: Heat Pump(s)
  • Fireplaces: 1, Wood,1 Fireplace
  • Floor:
  • Above Ground Sq Ft: 2190
  • Below Ground Sq Ft: 323
  • Basement:
  • Other: 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
  • Water: Public

Exterior Details

  • Lot Description: Adjoins - Open Space,Premium,Not New Construction,Horse Property: No,Waterfront,In City Limits
  • Garage Capacity: 1 car
  • Parking Spaces: 4
  • Zoning: C
  • Roof:
  • Others: BBQ Grill,Private Beach,Awning(s),Sidewalks,Beach,Pickleball Courts,Pool - Outdoor,Common Area Maintenance,Lawn Maintenance,Pool(s),Trash
  • Sewer: Public Sewer
  • Parking Features: Paved Driveway,Paved Parking,Private,Garage - Front Entry,Inside Access,Attached Garage,Parking Lot,Driveway,4+ Spaces,3+ Spaces,2+ Spaces,1+ Spaces

Financial Details

  • Tax Amount: $6,810
  • Taxes w/Assessments: N/A
  • Tax/Property ID: N/A
  • Tax Year: 2025

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8183 Windward Key Dr Chesapeake Beach, MD 20732

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Originating MLS: BRIGHT_MAIN

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