Under Contract

MLS: #MDCA2027960, Listed By: Sally Showalter, Deep Roots Real Estate, Source:Bright MLS

8183 Windward Key Drive

CHESAPEAKE BEACH, MD 20732
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Bed 4

Bed

Bath 5

Bath

SqFt2,513

Sqft

Acres0.04

Acre(Lot)

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 sh oreline, 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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Detail Ic Property Details

Property Type : Residential

Price : $885,000

AD Id : 85794247

MLS Id : MDCA2027960

Beds : 4

Lot Size : 0.04 Acre

Living Area Size : 2,513

Year Built : 1988

Garage : 1

County : CALVERT

Subdivision: Windward Key

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total beds: 4

    Bathroom Information

    Total Baths: 5 Full Baths: 4 Half Baths: 1
  • Flooring Information

    Carpet, Wood
  • Interior Features

    Ceiling Fan(s), Pantry, Walk-In Closet(s), Built-in Features, Open Floorplan Appliances: Cooktop, Electric Water Heater, Dishwasher, Disposal, Dryer, Ice Maker, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Microwave Window Features: Skylight(s)
  • Heating & Cooling

    Has Heating: Yes Heating: Electric, Heat Pump Has Cooling: Yes Cooling: Central Air, Heat Pump, Ceiling Fan(s), Electric Water front: 1

  • Building Information

    Year Built: 1988 Building Area Total: 3053 Construction Materials: Frame Frontage Length: 25 Pool Features: Community Private Pool: No View: Water, Bay, Panoramic, Scenic Association Fee Frequency: Monthly
  • Exterior Features

    Exterior Features: Barbecue, Awning(s)

  • Lot Information

    Lot Size Acres: 0.04 Lot Size Source: Assessor Lot Size Square Feet: 1743 Lot Description: Other, Cleared, Waterfront

    Property Information

    Subdivision: WINDWARD KEY Source Property Type: Residential Postal Code Plus 4: 3123 Property SubType: Townhouse Direction Faces: East Levels: Three Or More Property Age: 38

  • Listing Price Information

    Listing Price: $885000

  • Tax Information

    Parcel Number: 0503119378 Tax Lot: 66 Tax Year: 2025 Annual Tax: $6810

  • Parking Information

    Parking Total: 2 Private, Paved, Garage, Parking Lot, Driveway, Inside Entrance, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 1
    Homeowners Association Information
    Has Association: Yes Included Fees: Trash HOA: $410.00 Association Amenities: Beach Access Community Features: Pool, Sidewalks

  • School Information

    Elementary School: BEACH
    Junior High School: WINDY HILL
    Senior High School: NORTHERN
  • Location Information

    Direction: Bayside Rd. turn into Windward Key. Immediate left, 8183 on your right WaterSource: Public
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
8047 Windward Key Drive, Chesapeake Beach, MD, 20732 $849,900 4 5 2,632 2,632 SqFt
8054 Windward Key Drive.., Chesapeake Beach, MD, 20732 $774,900 4 5 2,876 2,876 SqFt
8048 Windward Key Drive, Chesapeake Beach, MD, 20732 $759,900 3 5 2,583 2,583 SqFt
8076 Windward Key Drive, Chesapeake Beach, MD, 20732 $749,900 4 5 2,950 2,950 SqFt
4013 Seagate Square, Chesapeake Beach, MD, 20732 $485,000 3 4 2,028 2,028 SqFt
7902 Delores Court, Chesapeake Beach, MD, 20732 $499,990 4 4 2,688 2,688 SqFt
2243 Ivy Lane #8, Chesapeake Beach, MD, 20732 $375,000 3 3 2,641 2,641 SqFt
2183 Ivy Lane #4, Chesapeake Beach, MD, 20732 $350,000 3 3 2,600 2,600 SqFt

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which ByOwner participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have closed or are no longer being offered for sale. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 07/01/2026 @ 15:50

MLS: MDCA2027960 LISTED BY: Sally Showalter, Deep Roots Real Estate 443-967-6687 SOURCE: Bright MLS

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