8183 Windward Key Drive Chesapeake Beach, MD $ 885,000
8183 Windward Key Drive
$ 885,000
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8183 Windward Key Drive

Chesapeake Beach, MD, 20732
$ 885,000
Bedrooms4 Baths4.1 Sq 2,513

Monthly Estimate*

$ 5,588

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Townhouse for sale in Chesapeake Beach, MD

for $885,000 with 4 bedrooms and 4 full baths, 1 half bath. This 2,513 square foot townhouse was built in 1988 on a lot size of 0.04.

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 shipsall 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 deckperfect 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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Townhouse Contingent

Price

$ 885,000

Bedrooms

4

Full Bath

4

Half Bath

1

Property Type

Townhouse

Taxes

$ 6,810

Style

Transitional

Lot Size

0.04

Year Built

1988

Town/City

Chesapeake Beach

County/Region

Calvert

MLS | Web ID

MDCA2027960

Features
General
Living Area 2513
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Heat Pump(s) Central A/C Ceiling Fan(s)
Possession Settlement
Appliances Built-In Microwave Dishwasher Disposal Dryer Extra Refrigerator/Freezer Icemaker Range Hood Refrigerator Six Burner Stove Stainless Steel Appliances Washer
Zoning C
HOA Fee 410.00
Garage Spaces 1.00
Association Fee Includes Common Area Maintenance Lawn Maintenance Pool(s) Trash
Architectural Style Transitional Other
Construction Materials Frame
School District CALVERT COUNTY PUBLIC SCHOOLS
Exclusions Dining Room light fixture
Year Built 1988
View Bay Panoramic Scenic Vista Water
Levels 4
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Municipality Chesapeake Beach
Waterfront Features Sandy Beach
Accessibility Other
Assoc Fee Paid Per Monthly
County CALVERT
New Construction N
Property Type Residential
Association Amenities Beach Pickleball Courts Pool - Outdoor
HOA Y
Subdivision Name WINDWARD KEY
Facing Direction East
Garage Y/N Y
Water Access Y/N Y
Other Structures Above Grade Below Grade
Full Baths 4
Status ACTIVE UNDER CONTRACT
Directions Bayside Rd. turn into Windward Key. Immediate left 8183 on your right
City CHESAPEAKE BEACH
Body of Water Chesapeake Bay
Disclosures Prop Disclaimer
Association Name SENTRY MANAGEMENT
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 1743.00
Tax Annual Amount 6810.0
Structure Type Interior Row/Townhouse
Condo/Coop Association fee Y/N N
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 404.11
Historic Y/N N
Lease Considered Y/N N
Vacation Rental Y/N N
Location Type Bayfront
Standard Status Active Under Contract
Year Built Source Assessor
Legal Subdivision WINDWARD KEY
Tax Lot 66
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Interior
Interior Amenities 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 Fro
Heating Fuel Electric
Total Fireplaces 1
Fireplace Features Wood
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 2190
Half Baths 1
Central Air Y/N Y
Total Bedrooms 4
Below Grade Finished Area 323
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 5
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Exterior
Exterior Amenities BBQ Grill Private Beach Awning(s) Sidewalks
Pool Yes - Community
Parking Features Paved Driveway Paved Parking Private
Lot Features Adjoins - Open Space Premium Other
Water Source Public
Garage Features Garage - Front Entry Inside Access
Type of Parking Attached Garage Parking Lot Driveway
Foundation Details Slab
Water View Y/N Y
Lot Size Acres 0.04
Water Body Type Bay
Lot Size Source Assessor
Waterfront Y/N Y
Water Access Features Private Beach Private Access
Horse Y/N N
Land Assessed Value 300000.00
Navigable Water Y/N Y
Water Oriented Y/N Y
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Internal Only
Street Number 1 8183
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* Excluded Features
List By
Deep Roots Real Estate

Broker

sallyshowalter@comcast.net

Email

Affordability Calculator

$6,155
Per Month
91%
9%
0%
Monthly Principal & Interest
$5,588
Monthly Property Taxes
$568
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3535382 Elementary School
3536303 Middle School
Northern High School High School
Pricing History
DatePricePrice ChangeDescription
6/23/2026$885,000 Listed Price

Map


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8183 Windward Key Drive, Chesapeake Beach, MD, 20732 is a Townhouse for sale at $885,000 with 2,513 sqft and a lot size of 0.04. 8183 Windward Key Drive has 4 bedrooms, 4.1 baths, and was built in 1988. The property's zip code is 20732 which is in Chesapeake Beach, MD