This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
$918,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
Property Description
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.
Full Property Details
Full Property Details for 8183 Windward Key Dr
General
- Sold For: $918,000
- HOA FEE: $410/month
- Taxes: $6,810 (2025)
- Status: Closed
- Type: Townhouse
- Source: BrightMLSMidAtlantic
- MLS ID: MDCA2027960
- Added to Site: 61 day(s) ago
Interior
- Interior 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
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Wood
- Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Extra Refrigerator/Freezer, Icemaker, Range Hood, Refrigerator, Six Burner Stove, Stainless Steel Appliances, Washer
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
- Upper 2 - Full Baths: 1
- Upper Floor Baths: 3
- Upper - Full Baths: 3
- Main Floor Baths: 1
- Main - 1/2 Baths: 1
- Lower Floor Baths: 1
- Lower - Full Baths: 1
Bedrooms
- Total Bedrooms: 4
- Bedrooms Upper: 4
- Bedrooms-Up2: 1
Additional Information
- Shared Amenities: Beach, Pickleball Courts, Pool - Outdoor
- Shared Pool: Yes
- Pool: Yes
Exterior
- Exterior Features: BBQ Grill, Private Beach, Awning(s), Sidewalks
Parking
- Garage: Yes
- Garage Spaces: 1
- Total Spaces: 4
- Parking Features: Paved Driveway, Paved Parking, Private
- Parking Type: Attached Garage, Parking Lot, Driveway
- Garage Description: Garage - Front Entry, Inside Access
Location
- Municipality: Chesapeake Beach
- County: CALVERT
- Subdivision: WINDWARD KEY
- Driving Directions: Bayside Rd. turn into Windward Key. Immediate left, 8183 on your right
- Direction Faces: East
- Location Details: Bayfront
- City Limits: Yes
School Information
- School District: Calvert County Public Schools
- Elementary School: Beach
- Middle School: Windy Hill
- High School: Northern
Community
- Association: Yes
- Assoc. Name: SENTRY MANAGEMENT
- Assoc. Fees Include: Common Area Maintenance, Lawn Maintenance, Pool(s), Trash
Heating & Cooling
- Central air: Yes
- Cooling Type: Heat Pump(s), Central A/C, Ceiling Fan(s)
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
Structural Information
- Architectural Style: Transitional, Other
- Structure Type: Interior Row/Townhouse
- Construction: Frame
- Foundation: Slab
- Stories Description: Lower 1, Main, Upper 1, Upper 2
- Square Feet: 3,053
- Sq. Ft. Source: Assessor
- Living Area: 2,513 Sq. Ft.
- Finished Above Grnd: 2,190 Sq. Ft.
- Finished Below Grnd: 323 Sq. Ft.
- Year Built: 1988
- Year Built Source: Assessor
Unit Information
Unit 1
- Bathrooms-Lower: 1
Lot Features
- Property View: Bay, Panoramic, Scenic Vista, Water
- Lot Size (Acres): 0.04
- Lot Size (Sq. Ft.): 1,743
- Lot Size Source: Assessor
- Zoning: C
- Lot Description: Adjoins - Open Space, Premium, Other
Water Features
- Water Front: Yes
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Access Desc: Private Beach, Private Access
- Water Front Type: Bay
- Water Front Name: Chesapeake Bay
Financial Considerations
- Price Per Sq. Ft.: $404.11
- Association Fee: $410
- Assoc Fee Freq.: Monthly
- Assessment Year: 2026
- City/TownTax: $1,830
- City/TownTax Freq: Annually
- County Tax: $4,569
- County Tax Freq: Annually
- Tax w/Assessment: $642,467
- Tax Amount: $6,810
- Tax Year: 2025
- Terms: Standard Sale
Disclosures and Reports
- Ownership: Fee Simple
- Exclusions: Dining Room light fixture
- Lot Number: 66
Listed by Deep Roots Real Estate, Sally L. D. Showalter
Sold by RE/MAX United Real Estate, Gail E Nyman
Get Pre-Approved Today
Schools
Schools serving 8183 Windward Key Dr
School District:Calvert County Public Schools
| Name | Grades | Distance |
|---|---|---|
Beach Elementary School 7900 Old Bayside Road, Chesapeake Beach, MD 20732 | PK-5 | 0.7 mi |
Windy Hill Middle School 9560 Boyd's Turn Rd, Owings, MD 20736 | 6-8 | 2.5 mi |
Northern High School 2950 Chaneyville Road, Owings, MD 20736 | 9-12 | 6.5 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 8183 Windward Key Dr
Date
Details
Price
Change
Source
8/10/2026
Sold
$918,000
3.73%
MLS
6/25/2026
Listed
$885,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
8183 Windward Key Drive, Chesapeake Beach, MD 20732 (MLS# MDCA2027960) is a Townhouse property that was sold at $918,000 on August 10, 2026. Want to learn more about 8183 Windward Key Drive? Do you have questions about finding other Townhouse real estate for sale in Chesapeake Beach? You can browse all Chesapeake Beach real estate or contact a Coldwell Banker agent to request more information.

