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107 Oak Leaf Drive, Chestertown, MD 21620

$295,000
  • 107 Oak Leaf Drive, Chestertown, MD 21620 Main Photo

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Price Reduced $3,000 on February 16th, 2026
BEDS3 BATHS2 full 1 partial SQUARE FEET1,947 MLS#MDKE2006114
STATUSACTIVE PROPERTY TYPEResidential - Townhouse SUBDIVISIONOAK HOLLOW SCHOOLKENT COUNTY PUBLIC SCHOOLS

Property Description

Desirable end-unit, 3-story townhome located in the heart of Chestertown, just moments from downtown and adjacent to the new YMCA. This well-maintained home features newer carpet and paint, a one-year-old stove (purchased new for $4,000), and a hot water heater just two years old. A newer full-size stackable washer and dryer adds convenience. Enjoy both sunrise and sunset views with an east-facing front that fills the home with beautiful morning light and a west-facing rear offering stunning evening sunsets. The balcony has been recently stained, and the first-floor patio has been thoughtfully converted into a deck with built-in wood flower boxes—perfect for outdoor enjoyment. The versatile first level offers flexible space ideal for a bedroom, office, or exercise room, complete with a gas fireplace and sliding door access to the deck. The garage includes a built-in loft, workbench, and shelving for added storage and functionality. Upstairs, the primary suite features a vaulted ceiling and a spacious en-suite bath with soaking tub and walk-in shower. A mature maple tree enhances the backyard setting, providing charm and seasonal beauty. Move-in ready and ideally located—this home offers comfort, updates, and convenience all in one.

107 Oak Leaf Drive | MLS# MDKE2006114

This townhouse located at 107 Oak Leaf Drive, Chestertown, MD 21620 is currently listed for sale with an asking price of $295,000. This property was built in 2004 and has 3 bedrooms and 2 full and 1 partial baths with 1947 sq. ft. Oak Leaf Drive is located in the OAK HOLLOW subdivision within the KENT COUNTY PUBLIC SCHOOLS school district. Search OAK HOLLOW real estate on www.tomboeshorerealtor.com today.

Property Features

Property Type: Residential - Townhouse
Fireplaces: 1
Fuel Type: Electric
Garage: 1
Heating: Heat Pump(s)
Home Style: Traditional
Lot Size: 0.09 Acres
Roof Type: Architectural Shingle
Stories: 3.0
Taxes: $3,521
Year Built: 2004

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Cooktop - Down Draft, Dishwasher, Dryer, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
Exterior: Brick, Concrete, Frame, Stick Built, Vinyl Siding
Exterior: Sidewalks, Street Lights, Other
Flooring: Carpet, Ceramic Tile, Hardwood
HOA Fee: $65.00/Monthly
Interior: Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Ceiling Fan(s), Combination Kitchen/Dining, Kitchen - Eat-In, Kitchen - Island, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting
Location: Corner Lot/Unit
Lot: Adjoins - Open Space, Corner, Level
Lot Dimensions: 0.09 Acre(S)
Municipality: Chestertown
Parking Notes: 3 Total Parking Spaces
Sewer: Public Sewer
Special View Info: Pond
SQFT Above Finished: 1947
SQFT Total Finished: 1947
Structure Type: End of Row/Townhouse
Total Garage/Parking Spaces: 3
Utilities: Propane
Water: Public

Local Schools

School District: KENT COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Chesapeake Real Estate Company
Agency Phone: 4107780330

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Estimated Payment

$ 1,036.00 per month $656.54 Principal & Interest $293.42 Property Tax $86.04 Homeowner's Insurance

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