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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.lancasterpahomesforsale.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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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/04/2026. The listing information on this page last changed on 03/04/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 03/04/2026 12:00:14 AM EST) or Bright MLS (last updated Tue 03/03/2026 11:50:12 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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The Ginger Volpone Stephen Burkett Team
Ginger Volpone, Stephen Burkett, Lauren Thompson 

215 S. Centerville Road, Lancaster, PA 17603
717-393-0100

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