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107 Oak Leaf Dr, 
Chestertown, MD 21620

$298,000


3

Beds


3

Baths


1,947

Sq Ft


Townhouse

Coming Soon

Last updated:

February 13, 2026, 04:34 PM

MLS#

MDKE2006114

Source:

BRIGHTMLS

Company Logo

About This Home

107 Oak Leaf Dr

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. PROFESSIONAL PICTURES TO COME!

Home Facts

Townhouse

3 Baths

3 Bedrooms

Built in 2004

Price Summary

298,000

$153 per Sq. Ft.

MLS #:

MDKE2006114

Last Updated:

February 13, 2026, 04:34 PM

Added:

1 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

1,947 Sq. Ft.


Structure

Structure

Architectural Style:

Traditional

Building Area:

1,947 Sq. Ft.

Year Built:

2004


Lot

Lot Size (Sq. Ft):

3,920


Finances & Disclosures

Finances

Price:

$298,000

Price per Sq. Ft:

$153 per Sq. Ft.

107 Oak Leaf Dr
Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.