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108 Oak Leaf Dr, 
Chestertown, MD 21620

$299,500


2

Beds


3

Baths


1,867

Sq Ft


Townhouse


Virtual Tour

Active

Listed by

Grace M Crockett

Doug Ashley Realtors, LLC.

Last updated:

April 20, 2026, 01:37 PM

MLS#

MDKE2006224

Source:

BRIGHTMLS

About This Home

108 Oak Leaf Dr

This beautifully maintained end-unit townhome, owned by its original owner, has been meticulously cared for and is now ready for its next chapter. The end-unit location provides additional natural light, creating a bright and inviting atmosphere throughout. The home has been freshly painted and features brand-new carpeting, while the ceramic tile and hardwood flooring in other areas are in excellent condition. The kitchen is equipped with a full set of newer appliances, offering both style and reliability, and the home also includes a newer washer and dryer—giving you the convenience of updated, move-in ready essentials from day one. Major systems have already been taken care of, including a new heating and cooling system (inside and out), a new hot water heater, and a newer roof and shutters. A flexible bonus room on the ground level currently houses the washer and dryer and can easily serve as a home office, TV room, or additional living space—whatever suits your needs. There is also an additional washer and dryer hookup on the upper level if preferred. Step out from the kitchen onto a private balcony, perfect for relaxing or entertaining. Truly move-in ready, this home offers a clean slate to make your own, along with the peace of mind that comes from years of thoughtful maintenance—making it feel like the perfect townhome.

Home Facts

Townhouse

3 Baths

2 Bedrooms

Built in 2004

Price Summary

299,500

$160 per Sq. Ft.

MLS #:

MDKE2006224

Last Updated:

April 20, 2026, 01:37 PM

Added:

5 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

1,867 Sq. Ft.


Structure

Structure

Architectural Style:

Traditional

Building Area:

1,867 Sq. Ft.

Year Built:

2004


Lot

Lot Size (Sq. Ft):

3,484


Finances & Disclosures

Finances

Price:

$299,500

Price per Sq. Ft:

$160 per Sq. Ft.

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.
See this home in person
108 Oak Leaf Dr
Attend an upcoming open house
Sat, Apr 25
11:00 AM01:00 PM

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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.