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108 OAK LEAF DR, CHESTERTOWN, MD 21620

2 Beds

3 Baths

1,867SqFt

Pending

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.

Property Details
Price$299,500
Bedrooms2
Full Baths2
Half Baths1
Total Baths3
Property StyleTraditional
Lot Size Area UnitsSquare Feet
Acres0.08
Property TypeResidential
Sub typeTownhouse
MLS Sub typeEnd of Row/Townhouse
Stories3
FeaturesBathroom - Stall Shower,Bathroom - Tub Shower,Carpet,Ceiling Fan(s),Combination Kitchen/Dining,Crown Moldings,Curved Staircase,Kitchen - Eat-In,Kitchen - Table Space,Pantry,Sprinkler System,Upgraded Countertops,Other
Exterior FeaturesSidewalks,Street Lights,Other,Exterior Lighting
Year Built2004
SubdivisionOAK HOLLOW
RoofArchitectural Shingle
HeatingHeat Pump(s)
FoundationBlock
AccessibilityNone
Parking DescriptionConcrete Driveway
Garage spaces1
Association Fee65
Geographic Data
Directions108 Oak Leaf Drive Chestertown GPS
CountyKENT
Latitude39.22789
Longitude-76.06699
Address Information
Address108 OAK LEAF DR, CHESTERTOWN, MD 21620
Postal Code21620
CityCHESTERTOWN
StateMD
CountryUnited States
Listing Information
Listing OfficeDoug Ashley Realtors, LLC
Listing AgentGrace Crockett
Special listing conditionsStandard
OwnershipFee Simple
TermsCash,Conventional,FHA,USDA,VA
Virtual Tour URLhttps://thru-the-lens-ivuf.view.property/2381363?idx=1
School Information
DistrictKENT COUNTY PUBLIC SCHOOLS
MLS Information
Days on market19
MLS StatusPending
Listing DateApr 16, 2026
Listing Last ModifiedMay 4, 2026
Tax ID1504027736
Tax Year2025
Tax Annual Amount3282
MLS #MDKE2006224

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Last updated: 2026-05-09T15:30:26.624906Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.