108 Oak Leaf Drive Chestertown, MD $ 299,500
108 Oak Leaf Drive
$ 299,500
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108 Oak Leaf Drive

Chestertown, MD, 21620
$ 299,500
Bedrooms2 Baths2.1 Sq 1,867

Monthly Estimate*

$ 1,844

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View a Virtual Tour

Townhouse for sale in Chestertown, MD

for $299,500 with 2 bedrooms and 2 full baths, 1 half bath. This 1,867 square foot townhouse was built in 2004 on a lot size of 0.08.

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 dryergiving 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 spacewhatever 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 maintenancemaking it feel like the perfect townhome.

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Townhouse Active

Price

$ 299,500

Bedrooms

2

Full Bath

2

Half Bath

1

Property Type

Townhouse

Taxes

$ 3,282

Style

Traditional

Lot Size

0.08

Year Built

2004

Town/City

Chestertown

County/Region

Kent

MLS | Web ID

MDKE2006224

Features
General
Living Area 1867
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Ceiling Fan(s) Heat Pump(s)
Possession Settlement
Roof Architectural Shingle
Appliances Cooktop Dishwasher Dryer - Front Loading Icemaker Microwave Oven - Single Refrigerator Stainless Steel Appliances Washer - Front Loading Water Heater
Zoning R3/R4
HOA Fee 65.00
Garage Spaces 1.00
Patio/Porch Features Deck(s)
Architectural Style Traditional
Construction Materials Brick Block Concrete Vinyl Siding Stick Built Blown-In Insulation
School District KENT COUNTY PUBLIC SCHOOLS
Year Built 2004
Levels 3
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Municipality Chestertown
Accessibility None
Assoc Fee Paid Per Monthly
County KENT
New Construction N
Property Type Residential
HOA Y
Subdivision Name OAK HOLLOW
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 2
Status ACTIVE
Directions 108 Oak Leaf Drive Chestertown GPS
City CHESTERTOWN
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 3672.00
Tax Annual Amount 3282.0
Property Condition Excellent
Structure Type End of Row/Townhouse
Condo/Coop Association fee Y/N N
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 160.42
Acceptable Financing Cash Conventional FHA USDA VA
Historic Y/N N
Lease Considered Y/N N
Vacation Rental Y/N N
Virtual Tour https://thru-the-lens-ivuf.view.property/2381363?idx=1
Standard Status Active
Year Built Source Assessor
Legal Subdivision OAKSTREET LLC
Tax Lot 30
Association Recreation Fee N
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Interior
Interior Amenities Bathroom - 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
Heating Fuel Electric
Flooring Carpet Ceramic Tile Hardwood
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N N
Above Grade Finished Area 1867
Half Baths 1
Central Air Y/N N
Total Bedrooms 2
Below Grade Finished Area 0
Room Type Living Room Kitchen Other Bonus Room
Below Grade Finished Area Unit Type Square Feet
Below Grade Finished Area Source Assessor
Above Grade Finished Area Source Assessor
Above Grade Finished Area Unit Type Square Feet
Total Baths 3
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Exterior
Exterior Amenities Sidewalks Street Lights Other Exterior Lighting
Pool No Pool
Parking Features Concrete Driveway
Water Source Public
Garage Features Oversized Garage - Front Entry Garage Door Opener Inside Access Additional Storage Area Other
Type of Parking Attached Garage Driveway
Foundation Details Block
Water View Y/N N
Lot Size Acres 0.08
Lot Size Source Assessor
Waterfront Y/N N
Road Responsibility City/County
Horse Y/N N
Land Assessed Value 60000.00
Navigable Water Y/N N
Water Oriented Y/N N
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Internal Only
Street Number 1 108
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* Excluded Features
List By
Doug Ashley Realtors, Llc

Broker

crockettgm@ymail.com

Email

Affordability Calculator

$2,118
Per Month
87%
13%
0%
Monthly Principal & Interest
$1,844
Monthly Property Taxes
$274
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3535796 Elementary School
3533824 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
4/16/2026$299,500 Listed Price

Map


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108 Oak Leaf Drive, Chestertown, MD, 21620 is a Townhouse for sale at $299,500 with 1,867 sqft and a lot size of 0.08. 108 Oak Leaf Drive has 2 bedrooms, 2.1 baths, and was built in 2004. The property's zip code is 21620 which is in Chestertown, MD