107 Oak Leaf Drive Chestertown, MD $ 298,000
107 Oak Leaf Drive
$ 298,000
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107 Oak Leaf Drive

Chestertown, MD, 21620
$ 298,000
Bedrooms3 Baths2.1 Sq 1,947

Monthly Estimate*

$ 1,835

107 Oak Leaf Drive, Chestertown, MD 21620 - Image 1
107 Oak Leaf Drive, Chestertown, MD 21620 - Image 2
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107 Oak Leaf Drive, Chestertown, MD 21620 - Image 4
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107 Oak Leaf Drive, Chestertown, MD 21620 - Image 8
107 Oak Leaf Drive, Chestertown, MD 21620 - Image 9
107 Oak Leaf Drive, Chestertown, MD 21620 - Image 10
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Townhouse for sale in Chestertown, MD

for $298,000 with 3 bedrooms and 2 full baths, 1 half bath. This 1,947 square foot townhouse was built in 2004 on a lot size of 0.09.

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 boxesperfect 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 locatedthis home offers comfort, updates, and convenience all in one. PROFESSIONAL PICTURES TO COME!

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Townhouse Coming Soon

Price

$ 298,000

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Townhouse

Taxes

$ 3,521

Style

Traditional

Lot Size

0.09

Year Built

2004

Town/City

Chestertown

County/Region

Kent

MLS | Web ID

MDKE2006114

Features
General
Living Area 1947
Sewer Public Sewer
Heating Heat Pump(s)
Cooling Other
Utilities Propane
Possession Settlement
Roof Architectural Shingle
Appliances Cooktop - Down Draft Dishwasher Dryer Refrigerator Stainless Steel Appliances Washer Water Heater
Zoning R3/R4
HOA Fee 65.00
Garage Spaces 1.00
Patio/Porch Features Deck(s) Balcony
Architectural Style Traditional
Construction Materials Brick Concrete Frame Stick Built Vinyl Siding
School District KENT COUNTY PUBLIC SCHOOLS
Year Built 2004
View Pond
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
Facing Direction East
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 2
Status COMING SOON
Directions Use GPS
City CHESTERTOWN
Association Name OAK HOLLOW
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 3740.00
Tax Annual Amount 3521.0
Property Condition Excellent
Structure Type End of Row/Townhouse
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 0
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 153.06
Vacation Rental Y/N N
Location Type Corner Lot/Unit
Standard Status Coming Soon
Year Built Source Assessor
Legal Subdivision OAKSTREET LLC
Tax Lot 4
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Interior
Interior Amenities 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
Heating Fuel Electric
Flooring Carpet Ceramic Tile Hardwood
Total Fireplaces 1
Hot Water Electric
Basement (Y/N) N
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 1947
Half Baths 1
Central Air Y/N N
Total Bedrooms 3
Below Grade Finished Area 0
Main Level Bedrooms 0
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
Pool No Pool
Lot Features Adjoins - Open Space Corner Level
Water Source Public
Garage Features Additional Storage Area Built In Garage - Front Entry Garage Door Opener Inside Access Oversized
Type of Parking Attached Garage Driveway
Foundation Details Slab
Water View Y/N Y
Lot Size Acres 0.09
Lot Size Source Assessor
Waterfront 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 1 107
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* Excluded Features
List By
Coldwell Banker Chesapeake Real Estate Company

Broker

kristina@cbchesapeake.com

Email

Affordability Calculator

$2,128
Per Month
86%
14%
0%
Monthly Principal & Interest
$1,835
Monthly Property Taxes
$293
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
2/12/2026$294,000 Listed Price

Map


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107 Oak Leaf Drive, Chestertown, MD, 21620 is a Townhouse for sale at $298,000 with 1,947 sqft and a lot size of 0.09. 107 Oak Leaf Drive has 3 bedrooms, 2.1 baths, and was built in 2004. The property's zip code is 21620 which is in Chestertown, MD