Property Photo: 107 Oak Leaf Drive MD 21620

Listing Courtesy of: BRIGHT IDX / Coldwell Banker Chesapeake Real Estate Company / Kristina Hyland

107 Oak Leaf Drive Chestertown, MD 21620

Active (5 Days)

$295,000 ^(USD)

BED

BATH

1,947

SQFT

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Description

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.

MLS #:
MDKE2006114

Taxes
$3,521(2025)

Lot Size
3,740 SQFT

Type
Townhouse

Year Built
2004

Style
Traditional

School District
Kent County Public Schools

County
Kent County

Listed By

Kristina Hyland, Coldwell Banker Chesapeake Real Estate Company

Source
BRIGHT IDX
Last checked Mar 2 2026 at 1:17 PM GMT+0000

Bathroom Details

Full Bathrooms: 2
Half Bathroom: 1

Interior Features

Dishwasher
Dryer
Washer
Refrigerator
Water Heater
Walls/Ceilings: High
Combination Kitchen/Dining
Kitchen - Eat-In
Walls/Ceilings: Cathedral Ceilings
Kitchen - Island
Walls/Ceilings: Dry Wall
Recessed Lighting
Kitchen - Table Space
Cooktop - Down Draft
Stainless Steel Appliances
Pantry
Ceiling Fan(s)
Primary Bath(s)
Bathroom - Tub Shower
Bathroom - Soaking Tub
Bathroom - Stall Shower
Bathroom - Walk-In Shower

Subdivision

Oak Hollow

Lot Information

Corner
Level
Adjoins - Open Space

Property Features

Above Grade
Below Grade
Foundation: Slab

Heating and Cooling

Heat Pump(s)
Other

Homeowners Association Information

Dues: $65

Flooring

Hardwood
Carpet
Ceramic Tile

Exterior Features

Brick
Frame
Vinyl Siding
Concrete
Stick Built
Roof: Architectural Shingle

Utility Information

Utilities: Propane
Sewer: Public Sewer
Fuel: Electric

Stories

Living Area

1,947 sqft

Listing Price History

Date

Event

Price

% Change

$ (+/-)

Feb 16, 2026

Price Changed

$295,000

-1%

-$3,000

Feb 12, 2026

Price Changed

$298,000

$4,000

Location

Map View | Street View

Listing to Address

Address to Listing

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Disclaimer: Copyright 2026 Bright MLS IDX. All rights reserved. This information is deemed reliable, but not guaranteed. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 3/2/26 05:17

107 Oak Leaf Drive Chestertown, MD 21620

Listed By

Listing Price History

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