Date
Details
Price
Change
Source
4/16/2026
Listed
$299,500
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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.
Full Property Details
Full Property Details for 108 Oak Leaf Dr
General
- Price: $299,500
- HOA FEE: $65/month
- Taxes: $3,282 (2025)
- Status: Active
- Type: Townhouse
- Source: BrightMLSMidAtlantic
- MLS ID: MDKE2006224
- Updated: 4/16/2026
- Added to Site: 3 day(s) ago
Interior
- Rooms/Areas: Living Room, Kitchen, Other, Bonus Room
- Interior Features: 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 Countertops, Other
- Appliances: Cooktop, Dishwasher, Dryer - Front Loading, Icemaker, Microwave, Oven - Single, Refrigerator, Stainless Steel Appliances, Washer - Front Loading, Water Heater
- Flooring: Carpet, Ceramic Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
- Upper Floor Baths: 2
- Upper - Full Baths: 2
- Main Floor Baths: 1
- Main - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 2
- Bedrooms Upper: 2
Exterior
- Exterior Features: Sidewalks, Street Lights, Other, Exterior Lighting
- Porch/Patio/Deck: Deck(s)
Parking
- Garage: Yes
- Garage Spaces: 1
- Total Spaces: 3
- Parking Features: Concrete Driveway
- Parking Type: Attached Garage, Driveway
- Garage Description: Oversized, Garage - Front Entry, Garage Door Opener, Inside Access, Additional Storage Area, Other
Location
- Municipality: Chestertown
- County: KENT
- Subdivision: OAK HOLLOW
- Driving Directions: 108 Oak Leaf Drive Chestertown GPS
- City Limits: Yes
School Information
- School District: Kent County Public Schools
Community
- Association: Yes
- Pets Allowed: Yes
- Pets: Cats OK, Dogs OK
Heating & Cooling
- Cooling Type: Ceiling Fan(s), Heat Pump(s)
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Public
Structural Information
- Architectural Style: Traditional
- Structure Type: End of Row/Townhouse
- Construction: Brick, Block, Concrete, Vinyl Siding, Stick Built, Blown-In Insulation
- Foundation: Block
- Roof: Architectural Shingle
- Stories Description: Main, Upper 1
- Square Feet: 1,867
- Sq. Ft. Source: Assessor
- Living Area: 1,867 Sq. Ft.
- Finished Above Grnd: 1,867 Sq. Ft.
- Year Built: 2004
- Year Built Source: Assessor
- Property Condition: Excellent
Lot Features
- Lot Size (Acres): 0.08
- Lot Size (Sq. Ft.): 3,672
- Lot Size Source: Assessor
- Zoning: R3/R4
Financial Considerations
- Price Per Sq. Ft.: $160.42
- Association Fee: $65
- Assoc Fee Freq.: Monthly
- Assessment Year: 2026
- City/TownTax: $907
- City/TownTax Freq: Annually
- County Tax: $2,375
- County Tax Freq: Annually
- Tax w/Assessment: $211,100
- Tax Amount: $3,282
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 1867
Disclosures and Reports
- Ownership: Fee Simple
- Lot Number: 30
Listed by Doug Ashley Realtors, LLC, Grace M Crockett
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Listing agent
— 108 Oak Leaf Dr —
Grace M Crockett
Doug Ashley Realtors, LLC
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 108 Oak Leaf Dr
School District:Kent County Public Schools
| Name | Grades | Distance |
|---|---|---|
H. H. Garnett Elementary School 320 Calvert Street, Chestertown, MD 21620 | PK-5 | 1 mi |
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620 | 6-8 | 0.8 mi |
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678 | 9-12 | 4.2 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 108 Oak Leaf Dr
Tax History
Tax History for 108 Oak Leaf Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,127
5%
$209,400
5%
2024
$2,978
11%
$199,300
5%
2023
$2,682
—
$189,200
6%
2022
$2,682
10%
$179,100
6%
2020
$2,444
6%
$168,833
14%
2019
$2,305
3%
$148,300
—
2018
$2,230
-1%
$148,300
-1%
2017
$2,258
307%
$150,100
—
2016
$555
-75%
$150,100
—
2015
$2,258
74%
$150,100
-13%
2014
$1,300
—
$172,900
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 108 Oak Leaf Dr
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108 Oak Leaf Drive, Chestertown, MD 21620 (MLS# MDKE2006224) is a Townhouse property with 2 bedrooms, 2 full bathrooms and 1 partial bathroom. 108 Oak Leaf Drive is currently listed for $299,500 and was received on April 16, 2026. Want to learn more about 108 Oak Leaf Drive? Do you have questions about finding other Townhouse real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.