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$295,000 -$3,000 (-1.01%) Price Reduced

  • For Sale
  • Coming Soon
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,947 Sq. Ft.
  • 1 Car Garage
  • Updated 13 hours ago

Next open house:

Open House: 12:00 PM - 2:00 PM

Sunday 3/1 12:00 PM - 2:00 PM

107 Oak Leaf Drive,Chestertown, MD 21620

107 Oak Leaf DriveChestertownMD21620

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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.

Full Property Details for 107 Oak Leaf Dr

General

  • Price: $295,000
  • HOA FEE: $65/month
  • Taxes: $3,521 (2025)
  • Status: Coming Soon
  • Type: Townhouse
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2006114
  • Updated: 2/19/2026
  • Added to Site: 8 day(s) ago
  • Expected Market Date: 2/27/2026

Interior

  • Interior Features: 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, Primary Bath(s), Recessed Lighting
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Cooktop - Down Draft, Dishwasher, Dryer, Refrigerator, Stainless Steel Appliances, Washer, 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: 3
  • Bedrooms Upper: 3

Exterior

  • Exterior Features: Sidewalks, Street Lights, Other
  • Porch/Patio/Deck: Deck(s), Balcony

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 3
  • Parking Type: Attached Garage, Driveway
  • Garage Description: Additional Storage Area, Built In, Garage - Front Entry, Garage Door Opener, Inside Access, Oversized

Location

  • Municipality: Chestertown
  • County: KENT
  • Subdivision: OAK HOLLOW
  • Driving Directions: Use GPS
  • Direction Faces: East
  • Location Details: Corner Lot/Unit
  • City Limits: Yes

School Information

  • School District: Kent County Public Schools

Community

  • Association: Yes
  • Assoc. Name: OAK HOLLOW

Heating & Cooling

  • Cooling Type: Other
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Propane

Structural Information

  • Architectural Style: Traditional
  • Structure Type: End of Row/Townhouse
  • Construction: Brick, Concrete, Frame, Stick Built, Vinyl Siding
  • Foundation: Slab
  • Roof: Architectural Shingle
  • Walls/Ceilings: Cathedral Ceilings, Dry Wall, High
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 1,947
  • Sq. Ft. Source: Assessor
  • Living Area: 1,947 Sq. Ft.
  • Finished Above Grnd: 1,947 Sq. Ft.
  • Year Built: 2004
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Property View: Pond
  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 3,740
  • Lot Size Source: Assessor
  • Zoning: R3/R4
  • Lot Description: Adjoins - Open Space, Corner, Level

Water Features

  • Water View: Yes

Financial Considerations

  • Price Per Sq. Ft.: $151.52
  • Association Fee: $65
  • Assoc Fee Freq.: Monthly
  • Assessment Year: 2026
  • City/TownTax: $973
  • City/TownTax Freq: Annually
  • County Tax: $2,548
  • County Tax Freq: Annually
  • Tax w/Assessment: $226,600
  • Tax Amount: $3,521
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1947

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 4

Listed by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland

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Listing agent

— 107 Oak Leaf Dr —

  • Kristina L Hyland

    Coldwell Banker Chesapeake Real Estate Company

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 107 Oak Leaf Dr

School District:Kent County Public Schools
NameGradesDistance
H. H. Garnett Elementary School
320 Calvert Street, Chestertown, MD 21620
PK-51 mi
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.8 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-124.2 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 107 Oak Leaf Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/16/2026
Price Reduced
$295,000
-1.01%
MLS
2/12/2026
Listed
$298,000
26.81%
MLS
10/20/2021
Sold
$235,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 107 Oak Leaf Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,522
7%
$224,700
7%
2024
$3,295
17%
$210,267
7%
2023
$2,825
—
$195,833
8%
2022
$2,825
14%
$181,400
6%
2020
$2,472
—
$170,933
7%
2021
$2,472
5%
$160,467
7%
2020
$2,346
1%
$150,000
—
2019
$2,331
3%
$150,000
—
2018
$2,256
-1%
$150,000
-1%
2017
$2,283
306%
$151,800
—
2016
$562
-75%
$151,800
—
2015
$2,283
74%
$151,800
-13%
2014
$1,314
—
$174,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland

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107 Oak Leaf Drive, Chestertown, MD 21620 (MLS# MDKE2006114) is a Townhouse property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 107 Oak Leaf Drive is currently listed for $295,000 and was received on February 12, 2026. Want to learn more about 107 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.

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