108 Oak Leaf Drive, Chestertown, MD 21620 - Photo 1

1/1

$296,500

Sold
Closed
Townhouse
2 Beds
2 Full Baths
1 Partial Bath
1,867 Sq. Ft.
1 Car Garage
Updated 11 days ago

1/1

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

Sold For: $296,500
HOA FEE: $65/month
Taxes: $3,282 (2025)
Status: Closed
Type: Townhouse
Source: BrightMLSMidAtlantic
MLS ID: MDKE2006224
Added to Site: 49 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
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 1867

Disclosures and Reports

Ownership: Fee Simple
Lot Number: 30

Listed by Doug Ashley Realtors, LLC, Grace M Crockett
Sold by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair

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Listing agent

— 108 Oak Leaf Dr —

Grace M Crockett

Doug Ashley Realtors, LLC

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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

Date

Details

Price

Change

Source

5/22/2026

Sold

$296,500

-1%

MLS

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.

11122 Boyer Ln, Worton, MD 21678 - Photo 1

Just Listed

$750,000

11122 Boyer Ln Worton, MD 21678

Single Family
Active
Updated 2 days ago

4
Beds
4
Total Baths
4,972
Sq. Ft.

Listed by TTR Sotheby's International Realty, Courtney Chipouras

10790 Worton Rd, Worton, MD 21678 - Photo 1

Just Listed

$410,000

10790 Worton Rd Worton, MD 21678

Single Family
Active
Updated 3 hours ago

3
Beds
2
Total Baths
1,484
Sq. Ft.

Listed by Doug Ashley Realtors, LLC, Retha J Arrabal

11054 Austin Ln, Worton, MD 21678 - Photo 1

Just Listed

$325,000

11054 Austin Ln Worton, MD 21678

Single Family
Active
Updated 2 days ago

3
Beds
2
Total Baths
1,376
Sq. Ft.

Listed by RE/MAX Chesapeake, Donnie M Horton

116 The Pond Way, Church Hill, MD 21623 - Photo 1

Just Listed

$279,900

116 The Pond Way #3C Church Hill, MD 21623

Townhouse
Active
Updated 5 hours ago

2
Beds
2
Total Baths
1,860
Sq. Ft.

Listed by Coldwell Banker Waterman Realty, Jonathan J Olsavsky and Coldwell Banker Waterman Realty, Steven S Saunders

11944 Augustine Herman Hwy, Kennedyville, MD 21645 - Photo 1

Price Reduced

-$20,000 (-4.26%)

$450,000

11944 Augustine Herman Hwy Kennedyville, MD 21645

Single Family
Active
Updated 4 days ago

4
Beds
2
Total Baths
2,604
Sq. Ft.

Listed by Coldwell Banker Chesapeake Real Estate Company, William Sutton and Coldwell Banker Chesapeake Real Estate Company, Lacey R Sutton

6416 Edesville Rd, Rock Hall, MD 21661 - Photo 1

Price Reduced

-$10,000 (-2.51%)

$389,000

6416 Edesville Rd Rock Hall, MD 21661

Single Family
Active
Updated 1 day ago

3
Beds
3
Total Baths
2,200
Sq. Ft.

Listed by Rock Hall Properties Real Estate, Sarah A Ulrick and Rock Hall Properties Real Estate, Cindy Genther

550 Bolton Woods Rd, Sudlersville, MD 21668 - Photo 1

Price Reduced

-$10,000 (-2.78%)

$349,900

550 Bolton Woods Rd Sudlersville, MD 21668

Single Family
Active
Updated 1 day ago

3
Beds
2
Total Baths
1,064
Sq. Ft.

Listed by RE/MAX Executive, Crystal M Smith

324 Kidwell Ave, Centreville, MD 21617 - Photo 1

Price Reduced

-$14,900 (-2.98%)

$485,000

324 Kidwell Ave Centreville, MD 21617

Single Family
Active
Updated 2 days ago

4
Beds
3
Total Baths
3,146
Sq. Ft.

Listed by Rhonda Dunmyer (410) 703-0246

107 Oak Leaf Dr, Chestertown, MD 21620 - Photo 1

Sold

$295,000

107 Oak Leaf Dr Chestertown, MD 21620

Townhouse
Closed

3
Beds
3
Total Baths
1,947
Sq. Ft.

Listed by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland
Sold by Coldwell Banker Chesapeake Real Estate Company, Joseph S. Ciganek

107 Metcalf Rd, Chestertown, MD 21620 - Photo 1

Sold

$259,900

107 Metcalf Rd Chestertown, MD 21620

Townhouse
Closed
Updated 12 days ago

3
Beds
2
Total Baths
1,200
Sq. Ft.

Listed by Real Broker, LLC, David J. Moore
Sold by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

109 Metcalf Rd, Chestertown, MD 21620 - Photo 1

Sold

$264,900

109 Metcalf Rd Chestertown, MD 21620

Townhouse
Closed
Updated 8 days ago

3
Beds
2
Total Baths
1,280
Sq. Ft.

Listed by Real Broker, LLC, David J. Moore
Sold by Real Broker, LLC, WALLACE G BOOTH Jr.

103 Flying Cloud Dr, Chestertown, MD 21620 - Photo 1

Sold

$339,900

103 Flying Cloud Dr Chestertown, MD 21620

Single Family
Closed

3
Beds
3
Total Baths
1,724
Sq. Ft.

Listed by American Premier Realty, LLC, Laura M Snyder
Sold by American Premier Realty, LLC, Priscilla J Anderson

108 Oak Leaf Drive, Chestertown, MD 21620 (MLS# MDKE2006224) is a Townhouse property that was sold at $296,500 on May 22, 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.

108 Oak Leaf Dr Chestertown, MD 21620