204 Rolling Road, Chestertown, MD 21620 - Photo 1

1/1

$340,000

Sold
Closed
Single Family
3,336 Sq. Ft.
Updated 10 days ago

1/1

Property Description

Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on the main floor and updated kitchen with tons of counter space were other valuable design updates. The basement provides ample partially finished storage space in a completely dry environment due to serious structural improvements, sump pump and french drain system. Bring your hobby down there or your trusty work bench. The roof, HVAC, and hot water heater are all less than 10 years old. The front yard provides a polished experience with tasteful landscaping. The rear yard is quite large for a house in town and includes a raised bed garden and tidy shed. Experience the relaxed lifestyle of Chestertown with the Historic District's shops, Washington College, and the Margo Bailey park just a short walk away.

Full Property Details

Full Property Details for 204 Rolling Rd

General

Sold For: $340,000
Taxes: $3,565 (2025)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDKE2005896
Added to Site: 128 day(s) ago

Interior

Fireplace: Yes
Number of Fireplaces: 1
Fireplace(s): Wood

Parking

Total Spaces: 3
Parking Type: Driveway

Location

Municipality: Chestertown
County: KENT
Subdivision: COLLEGE HEIGHTS
Driving Directions: From Washington Avenue turn onto Greenwood Avenue, This is opposite the entrance to Washington College. When you get to the end of Greenwood Avenue, take a right on Rolling Road then the house will be on your right.
City Limits: Yes

School Information

School District: Kent County Public Schools

Heating & Cooling

Central air: Yes
Cooling Type: Central A/C
Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric
Water Heater: Electric

Utilities

Sewer: Public Sewer
Water: Public

Structural Information

Architectural Style: Ranch/Rambler
Structure Type: Detached
Construction: Stick Built
Basement: Yes
Basement Desc.: Partially Finished, Poured Concrete
Foundation: Permanent
Stories Description: Main
Square Feet: 3,336
Sq. Ft. Source: Assessor
Living Area: 2,296 Sq. Ft.
Finished Above Grnd: 2,296 Sq. Ft.
Year Built: 1975
Year Built Source: Assessor

Lot Features

Lot Size (Acres): 0.34
Lot Size (Sq. Ft.): 14,875
Lot Size Source: Assessor
Zoning: R-2

Financial Considerations

Price Per Sq. Ft.: $150.26
Assessment Year: 2025
City/TownTax: $985
City/TownTax Freq: Annually
County Tax: $2,580
County Tax Freq: Annually
Tax w/Assessment: $227,500
Tax Amount: $3,565
Tax Year: 2025
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 2296

Disclosures and Reports

Ownership: Fee Simple

Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill
Sold by Select Land & Homes, LLC, Hayley A Norris

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Listing agent

— 204 Rolling Rd —

Michael ONeill

Coldwell Banker Chesapeake Real Estate Company

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Schools

Schools serving 204 Rolling Rd

School District:Kent County Public Schools

Name	Grades	Distance
Kent County Middle School 402 East Campus Avenue, Chestertown, MD 21620	6-8	0.2 mi
Kent County High School 25301 Lambs Meadow Road, Worton, MD 21678	9-12	4.7 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 204 Rolling Rd

Date

Details

Price

Change

Source

3/19/2026

Sold

$340,000

-1.45%

MLS

1/05/2026

Price Reduced

$345,000

-6.76%

MLS

11/22/2025

Listed

$370,000

—

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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Open House

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Single Family
Active
Updated 4 days ago

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

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Active
Updated 1 day ago

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Beds
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Total Baths
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Sq. Ft.

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Active
Updated 1 day ago

6
Beds
2
Total Baths
3,270
Sq. Ft.

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Just Listed

$1,100,000

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Single Family
Active
Updated 3 days ago

3
Beds
3
Total Baths
2,338
Sq. Ft.

Listed by Gunther-McClary Real Estate, Julia Hilfiker and Gunther-McClary Real Estate, Lynn M Hilfiker

Lambs Meadow Rd, Worton, MD 21678 - Photo 1

Price Reduced

-$15,001 (-20%)

$59,999

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Lots/Land
Active
Updated 5 days ago

1.09
Acres

Listed by EXP Realty, LLC, Micheal A Vakas

25044 Travis Trail, Worton, MD 21678 - Photo 1

Price Reduced

-$5,000 (-2.08%)

$235,000

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Single Family
Active
Updated 3 days ago

3
Beds
2
Total Baths
1,278
Sq. Ft.

Listed by Coldwell Banker Chesapeake Real Estate Company, Jyaire T McCall

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Price Reduced

-$15,000 (-3.85%)

$374,900

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Single Family
Active
Updated 5 days ago

3
Beds
2
Total Baths
2,114
Sq. Ft.

Listed by Redfin Corp, Jennifer L. Pogoda

118 Dabbling Ct, Church Hill, MD 21623 - Photo 1

118 Dabbling Ct Church Hill, MD 21623

Single Family
Active
Updated 4 days ago

6
Beds
4
Total Baths
5,781
Sq. Ft.

Listed by Chaney Homes, LLC, Jennifer S Chaney

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Sold

$325,000

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Single Family
Closed

3
Beds
3
Total Baths
2,577
Sq. Ft.

Listed by Select Land & Homes, LLC, Hayley A Norris and Select Land & Homes, LLC, Charles Coates
Sold by Cross Street Realtors LLC, Casey Scattergood

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Sold

$364,000

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Single Family
Closed

3
Beds
2
Total Baths
1,532
Sq. Ft.

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Sold

$335,000

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Single Family
Closed

3
Beds
3
Total Baths
1,856
Sq. Ft.

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Sold by Coldwell Banker Chesapeake Real Estate Company, Terri L Kulp

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Sold

$364,900

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Single Family
Closed

4
Beds
3
Total Baths
1,936
Sq. Ft.

Listed by Cross Street Realtors LLC, Casey Scattergood
Sold by Jenn Angel-Fuhlman

204 Rolling Road, Chestertown, MD 21620 (MLS# MDKE2005896) is a Single Family property that was sold at $340,000 on March 19, 2026. Want to learn more about 204 Rolling Road? Do you have questions about finding other Single Family real estate for sale in Chestertown? You can browse all Chestertown real estate or contact a Coldwell Banker agent to request more information.

204 Rolling Rd Chestertown, MD 21620