204 Rolling Road Chestertown, MD ^$ 370,000

204 Rolling Road

^$ 370,000

Back to search

204 Rolling Road

Chestertown, MD, 21620

^$ 370,000

Bedrooms3 Baths2.0 Sq 2,296

Monthly Estimate*

^$ 2,308

204 Rolling Road, Chestertown, MD 21620 - Image 1

204 Rolling Road, Chestertown, MD 21620 - Image 2

204 Rolling Road, Chestertown, MD 21620 - Image 3

204 Rolling Road, Chestertown, MD 21620 - Image 4

204 Rolling Road, Chestertown, MD 21620 - Image 5

204 Rolling Road, Chestertown, MD 21620 - Image 6

204 Rolling Road, Chestertown, MD 21620 - Image 7

204 Rolling Road, Chestertown, MD 21620 - Image 8

204 Rolling Road, Chestertown, MD 21620 - Image 9

204 Rolling Road, Chestertown, MD 21620 - Image 10

204 Rolling Road, Chestertown, MD 21620 - Image 11

204 Rolling Road, Chestertown, MD 21620 - Image 12

204 Rolling Road, Chestertown, MD 21620 - Image 13

204 Rolling Road, Chestertown, MD 21620 - Image 14

204 Rolling Road, Chestertown, MD 21620 - Image 15

204 Rolling Road, Chestertown, MD 21620 - Image 16

204 Rolling Road, Chestertown, MD 21620 - Image 17

204 Rolling Road, Chestertown, MD 21620 - Image 18

204 Rolling Road, Chestertown, MD 21620 - Image 19

204 Rolling Road, Chestertown, MD 21620 - Image 20

204 Rolling Road, Chestertown, MD 21620 - Image 21

204 Rolling Road, Chestertown, MD 21620 - Image 22

204 Rolling Road, Chestertown, MD 21620 - Image 23

204 Rolling Road, Chestertown, MD 21620 - Image 24

204 Rolling Road, Chestertown, MD 21620 - Image 25

204 Rolling Road, Chestertown, MD 21620 - Image 26

204 Rolling Road, Chestertown, MD 21620 - Image 27

204 Rolling Road, Chestertown, MD 21620 - Image 28

204 Rolling Road, Chestertown, MD 21620 - Image 29

204 Rolling Road, Chestertown, MD 21620 - Image 30

204 Rolling Road, Chestertown, MD 21620 - Image 31

204 Rolling Road, Chestertown, MD 21620 - Image 32

204 Rolling Road, Chestertown, MD 21620 - Image 33

204 Rolling Road, Chestertown, MD 21620 - Image 34

204 Rolling Road, Chestertown, MD 21620 - Image 35

204 Rolling Road, Chestertown, MD 21620 - Image 36

204 Rolling Road, Chestertown, MD 21620 - Image 37

204 Rolling Road, Chestertown, MD 21620 - Image 38

204 Rolling Road, Chestertown, MD 21620 - Image 39

204 Rolling Road, Chestertown, MD 21620 - Image 40

Single Family Home for sale in Chestertown, MD

for $370,000 with 3 bedrooms and 2 full baths. This 2,296 square foot home was built in 1975 on a lot size of 0.34.

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.

Single Family Active

Price

^$ 370,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 3,565

Style

Ranch/Rambler

Lot Size

0.34

Year Built

1975

Town/City

Chestertown

County/Region

Kent

MLS | Web ID

MDKE2005896

Features

General

Living Area 2296

Sewer Public Sewer

Heating Heat Pump(s)

Cooling Central A/C

Possession Settlement

Zoning R-2

Architectural Style Ranch/Rambler

Construction Materials Stick Built

School District KENT COUNTY PUBLIC SCHOOLS

Year Built 1975

Levels 2

Tax Year 2025

Ownership Fee Simple

Cool Fuel Electric

Municipality Chestertown

Accessibility Other

County KENT

New Construction N

Property Type Residential

HOA N

Subdivision Name COLLEGE HEIGHTS

Garage Y/N N

Water Access Y/N N

Other Structures Above Grade Below Grade

Full Baths 2

Status ACTIVE

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

City CHESTERTOWN

Senior Community Y/N N

Lot Size Units Square Feet

Lot Size Square Feet 14875.00

Tax Annual Amount 3565.0

Structure Type Detached

Condo/Coop Association Y/N N

Bathrooms Full Main Level 2

Bathrooms Count Main Level 2.00

Price Per Sq Ft Total AG 161.15

Vacation Rental Y/N N

Standard Status Active

Year Built Source Assessor

Legal Subdivision COLLEGE HEIGHTS

Interior

Heating Fuel Electric

Basement Partially Finished Poured Concrete

Total Fireplaces 1

Fireplace Features Wood

Hot Water Electric

Basement (Y/N) Y

Heating Y/N Y

Fireplace Y/N Y

Above Grade Finished Area 2296

Central Air Y/N Y

Total Bedrooms 3

Below Grade Finished Area 0

Main Level Bedrooms 3

Below Grade Finished Area Unit Type Square Feet

Below Grade Finished Area Source Assessor

Above Grade Finished Area Source Assessor

Above Grade Finished Area Unit Type Square Feet

Total Baths 2

Exterior

Pool No Pool

Water Source Public

Type of Parking Driveway

Foundation Details Permanent

Water View Y/N N

Lot Size Acres 0.34

Lot Size Source Assessor

Waterfront Y/N N

Land Assessed Value 91200.00

Navigable Water Y/N N

Water Oriented Y/N N

Internal Only

Street Number 1 204

* Excluded Features

List By

Coldwell Banker Chesapeake Real Estate Company

Broker

murphy@cbchesapeake.com

Affordability Calculator

$2,605

Per Month

Monthly Principal & Interest: $2,308
Monthly Property Taxes: $297
Monthly Home Insurance: --

Set your offer price

Down Payment

Loan Term

Interest Rate

Yearly Property Taxes

Yearly Home Insurance

Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

THE TIME TO SELL IS NOW! What's my home worth?

Nearby

Trends
Schools

Single family listings in Chestertown, MD

Average List Price ^$654,965

Percent of Sale Price 77%

About Chestertown, MD

5,312 Population

10% Since 2002

^$47,055 Median Income

32.86 Median Age

18% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

3535796 Elementary School

3533824 Middle School

Unknown High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
11/8/2025	$370,000		Listed Price

Map

More homes like this one

homes for you

See all

204 Rolling Road, Chestertown, MD, 21620 is a Single Family Home for sale at $370,000 with 2,296 sqft and a lot size of 0.34. 204 Rolling Road has 3 bedrooms, 2.0 baths, and was built in 1975. The property's zip code is 21620 which is in Chestertown, MD

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker Reciprocity^SM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

*Full Name

*Email

*Phone

I am interested in financing options

Get more info

By submitting the form, you agree that Weichert^® may contact you via phone or text about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our privacy policy.

Get more info

Looking for an Associate?

Already Working with an Associate?

204 Rolling Road

Single Family Home for sale in Chestertown, MD

Affordability Calculator

Map

More homes like this one

Get more info about this home