Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$345,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 3,336 Sq. Ft.
  • Updated 8 days ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 1/17 11:00 AM - 1:00 PM

204 Rolling Road,Chestertown, MD 21620

204 Rolling RoadChestertownMD21620

Get directions
See This Home
Save This Home
See This Home
Save This Home
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 for 204 Rolling Rd

General

  • Price: $345,000
  • Taxes: $3,565 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDKE2005896
  • Updated: 1/5/2026
  • Added to Site: 54 day(s) ago

Interior

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

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Main Floor Baths: 2
  • Main - Full Baths: 2

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Main & Up: 3

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
  • Tax Total Finished Sq. Ft.: 2296

Disclosures and Reports

  • Ownership: Fee Simple

Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 204 Rolling Rd —

  • Michael ONeill

    Coldwell Banker Chesapeake Real Estate Company

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 204 Rolling Rd

School District:Kent County Public Schools
NameGradesDistance
Kent County Middle School
402 East Campus Avenue, Chestertown, MD 21620
6-80.2 mi
Kent County High School
25301 Lambs Meadow Road, Worton, MD 21678
9-124.7 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 204 Rolling Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/05/2026
Price Reduced
$345,000
-6.76%
MLS
11/22/2025
Listed
$370,000
—
MLS
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 204 Rolling Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,565
7%
$227,500
7%
2024
$3,338
17%
$212,967
7%
2023
$2,864
—
$198,433
8%
2022
$2,864
2%
$183,900
1%
2020
$2,810
—
$181,600
1%
2021
$2,810
3%
$179,300
2%
2019
$2,731
4%
$175,767
1%
2018
$2,625
1%
$174,533
1%
2017
$2,606
307%
$173,300
—
2016
$641
-75%
$173,300
—
2015
$2,606
85%
$173,300
-7%
2014
$1,405
—
$186,800
—
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.

Estimate the Cost for 204 Rolling Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

Similar Properties near 204 Rolling Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

109 Wilton Rd, Chestertown, MD 21620 - Photo 1
$344,900

109 Wilton Rd  Chestertown, MD 21620

  • Single Family
  • Active
  • 3
    Beds
  • 2
    Total Baths
  • 1,392
    Sq. Ft.
Listed by Chesapeake Real Estate Associates, LLC, Amy L Larrauri
111 Cemetery Ln, Church Hill, MD 21623 - Photo 1
$344,500

111 Cemetery Ln  Church Hill, MD 21623

  • Single Family
  • Active
  • 3
    Beds
  • 1
    Total Bath
  • 1,449
    Sq. Ft.
Listed by Clark & Co Realty, LLC, Karen T Clark
23110 Old Fairlee Rd, Chestertown, MD 21620 - Photo 1
$349,900

23110 Old Fairlee Rd  Chestertown, MD 21620

  • Single Family
  • Active
  • Updated 8 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,805
    Sq. Ft.
Listed by Real Broker LLC, Thomas P Huston
121 Primrose Rd, Chestertown, MD 21620 - Photo 1
$350,000
Open House

121 Primrose Rd  Chestertown, MD 21620

  • Single Family
  • Active
  • Updated 9 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,871
    Sq. Ft.
Listed by Coldwell Banker Chesapeake Real Estate Company, William Sutton and Coldwell Banker Chesapeake Real Estate Company, Lacey R Sutton

Just Listed near 204 Rolling Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

10971 Bottom Rd, Worton, MD 21678 - Photo 1 Just Listed
$275,000

10971 Bottom Rd  Worton, MD 21678

  • Single Family
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 720
    Sq. Ft.
Listed by Keller Williams Select Realtors of Annapolis, Andrew F Batch Jr.
11047 Bottom Rd, Worton, MD 21678 - Photo 1 Just Listed
$315,000

11047 Bottom Rd  Worton, MD 21678

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,200
    Sq. Ft.
Listed by Taylor Properties, Jeff Guthrie
112 Browning Ln, Centreville, MD 21617 - Photo 1 Just Listed
$770,000

112 Browning Ln  Centreville, MD 21617

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 4
    Total Baths
  • 4,089
    Sq. Ft.
Listed by Coldwell Banker Chesapeake Real Estate Company, Ralph Wesley Russum and Coldwell Banker Chesapeake Real Estate Company, Kathryn P Moore
319 Red Lion Branch Rd, Millington, MD 21651 - Photo 1 Just Listed
$315,000

319 Red Lion Branch Rd  Millington, MD 21651

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,512
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Barbara M Wallace

Price Reduced near 204 Rolling Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

115 Cemetery Ln, Church Hill, MD 21623 - Photo 1 Price Reduced
-$29,100 (-6.78%)
$399,900

115 Cemetery Ln  Church Hill, MD 21623

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,114
    Sq. Ft.
Listed by Houwzer, LLC, Matthew Tyler Kalogeras
202 Church Street N, Sudlersville, MD 21668 - Photo 1 Price Reduced
-$19,100 (-8.72%)
$199,900

202 Church Street N  Sudlersville, MD 21668

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 3,336
    Sq. Ft.
Listed by RE/MAX Chesapeake, Brittany Fox and RE/MAX Chesapeake, Travis W Myers
119 Wye Knot Rd, Queenstown, MD 21658 - Photo 1 Price Reduced
-$31,000 (-4.77%)
$619,000

119 Wye Knot Rd  Queenstown, MD 21658

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,028
    Sq. Ft.
Listed by Benson & Mangold, LLC, Kimberly J Crouch
303 Purple Pl, Edgewood, MD 21040 - Photo 1 Price Reduced
-$9,000 (-2.37%)
$369,990

303 Purple Pl  Edgewood, MD 21040

  • Townhouse
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,440
    Sq. Ft.
Listed by Builder Solutions Realty, Terri E Hill

Recent Sales near 204 Rolling Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

205 Pine St, Chestertown, MD 21620 - Photo 1 Sold
$296,337

205 Pine St  Chestertown, MD 21620

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,576
    Sq. Ft.
Listed by Davis Real Estate, Inc., Robert L Davis Jr.
Sold by Doug Ashley Realtors, LLC, Retha J Arrabal
110 Flying Cloud Ct, Chestertown, MD 21620 - Photo 1 Sold
$335,000

110 Flying Cloud Ct  Chestertown, MD 21620

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,856
    Sq. Ft.
Listed by Berkshire Hathaway HomeServices Homesale Realty, Sandy Savani
Sold by Coldwell Banker Chesapeake Real Estate Company, Terri L Kulp
206 Silver Heel Dr, Chestertown, MD 21620 - Photo 1 Sold
$375,000

206 Silver Heel Dr  Chestertown, MD 21620

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 2,302
    Sq. Ft.
Listed by Samson Properties, Thomas Bennett and Samson Properties, Victoria W. King
Sold by RE/MAX Executive, Ralph S. Kennedy
517 High St, Chestertown, MD 21620 - Photo 1 Sold
$361,500

517 High St  Chestertown, MD 21620

  • Single Family
  • Closed
  • 1,728
    Sq. Ft.
Listed by L. C. Parker Real Estate, Kristie R Midash
Sold by Select Land & Homes, LLC, Hayley A Norris

204 Rolling Road, Chestertown, MD 21620 (MLS# MDKE2005896) is a Single Family property with 3 bedrooms and 2 full bathrooms. 204 Rolling Road is currently listed for $345,000 and was received on November 22, 2025. 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.

Tour this property