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-familyProperty Type
1975Year Built
0.34 acresLot Size
$148Price/Sq.Ft.
3 spacesParking
Listed by Murphy ONeill• Coldwell Banker Chesapeake Real Estate Company
•410-778-0330 (broker)
Bought with Hayley Norris• Select Land & Homes, LLC
Est. $2,868 per month, based on comparable rentals
Sale and tax history for 204 Rolling Rd
Sale History
Tax History
Date
Event
Price
BRIGHT MLS #MDKE2005896
Mar 19, 2026
Sold
$340,000
$148/sq ft
Jan 18, 2026
Contingent
—
Jan 5, 2026
Price Changed
$345,000
$150/sq ft
Nov 22, 2025
Listed
$370,000
$161/sq ft
Nov 7, 2025
Coming Soon
$370,000
$161/sq ft
Public Records
Aug 23, 1977
Sold
$33,500
$15/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$3,831 (+7.5%)
2025
$3,565 (+6.8%)
2024
$3,338 (+7.3%)
$91,200 + $136,300
$227,500
2023
$3,110 (+8.6%)
2022
$2,864 (+1.3%)
2021
$2,828 (+0.6%)
$91,200 + $92,700
$183,900
2020
$2,810 (+2.9%)
2019
$2,731
2018
$2,731 (+4.1%)
2017
$2,625 (+0.7%)
2015
$2,606 (+85.5%)
$101,200 + $72,100
$173,300
2014
$1,405 (−50.0%)
$101,200 + $85,600
$186,800
2013
$2,809
2012
$2,809 (−21.1%)
2011
$3,561 (+163.5%)
2010
$1,351 (−47.3%)
2009
$2,564
Public record
Beds
—
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
0.34 Acres
Year renovated
—
Sq. Ft.
2,296
Year built
1975
Style
Single Family Residential
County
Kent County
APN
04 003756
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 3, 2026.
Property details
Parking
Parking Information
# of Total Garage and Parking Spaces: 3
Driveway - # of Spaces: 3
Driveway
Interior
Bedroom Information
# of Bedrooms On Main Level: 3
Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2
Interior Information
Living Area Sq.Ft. Source: Assessor
Fireplace Information
Has Fireplace
# of Fireplaces: 1
Wood
Basement Information
Basement: Yes
Partially Finished, Poured Concrete
Exterior
Property Information
Total Below Grade Sq. Ft.: 1040
Accessibility Features: Other
Improvement Assessed Value: $136,300
Ownership Interest: Fee Simple
Year Built Source: Assessor
Building Information
Construction Materials: Stick Built
Foundation Details: Permanent
Other Structures: Above Grade, Below Grade
Structure Type: Detached
Lot Information
Tidal Water: No
Land Information
Land Assessed Value: $91,200
Above Grade Information
Finished Sq.Ft.: 2,296
Finished Sq.Ft. Source: Assessor
Below Grade Information
Unfinished Sq.Ft.: 1,040
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor
Financial
Tax Information
City/Town Tax: $985
County Tax: $2,580
Tax Assessed Value: $227,500
Tax Year: 2025
Tax Annual Amount: $3,565
Assessments Information
Year Assessed: 2025
Utilities
Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public
Location
School Information
School District Name: KENT COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent
Location Information
In City Limits
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.
Municipality: Chestertown
Public facts
Beds: —
Baths: 2.0
Sq. Ft.: 2,296
Stories: 1.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1975
Year Renovated: —
County: Kent County
APN: 04 003756
Home facts updated by county records on Aug 3, 2026
Around this home
Schools
H. H. Garnett Elementary School
Public PreK-5 • Assigned • 0.7mi
6/10
Kent County Middle School
Public 6-8 • Assigned • 0.2mi
3/10
Kent County High School
Public 9-12 • Assigned • 4.7mi
5/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
8/10 Heat Factor
7 days above 104° expected this year, 15 days in 30 years
6/10 Wind Factor
60% chance of strong winds in next 30 years
6/10 Air Factor
9 unhealthy days expected this year, 13 days in 30 years
Provided by First Street
Historical weather
Chestertown, MD • 21620
Average low and high temperatures (°F)
37
23
41
28
60
39
67
47
72
56
83
65
87
71
79
63
77
61
68
49
58
40
43
29
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 9.2 hours in
June and 4.7 hours in December, which is comparable to the
U.S. average for solar exposure.
9.2 hrs
4.7 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$384,000 – $464,000
Sell confidently with a local market expert in Chestertown.