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.
For sale
$370,000
204 Rolling Rd, Chestertown, MD 21620
3beds
2,296sqft
Est.:
Single Family Residence
Built in 1975
0.34 Acres Lot
$-- Zestimate®
$161/sqft
$-- HOA
What's special
Raised bed garden
- 23 days |
- 712 |
- 31 |
Likely to sell faster than
Zillow last checked: 8 hours ago
Listing updated: December 10, 2025 at 02:01pm
Listed by:
Murphy ONeill 443-480-4275,
Coldwell Banker Chesapeake Real Estate Company 410-778-0330
Source: Bright MLS,MLS#: MDKE2005896
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
- Main level bathrooms: 2
- Main level bedrooms: 3
Basement
- Area: 1040
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Electric Water Heater
Features
- Basement: Partially Finished,Concrete
- Number of fireplaces: 1
- Fireplace features: Wood Burning
Interior area
- Total structure area: 3,336
- Total interior livable area: 2,296 sqft
- Finished area above ground: 2,296
- Finished area below ground: 0
Property
Parking
- Total spaces: 3
- Parking features: Driveway
- Uncovered spaces: 3
Accessibility
- Accessibility features: Other
Features
- Levels: Two
- Stories: 2
- Pool features: None
Lot
- Size: 0.34 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1504003756
- Zoning: R-2
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Stick Built
- Foundation: Permanent
Condition
- New construction: No
- Year built: 1975
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Subdivision: College Heights
HOA
- Has HOA: No
Location
- Region: Chestertown
- Municipality: Chestertown
Financial & listing details
- Price per square foot: $161/sqft
- Tax assessed value: $227,500
- Annual tax amount: $3,565
- Date on market: 11/22/2025
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/22/2025 | Listed for sale | $370,000+1004.5%$161/sqft |
Source:  Bright MLS #MDKE2005896 Report a problem | ||
| 8/23/1977 | Sold | $33,500$15/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $227,500 +6.8% |
| 2024 | $3,338 +7.3% | $212,967 +7.3% |
| 2023 | $3,110 +8.6% | $198,433 +7.9% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$2,211/mo
Principal & interest
$1791
Property taxes
$290
Home insurance
$130
Climate risks
Neighborhood: 21620
Nearby schools
GreatSchools rating
- 7/10H. H. Garnett Elementary SchoolGrades: PK-5Distance: 0.7 mi
- 2/10Kent County Middle SchoolGrades: 6-8Distance: 0.2 mi
- 5/10Kent County High SchoolGrades: 9-12Distance: 4.7 mi
Schools provided by the listing agent
- District: Kent County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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