204 Rolling Rd

Chestertown, MD 21620

$370,000
Price
3
Beds
2,296 Sq. Ft.
$161 / Sq. Ft.
2,296
Sq. Ft.
$161
per Sq. Ft.
a view of a house with a yard
an aerial view of residential building with parking space
a kitchen with a sink a counter top space and stainless steel appliances
a kitchen that has a lot of cabinets and wooden floor
a dining room with furniture and window
a living room with furniture and a flat screen tv
a living room with furniture and large windows
a spacious bedroom with a bed a table and painting on the wall
a spacious bedroom with a bed and a chandelier
a bathroom with a toilet a sink and mirror
a view of walk in closet with clothes and shoes
a living room with furniture and large windows
a living room with furniture a large window with kitchen view
a utility room with dryer and washer
a bedroom with a bed rug and couch
a bedroom with furniture and a chandelier
a bathroom with a granite countertop sink a toilet and a mirror
a living room with furniture and a window
a bedroom with a bed and a table in it
a front view of house with yard and trees in the background
a front view of a house with a yard
a view of a yard with a house and large trees
a view of a house with a yard
a front view of a house with a big yard
a view of a garage with storage
a view of a garage with storage
a view of a city
a view of ocean and city
an aerial view of a city with lots of residential buildings ocean and mountain view in back
front view of a house with a yard
a view of a house with snow on the side of it

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...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.
  1. Listed by Michael ONeill • Coldwell Banker Chesapeake Real Estate Company
    P: (443)-480-4275 murphy@cbchesapeake.com

Property Details for 204 Rolling Road

Tax ID Number
1504003756
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Ranch/Rambler
Levels/Stories
2
Waterfront
No
LISTING UPDATED: 12/10/2025 10:01 PM

Property Details for 204 Rolling Road

StatusActive
MLS #MDKE2005896
Days on Market32
Taxes$3,565 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1975
Lot Size0.34 AC / 14,875 SF
CountyKent County

Location

Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company
Add your commute

Building Information for 204 Rolling Road

Stories2Year Built1975Building Size-Lot Size0.34 AC / 14,875 SF

Payment Calculator

$2,125 per month

30 year fixed, 6.28% Interest

Principal and Interest

$1,828

Property Taxes

$297

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 204 Rolling Road

Location
Location
  • In City Limits: Yes
  • School District Name: KENT COUNTY PUBLIC SCHOOLS
  • School District County ID: 121139164602
  • SchoolDistrictSource: Listing Agent
  • County: KENT
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: No
  • Navigable Water: No
  • Tidal Water: No
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Senior Community: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $227,500
  • Year Assessed: 2025
  • County Tax: $2,580
  • Improvement Assessed Value: $136,300
  • City Town Tax: $985
  • Land Assessed Value: $91,200
  • Clean Green Assessed: No
  • Land Use Code: R
  • Zoning: R-2
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 3
  • # Bathrooms Count Main Level: 2
  • # Bathrooms Full Main Level: 2
Rooms
  • Stories: Main
Building Info
Building Info
  • Total Finished SQFT: 2,296.00
  • Total Finished SQFT Source: Assessor
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Parcel ID: 4504483
Parking
Parking
  • Type Of Parking: Driveway
  • Driveway - # of Spaces: 3
Interior Features
Interior Features
  • Fireplace: Yes
  • Fireplaces Count: 1
  • Fireplace Features: Wood
  • Accessibility Features: Other
Exterior Features
Exterior Features
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Public
  • Sewer Septic: Public Sewer
Confidential Data
Listing Office
  • List Agent AOR: Mid-Shore Board of REALTORS

Property History for 204 Rolling Road

DateEvent & SourcePriceAppreciation
Nov 22, 2025

Listed (Active)

BRIGHT #MDKE2005896

$370,000—
DateEvent & SourcePrice
11/22/2025

Listed (Active)

BRIGHT #MDKE2005896

$370,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 204 Rolling Road

Taxable ValueLand$91,200Additions$136,300Total$227,500
Tax Record2025$3,565 ($297 / month)
Home Facts
Beds0Baths2Total Finished SqFt2,296 SqFtAbove Grade Finished SqFt2,296 SqFtStories1Lot Size14,875 SqFtStyleSingle Family ResidenceYear Built1975ZoningR-2CountyKENTAPN04-003756Fireplace TypeHas Fireplace

Schools near 204 Rolling Road

This home is within Kent County Public Schools.
Rating
School
Type
Grades
Distance
H. H. Garnett Elementary School
Public - PK to 5
Kent County Middle School
Public - 6 to 8
Kent County High School
Public - 9 to 12
Worton Elementary School
Public - PK to 5
Rating
School
Distance
H. H. Garnett Elementary School
PublicPK to 5

Kent County Middle School
Public6 to 8

Kent County High School
Public9 to 12

Worton Elementary School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 204 Rolling Road, Chestertown, MD 21620

204 Rolling Road is a single family home for sale in Chestertown, MD 21620. This property was listed for sale on November 22, 2025 by Coldwell Banker Chesapeake Real Estate Company, it's currently listed at $370,000. This listing's school district is Kent County Public Schools. Nearby schools include H. H. Garnett Elementary School, Kent County Middle School and Kent County High School. 204 Rolling Road is a 3-bed, 2-bath, 2,296 sqft single family home built in 1975.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company

© 2025 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 12/10/2025 10:01 PM