204 Rolling Rd, Chestertown, MD 21620
Property image
Property image
SOLD
MAR 19, 2026

$340,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,296 sqft (on 0.34 acres)

204 Rolling Rd, Chestertown, MD 21620

Est. Refi. Payment $2,137/mo*
Refinance Your Home
Currently Off Market - Sold Mar 19, 2026 for $340,000 (1% below list price)

Home Value

Trulia Estimate
$341K
Since last month
$100 (0%)
Since last year
Increased$2K (+0.7%)
Since last sale
$100 (0%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +61% in the last 10 years
MonthEstimated value
2026
September 2026$340K
August 2026$340K
July 2026$344K
June 2026$345K
May 2026$342K
April 2026$340K
March 2026$340K
February 2026$331K
January 2026$329K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
224 Valley Rd, Chestertown, MD
0.11
Single-Family Home
$455,000
10/21/25
3
2
1,886
205 Pine St, Chestertown, MD
0.24
Single-Family Home
$296,337
09/30/25
3
1.5
2,212
411 Greenwood Ave, Chestertown, MD
0.08
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
303 Cedar St, Chestertown, MD
0.16
Single-Family Home
$325,000
01/30/26
3
2.5
2,577
303 E Campus Ave, Chestertown, MD
0.32
Single-Family Home
$364,000
01/16/26
3
2
1,532
109 Cedar St, Chestertown, MD
0.17
Single-Family Home
$318,000
08/14/26
3
2
1,397
206 Barroll Dr, Chestertown, MD
0.37
Single-Family Home
$438,000
09/30/25
3
2
1,820
101 Birch Run Rd, Chestertown, MD
0.33
Single-Family Home
$475,000
12/11/25
3
2
1,961
201 Birch Run Rd, Chestertown, MD
0.32
Single-Family Home
$430,000
05/29/26
3
2
1,588

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
202 Glen St, Chestertown, MD 21620
0.08
$291,500
3
1
1,252
Off Market
411 Greenwood Ave, Chestertown, MD 21620
0.08
$415,000
3
2.5
1,676
Recently Sold
207 Glen St, Chestertown, MD 21620
0.07
$410,300
4
2
2,236
Off Market
114 School Rd, Chestertown, MD 21620
0.09
$292,200
3
1.5
1,102
Off Market
224 Valley Rd, Chestertown, MD 21620
0.11
$460,700
3
2
1,886
Off Market
303 Cedar St, Chestertown, MD 21620
0.16
$325,000
3
2.5
2,577
Recently Sold
109 Cedar St, Chestertown, MD 21620
0.17
$318,000
3
2
1,397
Recently Sold
101 School Rd, Chestertown, MD 21620
0.18
$364,600
3
1.5
1,424
Off Market
206 Valley Rd, Chestertown, MD 21620
0.20
$590,000
4
2
2,869
Recently Sold
111 Elm St, Chestertown, MD 21620
0.21
$249,400
3
1
1,275
Off Market
118 Elm St, Chestertown, MD 21620
0.22
$445,900
3
2.5
2,008
Off Market

Local Information

  • Map ViewExplore the area around 204 Rolling Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1975
0.34 acre lot
2,296 sqft
$148/sqft
3 Open Spaces

About this House

What's unique:Raised bed garden
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.
204 Rolling Rd, Chestertown, MD 21620 is a 3 bedroom, 2 bathroom, 2,296 sqft single-family home built in 1975. It last sold for $340,000 on Mar 19, 2026 (1% below the $345,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $340,500, with a rent estimate of $2,235/month.
Last check for updates: about 3 hours ago
Listed by Murphy ONeill, (443) 480-4275
Coldwell Banker Chesapeake Real Estate Company
Bought with: Hayley Norris, (443) 480-4157, Select Land & Homes, LLC
Source: Bright MLS, MLS#MDKE2005896

Home Details for 204 Rolling Rd

Interior Features

Interior Details
Basement: Partially Finished,ConcreteNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 2296 Square Feet
Appliances & Utilities
Appliances: Electric Water Heater
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood BurningHas a Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: Other
View
No View

Exterior Features

Exterior Home Features
Other Structures: Above Grade, Below GradeFoundation: PermanentNo Private Pool
Parking & Garage
Open Parking Spaces: 3No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 3Parking: Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2296 Square Feet

Property Information

Year Built
Year Built: 1975
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building
Construction Materials: Stick BuiltNot a New Construction
Property Information
Parcel Number: 1504003756

Price & Status

Price
List Price: $345,000Price Per Sqft: $148/sqft
Status Change & Dates
Off Market Date: Thu Mar 19 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: CHESTERTOWNCommunity: College Heights
School Information
Elementary School District: Kent County Public SchoolsJr High / Middle School District: Kent County Public SchoolsHigh School District: Kent County Public Schools

Building

Building Area
Building Area: 3336 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.34 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDKE2005896Municipality: ChestertownAbove Grade Unfinished Area: 2296

Additional Information

Source Internet Entire Listing Display: Y

Price and Tax history

DateEventPrice
Mar 19, 2026
Source: Bright MLS #MDKE2005896
Sold
$340,000
Jan 18, 2026
Source: Bright MLS #MDKE2005896
Contingent
$345,000
Jan 5, 2026
Source: Bright MLS #MDKE2005896
PriceChange
$345,000
Price decreased by 7%
Nov 22, 2025
Source: Bright MLS #MDKE2005896
Listed For Sale
$370,000

Market trends in Chestertown

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
5MoM

Around this home

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 204 Rolling Rd

  • What is 204 Rolling Rd estimated to be worth?
    Trulia's estimated value for 204 Rolling Rd in Chestertown, MD is $340,500.
  • What is the price history for 204 Rolling Rd?
    204 Rolling Rd in Chestertown, MD last sold for $340,000 in March 2026.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • Does 204 Rolling Rd have air conditioning?
    Yes, 204 Rolling Rd in Chestertown, MD has air conditioning.
  • How big is the lot at 204 Rolling Rd?
    The lot at 204 Rolling Rd in Chestertown, MD is about 0.34 acres (14,875 sq ft).

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