202 Rolling Rd, Chestertown, MD 21620
OFF MARKET

$335,600

Trulia Estimate
  • Studio
  • 2 Baths
  • 1,806 sqft (on 0.30 acres)

202 Rolling Rd, Chestertown, MD 21620

Est. Refi. Payment $2,082/mo*
Refinance Your Home
Currently Off Market - Sold Oct 29, 2001 for $120,100

Home Value

Trulia Estimate
$336K
Since last month
Decreased$8K (-2.4%)
Since last year
Decreased$3K (-0.9%)
Since last sale
Increased$214K (+178.2%)
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 +44% in the last 10 years
MonthEstimated value
2026
September 2026$334K
August 2026$336K
July 2026$342K
June 2026$342K
May 2026$343K
April 2026$336K
March 2026$334K
February 2026$332K
January 2026$338K
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
204 Rolling Rd, Chestertown, MD
0.02
Single-Family Home
$340,000
03/19/26
3
2
2,296
224 Valley Rd, Chestertown, MD
0.12
Single-Family Home
$455,000
10/21/25
3
2
1,886
205 Pine St, Chestertown, MD
0.23
Single-Family Home
$296,337
09/30/25
3
1.5
2,212
411 Greenwood Ave, Chestertown, MD
0.07
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
109 Cedar St, Chestertown, MD
0.16
Single-Family Home
$318,000
08/14/26
3
2
1,397
304 Hadaway Dr, Chestertown, MD
0.25
Single-Family Home
$300,000
07/30/26
4
2
1,325
303 E Campus Ave, Chestertown, MD
0.34
Single-Family Home
$364,000
01/16/26
3
2
1,532
202 Pine St, Chestertown, MD
0.27
Single-Family Home
$222,000
09/08/26
3
1
1,341
206 Barroll Dr, Chestertown, MD
0.39
Single-Family Home
$438,000
09/30/25
3
2
1,820
112 Elm St, Chestertown, MD
0.23
Single-Family Home
$249,000
06/12/26
3
1
1,356

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
204 Rolling Rd, Chestertown, MD 21620
0.02
$340,000
3
2
2,296
Recently Sold
202 Glen St, Chestertown, MD 21620
0.07
$290,500
3
1
1,252
Off Market
411 Greenwood Ave, Chestertown, MD 21620
0.07
$415,000
3
2.5
1,676
Recently Sold
207 Glen St, Chestertown, MD 21620
0.08
$410,300
4
2
2,236
Off Market
114 School Rd, Chestertown, MD 21620
0.10
$290,400
3
1.5
1,102
Off Market
224 Valley Rd, Chestertown, MD 21620
0.12
$457,400
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
0.16
$318,000
3
2
1,397
Recently Sold
101 School Rd, Chestertown, MD 21620
0.19
$364,200
3
1.5
1,424
Off Market
206 Valley Rd, Chestertown, MD 21620
0.21
$590,000
4
2
2,869
Recently Sold
111 Elm St, Chestertown, MD 21620
0.20
$242,800
3
1
1,275
Off Market
118 Elm St, Chestertown, MD 21620
0.21
$451,500
3
2.5
2,008
Off Market

Local Information

  • Map ViewExplore the area around 202 Rolling Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1970
0.3 acre lot
1,806 sqft
$186/sqft
Garage

About this House

This single-family home is located at 202 Rolling Rd, Chestertown, MD. 202 Rolling Rd is in Chestertown, MD and in ZIP code 21620. This property has 2 bathrooms and approximately 1,806 sqft of floor space. This property has a lot size of 0.30 acres and was built in 1970.
202 Rolling Rd, Chestertown, MD 21620 is a studio, 2 bathroom, 1,806 sqft single-family home built in 1970. It last sold for $120,100 on Oct 29, 2001. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $335,600, with a rent estimate of $1,524/month.

Home Details for 202 Rolling Rd

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1970
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.30 acres

Price and Tax history

DateEventPrice
Oct 29, 2001
Source: N/A
Sold
$120,100

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

LGBTQ Local Legal Protections

Frequently asked questions about 202 Rolling Rd

  • What is 202 Rolling Rd estimated to be worth?
    Trulia's estimated value for 202 Rolling Rd in Chestertown, MD is $335,600.
  • What is the price history for 202 Rolling Rd?
    202 Rolling Rd in Chestertown, MD last sold for $120,100 in October 2001.
  • 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.
  • How big is the lot at 202 Rolling Rd?
    The lot at 202 Rolling Rd in Chestertown, MD is about 0.30 acres (13,202 sq ft).
  • Does 202 Rolling Rd have a garage?
    Yes, 202 Rolling Rd in Chestertown, MD has a garage.

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