209 Rolling Rd, Chestertown, MD 21620
OFF MARKET

$251,000

Trulia Estimate
  • Studio
  • 1 Bath
  • 1,120 sqft (on 0.25 acres)

209 Rolling Rd, Chestertown, MD 21620

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Home Value

Trulia Estimate
$251K
Since last month
Decreased$7K (-2.6%)
Since last year
Decreased$1K (-0.5%)
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 +74% in the last 10 years
MonthEstimated value
2026
August 2026$250K
August 2026$250K
July 2026$257K
June 2026$259K
May 2026$253K
April 2026$243K
March 2026$249K
February 2026$241K
January 2026$246K
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
112 Elm St, Chestertown, MD
0.31
Single-Family Home
$249,000
06/12/26
3
1
1,356
111 Pine St, Chestertown, MD
0.34
Single-Family Home
$347,000
05/05/26
5
1
1,645
202 Valley Rd, Chestertown, MD
0.29
Single-Family Home
$325,000
06/17/26
3
1
1,427
108 Pine St, Chestertown, MD
0.39
Single-Family Home
$85,000
06/30/26
3
1
910
204 Rolling Rd, Chestertown, MD
0.07
Single-Family Home
$340,000
03/19/26
3
2
2,296
411 Greenwood Ave, Chestertown, MD
0.15
Single-Family Home
$415,000
01/07/26
3
2.5
1,676
224 Valley Rd, Chestertown, MD
0.15
Single-Family Home
$455,000
10/21/25
3
2
1,886
109 Cedar St, Chestertown, MD
0.24
Single-Family Home
$318,000
08/14/26
3
2
1,397
303 E Campus Ave, Chestertown, MD
0.31
Single-Family Home
$364,000
01/16/26
3
2
1,532
201 Birch Run Rd, Chestertown, MD
0.26
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
204 Rolling Rd, Chestertown, MD 21620
0.07
$340,000
3
2
2,296
Recently Sold
114 School Rd, Chestertown, MD 21620
0.07
$292,000
3
1.5
1,102
Off Market
207 Glen St, Chestertown, MD 21620
0.08
$410,300
4
2
2,236
Off Market
5 Rolling Rd, Chestertown, MD 21620
0.14
$279,800
3
1
1,202
Off Market
411 Greenwood Ave, Chestertown, MD 21620
0.15
$415,000
3
2.5
1,676
Recently Sold
202 Glen St, Chestertown, MD 21620
0.15
$290,500
3
1
1,252
Off Market
224 Valley Rd, Chestertown, MD 21620
0.15
$457,400
3
2
1,886
Off Market
303 Cedar St, Chestertown, MD 21620
0.19
$325,000
3
2.5
2,577
Recently Sold
1 Reed Ct, Chestertown, MD 21620
0.21
$420,400
4
2.5
1,854
Off Market
101 School Rd, Chestertown, MD 21620
0.20
$364,200
3
1.5
1,424
Off Market
307 Cedar St, Chestertown, MD 21620
0.21
$308,800
3
1
1,472
Off Market
109 Cedar St, Chestertown, MD 21620
0.24
$318,000
3
2
1,397
Recently Sold

Local Information

  • Map ViewExplore the area around 209 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
0.25 acre lot
1,120 sqft
$224/sqft

About this House

This single-family home is located at 209 Rolling Rd, Chestertown, MD. 209 Rolling Rd is in Chestertown, MD and in ZIP code 21620. This property has 1 bathroom and approximately 1,120 sqft of floor space. This property has a lot size of 10824 sqft and was built in 1975.
209 Rolling Rd, Chestertown, MD 21620 is a studio, 1 bathroom, 1,120 sqft single-family home built in 1975. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $251,000, with a rent estimate of $1,631/month.

Home Details for 209 Rolling Rd

Interior Features

Heating & Cooling
Heating: ElectricHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Other

Property Information

Year Built
Year Built: 1975
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 10824 sqft

Price and Tax history

YearProperty taxTax assessment
2025
$4,934
$157,400
Home facts updated by county records

Market trends in Chestertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
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 209 Rolling Rd

  • What is 209 Rolling Rd estimated to be worth?
    Trulia's estimated value for 209 Rolling Rd in Chestertown, MD is $251,000.
  • 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.
  • What are the closest schools to 209 Rolling Rd?
    The closest schools to 209 Rolling Rd in Chestertown, MD are H. H. Garnett Elementary School (Pre-K, rated 6/10), Kent County High School (rated 5/10), Kent County Middle School (rated 3/10).
  • How big is the lot at 209 Rolling Rd?
    The lot at 209 Rolling Rd in Chestertown, MD is about 0.25 acres (10,824 sq ft).

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