1 Rolling Rd, Chestertown, MD 21620
OFF MARKET

$128,000

Last sold price
  • 1 Bath
  • 888 sqft

1 Rolling Rd, Chestertown, MD 21620

Currently Off Market - Sold May 25, 2016 for $128,000

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
108 Pine St, Chestertown, MD
0.52
Single-Family Home
$85,000
06/30/26
3
1
910
112 Elm St, Chestertown, MD
0.45
Single-Family Home
$249,000
06/12/26
3
1
1,356
202 Valley Rd, Chestertown, MD
0.35
Single-Family Home
$325,000
06/17/26
3
1
1,427
201 Birch Run Rd, Chestertown, MD
0.09
Single-Family Home
$430,000
05/29/26
3
2
1,588
303 E Campus Ave, Chestertown, MD
0.24
Single-Family Home
$364,000
01/16/26
3
2
1,532
139 Prospect St, Chestertown, MD
0.75
Single-Family Home
$195,000
07/31/26
3
1
1,200
217 Philosophers Ter, Chestertown, MD
0.39
Single-Family Home
$370,000
05/01/26
3
1.5
1,404
111 Pine St, Chestertown, MD
0.47
Single-Family Home
$347,000
05/05/26
5
1
1,645
206 Barroll Dr, Chestertown, MD
0.20
Single-Family Home
$438,000
09/30/25
3
2
1,820
141 Prospect St, Chestertown, MD
0.76
Single-Family Home
$120,000
02/27/26
4
1.5
1,156

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
1 Reed Ct, Chestertown, MD 21620
0.03
$420,400
4
2.5
1,854
Off Market
5 Rolling Rd, Chestertown, MD 21620
0.04
$279,800
3
1
1,202
Off Market
201 Birch Run Rd, Chestertown, MD 21620
0.09
$430,000
3
2
1,588
Recently Sold
109 Birch Run Rd, Chestertown, MD 21620
0.11
$483,500
3
2.5
1,428
Off Market
110 Birch Run Rd, Chestertown, MD 21620
0.13
$619,900
4
3
2,672
Off Market
209 Birch Run Rd, Chestertown, MD 21620
0.10
$597,000
4
3
2,488
Off Market
101 Birch Run Rd, Chestertown, MD 21620
0.16
$475,000
3
2
1,961
Recently Sold
403 E Campus Ave, Chestertown, MD 21620
0.16
$304,200
3
1
1,248
Off Market
211 David Dr, Chestertown, MD 21620
0.19
$797,600
4
4
4,401
Off Market
206 Barroll Dr, Chestertown, MD 21620
0.20
$440,300
3
2
1,820
Off Market
114 School Rd, Chestertown, MD 21620
0.17
$292,000
3
1.5
1,102
Off Market
217 Birch Run Rd, Chestertown, MD 21620
0.18
$548,600
4
2.5
2,208
Off Market

Local Information

  • Map ViewExplore the area around 1 Rolling Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Built in 1961
888 sqft

About this House

1 Rolling Rd is in Chestertown, MD and in ZIP code 21620. This property has 1 bathroom and approximately 888 sqft of floor space. This property has a lot size of 9100 sqft and was built in 1961.
1 Rolling Rd, Chestertown, MD 21620 is a 1 bathroom, 888 sqft unknown built in 1961. It last sold for $128,000 on May 25, 2016. This property is not currently displayed as for sale or rent on Trulia.

Home Details for 1 Rolling Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Brick

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: UnknownArchitecture: Conventional

Lot Information

Lot Area: 9100 sqft

Price and Tax history

DateEventPrice
May 25, 2016
Source: N/A
Sold
$128,000

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 1 Rolling Rd

  • What is the price history for 1 Rolling Rd?
    1 Rolling Rd in Chestertown, MD last sold for $128,000 in May 2016.
  • 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 1 Rolling Rd?
    The closest schools to 1 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).

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