7 Rolling Rd, Chestertown, MD 21620
Property image
Property image
OFF MARKET

$280,400

Trulia Estimate
  • 3 Beds
  • 1 Bath
  • 1,300 sqft

7 Rolling Rd, Chestertown, MD 21620

Est. Refi. Payment $1,688/mo*
Refinance Your Home
Currently Off Market - Sold Dec 18, 2020 for $168,000

Home Value

Trulia Estimate
$280K
Since last month
Decreased$4K (-1.2%)
Since last year
Increased$8K (+2.8%)
Since last sale
Increased$112K (+66.9%)
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 +115% in the last 10 years
MonthEstimated value
2026
August 2026$280K
August 2026$280K
July 2026$284K
June 2026$287K
May 2026$284K
April 2026$281K
March 2026$279K
February 2026$274K
January 2026$277K
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
0.39
Single-Family Home
$249,000
06/12/26
3
1
1,356
202 Valley Rd, Chestertown, MD
0.31
Single-Family Home
$325,000
06/17/26
3
1
1,427
108 Pine St, Chestertown, MD
0.46
Single-Family Home
$85,000
06/30/26
3
1
910
303 E Campus Ave, Chestertown, MD
0.26
Single-Family Home
$364,000
01/16/26
3
2
1,532
201 Birch Run Rd, Chestertown, MD
0.16
Single-Family Home
$430,000
05/29/26
3
2
1,588
204 Rolling Rd, Chestertown, MD
0.17
Single-Family Home
$340,000
03/19/26
3
2
2,296
217 Philosophers Ter, Chestertown, MD
0.40
Single-Family Home
$370,000
05/01/26
3
1.5
1,404
139 Prospect St, Chestertown, MD
0.74
Single-Family Home
$195,000
07/31/26
3
1
1,200
109 Cedar St, Chestertown, MD
0.34
Single-Family Home
$318,000
08/14/26
3
2
1,397
224 Valley Rd, Chestertown, MD
0.18
Single-Family Home
$455,000
10/21/25
3
2
1,886

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
5 Rolling Rd, Chestertown, MD 21620
0.04
$279,800
3
1
1,202
Off Market
1 Reed Ct, Chestertown, MD 21620
0.10
$420,400
4
2.5
1,854
Off Market
114 School Rd, Chestertown, MD 21620
0.10
$292,000
3
1.5
1,102
Off Market
201 Birch Run Rd, Chestertown, MD 21620
0.16
$430,000
3
2
1,588
Recently Sold
209 Birch Run Rd, Chestertown, MD 21620
0.17
$597,000
4
3
2,488
Off Market
109 Birch Run Rd, Chestertown, MD 21620
0.17
$483,500
3
2.5
1,428
Off Market
207 Glen St, Chestertown, MD 21620
0.13
$410,300
4
2
2,236
Off Market
110 Birch Run Rd, Chestertown, MD 21620
0.20
$619,900
4
3
2,672
Off Market
403 E Campus Ave, Chestertown, MD 21620
0.19
$304,200
3
1
1,248
Off Market
101 Birch Run Rd, Chestertown, MD 21620
0.20
$475,000
3
2
1,961
Recently Sold
204 Rolling Rd, Chestertown, MD 21620
0.17
$340,000
3
2
2,296
Recently Sold
101 School Rd, Chestertown, MD 21620
0.19
$364,200
3
1.5
1,424
Off Market

Local Information

  • Map ViewExplore the area around 7 Rolling Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1961
1,300 sqft
$216/sqft

About this House

Take a gamble on Lucky No. 7!! Investors this home has tenants in place and willing to stay. This three bedroom, one bath brick home is looking for it's next lucky owner. Located in the College Heights area of Chestertown, it is close to college, schools, hospital, medical offices, dog parks and play grounds. Mature trees line the streets in this pet friendly neighborhood. Inside, you walk into the traditional floor plan offering a living room, three bedrooms all with original hardwood flooring, Kitchen with the essential appliances and hall bath with retro tile. The unfinished basement houses the laundry and offers plenty of storage. Outside the yard is a manageable size with room to garden and play. The driveway allows for off street parking. The new roof is on order and scheduled for early November 2020. Sellers have attended to several other items through the years making this home easy to move right in and ability to add your own cosmetic touches. No matter if you are looking for your first home, looking to scale down or maybe just an a place to invest in, this home will fill your needs. Schedule your personal tour today!
7 Rolling Rd, Chestertown, MD 21620 is a 3 bedroom, 1 bathroom, 1,300 sqft single-family home built in 1961. It last sold for $168,000 on Dec 18, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $280,400, with a rent estimate of $1,445/month.

Home Details for 7 Rolling Rd

Interior Features

Interior Details
Basement
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Brick

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 9147 sqft

Price and Tax history

DateEventPrice
Dec 18, 2020
Source: N/A
Sold
$168,000
Oct 27, 2020
Source: Agent Provided
Pending
$170,000
Oct 22, 2020
Source: Agent Provided
Listed For Sale
$170,000

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 7 Rolling Rd

  • What is 7 Rolling Rd estimated to be worth?
    Trulia's estimated value for 7 Rolling Rd in Chestertown, MD is $280,400.
  • What is the price history for 7 Rolling Rd?
    7 Rolling Rd in Chestertown, MD last sold for $168,000 in December 2020.
  • 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 7 Rolling Rd have laundry facilities?
    Yes, 7 Rolling Rd in Chestertown, MD has in-unit laundry.
  • How big is the lot at 7 Rolling Rd?
    The lot at 7 Rolling Rd in Chestertown, MD is about 0.21 acres (9,147 sq ft).

Explore by feature - Air Conditioning

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 7 Rolling Rd

Skip to last item
Skip to first item

Homes for sale near 7 Rolling Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item