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

5 Rolling Rd
Chestertown, MD 21620

  • 3 Beds
  • 1 Bath
  • 1,202 sqft

$266,700

Trulia Estimate
as of Jul 29, 2026

$266,700

Trulia Estimate
as of Jul 29, 2026
3 Beds
1 Bath
1,202 sqft

Local Information

  • Map ViewExplore the area around 5 Rolling Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1961
Living Area
1,202 sqft
Price/Sqft
$222
Parking
Open Parking

About this House

Brick rancher located in College Heights! There are 3 bedrooms and living room, all with wood floors. There is a large family room with built-ins. There is a full unfinished basement with connecting interior stairs and exterior stairs. The rear porch is ready to be screened in. Property backs up to woods. Close to hospital, parks and schools. This home will require a little TLC however the efforts made to renovate an upgrade will be well worth it.
5 Rolling Rd, Chestertown, MD 21620 is a 3 bedroom, 1 bathroom, 1,202 sqft single-family home built in 1961. It last sold for the $239,000 asking price on Nov 25, 2024. It is currently off market. The Trulia Estimate is $266,700, with a rent estimate of $1,653/month.

Home Details for 5 Rolling Rd

Interior Features

Interior Details
Basement: Connecting Stairway,Walk-Out AccessNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1202 Square Feet
Appliances & Utilities
Appliances: Dryer, Refrigerator, Cooktop, Washer, Water Heater, Electric Water HeaterDryerLaundry: In BasementRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Skylight(s)Door: Storm Door(s)Flooring: Carpet, Vinyl, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Carpet, Vinyl, Wood
View
No View

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PorchOther Structures: Above Grade, Below GradeFoundation: BlockNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Crushed Stone,Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1202 Square Feet

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building
Construction Materials: BrickNot a New Construction
Property Information
Condition: AverageParcel Number: 1504011279

Price & Status

Price
List Price: $239,000
Status Change & Dates
Off Market Date: Tue Nov 26 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Media

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: 2114 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 9100 sqft

Listing Info

Special Conditions: Standard

Offer

Contingencies: Financing ApprovalListing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDKE2004448Municipality: ChestertownAbove Grade Unfinished Area: 1202
Last check for updates: about 19 hours ago
Listed by Doug Ashley, (410) 708-0480
Doug Ashley Realtors, LLC
Bought with: FRED NGUYEN, (301) 331-9989, Real Broker, LLC
Source: Bright MLS, MLS#MDKE2004448

Price History for 5 Rolling Rd

DatePriceEventSource
11/25/2024$239,000Sold
Bright MLS #MDKE2004448
11/21/2024$239,000PendingBright MLS #MDKE2004448
09/25/2024$239,000ContingentBright MLS #MDKE2004448
09/17/2024$239,000Listed For SaleBright MLS #MDKE2004448

Market trends in Chestertown

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

Year2025
Tax$5,401
Assessment$172,300
Home facts updated by county records

Comparable Sales for 5 Rolling Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
112 Elm St, Chestertown, MD
0.41
Single-Family Home
$249,000
06/12/26
3
1
1,356
202 Valley Rd, Chestertown, MD
0.32
Single-Family Home
$325,000
06/17/26
3
1
1,427
201 Birch Run Rd, Chestertown, MD
0.12
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
217 Philosophers Ter, Chestertown, MD
0.39
Single-Family Home
$370,000
05/01/26
3
1.5
1,404
204 Rolling Rd, Chestertown, MD
0.20
Single-Family Home
$340,000
03/19/26
3
2
2,296
206 Barroll Dr, Chestertown, MD
0.22
Single-Family Home
$438,000
09/30/25
3
2
1,820
205 Pine St, Chestertown, MD
0.35
Single-Family Home
$296,337
09/30/25
3
1.5
2,212
224 Valley Rd, Chestertown, MD
0.20
Single-Family Home
$455,000
10/21/25
3
2
1,886
304 Hadaway Dr, Chestertown, MD
0.46
Single-Family Home
$250,000
07/31/25
4
2
1,325

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Rolling Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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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Homes for sale near 5 Rolling Rd

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Off Market Homes Near 5 Rolling Rd

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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