OFF MARKET

Off Market Nov 2024 for $239K

$254,257

Est. refi paymentEst. refi $1,551/mo

•

1,202

sq ft

5 Rolling Rd, Chestertown, MD 21620

About this home

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.

Single-familyProperty Type

1961Year Built

9,100 sq ftLot Size

$212Est. Price/Sq.Ft.

Listed by Doug Ashley • Doug Ashley Realtors, LLC

•410-810-0010 (broker)

Bought with FRED NGUYEN • Real Broker, LLC

•855-450-0442 (broker)

•dmvbroker@therealbrokerage.com (broker)

Redfin checked: a few seconds ago

•Source:BRIGHT MLS #MDKE2004448

Redfin Estimate

$254,257

$15K since sold in November 2024$1,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 12.9% higher than the average sale price ($225K) of 6 comparable homes.

SOLD AUG 14, 2026
$318,000
A
3 beds2 baths1,397 sq ft
109 Cedar St, Chestertown, MD 21620
SOLD AUG 21, 2026
$289,000
B
3 beds1 bath1,248 sq ft
517 Round Top Rd, Chestertown, MD 21620
SOLD JUN 30, 2026
$85,000
C
3 beds1 bath910 sq ft
108 Pine St, Chestertown, MD 21620
SOLD JUN 12, 2026
$249,000
D
3 beds1 bath1,356 sq ft
112 Elm St, Chestertown, MD 21620
SOLD JUL 21, 2026
$215,000
E
3 beds1 bath1,373 sq ft
100 Prospect St, Chestertown, MD 21620
SOLD BY REDFIN JUL 31, 2026
$195,000
F
3 beds1 bath1,200 sq ft
139 Prospect St, Chestertown, MD 21620

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Earn from this home

Refinance

Est. cash available

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Rent

$2,027/mo

Redfin rental estimate

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Market trends in 21620, MD

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.0%

+0.0% MoM

Median sale price

$347K

$15K MoM

Avg. days on market

48d

2 days MoM

Recently sold homes

1 MoM

New listings for sale

$263,000
3 beds2 baths1,140 sq ft
115 Chester Arms Dr, Chestertown, MD 21620
(703) 378-8810
NEW 27 HRS AGO
$229,000
3 beds1 bath936 sq ft
7415 Wilkins Ln, Chestertown, MD 21620
(410) 810-0010
COMING SOON
$275,000
3 beds1 bath975 sq ft
7482 Poplar Ave, Chestertown, MD 21620
(301) 970-2447
COMING SOON
$315,000
3 beds1 bath1,008 sq ft
24775 Langford Rd, Chestertown, MD 21620
(410) 398-9200
COMING SOON
$300,000
3 beds1 bath960 sq ft
104 Lincoln Dr, Chestertown, MD 21620
(443) 274-1900
OPEN SAT, 10AM TO 12PM
$315,000
3 beds2 baths1,288 sq ft
109 Parma Rd, Chestertown, MD 21620
(410) 778-0330
OPEN SAT, 11AM TO 1PM
$225,000
4 beds1.5 baths1,800 sq ft
533 Round Top Rd, Chestertown, MD 21620
(833) 335-7433
$304,000
3 beds2 baths1,232 sq ft
7464 Shortall St, Chestertown, MD 21620
(410) 476-2201
COMING SOON
$675,000
5 beds3 baths2,838 sq ft
212 Washington Ave, Chestertown, MD 21620
(410) 778-0330
$38,200,000
4 beds2 baths2,330 sq ft
8184 Rock Hall Rd, Chestertown, MD 21620
(410) 778-3779
See all

Provided by Redfin

Sale history for 5 Rolling Rd

Year

Property tax

Land + Additions

Assessment*

2026

$2,875 (+6.5%)

2025

$2,700 (+8.7%)

2024

$2,484 (+5.1%)

$81,900 + $90,400

$172,300

2023

$2,364 (+5.8%)

2022

$2,235 (+0.7%)

2021

$2,218 (+0.1%)

$81,900 + $61,600

$143,500

2020

$2,216 (+1.0%)

2019

$2,194 (+0.9%)

2018

$2,175 (+3.6%)

2017

$2,099 (+0.3%)

2015

$2,093 (+80.1%)

$91,000 + $48,200

$139,200

2014

$1,162 (−48.8%)

$91,000 + $63,500

$154,500

2013

$2,271 (+3.3%)

2012

$2,199 (−27.2%)

2011

$3,020 (+208.0%)

2010

$980 (−47.3%)

2009

$1,859

Tax history for 5 Rolling Rd

Year

Property tax

Land + Additions

Assessment*

2026

$2,875 (+6.5%)

2025

$2,700 (+8.7%)

2024

$2,484 (+5.1%)

$81,900 + $90,400

$172,300

2023

$2,364 (+5.8%)

2022

$2,235 (+0.7%)

2021

$2,218 (+0.1%)

$81,900 + $61,600

$143,500

2020

$2,216 (+1.0%)

2019

$2,194 (+0.9%)

2018

$2,175 (+3.6%)

2017

$2,099 (+0.3%)

2015

$2,093 (+80.1%)

$91,000 + $48,200

$139,200

2014

$1,162 (−48.8%)

$91,000 + $63,500

$154,500

2013

$2,271 (+3.3%)

2012

$2,199 (−27.2%)

2011

$3,020 (+208.0%)

2010

$980 (−47.3%)

2009

$1,859

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

9,100 Sq. Ft.

Year renovated

—

Sq. Ft.

1,202

Year built

1961

Style

Single Family Residential

County

Kent County

APN

04 011279

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 3, 2026.

Property details

Parking

Parking Information
Crushed Stone
Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full): 1

Interior Information
Appliances: Dryer, Refrigerator, Stove, Washer, Water Heater
Door Features: Storm
Flooring Type: Carpet, Vinyl, Wood
Interior Features: Attic, Built-Ins, Carpet, CeilngFan(s), Family Room Off Kitchen, Floor Plan - Traditional, Kitchen - Country, Skylight(s), Wood Floors
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: Dry Wall

Room Information
Living Room, Bedroom 2, Bedroom 3, Kitchen, Family Room, Basement, Bedroom 1
Laundry Type: Basement

Basement Information
Basement: Yes
Connecting Stairway, Walkout Stairs

Exterior

Property Information
Total Below Grade Sq. Ft.: 912
Improvement Assessed Value: $61,600
Ownership Interest: Fee Simple
Property Condition: Average
Year Built Source: Assessor

Building Information
Construction Materials: Brick
Foundation Details: Block
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Porch(es)
Roof: Asphalt
Structure Type: Detached
Window Features: Double Pane
Other Structures: Shed

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $81,900

Above Grade Information
Finished Sq.Ft.: 1,202
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft.: 912
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
City/Town Tax: $704
County Tax: $1,845
Tax Assessed Value: $162,700
Tax Year: 2024
Tax Annual Amount: $2,550

Assessments Information
Year Assessed: 2024

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Baseboard - Electric
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public

Location

School Information
School District Name: KENT COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
In City Limits
Directions: From Chester River Bridge make a right on Campus Avenue. Make a left on Rolling Road. House on right.
Municipality: Chestertown

Public facts

Beds: —
Baths: 1.0
Sq. Ft.: 1,202
Stories: 1.0
Lot Size: 9,100 square feet
Style: Single Family Residential
Year Built: 1961
Year Renovated: —
County: Kent County
APN: 04 011279

Home facts updated by county records on Aug 3, 2026

Around this home

Schools

H. H. Garnett Elementary School

Public PreK-5 • Assigned • 0.7mi

6/10

Kent County Middle School

Public 6-8 • Assigned • 0.2mi

3/10

Kent County High School

Public 9-12 • Assigned • 4.9mi

5/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 104° expected this year, 15 days in 30 years

6/10 Wind Factor

60% chance of strong winds in next 30 years

6/10 Air Factor

9 unhealthy days expected this year, 13 days in 30 years

Provided by First Street

Historical weather

Chestertown, MD • 21620

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.7 hours in December, which is comparable to the U.S. average for solar exposure.

9.2 hrs

4.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$242,000 – $293,000

Sell confidently with a local market expert in Chestertown. 3 minutes to get started.

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New listings for sale in 21620

$263,000

3 beds2 baths1,140 sq ft

115 Chester Arms Dr, Chestertown, MD 21620

(703) 378-8810

NEW 27 HRS AGO

$229,000

3 beds1 bath936 sq ft

7415 Wilkins Ln, Chestertown, MD 21620

(410) 810-0010

COMING SOON

$275,000

3 beds1 bath975 sq ft

7482 Poplar Ave, Chestertown, MD 21620

(301) 970-2447

COMING SOON

$315,000

3 beds1 bath1,008 sq ft

24775 Langford Rd, Chestertown, MD 21620

(410) 398-9200

COMING SOON

$300,000

3 beds1 bath960 sq ft

104 Lincoln Dr, Chestertown, MD 21620

(443) 274-1900

OPEN SAT, 10AM TO 12PM

$315,000

3 beds2 baths1,288 sq ft

109 Parma Rd, Chestertown, MD 21620

(410) 778-0330

OPEN SAT, 11AM TO 1PM

$225,000

4 beds1.5 baths1,800 sq ft

533 Round Top Rd, Chestertown, MD 21620

(833) 335-7433

$304,000

3 beds2 baths1,232 sq ft

7464 Shortall St, Chestertown, MD 21620

(410) 476-2201

COMING SOON

$675,000

5 beds3 baths2,838 sq ft

212 Washington Ave, Chestertown, MD 21620

(410) 778-0330

Home values near 5 Rolling Rd

Data from public records.

Address	Redfin Estimate
213 Rolling Rd, Chestertown, MD - Beds \| 1 Baths \| 1716 Sq. Ft.	$337,977
2 Rolling Rd, Chestertown, MD - Beds \| 1 Baths \| 1776 Sq. Ft.	$259,914

Address	Redfin Estimate
212 Rolling Rd, Chestertown, MD 3 Beds \| 1.5 Baths \| 1148 Sq. Ft.	$356,853
8 Rolling Rd, Chestertown, MD - Beds \| 1 Baths \| 1523 Sq. Ft.	$275,700

Address	Redfin Estimate
6 Rolling Rd, Chestertown, MD - Beds \| 1 Baths \| 975 Sq. Ft.	$242,680
4 Rolling Rd, Chestertown, MD 4 Beds \| 2 Baths \| 1950 Sq. Ft.	$318,429

Property information provided by BRIGHT MLS when last listed in 2024. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 21620, MD

Sale history for 5 Rolling Rd

Tax history for 5 Rolling Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21620

Home values near 5 Rolling Rd

More real estate resources