OFF MARKET

Off Market Jun 2021 for $220K

$340,441

Est. refi paymentEst. refi $1,771/mo

•

1,728

sq ft

206 Rolling Rd, Chestertown, MD 21620

About this home

Chestertown - This 3 bedroom 2 bath home sits in a beautiful family neighborhood walking distance from the Washington College campus. This home has had new windows installed, new gutters, a new water heater and new laminate flooring in the kitchen and dining room all within the last 2 years. A new central air and heating system was installed within the last 5 years. The solar panels produce plenty of energy and have no outstanding lease. There is a large back deck off the family room entrance perfect for entertaining. The back deck opens up to a large fenced in backyard. This home offers a Jack and Jill bath in addition to the master suite that has an attached dressing room. There is a full unfinished basement and a large attic with outside stair access that offers additional storage. The large living room offers plenty of space for family time in addition to the family room with a wood burning fireplace. The washer and dryer are on the main level of the house. An attached carport provides protection for your vehicle. Call today for your private showing!

Single-familyProperty Type

1970Year Built

0.35 acresLot Size

$197Est. Price/Sq.Ft.

2 spacesParking

Listed by Linda Austin • Long & Foster Real Estate, Inc.

•410-643-2244 (broker)

Bought with Lacey Sutton • Coldwell Banker Chesapeake Real Estate Company

•410-778-0330 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDKE117860

Redfin Estimate

$340,441

$120K since sold in June 2021$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.9% lower than the average sale price ($382K) of 6 comparable homes.

SOLD JUL 22, 2026
$365,000
A
3 beds2 baths1,934 sq ft
521 N Kent St, Chestertown, MD 21620
SOLD MAY 29, 2026
$430,000
B
3 beds2 baths1,588 sq ft
201 Birch Run Rd, Chestertown, MD 21620
SOLD AUG 14, 2026
$318,000
C
3 beds2 baths1,397 sq ft
109 Cedar St, Chestertown, MD 21620
SOLD JAN 16, 2026
$364,000
D
3 beds2 baths1,532 sq ft
303 E Campus Ave, Chestertown, MD 21620
SOLD MAR 19, 2026
$340,000
E
3 beds2 baths2,296 sq ft
204 Rolling Rd, Chestertown, MD 21620
SOLD DEC 11, 2025
$475,000
F
3 beds2 baths1,961 sq ft
101 Birch Run Rd, Chestertown, MD 21620

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Earn from this home

Refinance

Est. cash available

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Rent

$2,630/mo

Redfin rental estimate

List your home for rent

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

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
$1,195,000
2 beds1 bath806 sq ft
302 S Mill St, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$345,000
3 beds1.5 baths1,398 sq ft
217 Edmore Rd, Chestertown, MD 21620
(410) 810-0010
$369,000
2 beds1.5 baths1,036 sq ft
101 S College Ave, Chestertown, MD 21620
(410) 810-0010
$649,000
4 beds3 baths2,864 sq ft
22400 Great Oak Landing Rd, Chestertown, MD 21620
(410) 778-0330
FOR SALE BY OWNER
$435,000
3 beds2 baths1,956 sq ft
233 Duke of Kent St, Chestertown, MD 21620
See all

Provided by Redfin

Sale history for 206 Rolling Rd

Year

Property tax

Land + Additions

Assessment*

2026

$3,587 (+5.9%)

2025

$3,388 (+7.6%)

2024

$3,149 (+8.2%)

$91,300 + $124,900

$216,200

2023

$2,909 (+9.7%)

2022

$2,652 (+0.9%)

2021

$2,629 (+0.2%)

$91,300 + $79,000

$170,300

2020

$2,623 (+1.1%)

2019

$2,595 (+1.0%)

2018

$2,570 (+3.7%)

2017

$2,479 (+0.3%)

2015

$2,471 (+81.0%)

$101,300 + $63,000

$164,300

2014

$1,365 (−40.6%)

$101,300 + $80,200

$181,500

2013

$2,297 (−13.3%)

2012

$2,649 (−25.2%)

2011

$3,541 (+194.0%)

2010

$1,204 (−47.3%)

2009

$2,284

Tax history for 206 Rolling Rd

Year

Property tax

Land + Additions

Assessment*

2026

$3,587 (+5.9%)

2025

$3,388 (+7.6%)

2024

$3,149 (+8.2%)

$91,300 + $124,900

$216,200

2023

$2,909 (+9.7%)

2022

$2,652 (+0.9%)

2021

$2,629 (+0.2%)

$91,300 + $79,000

$170,300

2020

$2,623 (+1.1%)

2019

$2,595 (+1.0%)

2018

$2,570 (+3.7%)

2017

$2,479 (+0.3%)

2015

$2,471 (+81.0%)

$101,300 + $63,000

$164,300

2014

$1,365 (−40.6%)

$101,300 + $80,200

$181,500

2013

$2,297 (−13.3%)

2012

$2,649 (−25.2%)

2011

$3,541 (+194.0%)

2010

$1,204 (−47.3%)

2009

$2,284

*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

0.35 Acres

Year renovated

—

Sq. Ft.

1,728

Year built

1970

Style

Single Family Residential

County

Kent County

APN

04 017595

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 3, 2026.

Property details

Parking

Parking Information
# of Attached Carport Spaces: 2
# of Total Garage and Parking Spaces: 2
# of Carport Spaces: 2
Driveway, On Street, Attached Carport

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2

Interior Information
Appliances: Dishwasher, Dryer, Exhaust Fan, Icemaker, Microwave, Refrigerator, Stove, Washer, Water Heater
Interior Features: Attic, Attic/House Fan, Carpet, CeilngFan(s), Combination Kitchen/Dining, Entry Level Bedroom, Floor Plan - Open, Kitchen - Country, Recessed Lighting
Living Area Sq.Ft. Source: Assessor

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

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Wood

Basement Information
Basement: Yes
Other

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $79,000
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Assessor

Building Information
Construction Materials: Aluminum Siding
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s)
Roof: Architectural Shingle
Structure Type: Detached

Exterior Information
Sidewalks

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $91,300

Above Grade Information
Finished Sq.Ft.: 1,728
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
City/Town Tax: $725
County Tax: $1,897
Tax Assessed Value: $168,833
Tax Year: 2021
Tax Annual Amount: $2,622

Assessments Information
Year Assessed: 2021

Utilities

Utilities Information
Central Air
Cooling Type: Ceiling Fan(s), Central A/C
Cooling Fuel: Electric
Baseboard - Electric, Heat Pump(s)
Heating Fuel: Electric, Wood
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public

Location

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

Location Information
Outside City Limits
Directions: Route 213 to Greenwood Avenue, left to Rolling Road and property is on the right.
Municipality: Chestertown

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,728
Stories: 1.0
Lot Size: 0.35 acres
Style: Single Family Residential
Year Built: 1970
Year Renovated: —
County: Kent County
APN: 04 017595

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 • 4.7mi

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

64% 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

$324,000 – $392,000

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

Nearby similar homes

$1,195,000

2 beds1 bath806 sq ft

302 S Mill St, Chestertown, MD 21620

(410) 778-0330

NEW CONSTRUCTION

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3 beds2.5 baths1,964 sq ft

#37 Landing Ln, Chestertown, MD 21620

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Land— sq ft

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NEW CONSTRUCTION

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NEW CONSTRUCTION

$799,900

3 beds3.5 baths2,092 sq ft

106 Landing Ln, Chestertown, MD 21620

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New listings for sale in 21620

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

$1,195,000

2 beds1 bath806 sq ft

302 S Mill St, Chestertown, MD 21620

(410) 778-0330

COMING SOON

$345,000

3 beds1.5 baths1,398 sq ft

217 Edmore Rd, Chestertown, MD 21620

(410) 810-0010

$369,000

2 beds1.5 baths1,036 sq ft

101 S College Ave, Chestertown, MD 21620

(410) 810-0010

$649,000

4 beds3 baths2,864 sq ft

22400 Great Oak Landing Rd, Chestertown, MD 21620

(410) 778-0330

Home values near 206 Rolling Rd

Data from public records.

Address	Redfin Estimate
213 Rolling Road, Chestertown, MD - Beds \| 1 Baths \| 1716 Sq. Ft.	$338,205
201 Rolling Road, Chestertown, MD 4 Beds \| 2 Baths \| 2652 Sq. Ft.	$392,378

Address	Redfin Estimate
207 Rolling Road, Chestertown, MD 3 Beds \| 1 Baths \| 1196 Sq. Ft.	$316,381
202 Rolling Road, Chestertown, MD - Beds \| 1.5 Baths \| 1806 Sq. Ft.	$349,354

Address	Redfin Estimate
203 Rolling Road, Chestertown, MD - Beds \| 2.5 Baths \| 2508 Sq. Ft.	$415,919
210 Rolling Road, Chestertown, MD - Beds \| 2 Baths \| 1344 Sq. Ft.	$278,855

Property information provided by BRIGHT MLS when last listed in 2021. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 21620, MD

Sale history for 206 Rolling Rd

Tax history for 206 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 206 Rolling Rd

More real estate resources