OFF MARKET

Off Market Jan 2022 for $299K

$388,746

Est. refi paymentEst. refi $2,137/mo

•

2,652

sq ft

201 Rolling Rd, Chestertown, MD 21620

About this home

Very nice Colonial Style home in College Heights Chestertown. Kitchen with center island which opens to dining area. Large family room with access to screened in porch overlooking fenced in ground pool. Plus den or private office space and half bath on first floor. Second floor features 4 bedrooms and full bath. Property backs to park like setting. Private driveway via shared access of easement between adjacent property.

Single-familyProperty Type

1975Year Built

0.45 acresLot Size

$147Est. Price/Sq.Ft.

Listed by Mark McGuire • Benson & Mangold, LLC

•410-822-6665 (broker)

•info@bensonandmangold.com (broker)

Bought with audrianna goddard • Rosendale Realty

•410-758-0333 (broker)

•info@rosendalerealtyonline.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDKE2000754

Redfin Estimate

$388,746

$90K since sold in January 2022$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 1.8% higher than the average sale price ($382K) of 5 comparable homes.

SOLD JUL 22, 2026
$365,000
A
3 beds2 baths1,934 sq ft
521 N Kent St, Chestertown, MD 21620
SOLD MAR 19, 2026
$340,000
B
3 beds2 baths2,296 sq ft
204 Rolling Rd, Chestertown, MD 21620
SOLD BY REDFIN JUL 30, 2026
$300,000
C
4 beds2 baths1,325 sq ft
304 Hadaway Dr, Chestertown, MD 21620
SOLD MAY 29, 2026
$430,000
D
3 beds2 baths1,588 sq ft
201 Birch Run Rd, Chestertown, MD 21620
SOLD DEC 11, 2025
$475,000
E
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

$2,935/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%

1.0% MoM

Median sale price

$362K

$17K MoM

Avg. days on market

46d

14 days MoM

Recently sold homes

9 MoM

New listings for sale

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
$524,900
3 beds2.5 baths2,076 sq ft
1003 Twin Ct, Chestertown, MD 21620
(410) 778-3779
See all

Provided by Redfin

Sale history for 201 Rolling Rd

Date

Event

Price

BRIGHT MLS #MDKE2000754

Jan 31, 2022

Sold

$299,000

$113/sq ft

Jan 4, 2022

Pending

—

Dec 1, 2021

Listed

$299,000

$113/sq ft

BRIGHT MLS #1000479421

Nov 18, 2015

Sold

$210,000

$79/sq ft

+19

MRIS #KE8693096

Nov 18, 2015

Sold

$210,000

$79/sq ft

Sep 23, 2015

Pending

—

Jul 13, 2015

Listed

$87/sq ft

+19

MRIS #KE7927535

Sep 11, 2013

Delisted

—

May 9, 2013

Price Changed

Apr 29, 2013

Price Changed

Sep 14, 2012

Listed

BRIGHT MLS #1009686580

Sep 11, 2013

Listing Removed

—

Sep 14, 2012

Listed

$216,000

$81/sq ft

MRIS #KE7555772

Sep 18, 2011

Delisted

—

Mar 18, 2011

Listed

BRIGHT MLS #1006808754

Sep 18, 2011

Listing Removed

—

Mar 18, 2011

Listed

$235,000

$89/sq ft

MRIS #KE7282183

Sep 18, 2010

Delisted

—

Apr 21, 2010

Price Changed

Mar 17, 2010

Listed

BRIGHT MLS #1006671916

Sep 18, 2010

Listing Removed

—

Mar 17, 2010

Listed

$265,500

$100/sq ft

MRIS #KE7156465

Mar 11, 2010

Delisted

—

Sep 10, 2009

Listed

BRIGHT MLS #1006600206

Mar 11, 2010

Listing Removed

—

Sep 10, 2009

Listed

$279,500

$105/sq ft

Public Records

Jul 5, 2002

Sold

$145,000

$55/sq ft

MRIS #KE4199756

May 23, 2002

Delisted

—

Apr 30, 2002

Listed

$58/sq ft

Public Records

Feb 27, 1996

Sold

$37,500

$14/sq ft

Public Records

Mar 27, 1989

Sold

$124,000

$47/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2026

$4,603 (+2.2%)

2025

$4,504 (+8.2%)

2024

$4,163 (+8.9%)

$92,400 + $195,000

$287,400

2023

$3,822 (+10.5%)

2022

$3,459 (−0.6%)

2020

$3,481 (−2.5%)

$92,400 + $129,700

$222,100

2019

$3,570 (+2.0%)

$92,400 + $129,700

$222,100

2018

$3,501 (+3.3%)

$102,400 + $122,900

$225,300

2017

$3,389 (−1.0%)

$102,400 + $122,900

$225,300

2015

$3,424 (−2.5%)

$102,400 + $125,300

$227,700

2014

$3,512

$102,400 + $131,100

$233,500

2013

$3,512

2012

$3,512 (−9.3%)

2011

$3,874 (+171.7%)

2010

$1,426 (−47.3%)

2009

$2,705

Tax history for 201 Rolling Rd

Year

Property tax

Land + Additions

Assessment*

2026

$4,603 (+2.2%)

2025

$4,504 (+8.2%)

2024

$4,163 (+8.9%)

$92,400 + $195,000

$287,400

2023

$3,822 (+10.5%)

2022

$3,459 (−0.6%)

2020

$3,481 (−2.5%)

$92,400 + $129,700

$222,100

2019

$3,570 (+2.0%)

$92,400 + $129,700

$222,100

2018

$3,501 (+3.3%)

$102,400 + $122,900

$225,300

2017

$3,389 (−1.0%)

$102,400 + $122,900

$225,300

2015

$3,424 (−2.5%)

$102,400 + $125,300

$227,700

2014

$3,512

$102,400 + $131,100

$233,500

2013

$3,512

2012

$3,512 (−9.3%)

2011

$3,874 (+171.7%)

2010

$1,426 (−47.3%)

2009

$2,705

*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

0.45 Acres

Year renovated

—

Sq. Ft.

2,652

Year built

1975

Style

Single Family Residential

County

Kent County

APN

04 012526

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 3, 2026.

Property details

Parking

Parking Information
Shared Driveway
Off Street

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 4

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Full): 2

Interior Information
Appliances: Dishwasher, Dryer, Refrigerator, Stove, Washer
Interior Features: Kitchen - Table Space, Combination Kitchen/Dining, Wood Floors, Recessed Lighting, Floor Plan - Traditional
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: Dry Wall, Beamed Ceilings

Room Information
Living Room, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Den, Bedroom 1, Laundry

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $129,700
Ownership Interest: Fee Simple
Property Condition: Excellent
Year Built Source: Assessor

Building Information
Construction Completed
Construction Materials: Combination, Brick
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Screened
Roof: Asphalt
Structure Type: Detached
Window Features: Double Pane, Screens, Skylights
Other Structures: Shed

Exterior Information
Outbuilding(s)
Fencing: Partially

Pool Information
Personal Pool
In Ground, Vinyl

Lot Information
Lot Features: Landscaping
Tidal Water: No

Land Information
Land Assessed Value: $92,400

Above Grade Information
Finished Sq.Ft.: 2,652
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
City/Town Tax: $842.49
County Tax: $2,582.12
Tax Assessed Value: $222,100
Tax Year: 2014
Tax Annual Amount: $3,424.61

Assessments Information
Year Assessed: 2020

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C, Ceiling Fan(s)
Cooling Fuel: Electric
Forced Air
Heating Fuel: Electric
Hot Water: Bottled Gas
Sewer Septic: Public Sewer
Water Source: Public

Location

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

Location Information
In City Limits
Directions: MD Rt 213 North from MD Rt 301, Cross over Chester River Bridge, road becomes Washington Ave, turn right on Greenwood then right on Rolling , property will be on the left.
Municipality: CHESTERTOWN

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 2,652
Stories: 2.0
Lot Size: 0.45 acres
Style: Single Family Residential
Year Built: 1975
Year Renovated: —
County: Kent County
APN: 04 012526

Home facts updated by county records on Aug 3, 2026

Around this home

Schools

H. H. Garnett Elementary School

Public PreK-5 • Assigned • 0.8mi

6/10

Kent County Middle School

Public 6-8 • Assigned • 0.3mi

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

$370,000 – $448,000

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

Nearby similar homes

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NEW CONSTRUCTION

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Land— sq ft

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New listings for sale in 21620

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

Home values near 201 Rolling Rd

Data from public records.

Address	Redfin Estimate
213 Rolling Rd, Chestertown, MD - Beds \| 1 Baths \| 1716 Sq. Ft.	$338,205
206 Rolling Rd, Chestertown, MD 3 Beds \| 2 Baths \| 1728 Sq. Ft.	$333,657

Address	Redfin Estimate
207 Rolling Rd, Chestertown, MD 3 Beds \| 1 Baths \| 1196 Sq. Ft.	$316,381
111 Rolling Rd, Chestertown, MD - Beds \| 3 Baths \| 2100 Sq. Ft.	$407,314

Address	Redfin Estimate
203 Rolling Rd, Chestertown, MD - Beds \| 2.5 Baths \| 2508 Sq. Ft.	$415,919
202 Rolling Rd, Chestertown, MD - Beds \| 1.5 Baths \| 1806 Sq. Ft.	$355,352

Property information provided by BRIGHT MLS when last listed in 2021. 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 201 Rolling Rd

Tax history for 201 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 201 Rolling Rd

More real estate resources