OFF MARKET

Off Market Oct 2021 for $337K

$411,424

Est. refi paymentEst. refi $2,590/mo

•

1,756

sq ft

107 Rolling Rd, Chestertown, MD 21620

About this home

This home has been renovated top to bottom in recent years. Gleaming wood floors are throughout most of the main level. The kitchen/dining area combination has a slider that exits to the rear deck. The lower level offers two very spacious rooms that act as family and rec rooms. There is even a bedroom on the lower level and a separate full bath. Sliders in lower level take you to the patio under the deck and to the nice semi-private backyard. Freshly painted and ready for you just to move right in!!!

Single-familyProperty Type

1970Year Built

0.37 acresLot Size

$234Est. Price/Sq.Ft.

Listed by Doug Ashley • Doug Ashley Realtors, LLC

•410-810-0010 (broker)

Bought with Jay McCall • Coldwell Banker Chesapeake Real Estate Company

•410-822-9000 (broker)

Redfin checked: a few seconds ago

•Source:BRIGHT MLS #MDKE2000200

Redfin Estimate

$411,424

$74K since sold in October 2021$1,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.7% higher than the average sale price ($379K) 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 APR 17, 2026
$495,000
B
4 beds2.5 baths2,220 sq ft
515 N Kent St, Chestertown, MD 21620
SOLD AUG 14, 2026
$318,000
C
3 beds2 baths1,397 sq ft
109 Cedar St, Chestertown, MD 21620
SOLD BY REDFIN JUL 30, 2026
$300,000
D
4 beds2 baths1,325 sq ft
304 Hadaway Dr, Chestertown, MD 21620
SOLD MAY 29, 2026
$430,000
E
3 beds2 baths1,588 sq ft
201 Birch Run Rd, Chestertown, MD 21620
SOLD JAN 16, 2026
$364,000
F
3 beds2 baths1,532 sq ft
303 E Campus Ave, Chestertown, MD 21620

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Refinance

Est. cash available

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Rent

$3,194/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

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
$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
See all

Provided by Redfin

Sale history for 107 Rolling Rd

Date

Event

Price

Public Records

Dec 16, 2021

Sold

$337,500

$192/sq ft

BRIGHT MLS #MDKE2000200

Oct 21, 2021

Sold

$337,500

$192/sq ft

Oct 15, 2021

Pending

—

Aug 22, 2021

Contingent

—

Jul 16, 2021

Listed

$337,500

$192/sq ft

MRIS #KE7747144

May 24, 2012

Sold

$167,860

$96/sq ft

Apr 11, 2012

Pending

—

Jan 2, 2012

Listed

$114/sq ft

BRIGHT MLS #1003802830

May 24, 2012

Sold

$167,860

$96/sq ft

Apr 6, 2012

Listing Removed

—

Jan 2, 2012

Listed

$200,000

$114/sq ft

Public Records

Aug 6, 1984

Sold

$77,500

$44/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2026

$4,359 (+5.3%)

2025

$4,140 (+5.4%)

2024

$3,929 (+5.4%)

$91,500 + $231,900

$323,400

2023

$3,728 (+6.0%)

2022

$3,516

2021

$3,516 (−0.6%)

$91,500 + $134,300

$225,800

2020

$3,539 (−1.4%)

$91,500 + $134,300

$225,800

2019

$3,589 (+0.6%)

$91,500 + $134,300

$225,800

2018

$3,566 (+3.3%)

$101,500 + $128,000

$229,500

2017

$3,452 (−0.2%)

$101,500 + $128,000

$229,500

2015

$3,459 (+0.8%)

2014

$3,432

$101,500 + $126,700

$228,200

2013

$3,432

2012

$3,432 (−6.9%)

2011

$3,688 (+162.2%)

2010

$1,406 (−47.3%)

2009

$2,668

Tax history for 107 Rolling Rd

Year

Property tax

Land + Additions

Assessment*

2026

$4,359 (+5.3%)

2025

$4,140 (+5.4%)

2024

$3,929 (+5.4%)

$91,500 + $231,900

$323,400

2023

$3,728 (+6.0%)

2022

$3,516

2021

$3,516 (−0.6%)

$91,500 + $134,300

$225,800

2020

$3,539 (−1.4%)

$91,500 + $134,300

$225,800

2019

$3,589 (+0.6%)

$91,500 + $134,300

$225,800

2018

$3,566 (+3.3%)

$101,500 + $128,000

$229,500

2017

$3,452 (−0.2%)

$101,500 + $128,000

$229,500

2015

$3,459 (+0.8%)

2014

$3,432

$101,500 + $126,700

$228,200

2013

$3,432

2012

$3,432 (−6.9%)

2011

$3,688 (+162.2%)

2010

$1,406 (−47.3%)

2009

$2,668

*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

0.37 Acres

Year renovated

—

Sq. Ft.

1,756

Year built

1970

Style

Single Family Residential

County

Kent County

APN

04 012488

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 3, 2026.

Property details

Parking

Parking Information
Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 3
# of Bedrooms On 1st Lower Level: 1

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full) On 1st Lower Level: 1
# of Bathrooms (Full) On All Lower Levels: 1
# of Bathrooms (Full): 3

Interior Information
Appliances: Built-In Microwave, Dishwasher, Dryer, Refrigerator, Stove, Washer, Water Heater, Disposal
Door Features: Sliding Glass
Flooring Type: Hardwood, Concrete
Interior Features: Attic, Combination Kitchen/Dining, Floor Plan - Open, Wood Floors
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: Dry Wall

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Recreation Room

Basement Information
Basement: Yes
Heated, Connecting Stairway, Full, Fully Finished, Walkout Level, Windows

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $134,300
Ownership Interest: Fee Simple
Property Condition: Excellent
Year Built Source: Assessor

Building Information
Construction Materials: Aluminum Siding, Brick, HardiPlank Type
Foundation Details: Block
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Patio(s)
Roof: Architectural Shingle
Structure Type: Detached
Window Features: Double Pane

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $91,500

Above Grade Information
Finished Sq.Ft.: 1,756
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
City/Town Tax: $978
County Tax: $2,560
Tax Assessed Value: $225,800
Tax Year: 2021
Tax Annual Amount: $3,538

Assessments Information
Year Assessed: 2021

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
200+ Amp Service
Forced Air
Heating Fuel: Propane - Owned
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public
Municipal Trash: Yes

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 follow Washington Avenue and make a right onto Greenwood Avenue. Make a left onto Rolling Road. Last home on right before the bend.
Municipality: Chestertown

Public facts

Beds: —
Baths: 3.0
Sq. Ft.: 1,756
Stories: —
Lot Size: 0.37 acres
Style: Single Family Residential
Year Built: 1970
Year Renovated: —
County: Kent County
APN: 04 012488

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 • 0.4mi

3/10

Kent County High School

Public 9-12 • Assigned • 4.6mi

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

$391,000 – $474,000

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

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OPEN SAT, 11AM TO 1PM

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COMING SOON

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(410) 778-0330

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Home values near 107 Rolling Rd

Data from public records.

Address	Redfin Estimate
111 Rolling Road, Chestertown, MD - Beds \| 3 Baths \| 2100 Sq. Ft.	$409,293
117 Rolling Road, Chestertown, MD - Beds \| 3.5 Baths \| 2122 Sq. Ft.	$380,999

Address	Redfin Estimate
201 Rolling Road, Chestertown, MD 4 Beds \| 2 Baths \| 2652 Sq. Ft.	$392,378
199 Rolling Road, Chestertown, MD - Beds \| 1.5 Baths \| 2223 Sq. Ft.	$392,330

Address	Redfin Estimate
109 Rolling Road, Chestertown, MD - Beds \| 1.5 Baths \| 1152 Sq. Ft.	$323,485
115 Rolling Road, Chestertown, MD - Beds \| 2.5 Baths \| 1108 Sq. Ft.	$362,390

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 107 Rolling Rd

Tax history for 107 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 107 Rolling Rd

More real estate resources