4 Rolling Road

Closed 5/1/20

Last Sold Price

$145,000

3 beds2 baths1,950 sqft$74/sqft

4 Rolling Rd, Chestertown, MD 21620

Description

Own this home less than the cost to rent! 3 bedrooms, a remodeled full bathroom, living room, office, and wood floors complete the main level. The lower level features a spacious kitchen opening to the family room, another full bathroom, laundry room and ceramic tile floors. Outside is a driveway for off street parking, a fully fenced backyard, and large shed with workbench and electric. Within walking distance to Downtown, Washington College, the hospital, and the Chestertown dog park, this is a...Own this home less than the cost to rent! 3 bedrooms, a remodeled full bathroom, living room, office, and wood floors complete the main level. The lower level features a spacious kitchen opening to the family room, another full bathroom, laundry room and ceramic tile floors. Outside is a driveway for off street parking, a fully fenced backyard, and large shed with workbench and electric. Within walking distance to Downtown, Washington College, the hospital, and the Chestertown dog park, this is a great home for first time home buyers or investors looking for great return!

LISTING CLOSED: 05/01/2020 12:00 AM

Property Details for 4 Rolling Road

Status

Closed

MLS #

MDKE116100

Days on Market

Taxes

$2,081 / year

HOA Fees

Condo/Co-op Fees

Property Type

Single Family

MLS Type

Residential / Fee Simple

Year Built

1961

Lot Size

0.21 AC / 9,100 SF

County

Kent County

Tax ID Number

1504009622

Ownership

Fee Simple

Condo Coop Association

HOA

Structure Type

Detached

Style

Ranch/Rambler

Levels/Stories

Furnished

Waterfront

Garage

Subdivision

COLLEGE HEIGHTS

Subdivision

COLLEGE HEIGHTS (KENT MD)

Legal Subdivision

COLLEGE HEIGHTS

Municipality

Chestertown

Central Air

Yes

Basement

Yes

Room Count

Above Grade Finished SQFT

975.00

Above Grade Fin SQFT Source

Assessor

Below Grade Finished SQFT

975.00

Below Grade Fin SQFT Source

Estimated

Below Grade Unfinished SQFT

.00

Below Grade Unfin SQFT Source

Assessor

Total Below Grade SQFT

975.00

Total Below Grade SQFT Source

Estimated

New Construction

Property Condition

Very Good, Good

Recent comparable sales

Median sold price

$398,000

Avg days on market

Sale-to-list ratio

96.0%

1/39

$475,000

Sold 12/11/25

3
Bedrooms: 2
Bathrooms: 1,961
Square Feet: 0.42
Acres

101 Birch Run Road, Chestertown, MD 21620

1/35

$438,000

Sold 09/30/25

3
Bedrooms: 2
Bathrooms: 1,820
Square Feet: 0.34
Acres

206 Barroll Drive, Chestertown, MD 21620

1/25

$455,000

Sold 10/21/25

3
Bedrooms: 2
Bathrooms: 1,886
Square Feet: 0.37
Acres

224 Valley Road, Chestertown, MD 21620

1/2

$365,000

Sold 07/22/26

3
Bedrooms: 2
Bathrooms: 1,934
Square Feet: 0.4
Acres

521 North Kent Street, Chestertown, MD 21620

a view of a house with backyard sitting area and garden

1/2

$1,125,000

Sold 06/10/25

3
Bedrooms: 2
Bathrooms: 1,968
Square Feet: 0.81
Acres

101 Rivershore Road, Chestertown, MD 21620

1/30

$359,900

Sold 11/24/25

3
Bedrooms: 2
Bathrooms: 1,851
Square Feet: 0.51
Acres

221 Old Bridge Road, Chestertown, MD 21620

1/30

$380,000

Sold 03/14/25

3
Bedrooms: 2
Bathrooms: 1,800
Square Feet: 0.31
Acres

409 Riverview Road, Chestertown, MD 21620

1/27

$398,000

Sold 09/27/24

3
Bedrooms: 2
Bathrooms: 1,776
Square Feet: 0.69
Acres

209 Princess Anne Drive, Chestertown, MD 21620

1/37

$370,247

Sold 11/15/24

3
Bedrooms: 2
Bathrooms: 2,092
Square Feet: 0.76
Acres

201 Princess Anne Drive, Chestertown, MD 21620

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Location

Listing Courtesy of Select Land & Homes, LLC

Sold By Doug Ashley Realtors, LLC

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Building Information for 4 Rolling Road

Stories2Year Built1961Building Size-Lot Size0.21 AC / 9,100 SF

Payment Calculator

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OriginPoint Mortgage or Rocket Mortgage¹

$910 per month

30 year fixed, 6.55% Interest

Principal and Interest

$737

Property Taxes

$173

HOA Dues

The Payment Calculator is for illustrative purposes only.

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Property Information for 4 Rolling Road

Location

In City Limits: Yes
School District Name: KENT COUNTY PUBLIC SCHOOLS

School District County ID: 121139164602
SchoolDistrictSource: Listing Agent
County: KENT

Waterfront / Water Access

Water View: No
Water Access: No

Water Oriented: No
Navigable Water: No
Tidal Water: No
Riparian Rights Y/N: No

Association / Community Info

Senior Community: No

Taxes and Assessment

Tax Year: 2020
Tax Assessed Value: $133,100

Year Assessed: 2020
County Tax: $1,509
Improvement Assessed Value: $51,200
City Town Tax: $572
Land Assessed Value: $81,900
Clean Green Assessed: No
Land Use Code: 110
Agricultural Tax Due: No
Historic: No
Zoning: R-2
Tax Lot: 4
Automatically Update Tax Values Y/N: Yes
TaxDataUpdatedYN: Yes

Lease Information

Concessions: Yes
Concessions Amount: $4,400

Rooms

Main

# Bedrooms Count Main Level: 3
# Bathrooms Count Main Level: 1

# Bathrooms Full Main Level: 1

All Lower Levels

# Bathrooms All Lower Levels: 1
# Bathrooms Full All Lower Levels: 1

Lower Level 1

# Bathrooms Lower Level: 1
# Bathrooms Full Lower Level: 1

Rooms

Room List: Living Room, Bedroom 2, Bedroom 3, Kitchen, Family Room, Bedroom 1, Office
Stories: Lower 1, Main

Building Info

Building Level Count: 2
Total Finished SQFT: 1,950.00

Total Finished SQFT Source: Estimated
Tax Total Finished SQFT: 975.00
Total SQFT: 1,950.00
Total SQFT Source: Estimated
Construction Materials: Brick
Roof: Asphalt
Ext Main Mid-res: http://bright-media.brightmls.com/bright/images/0000/3022/0167/1035/302201671035_512_384_WM_J6DCUiXOGkpyt1yO.jpg
Wall and Ceiling Types: Dry Wall
Flooring Type: Ceramic Tile, Hardwood, Carpet
Basement Type: Daylight, Full, Fully Finished, Heated, Improved, Interior Access, Sump Pump, Windows
Basement Finished Percent: 100.00
Basement Footprint Percent: 100.00
Foundation Details: Block
Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bedrooms-Main Level-3, Bathrooms Full-Main Level-1, Bathrooms Full-Lower Level 1-1
# Bathrooms Full: 2
Other Structure: Above Grade, Below Grade

Lot / Land Information

Lot Size Source: Assessor
Lot Features: Front Yard, Rear Yard, Road Frontage

Road Surface Type: Gravel
Fencing: Rear
Parcel ID: 4504872
Additional Parcels: No

Parking

Type Of Parking: Driveway, Off Street

Interior Features

Interior Features: Attic, Bar, Carpet, Ceiling Fan(s), Family Room Off Kitchen, Pantry, Recessed Lighting, Wood Floors
Fireplace: No

Appliances: Dishwasher, Dryer, Cooktop, Microwave, Oven - Wall, Refrigerator, Water Heater
Accessibility Features: Doors - Swing In
Door Features: Double Entry
Window Features: Double Hung
Laundry Type: Lower Floor

Exterior Features

Exterior Features: Outbuilding(s), Sidewalks
Pool: No Pool

Utilities

Heating: Yes
Cooling Type: Heat Pump(s), Central A/C

Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Water Source: Public
Sewer Septic: Public Sewer

Confidential Data

Listing Office

List Agent AOR: Bay Area Association of REALTORS

Property History for 4 Rolling Road

Date	Event & Source	Price	Appreciation
May 1, 2020	Closed (Public Record) Public Record #672990205	$145,000	+0.2% / yr
May 1, 2020	Closed BRIGHT #MDKE116100	$145,000	—
Mar 3, 2020	Pending BRIGHT #MDKE116100		—
Jan 10, 2020	Listed (Active) BRIGHT #MDKE116100	$147,700	—
Oct 11, 2017	Withdrawn BRIGHT #1000083751	$149,000	—
Oct 11, 2017	Withdrawn BRIGHT #1000083751		—
Sep 20, 2016	Listed (Active) BRIGHT #1000083751	$174,900	—
Apr 19, 2006	Withdrawn BRIGHT #MDKE114180	$1,200	—
Apr 19, 2006	Withdrawn BRIGHT #MDKE114180		—
Sep 16, 2005	Listed (Active) BRIGHT #MDKE114180	$289,000	—
Jan 30, 2004	Closed BRIGHT #MDKE104272	$140,000	—
Jan 23, 2004	Closed (Public Record) Public Record #132905166	$140,000	+9.4% / yr
Nov 28, 2003	Pending BRIGHT #MDKE104272		—
Nov 5, 2003	Listed (Active) BRIGHT #MDKE104272	$150,000	—
Apr 5, 2002	Closed (Public Record) Public Record #85871915	$119,000	—
Apr 3, 2002	Closed BRIGHT #MDKE103082	$119,000	—
Mar 7, 2002	Pending BRIGHT #MDKE103082		—
Feb 13, 2002	Listed (Active) BRIGHT #MDKE103082	$115,000	—

Date	Event & Source	Price
05/01/2020	Closed (Public Record) Public Record #672990205	$145,000 +0.2% / yr
05/01/2020	Closed BRIGHT #MDKE116100	$145,000
03/03/2020	Pending BRIGHT #MDKE116100	—
01/10/2020	Listed (Active) BRIGHT #MDKE116100	$147,700
10/11/2017	Withdrawn BRIGHT #1000083751	$149,000
10/11/2017	Withdrawn BRIGHT #1000083751	—
09/20/2016	Listed (Active) BRIGHT #1000083751	$174,900
04/19/2006	Withdrawn BRIGHT #MDKE114180	$1,200
04/19/2006	Withdrawn BRIGHT #MDKE114180	—
09/16/2005	Listed (Active) BRIGHT #MDKE114180	$289,000
01/30/2004	Closed BRIGHT #MDKE104272	$140,000
01/23/2004	Closed (Public Record) Public Record #132905166	$140,000 +9.4% / yr
11/28/2003	Pending BRIGHT #MDKE104272	—
11/05/2003	Listed (Active) BRIGHT #MDKE104272	$150,000
04/05/2002	Closed (Public Record) Public Record #85871915	$119,000
04/03/2002	Closed BRIGHT #MDKE103082	$119,000
03/07/2002	Pending BRIGHT #MDKE103082	—
02/13/2002	Listed (Active) BRIGHT #MDKE103082	$115,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 4 Rolling Road

Taxable ValueLand-Additions-Total-

Tax Record2025$2,189 ($182 / month)

Home Facts

Beds0Baths1Total Finished SqFt975 SqFtAbove Grade Finished SqFt975 SqFtStories1Lot Size9,100 SqFtStyleSingle Family ResidenceYear Built1961Year Renovated1961ZoningR-2CountyKENTAPN04-009622

Schools near 4 Rolling Road

This home is within Kent County Public Schools.


Rating	School	Type	Grades	Distance
6/10	H. H. Garnett Elementary School	Public - Nearby school	PK to 5	0.7 mi
3/10	Kent County Middle School	Public - Serves this home	6 to 8	0.2 mi
5/10	Kent County High School	Public - Serves this home	9 to 12	4.9 mi
8/10	Rock Hall Elementary School	Public - Nearby school	PK to 5	11.2 mi
4/10	Galena Elementary School	Public - Nearby school	PK to 5	12.7 mi
NR	Chestertown Christian Academy	Private - Nearby school	PK to 12	0.4 mi
NR	Chester River Adventist School	Private - Nearby school	1 to 8	0.5 mi
NR	Radcliffe Creek School	Private - Nearby school	K to 8	1.1 mi


Rating	School	Distance
6/10	H. H. Garnett Elementary School PublicPK to 5 Nearby school	0.7 mi
3/10	Kent County Middle School Public6 to 8 Serves this home	0.2 mi
5/10	Kent County High School Public9 to 12 Serves this home	4.9 mi
8/10	Rock Hall Elementary School PublicPK to 5 Nearby school	11.2 mi
4/10	Galena Elementary School PublicPK to 5 Nearby school	12.7 mi
NR	Chestertown Christian Academy PrivatePK to 12 Nearby school	0.4 mi
NR	Chester River Adventist School Private1 to 8 Nearby school	0.5 mi
NR	Radcliffe Creek School PrivateK to 8 Nearby school	1.1 mi

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

Address	Sold price	Beds	Baths	Sqft	Lot (Sqft)
This home: 4 Rolling Road, Chestertown, MD 21620	$145,000	3	2	1,950	9,100
2 Rolling Road, Chestertown, MD 21620	–	–	1	888	9,100
1 Rolling Road, Chestertown, MD 21620	–	–	–	–	9,100
6 Rolling Road, Chestertown, MD 21620	$92,000	–	1	975	9,100
5 Rolling Road, Chestertown, MD 21620	$239,000	3	1	1,202	9,100
7 Rolling Road, Chestertown, MD 21620	$168,000	3	1	1,300	9,100
1 Reed Court, Chestertown, MD 21620	$398,000	4	3	1,854	11,567
415 East Campus Avenue, Chestertown, MD 21620	$14,000	–	1	1,813	21,750
3 Reed Court, Chestertown, MD 21620	$415,000	3	3	1,828	13,747
413 East Campus Avenue, Chestertown, MD 21620	–	–	1	1,468	21,750
2 Reed Court, Chestertown, MD 21620	$269,000	5	3	2,552	13,581
8 Rolling Road, Chestertown, MD 21620	–	–	1	1,523	9,100
5 Reed Court, Chestertown, MD 21620	$283,500	3	2	2,052	11,039
411 East Campus Avenue, Chestertown, MD 21620	$325,000	4	3	2,942	43,500
4 Reed Court, Chestertown, MD 21620	–	–	2.5	1,953	13,428
317 Rolling Road, Chestertown, MD 21620	–	–	2	1,192	15,000

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Listing Courtesy of Select Land & Homes, LLC

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 08/18/2022 02:34 AM

Chestertown, MD

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