107 Rolling Road

Closed 10/21/21

Sold

Last Sold Price

$337,500

4 beds3 baths1,756 sqft

107 Rolling Rd, Chestertown, MD 21620

Single FamilyProperty Type

0.37 acresLot Size

1970Year Built

$192/sq ftPrice per sq ft

Description

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!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!

Listed by: Douglas J Ashley 410.708.0480 doug@dougashleyrealtors.com • Doug Ashley Realtors, LLC

Listing closed: 10/21/2021 12:00 AM • Source: BRIGHT, MLS#: MDKE2000200

Recent comparable sales

Median sold price

$359,900

Avg days on market

Sale-to-list ratio

94.6%

a living room with furniture and a flat screen tv

1/22

$364,900

Sold 02/26/26

4
Bedrooms: 3
Bathrooms: 1,936
Square Feet: 0.09
Acres

108 Flying Cloud Drive, Chestertown, MD 21620

1/34

$250,000

Sold 12/06/24

4
Bedrooms: 3
Bathrooms: 1,632
Square Feet: 0.55
Acres

305 Lincoln Drive, Chestertown, MD 21620

1/84

$440,000

Sold 03/13/25

4
Bedrooms: 3
Bathrooms: 1,848
Square Feet: 0.49
Acres

312 Princess Anne Drive, Chestertown, MD 21620

1/27

$325,000

Sold 12/12/24

4
Bedrooms: 2
Bathrooms: 1,500
Square Feet: 0.34
Acres

228 Concord Road, Chestertown, MD 21620

a front view of a house with a yard and trees

1/30

$433,000

Sold 09/01/26

4
Bedrooms: 2
Bathrooms: 1,656
Square Feet: 0.15
Acres

222 Mt Vernon Avenue, Chestertown, MD 21620

1/25

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3
Bedrooms: 3
Bathrooms: 1,512
Square Feet: 0.34
Acres

473 Pear Tree Point Road, Chestertown, MD 21620

a front view of a house with a yard and garage

1/33

$360,000

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3
Bedrooms: 3
Bathrooms: 1,724
Square Feet: 0.11
Acres

216 Silver Heel Road, Chestertown, MD 21620

1/18

$335,000

Sold 10/03/25

3
Bedrooms: 3
Bathrooms: 1,856
Square Feet: 0.09
Acres

110 Flying Cloud Drive, Chestertown, MD 21620

1/42

$324,000

Sold 08/14/26

3
Bedrooms: 3
Bathrooms: 1,896
Square Feet: 0.09
Acres

102 Flying Cloud Drive, Chestertown, MD 21620

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Location

Listing Courtesy of Doug Ashley Realtors, LLC

Sold By Coldwell Banker Chesapeake Real Estate Company

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$2,039 per month

30 year fixed, 6.71% Interest

Principal and Interest

$1,744

Property Taxes

$295

HOA Dues

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Property Information for 107 Rolling Road

Property Details

Taxes: $3,538 / year
MLS Type: Residential / Fee Simple
County: Kent County
Tax ID Number: 1504012488
Ownership: Fee Simple
Condo Coop Association: No
HOA: No
Structure Type: Detached
Style: Split Level
Levels/Stories: 2
Waterfront: No
Garage: No
Subdivision: COLLEGE HEIGHTS
Subdivision: COLLEGE HEIGHTS (KENT MD)
Legal Subdivision: COLLEGE HEIGHTS
Municipality: Chestertown
Central Air: Yes
Basement: Yes
Above Grade Finished SQFT: 1,756.00
Above Grade Fin SQFT Source: Assessor
Below Grade Finished SQFT: .00
Below Grade Fin SQFT Source: Assessor
Below Grade Unfinished SQFT: .00
Below Grade Unfin SQFT Source: Assessor
Total Below Grade SQFT: .00
Total Below Grade SQFT Source: Assessor
New Construction: No
Property Condition: Excellent

Building Information

Stories: 2
Year Built: 1970
Lot Size: 0.37 AC / 16,150 SF

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: 2021
Tax Assessed Value: $225,800

Year Assessed: 2021
County Tax: $2,560
Improvement Assessed Value: $134,300
City Town Tax: $978
Land Assessed Value: $91,500
Clean Green Assessed: No
Municipal Trash: Yes
Land Use Code: 110
Zoning: R-2
Tax Lot: 23
Automatically Update Tax Values Y/N: Yes
TaxDataUpdatedYN: Yes

Lease Information

Concessions: No

Rooms

Main

# Bedrooms Count Main Level: 3
# Bathrooms Count Main Level: 2

# Bathrooms Full Main Level: 2

All Lower Levels

# Bedrooms All Lower Levels: 1
# Bathrooms All Lower Levels: 1

# Bathrooms Full All Lower Levels: 1

Lower Level 1

# Bedrooms Lower Level: 1
# Bathrooms Lower Level: 1

# Bathrooms Full Lower Level: 1

Rooms

Room List: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Recreation Room
Stories: Lower 1, Main

Building Info

Total Finished SQFT: 1,756.00
Total Finished SQFT Source: Assessor

Tax Total Finished SQFT: 1,756.00
Total SQFT: 1,756.00
Total SQFT Source: Assessor
Construction Materials: Aluminum Siding, Brick, HardiPlank Type
Roof: Architectural Shingle
Ext Main Mid-res: http://bright-media01.prd.brightmls.com/bright/images/0000/8008/6264/2262/800862642262_512_384_WM_VTc1w2nQ7qVRARct.jpg
Wall and Ceiling Types: Dry Wall
Flooring Type: Hardwood, Concrete
Basement Type: Heated, Connecting Stairway, Full, Fully Finished, Walkout Level, Windows
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-Main Level-2, Bedrooms-Lower Level 1-1, Bathrooms Full-Lower Level 1-1
# Bathrooms Full: 3
Other Structure: Above Grade, Below Grade

Lot / Land Information

Lot Size Source: Assessor
Parcel ID: 4505066

Parking

Type Of Parking: Driveway

Interior Features

Interior Features: Attic, Combination Kitchen/Dining, Floor Plan - Open, Wood Floors
Appliances: Built-In Microwave, Dishwasher, Dryer, Refrigerator, Stove, Washer, Water Heater, Disposal

Accessibility Features: None
Door Features: Sliding Glass
Window Features: Double Pane
Virtual Tour URL Unbranded: https://my.matterport.com/show/?m=tHqGEBdBZyk&mls=1

Exterior Features

Outdoor Living Structures: Deck(s), Patio(s)
Pool: No Pool

Utilities

Heating: Yes
Cooling Type: Central A/C

Cooling Fuel: Electric
Heating Type: Forced Air
Heating Fuel: Propane - Owned
Hot Water: Electric
Water Source: Public
Sewer Septic: Public Sewer
Electric Service: 200+ Amp Service

Confidential Data

Listing Office

List Agent AOR: Bay Area Association of REALTORS
List Agent URL: www.dougashleyrealtors.com

Property History for 107 Rolling Road

Date	Event & Source	Price	Appreciation
Oct 21, 2021	Closed (Public Record) Public Record #1479729704	$337,500	+7.7% / yr
Oct 21, 2021	Closed BRIGHT #MDKE2000200	$337,500	—
Oct 15, 2021	Pending BRIGHT #MDKE2000200		—
Aug 22, 2021	Active Under Contract BRIGHT #MDKE2000200		—
Aug 21, 2021	Pending BRIGHT #MDKE2000200		—
Aug 21, 2021	Active Under Contract BRIGHT #MDKE2000200		—
Jul 16, 2021	Listed (Active) BRIGHT #MDKE2000200	$337,500	—
May 24, 2012	Closed (Public Record) Public Record #332101343	$167,860	—
May 24, 2012	Closed BRIGHT #1003802830	$167,860	—
Apr 6, 2012	Pending BRIGHT #1003802830		—
Jan 2, 2012	Listed (Active) BRIGHT #1003802830	$200,000	—

Date	Event & Source	Price
10/21/2021	Closed (Public Record) Public Record #1479729704	$337,500 +7.7% / yr
10/21/2021	Closed BRIGHT #MDKE2000200	$337,500
10/15/2021	Pending BRIGHT #MDKE2000200	—
08/22/2021	Active Under Contract BRIGHT #MDKE2000200	—
08/21/2021	Pending BRIGHT #MDKE2000200	—
08/21/2021	Active Under Contract BRIGHT #MDKE2000200	—
07/16/2021	Listed (Active) BRIGHT #MDKE2000200	$337,500
05/24/2012	Closed (Public Record) Public Record #332101343	$167,860
05/24/2012	Closed BRIGHT #1003802830	$167,860
04/06/2012	Pending BRIGHT #1003802830	—
01/02/2012	Listed (Active) BRIGHT #1003802830	$200,000

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

Public Records for 107 Rolling Road

Taxable ValueLand-Additions-Total-

Tax Record2026$4,359 ($363 / month)

Home Facts

Beds0Baths3Total Finished SqFt1,756 SqFtAbove Grade Finished SqFt1,756 SqFtLot Size16,150 SqFtStyleSingle Family ResidenceYear Built1970Year Renovated1970ZoningR-2CountyKENTAPN04-012488

Schools near 107 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	0.8 mi
3/10	Kent County Middle School	Public - Serves this home	6 to 8	0.4 mi
5/10	Kent County High School	Public - Serves this home	9 to 12	4.6 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	0.1 mi
NR	Chester River Adventist School	Private - Nearby school	1 to 8	0.7 mi
NR	Radcliffe Creek School	Private - Nearby school	K to 8	0.9 mi


Rating	School	Distance
6/10	H. H. Garnett Elementary School PublicPK to 5 Nearby school	0.8 mi
3/10	Kent County Middle School Public6 to 8 Serves this home	0.4 mi
5/10	Kent County High School Public9 to 12 Serves this home	4.6 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	0.1 mi
NR	Chester River Adventist School Private1 to 8 Nearby school	0.7 mi
NR	Radcliffe Creek School PrivateK to 8 Nearby school	0.9 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: 107 Rolling Road, Chestertown, MD 21620	$337,500	4	3	1,756	16,150
414 Bell Avenue, Chestertown, MD 21620	$237,000	4	3	2,080	17,290
105 Holly Court, Chestertown, MD 21620	$425,000	3	2	2,285	43,996
115 Rolling Road, Chestertown, MD 21620	–	–	2.5	1,108	18,079
111 Rolling Road, Chestertown, MD 21620	–	–	3	1,120	16,150
412 Bell Avenue, Chestertown, MD 21620	–	–	1.5	1,720	13,500
411 Bell Avenue, Chestertown, MD 21620	$318,000	3	3	2,146	19,575
103 Holly Court, Chestertown, MD 21620	$250,000	–	2.5	1,524	13,600
410 Bell Avenue, Chestertown, MD 21620	$205,000	3	2	1,248	14,000
415 Greenwood Avenue, Chestertown, MD 21620	$310,000	3	2	1,198	11,211
501 Morgnec Road, Chestertown, MD 21620	$116,000	–	–	–	173,804
401 Morgnec Road, Chestertown, MD 21620	–	–	–	18,144	310,147
413 Greenwood Avenue, Chestertown, MD 21620	$235,000	4	2	1,590	14,500
409 Bell Avenue, Chestertown, MD 21620	$369,000	5	3	3,500	25,375
411 Greenwood Avenue, Chestertown, MD 21620	$415,000	3	3	1,676	12,250
111 Cedar Street, Chestertown, MD 21620	$200,000	3	2	1,800	12,600

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Listing Courtesy of Doug Ashley Realtors, 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 08/27/2022 05:54 AM

Chestertown, MD

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