OFF MARKET

Off Market Oct 2023 for $349K

$392,352

Est. refi paymentEst. refi $2,329/mo

•

1,424

sq ft

101 School Rd, Chestertown, MD 21620

About this home

This house is adorable, immaculate and in move in condition. There are three bedrooms, 1.5 baths, with one bedroom being used as a den. The house and yard have been meticulously maintained, and it shows. The kitchen has been updated, and there is room for a cafe style table, just in case you don't want to use the more formal dining room. Major systems for the house have been updated as well. The living room is charming and is just off the kitchen and dining area. The bedrooms are generous, and the hallway bath has been updated. There is a sitting room, two large closets in the primary bathroom, which makes for a cozy oasis. This is truly a turnkey home with low maintenance, and such amazing curb appeal! The back shed is relatively new. Hardwood floors are in great condition - and the landscaping and curb appeal completes the picture! Improvements include bathroom was updated and radiant floor heating added, all of the windows have been replaced and are tilt-out (done 2016). Both doors and jams replaced in 2017. New roof in 2020, new AC in 2023, New furnace in 2015, and stove and refrigerator were replaced in 2019.

Single-familyProperty Type

1961Year Built

0.31 acresLot Size

$276Est. Price/Sq.Ft.

Listed by Retha Arrabal • Doug Ashley Realtors, LLC

•410-810-0010 (broker)

Bought with Grace Crockett • Doug Ashley Realtors, LLC

•410-810-0010 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDKE2003030

Redfin Estimate

$392,352

$43K since sold in October 2023$0 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.9% higher than the average sale price ($319K) of 6 comparable homes.

SOLD AUG 14, 2026
$318,000
A
3 beds2 baths1,397 sq ft
109 Cedar St, Chestertown, MD 21620
SOLD AUG 21, 2026
$289,000
B
3 beds1 bath1,248 sq ft
517 Round Top Rd, Chestertown, MD 21620
SOLD JUN 12, 2026
$249,000
C
3 beds1 bath1,356 sq ft
112 Elm St, Chestertown, MD 21620
SOLD JUN 17, 2026
$325,000
D
3 beds1 bath1,427 sq ft
202 Valley Rd, Chestertown, MD 21620
SOLD JAN 16, 2026
$364,000
E
3 beds2 baths1,532 sq ft
303 E Campus Ave, Chestertown, MD 21620
SOLD MAY 1, 2026
$370,000
F
3 beds1.5 baths1,404 sq ft
217 Philosophers Ter, Chestertown, MD 21620

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Earn from this home

Refinance

Est. cash available

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Rent

$2,280/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

98.4%

+0.3% MoM

Median sale price

$355K

$7K MoM

Avg. days on market

48d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

NEW 14 HRS AGO
$289,000
3 beds2 baths1,056 sq ft
8732 Elm Rd, Chestertown, MD 21620
(410) 778-0330
NEW 23 HRS AGO
$1,295,000
4 beds3.5 baths3,383 sq ft
8276 Broad Neck Rd, Chestertown, MD 21620
(410) 810-3900
COMING SOON
$200,000
4 beds1 bath1,816 sq ft
223 Mount Vernon Ave, Chestertown, MD 21620
(443) 215-4663
$300,000
3 beds1 bath960 sq ft
104 Lincoln Dr, Chestertown, MD 21620
(443) 274-1900
COMING SOON
$568,900
4 beds2.5 baths2,464 sq ft
329 Union Church Rd, Chestertown, MD 21620
(443) 215-4663
$275,000
3 beds1 bath975 sq ft
7482 Poplar Ave, Chestertown, MD 21620
(301) 970-2447
$345,000
3 beds1.5 baths1,398 sq ft
217 Edmore Rd, Chestertown, MD 21620
(410) 810-0010
$263,000
3 beds2 baths1,140 sq ft
115 Chester Arms Dr, Chestertown, MD 21620
(703) 378-8810
See all

Provided by Redfin

Sale history for 101 School Rd

Year

Property tax

Land + Additions

Assessment*

2026

$2,782 (+5.4%)

2025

$2,640 (+5.0%)

2024

$2,514 (+6.1%)

$90,800 + $77,900

$168,700

2023

$2,369 (+5.7%)

2022

$2,241

2021

$2,241 (−0.6%)

$90,800 + $53,100

$143,900

2020

$2,255

$90,800 + $53,100

$143,900

2019

$2,257 (+0.6%)

$90,800 + $53,100

$143,900

2018

$2,242 (+3.3%)

$100,800 + $43,500

$144,300

2017

$2,170 (−0.7%)

$100,800 + $43,500

$144,300

2015

$2,185 (+95.9%)

$100,800 + $44,500

$145,300

2014

$1,115 (−47.9%)

$100,800 + $55,400

$156,200

2013

$2,142 (+4.6%)

2012

$2,048 (−27.6%)

2011

$2,829 (+213.0%)

2010

$904 (−47.3%)

2009

$1,714

Tax history for 101 School Rd

Year

Property tax

Land + Additions

Assessment*

2026

$2,782 (+5.4%)

2025

$2,640 (+5.0%)

2024

$2,514 (+6.1%)

$90,800 + $77,900

$168,700

2023

$2,369 (+5.7%)

2022

$2,241

2021

$2,241 (−0.6%)

$90,800 + $53,100

$143,900

2020

$2,255

$90,800 + $53,100

$143,900

2019

$2,257 (+0.6%)

$90,800 + $53,100

$143,900

2018

$2,242 (+3.3%)

$100,800 + $43,500

$144,300

2017

$2,170 (−0.7%)

$100,800 + $43,500

$144,300

2015

$2,185 (+95.9%)

$100,800 + $44,500

$145,300

2014

$1,115 (−47.9%)

$100,800 + $55,400

$156,200

2013

$2,142 (+4.6%)

2012

$2,048 (−27.6%)

2011

$2,829 (+213.0%)

2010

$904 (−47.3%)

2009

$1,714

*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

1.5

Stories

Lot width

—

Lot depth

—

Lot size

0.31 Acres

Year renovated

—

Sq. Ft.

1,424

Year built

1961

Style

Single Family Residential

County

Kent County

APN

04 010205

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 3, 2026.

Property details

Parking

Parking Information
Paved Driveway
Driveway, On Street

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 1

Interior Information
Appliances: Dishwasher, Washer/Dryer Stacked, Exhaust Fan, Range Hood, Refrigerator, Stove
Interior Features: Floor Plan - Traditional, Kitchen - Eat-In, Wainscotting, Kitchen - Table Space, Wood Floors, Dining Area
Living Area Sq.Ft. Source: Assessor

Room Information
Laundry Type: Main Floor

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Horse: No
Improvement Assessed Value: $77,900
Ownership Interest: Fee Simple
Property Condition: Excellent
Year Built Source: Assessor

Building Information
Construction Materials: Mixed, Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Structure Type: Detached
Other Structures: Shed
Building Not Winterized

Exterior Information
Street Lights

Lot Information
Lot Features: Front Yard, Landscaping, Level, Rear Yard
Tidal Water: No

Land Information
Land Assessed Value: $90,800

Above Grade Information
Finished Sq.Ft.: 1,424
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
City/Town Tax: $623
County Tax: $1,617
Tax Assessed Value: $152,167
Tax Year: 2022
Tax Annual Amount: $2,241

Assessments Information
Year Assessed: 2023

Utilities

Utilities Information
Fiber Optic
Central Air
Cooling Type: Central A/C, Ceiling Fan(s)
Cooling Fuel: Electric
Heat Pump(s), Baseboard - Hot Water, Radiant
Heating Fuel: Oil
Hot Water: Oil
Sewer Septic: Public Sewer
Under Ground
Water Source: Public
Municipal Trash: Yes

Location

School Information
Elementary School: GARNETT
Middle Or Junior School: CHESTERTOWN
High School: KENT
School District Name: KENT COUNTY PUBLIC SCHOOLS
Elementary School Source: Listing Agent
Middle School Source: Listing Agent
High School Source: Listing Agent
School District Source: Listing Agent

Location Information
In City Limits
Directions: Follow 213 N from Centreville to Chestertown, make a right onto Philosophers Terrace and make a right on Campus Ave. Follow to a left onto Rolling Rd, and the first left is School Rd. Property is on the left.
Municipality: Chestertown

Public facts

Beds: —
Baths: 1.5
Sq. Ft.: 1,424
Stories: 1.0
Lot Size: 0.31 acres
Style: Single Family Residential
Year Built: 1961
Year Renovated: —
County: Kent County
APN: 04 010205

Home facts updated by county records on Aug 3, 2026

Around this home

Schools

H. H. Garnett Elementary School

Public PreK-5 • Assigned • 0.6mi

6/10

Kent County Middle School

Public 6-8 • Assigned • 0.1mi

3/10

Kent County High School

Public 9-12 • Assigned • 4.8mi

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

$373,000 – $452,000

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

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New listings for sale in 21620

NEW 14 HRS AGO

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8732 Elm Rd, Chestertown, MD 21620

(410) 778-0330

NEW 23 HRS AGO

$1,295,000

4 beds3.5 baths3,383 sq ft

8276 Broad Neck Rd, Chestertown, MD 21620

(410) 810-3900

COMING SOON

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223 Mount Vernon Ave, Chestertown, MD 21620

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COMING SOON

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329 Union Church Rd, Chestertown, MD 21620

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7482 Poplar Ave, Chestertown, MD 21620

(301) 970-2447

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3 beds1.5 baths1,398 sq ft

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(410) 810-0010

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(703) 378-8810

Home values near 101 School Rd

Data from public records.

Address	Redfin Estimate
107 School Road, Chestertown, MD 3 Beds \| 1 Baths \| 1356 Sq. Ft.	$304,934
111 School Road, Chestertown, MD 3 Beds \| 1 Baths \| 1296 Sq. Ft.	$280,993

Address	Redfin Estimate
113 School Road, Chestertown, MD 3 Beds \| 1 Baths \| 988 Sq. Ft.	$246,841
109 School Road, Chestertown, MD - Beds \| 2 Baths \| 1230 Sq. Ft.	$353,893

Address	Redfin Estimate
102 School Road, Chestertown, MD - Beds \| 1.5 Baths \| 1674 Sq. Ft.	$331,482
103 School Road, Chestertown, MD 2 Beds \| 1 Baths \| 1232 Sq. Ft.	$304,264

Property information provided by BRIGHT MLS when last listed in 2023. 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 101 School Rd

Tax history for 101 School 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 101 School Rd

More real estate resources