Google satellite image for 21169 Chesapeake Rd, Chestertown, MD 21620

Off market aug 1986 for $14K

$501,461

Est. refi paymentEst. refi $99/mo

—

•

2 ba

•

1,920

sq ft

21169 Chesapeake Rd, Chestertown, MD 21620

About this home

21169 Chesapeake Rd is a 1,920 square foot house on a 0.55 acre lot with 2 bathrooms. - it last sold on August 08, 1986 for $14,500. Based on Redfin's Chestertown data, we estimate the home's value is $501,461.

Single-familyProperty Type

1991Year Built

0.55 acresLot Size

$261Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$501,461

$487K since sold in August 1986$5,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 53.8% higher than the average sale price ($326K) of 6 comparable homes.

SOLD SEP 11, 2026
$290,000
A
2 beds1.5 baths1,500 sq ft
21146 Montana Ave, Chestertown, MD 21620
SOLD MAR 5, 2026
$350,000
B
3 beds2 baths1,680 sq ft
21111 Texas Ave, Chestertown, MD 21620
SOLD OCT 2, 2026
$325,000
C
3 beds2 baths1,568 sq ft
5925 Williams St, Rock Hall, MD 21661
SOLD MAR 27, 2026
$350,000
D
3 beds2 baths1,942 sq ft
10751 Millbrook Dr, Chestertown, MD 21620
SOLD SEP 1, 2026
$316,000
E
3 beds2 baths1,412 sq ft
10720 Foreston Rd, Chestertown, MD 21620
SOLD JUL 16, 2026
$325,000
F
3 beds2 baths1,404 sq ft
10572 Watonga Rd, Chestertown, MD 21620

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Earn from this home

Sell

$470,592

Est. take-home

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Est. cash available

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Market trends in 21620, MD

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.4%

+0.3% MoM

Median sale price

$355K

$8K MoM

Avg. days on market

48d

0 days MoM

Recently sold homes

2 MoM

New listings for sale

3D WALKTHROUGH
$430,000
3 beds2.5 baths1,520 sq ft
206 N Mill St, Chestertown, MD 21620
(410) 778-0330
$325,000
5 beds2 baths1,802 sq ft
234 N Kent St, Chestertown, MD 21620
(410) 673-3344
$568,900
4 beds2.5 baths2,464 sq ft
329 Union Church Rd, Chestertown, MD 21620
(443) 215-4663
COMING SOON
$679,900
3 beds3.5 baths3,228 sq ft
8986 Orchard Dr, Chestertown, MD 21620
(410) 822-6665
$675,000
5 beds3 baths2,838 sq ft
212 Washington Ave, Chestertown, MD 21620
(410) 778-0330
$489,000
2 beds2 baths1,098 sq ft
105 N Water St #3, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$499,999
4 beds3.5 baths3,506 sq ft
331 Devon Dr, Chestertown, MD 21620
(410) 778-0330
See all

Provided by Redfin

Sale history for 21169 Chesapeake Rd

Year

Property tax

Land + Additions

Assessment*

2026

$6,418 (+2.8%)

2025

$6,241 (+2.9%)

2024

$6,064 (+0.4%)

2023

$6,037 (+1.3%)

$327,200 + $207,500

$534,700

2022

$5,957 (+0.4%)

2021

$5,930 (−0.5%)

2020

$5,961 (+0.4%)

$327,200 + $200,400

$527,600

2019

$5,938 (+0.4%)

2018

$5,916

$327,200 + $194,500

$521,700

2017

$5,916 (−0.2%)

$327,200 + $194,500

$521,700

2015

$5,930 (+0.5%)

2014

$5,900 (+0.5%)

2013

$5,870

2012

$5,870

2011

$5,870 (−14.5%)

2010

$6,862 (+19.1%)

2009

$5,763

Tax history for 21169 Chesapeake Rd

Year

Property tax

Land + Additions

Assessment*

2026

$6,418 (+2.8%)

2025

$6,241 (+2.9%)

2024

$6,064 (+0.4%)

2023

$6,037 (+1.3%)

$327,200 + $207,500

$534,700

2022

$5,957 (+0.4%)

2021

$5,930 (−0.5%)

2020

$5,961 (+0.4%)

$327,200 + $200,400

$527,600

2019

$5,938 (+0.4%)

2018

$5,916

$327,200 + $194,500

$521,700

2017

$5,916 (−0.2%)

$327,200 + $194,500

$521,700

2015

$5,930 (+0.5%)

2014

$5,900 (+0.5%)

2013

$5,870

2012

$5,870

2011

$5,870 (−14.5%)

2010

$6,862 (+19.1%)

2009

$5,763

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Property details

Interior

Bathroom Information
# of Full Baths: 2

Heating & Cooling
Air Conditioning Type: Split System
Heating Type: Hot Air

Fireplace Information
# of Fireplaces: 1
Fireplace Type: 3 Story Brick
Has Fireplace

Exterior

Exterior Information
Building Style Type: Conventional
Building Construction Quality: Fair
Exterior Wall: Frame
Building Type: Single Family

Property Information
Subdivision Name: TOLCHESTER ESTATES
Living Sq. Ft: 1,920
Building Sq. Ft: 1,920
# of Stories: 2.5
Stories Type: 2 1/2
Legal Description: L 6 BK H & 0.368 PL2 21169 CHESAPEAKE RD TOLCHESTER ESTATES

Lot Information
# of Buildings: 2
Land Sq. Ft: 24,000
Legal Lot Number: 6
Acres: 0.551
Zoning Code: CAR
State Use Description: RESIDENTIAL

Location Information
Parcel Location Influence: Waterfront

Utility Information
Sewer Type: Public
Water Service Type: Private

Financial

Assessor Information
Assessment Year: 2026
Tax District County: 06

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,920
Stories: 2.5
Lot Size: 0.55 acres
Style: Single Family Residential
Year Built: 1991
Year Renovated: —
County: Kent County
APN: 06 008003

Home facts updated by county records on Aug 3, 2026

Around this home

Schools

Rock Hall Elementary School

Public PreK-5 • Assigned • 6.1mi

8/10

Kent County Middle School

Public 6-8 • Assigned • 9.5mi

3/10

Kent County High School

Public 9-12 • Assigned • 8.9mi

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 105° expected this year, 15 days in 30 years

6/10 Wind Factor

70% 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 9.3 hours in June and 4.6 hours in December, which is comparable to the U.S. average for solar exposure.

9.3 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$477,000 – $577,000

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Nearby similar homes

$375,000

3 beds2 baths1,326 sq ft

5686 S Main St, Rock Hall, MD 21661

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5 beds3.5 baths3,816 sq ft

103 Sutton Way, Chestertown, MD 21620

(410) 673-3344

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3 beds1 bath1,056 sq ft

10540 Worton Rd, Worton, MD 21678

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3 beds2 baths1,232 sq ft

8706 Elm Rd, Chestertown, MD 21620

(410) 810-0010

NEW CONSTRUCTION

$1,099,900

4 beds3.5 baths2,784 sq ft

#25 Landing Ln, Chestertown, MD 21620

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$635,000

Land— sq ft

108 Little Harbor Way, Chestertown, MD 21620

(410) 275-2118

New listings for sale in 21620

3D WALKTHROUGH

$430,000

3 beds2.5 baths1,520 sq ft

206 N Mill St, Chestertown, MD 21620

(410) 778-0330

$325,000

5 beds2 baths1,802 sq ft

234 N Kent St, Chestertown, MD 21620

(410) 673-3344

$568,900

4 beds2.5 baths2,464 sq ft

329 Union Church Rd, Chestertown, MD 21620

(443) 215-4663

COMING SOON

$679,900

3 beds3.5 baths3,228 sq ft

8986 Orchard Dr, Chestertown, MD 21620

(410) 822-6665

$675,000

5 beds3 baths2,838 sq ft

212 Washington Ave, Chestertown, MD 21620

(410) 778-0330

$489,000

2 beds2 baths1,098 sq ft

105 N Water St #3, Chestertown, MD 21620

(410) 778-0330

COMING SOON

$499,999

4 beds3.5 baths3,506 sq ft

331 Devon Dr, Chestertown, MD 21620

(410) 778-0330

Home values near 21169 Chesapeake Rd

Data from public records.

Address	Redfin Estimate
21179 Chesapeake Road, Chestertown, MD 1 Beds \| 1 Baths \| 624 Sq. Ft.	$207,011
21154 Alabama Avenue, Chestertown, MD - Beds \| 2 Baths \| 2258 Sq. Ft.	$347,510

Address	Redfin Estimate
21180 Chesapeake Road, Chestertown, MD 3 Beds \| 2 Baths \| 1456 Sq. Ft.	$356,913
8901 S Bayview Drive, Chestertown, MD - Beds \| 2.5 Baths \| 1833 Sq. Ft.	$362,501

Address	Redfin Estimate
21254 Chesapeake Road, Chestertown, MD - Beds \| 1 Baths \| 784 Sq. Ft.	$221,642
21174 Georgia Avenue, Chestertown, MD 4 Beds \| 3 Baths \| 2643 Sq. Ft.	$1,126,984

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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 21169 Chesapeake Rd

Tax history for 21169 Chesapeake Rd

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 21169 Chesapeake Rd

More real estate resources