Google street view image for 444 Pear Tree Point Rd, Chestertown, MD 21620

OFF MARKET

$398,627

—

•

1 ba

•

1,204

sq ft

444 Pear Tree Point Rd, Chestertown, MD 21620

About this home

444 Pear Tree Point Rd is a 1,204 square foot house on a 0.43 acre lot with 1 bathroom. Based on Redfin's Chestertown data, we estimate the home's value is $398,627.

Single-familyProperty Type

1953Year Built

0.43 acresLot Size

$331Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$398,627

$14K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 43% higher than the average sale price ($279K) of 6 comparable homes.

SOLD APR 14, 2026
$220,000
A
4 beds1 bath1,248 sq ft
513 Round Top Rd, Chestertown, MD 21620
SOLD BY REDFIN JUL 30, 2026
$300,000
B
4 beds2 baths1,325 sq ft
304 Hadaway Dr, Chestertown, MD 21620
SOLD JUN 17, 2026
$325,000
C
3 beds1 bath1,427 sq ft
202 Valley Rd, Chestertown, MD 21620
SOLD MAY 14, 2026
$278,500
D
3 beds1 bath— sq ft
107 Longfellow Dr, Chestertown, MD 21620
SOLD MAY 27, 2026
$300,000
E
3 beds1 bath1,408 sq ft
154 Longfellow Dr, Chestertown, MD 21620
SOLD JUN 12, 2026
$249,000
F
3 beds1 bath1,356 sq ft
112 Elm St, Chestertown, MD 21620

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

Market trends in 21620, MD

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.0%

1.0% MoM

Median sale price

$362K

$17K MoM

Avg. days on market

46d

14 days MoM

Recently sold homes

9 MoM

New listings for sale

VIDEO TOUR
$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
$369,000
2 beds1.5 baths1,036 sq ft
101 S College Ave, Chestertown, MD 21620
(410) 810-0010
$649,000
4 beds3 baths2,864 sq ft
22400 Great Oak Landing Rd, Chestertown, MD 21620
(410) 778-0330
FOR SALE BY OWNER
$435,000
3 beds2 baths1,956 sq ft
233 Duke of Kent St, Chestertown, MD 21620
$524,900
3 beds2.5 baths2,076 sq ft
1003 Twin Ct, Chestertown, MD 21620
(410) 778-3779
$295,000
1 bed1 bath— sq ft
117 N Water St Unit 3B, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$304,000
3 beds2 baths1,232 sq ft
7464 Shortall St, Chestertown, MD 21620
(410) 476-2201
$299,900
3 beds1 bath1,056 sq ft
124 Wilton Rd, Chestertown, MD 21620
(410) 810-0010
See all

Provided by Redfin

Sale history for 444 Pear Tree Point Rd

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2025

$4,167 (+8.2%)

2024

$3,851 (+8.9%)

$309,300 + $126,700

$436,000

2023

$3,535 (+9.8%)

2022

$3,219 (−1.8%)

2021

$3,277

$234,300 + $101,100

$335,400

2020

$3,277 (−11.9%)

$234,300 + $101,100

$335,400

2019

$3,720 (+5.4%)

$234,300 + $101,100

$335,400

2018

$3,530 (+5.7%)

$291,100 + $90,500

$381,600

2017

$3,339 (+6.0%)

2016

$3,149

$234,300 + $87,800

$322,100

2015

$3,149 (−22.0%)

$234,300 + $87,800

$322,100

2014

$4,036

$328,100 + $86,500

$414,600

2013

$4,036 (+0.7%)

2012

$4,006 (−14.1%)

2011

$4,664 (+8.8%)

2010

$4,289 (+10.9%)

2009

$3,868

Tax history for 444 Pear Tree Point Rd

Year

Property tax

Land + Additions

Assessment*

2025

$4,167 (+8.2%)

2024

$3,851 (+8.9%)

$309,300 + $126,700

$436,000

2023

$3,535 (+9.8%)

2022

$3,219 (−1.8%)

2021

$3,277

$234,300 + $101,100

$335,400

2020

$3,277 (−11.9%)

$234,300 + $101,100

$335,400

2019

$3,720 (+5.4%)

$234,300 + $101,100

$335,400

2018

$3,530 (+5.7%)

$291,100 + $90,500

$381,600

2017

$3,339 (+6.0%)

2016

$3,149

$234,300 + $87,800

$322,100

2015

$3,149 (−22.0%)

$234,300 + $87,800

$322,100

2014

$4,036

$328,100 + $86,500

$414,600

2013

$4,036 (+0.7%)

2012

$4,006 (−14.1%)

2011

$4,664 (+8.8%)

2010

$4,289 (+10.9%)

2009

$3,868

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

Zoning

NC-20

Neighborhood Conservation-20 District

There are several varieties of NC Districts. The NC Districts are intended to preserve the character, density, and scale of existing residential neighborhoods. The NC Districts allow existing neighborhoods to conform to this Chapter 18:1, and they allow for in-fill development to be compatible with the surrounding area. NC Districts are designated for existing residential developments as follows: NC-20: 20,000 sq ft average lot size.; All NC District regulations apply to NC Districts with a T designation on the Zoning Maps; except that single-wide manufactured homes are a permitted use within NC-T Districts.

Permitted uses

Include but are not limited to:

Equestrian facility
Housing-Single unit
Housing-Multiple units
Public service
Recreation
Housing-Mobile home park

Property details

Interior

Bathroom Information
# of Full Baths: 1

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

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

Exterior

Exterior Information
Building Construction Quality: Fair
Exterior Wall: Aluminum/Vinyl
Building Type: Single Family

Property Information
Subdivision Name: PEAR TREE POINT FARM
Living Sq. Ft: 1,204
Building Sq. Ft: 1,204
# of Stories: 1
Stories Type: 1
Legal Description: LOT 18750 SQ FT PEAR TREE PT RD E/CHESTERTOWN

Parking & Garage Information
Parking Type: Detached Frame Garage
Garage/Parking Sq. Ft: 483
Garage / Carport Type: Detached Frame

Lot Information
# of Buildings: 1
Land Sq. Ft: 18,750
Legal Lot Number: 8
Acres: 0.4304
Depth Footage: 250
Front Footage: 75
Zoning Code: NC20
State Use Description: RESIDENTIAL

Location Information
Parcel Location Influence: Waterfront

Utility Information
Sewer Type: Private
Water Service Type: Private

Financial

Assessor Information
Assessment Year: 2026
Tax District County: 07

Public facts

Beds: —
Baths: 1.0
Sq. Ft.: 1,204
Stories: 1.0
Lot Size: 0.43 acres
Style: Single Family Residential
Year Built: 1953
Year Renovated: —
County: Queen Anne's County
APN: 07 010818

Home facts updated by county records on Jul 18, 2026

Around this home

Schools

Church Hill Elementary School

Public PreK-4 • Assigned • 5.7mi

5/10

Sudlersville Middle School

Public 5-8 • Assigned • 9.5mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 12.9mi

7/10

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

27% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 4 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

$379,000 – $459,000

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

Nearby similar homes

$135,000

Land— sq ft

109 2nd St, Chestertown, MD 21620

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3 beds1.5 baths2,206 sq ft

107 2nd St, Crumpton, MD 21628

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$100,000

3 beds1 bath1,896 sq ft

10520 Worton Rd, Worton, MD 21678

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$375,000

4 beds2.5 baths2,504 sq ft

123 Trafford Dr, Chestertown, MD 21620

(443) 215-4663

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4 beds3 baths2,208 sq ft

25133 Smithville Rd, Worton, MD 21678

(443) 320-1344

New listings for sale in 21620

VIDEO TOUR

$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

$369,000

2 beds1.5 baths1,036 sq ft

101 S College Ave, Chestertown, MD 21620

(410) 810-0010

$649,000

4 beds3 baths2,864 sq ft

22400 Great Oak Landing Rd, Chestertown, MD 21620

(410) 778-0330

FOR SALE BY OWNER

$435,000

3 beds2 baths1,956 sq ft

233 Duke of Kent St, Chestertown, MD 21620

$524,900

3 beds2.5 baths2,076 sq ft

1003 Twin Ct, Chestertown, MD 21620

(410) 778-3779

$295,000

1 bed1 bath— sq ft

117 N Water St Unit 3B, Chestertown, MD 21620

(410) 778-0330

COMING SOON

$304,000

3 beds2 baths1,232 sq ft

7464 Shortall St, Chestertown, MD 21620

(410) 476-2201

Home values near 444 Pear Tree Point Rd

Data from public records.

Address	Redfin Estimate
464 Pear Tree Point Road, Chestertown, MD - Beds \| 1 Baths \| 1008 Sq. Ft.	$571,574
415 Pear Tree Point Road, Chestertown, MD - Beds \| 2 Baths \| 1848 Sq. Ft.	$405,297

Address	Redfin Estimate
437 Pear Tree Point Road, Chestertown, MD - Beds \| 2 Baths \| 1680 Sq. Ft.	$422,158
424 Pear Tree Point Road, Chestertown, MD - Beds \| 2.5 Baths \| 3589 Sq. Ft.	$1,096,123

Address	Redfin Estimate
456 Pear Tree Point Road, Chestertown, MD 3 Beds \| 2 Baths \| 1834 Sq. Ft.	$860,176
421 Pear Tree Point Road, Chestertown, MD 2 Beds \| 1 Baths \| 997 Sq. Ft.	$308,980

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Market trends in 21620, MD

Sale history for 444 Pear Tree Point Rd

Tax history for 444 Pear Tree Point Rd

Zoning

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 444 Pear Tree Point Rd

More real estate resources