OFF MARKET

Off Market Dec 2021 for $249K

$308,980

Est. refi paymentEst. refi $1,550/mo

•

997

sq ft

421 Pear Tree Point Rd W, Chestertown, MD 21620

About this home

This delightful 2 BR, 1 BA cottage style residence offers affordable living and low maintenance with an open kitchen/dining/living area, breakfast bar, wood burning fireplace, freshly painted throughout, polished hardwood floors, a 1-car attached garage and deeded water access to the Chester River. All within biking distance or a quick drive to everything Chestertown has to offer; Farmers Market every Saturday morning, Arts & Entertainment district, Washington College, restaurants, local shops, and much more. Nothing to do but move in and enjoy the Eastern Shore charm!

Single-familyProperty Type

1980Year Built

0.37 acresLot Size

$310Est. Price/Sq.Ft.

1 car garageParking

Listed by Jody Baker • Cross Street Realtors LLC

•410-778-3779 (broker)

•stacy@csrealtors.com (broker)

Bought with Mary Carlisle • Coldwell Banker Chesapeake Real Estate Company

•410-778-0330 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDQA2001174

Redfin Estimate

$308,980

$60K since sold in December 2021$1,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 3.3% higher than the average sale price ($299K) of 6 comparable homes.

SOLD MAY 14, 2026
$278,500
A
3 beds1 bath— sq ft
107 Longfellow Dr, Chestertown, MD 21620
SOLD MAY 27, 2026
$300,000
B
3 beds1 bath1,408 sq ft
154 Longfellow Dr, Chestertown, MD 21620
SOLD MAR 31, 2026
$330,000
C
3 beds2 baths1,170 sq ft
129 Parma Rd, Chestertown, MD 21620
SOLD SEP 26, 2025
$300,000
D
3 beds1 bath1,056 sq ft
925 Round Top Rd, Chestertown, MD 21620
SOLD MAR 9, 2026
$317,000
E
3 beds2 baths1,232 sq ft
213 Central Dr, Chestertown, MD 21620
SOLD AUG 25, 2025
$270,000
F
3 beds1 bath1,056 sq ft
114 Darden Rd, Chestertown, MD 21620

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Earn from this home

Refinance

Est. cash available

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Rent

$1,758/mo

Redfin rental estimate

List your home for rent

Market trends in 21620, MD

Last updated July 2026

Buyer's Market

Seller's Market

Balanced 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

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
$750,000
3 beds2.5 baths2,176 sq ft
216 Birch Run Rd, Chestertown, MD 21620
(410) 673-3344
$440,000
2 beds1.5 baths1,058 sq ft
104 Church Aly, Chestertown, MD 21620
(410) 778-0330
See all

Provided by Redfin

Sale history for 421 Pear Tree Point Rd W

Date

Event

Price

BRIGHT MLS #MDQA2001174

Dec 10, 2021

Sold

$249,000

$250/sq ft

Dec 6, 2021

Pending

—

Nov 2, 2021

Contingent

—

Oct 19, 2021

Listed

$249,000

$250/sq ft

MRIS #QA7909284

Oct 24, 2012

Delisted

—

Oct 3, 2012

Price Changed

Aug 17, 2012

Listed

MRIS #QA6572064

Jul 28, 2008

Delisted

—

Oct 20, 2007

Listed

Public Records

Nov 13, 2006

Sold

$200,000

$201/sq ft

MRIS #QA6120567

Sep 29, 2006

Delisted

—

Jul 12, 2006

Listed

$219/sq ft

Public Records

Jun 30, 1999

Sold

$66,500

$67/sq ft

MRIS #QA2495544

Jan 3, 1999

Delisted

—

Jun 2, 1998

Listed

$69/sq ft

Public Records

Sep 19, 1996

Sold

$50,000

$50/sq ft

MRIS #QA043399C

Sep 9, 1996

Delisted

—

May 28, 1996

Listed

$59/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$2,272 (+13.4%)

2024

$2,003 (+15.5%)

$71,100 + $163,700

$234,800

2023

$1,734 (+18.3%)

2022

$1,465 (−0.8%)

2021

$1,477 (+1.0%)

$61,100 + $88,100

$149,200

2020

$1,462 (+1.0%)

2019

$1,448

2018

$1,448

$62,200 + $82,500

$144,700

2017

$1,448 (−0.4%)

$62,200 + $82,500

$144,700

2016

$1,454 (+0.5%)

2015

$1,447 (+0.5%)

2014

$1,440

$62,200 + $81,700

$143,900

2013

$1,440 (+2.1%)

2012

$1,410 (−23.7%)

2011

$1,849 (+8.4%)

2010

$1,706 (+11.7%)

2009

$1,527

Tax history for 421 Pear Tree Point Rd W

Year

Property tax

Land + Additions

Assessment*

2025

$2,272 (+13.4%)

2024

$2,003 (+15.5%)

$71,100 + $163,700

$234,800

2023

$1,734 (+18.3%)

2022

$1,465 (−0.8%)

2021

$1,477 (+1.0%)

$61,100 + $88,100

$149,200

2020

$1,462 (+1.0%)

2019

$1,448

2018

$1,448

$62,200 + $82,500

$144,700

2017

$1,448 (−0.4%)

$62,200 + $82,500

$144,700

2016

$1,454 (+0.5%)

2015

$1,447 (+0.5%)

2014

$1,440

$62,200 + $81,700

$143,900

2013

$1,440 (+2.1%)

2012

$1,410 (−23.7%)

2011

$1,849 (+8.4%)

2010

$1,706 (+11.7%)

2009

$1,527

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

Public record

Public record
Zoning

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.37 Acres

Year renovated

—

Sq. Ft.

997

Year built

1980

Style

Single Family Residential

County

Queen Anne's County

APN

07 007973

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

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

Parking

Parking Information
# of Attached Garage Spaces: 1
Garage Features: Garage Door Opener, Garage - Front Entry
# of Total Garage and Parking Spaces: 1
Has Garage
# of Garage Spaces: 1
Stone Driveway, Private
Attached Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 2

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

Interior Information
Appliances: Oven/Range - Electric, Refrigerator, Dryer - Electric, Washer
Door Features: Sliding Glass, Storm
Flooring Type: Hardwood, Vinyl
Not Furnished
Interior Features: Family Room Off Kitchen, Breakfast Area, Combination Kitchen/Dining, Wood Floors, Entry Level Bedroom
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: Dry Wall

Room Information
Living Room, Dining Room, Master Bedroom, Kitchen, Bedroom 1
Laundry Type: Has Laundry, Washer In Unit

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Equipment, Mantel(s), Wood

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Horse: No
Improvement Assessed Value: $88,100
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Assessor
Year Major Reno/Remodel: 2002

Building Information
Construction Materials: Vinyl Siding
Foundation Details: Slab
Other Structures: Above Grade, Below Grade
Roof: Shingle
Structure Type: Detached
Other Structures: Shed
Building Not Winterized

Exterior Information
Fencing: Partially, Chain Link

Lot Information
Lot Features: Backs to Trees
Navigable Water
Tidal Water: No

Land Information
Land Assessed Value: $61,100

Above Grade Information
Finished Sq.Ft.: 997
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
Agricultural Tax Due: No
County Tax: $1,402
Tax Assessed Value: $147,700
Tax Year: 2020
Tax Annual Amount: $1,462

Assessments Information
Year Assessed: 2021

Lease Information
Lease Considered: No

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Private Septic Tank
Water Source: Well
Municipal Trash: No

Location

School Information
School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: From the Chester River Bridge traveling South, turn Left on Round Top Rd. , follow to Pear Tree Point Rd, which is the next left after Round Top Park. Follow to 421, which will be on your Left. Sign Posted.
Mean Low Water Feet: 2
Road Surface Type: Tar and Chip

Waterfrontage Information
Water Access Features: Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Swimming Allowed, Waterski/Wakeboard, Boat - Powered
Water Access
Water Oriented
Water Body Type: River
Water Body Name: CHESTER RIVER

Public facts

Beds: —
Baths: 1.0
Sq. Ft.: 997
Stories: 1.0
Lot Size: 0.37 acres
Style: Single Family Residential
Year Built: 1980
Year Renovated: —
County: Queen Anne's County
APN: 07 007973

Home facts updated by county records on Jul 18, 2026

Around this home

Schools

Church Hill Elementary School

Public PreK-4 • Assigned • 5.6mi

4/10

Sudlersville Middle School

Public 5-8 • Assigned • 9.4mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 12.9mi

4/10

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

$294,000 – $356,000

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

Nearby similar homes

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NEW CONSTRUCTION

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Land— sq ft

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New listings for sale in 21620

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

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Home values near 421 Pear Tree Point Rd W

Data from public records.

Address	Redfin Estimate
464 Pear Tree Point Road, Chestertown, MD - Beds \| 1 Baths \| 1008 Sq. Ft.	$571,574
400 Pear Tree Point Road, Chestertown, MD - Beds \| 2 Baths \| 2224 Sq. Ft.	$586,017

Address	Redfin Estimate
437 Pear Tree Point Road, Chestertown, MD - Beds \| 2 Baths \| 1680 Sq. Ft.	$422,158
456 Pear Tree Point Road, Chestertown, MD 3 Beds \| 2 Baths \| 1834 Sq. Ft.	$860,176

Address	Redfin Estimate
301 Pear Tree Point Road, Chestertown, MD - Beds \| 1 Baths \| 1120 Sq. Ft.	$278,566
311 Pear Tree Point Road, Chestertown, MD - Beds \| 2 Baths \| 1568 Sq. Ft.	$333,620

Property information provided by BRIGHT MLS when last listed in 2021. 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 421 Pear Tree Point Rd W

Tax history for 421 Pear Tree Point Rd W

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 421 Pear Tree Point Rd W

More real estate resources