OFF MARKET

Off Market Apr 2021 for $715K

$1,162,521

Est. refi paymentEst. refi $3,554/mo

•

5,563

sq ft

265 Pear Tree Point Rd, Chestertown, MD 21620

About this home

Your Staycation Dream Home Has Never Felt So Perfect - From Horses To Vineyards', Farming To Local Waterways - The Choice is Yours - Perfect Location For Whatever You Fancy - With Ample Room The Choices Are Endless - 5 Bedroom 3.5 Bath - Over 5500 Sq Feet - Over 21 Acres - Raised Ceilings Through Out - Main Level Master With Walk In Closet and Spa Like Master En-Suite - Large Living Room With Access Doors to Rear Patio - Formal Dining Room - Gourmet Kitchen With Large Island and Plenty Of Counter Space For Exquisite Meals and Entertainment - Large Theatre Room Off Of Kitchen To Hunker Down In For Family Fun Night or Convert To A Perfect In-Law Suite - Rear Family/ Rec Room With Outside Access To Concrete Pool and Extra Large Patio - Enjoy Horses With 2 Stalls - Barn Convertible To A Workshop Area If So Desired - Large Fenced Pasture Could House Livestock Or Be Converted Back to Prior Use As A Vineyard - With Over 21 Acres, It's Up To You To Decide. .. What's Your Desire? Close to Art and Entertainment Of Downtown Chestertown - Bring Your Deep Water Boat and Dock It In Slip At the Local Chestertown Marina - Country Club Offers Golf Galore - Minutes From Middletown Or Centreville and 30 minutes to the Bay Bridge - Installed Solar Panels Help Cover Electric With Money To Spare - Why Choose One or The Other When You Can Have It All? Get In Line Today as This One Is Already Creating A BUZZ! Don't miss your chance!

Single-familyProperty Type

2005Year Built

21.06 acresLot Size

$209Est. Price/Sq.Ft.

3 garage spacesParking

Listed by Joelle Dolch • Chaney Homes, LLC

•443-249-7653 (broker)

•jchaney@chaneyhomes.com (broker)

Bought with Joelle Dolch • Chaney Homes, LLC

•443-249-7653 (broker)

•jchaney@chaneyhomes.com (broker)

Redfin checked: a few seconds ago

•Source:BRIGHT MLS #MDQA146530

Redfin Estimate

$1,162,521

$448K since sold in April 2021$75K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 73.4% higher than the average sale price ($670K) of 6 comparable homes.

SOLD AUG 16, 2026
$525,000
A
3 beds3 baths2,824 sq ft
Preston Ln, 2, Kennedyville, MD 21620
SOLD JUL 29, 2026
$640,000
B
4 beds2.5 baths3,248 sq ft
7844 Chester Ct, Chestertown, MD 21620
SOLD APR 8, 2026
$512,500
C
4 beds3.5 baths3,000 sq ft
206 Flyway Ln, Chestertown, MD 21620
SOLD DEC 5, 2025
$550,000
D
5 beds4 baths3,877 sq ft
302 Rosin Dr, Chestertown, MD 21620
SOLD JUN 26, 2026
$1,050,000
E
5 beds3 baths2,956 sq ft
231 Richard Dr, Chestertown, MD 21620
SOLD JUL 20, 2026
$745,000
F
4 beds4 baths3,180 sq ft
11122 Boyer Ln, Worton, MD 21678

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Earn from this home

Sell

$581,708

Est. take-home

List your home with Redfin and save $11,625

Refinance

Est. cash available

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Rent

$4,346/mo

Redfin rental estimate

List your home for rent

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 265 Pear Tree Point Rd

Date

Event

Price

Public Records

Apr 23, 2021

Sold

$715,000

$129/sq ft

BRIGHT MLS #MDQA146530

Apr 21, 2021

Listing Removed

—

Apr 20, 2021

Sold

$715,000

$129/sq ft

Apr 11, 2021

Pending

—

Feb 21, 2021

Contingent

—

Feb 12, 2021

Listed

$699,000

$126/sq ft

BRIGHT MLS #1009997800

Jul 5, 2019

Listing Removed

—

Oct 25, 2018

Listed

$699,000

$126/sq ft

BRIGHT MLS #1002071386

Jul 5, 2019

Listing Removed

—

Sep 9, 2018

Price Changed

$699,000

$126/sq ft

Aug 22, 2018

Price Changed

$715,000

$129/sq ft

Jul 19, 2018

Listed

$750,000

$135/sq ft

Public Records

Nov 25, 2002

Sold

$152,650

$27/sq ft

Tax history for 265 Pear Tree Point Rd

*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

4.25

Stories

Lot width

—

Lot depth

—

Lot size

917,374

Year renovated

—

Sq. Ft.

5,563

Year built

2005

Style

Single Family Residential

County

Kent County

APN

07019092

Parking Spaces

Basement

Accessible

Yes

HOA Dues

—

Garage

Yes

Features

Views, Pool

Last updated by owner on Jul 31, 2023.

Countryside District

The Countryside CS District is intended to preserve and protect the rural and agricultural areas of the County that generally lie within the Chesapeake Bay Critical Area and contain extremely sensitive natural resources. Residential development densities and design standards shall ensure resource protection and preservation of open space. This district shall be predominately characterized by open space, farmettes, and very low-density residential uses or small single-family cluster developments with significant associated open space.

Permitted uses

Include but are not limited to:

Agriculture
Equestrian facility
Greenhouse / nursery
Housing-Single unit
Housing-Multiple units
Bed & breakfast
Public service
Recreation
Kennel
Housing-Mobile home park

Property details

Parking

Parking Information
# of Attached Garage Spaces: 3
Garage Features: Garage - Side Entry, Built In, Inside Access
# of Total Garage and Parking Spaces: 9
Has Garage
# of Garage Spaces: 3
Driveway - # of Spaces: 3
Off Street - # of Spaces: 3
Fenced, Gravel Driveway, Private
Attached Garage, Driveway, Off Street

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On 1st Upper Level: 4
# of Bedrooms On Main Level: 1

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 2
# of Bathrooms (Half): 1
# of Bathrooms (Full): 3

Interior Information
Appliances: Built-In Microwave, Commercial Range, Dishwasher, Dryer, Microwave, Oven - Double, Refrigerator, Six Burner Stove, Washer, Water Heater
Flooring Type: Hardwood
Living Area Sq.Ft. Source: Assessor

Room Information
Master Bedroom, Attic
Laundry Type: Dryer In Unit, Washer In Unit, Main Floor, Upper Floor

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Accessibility Features: 2+ Access Exits
Horse: Yes
Horse Amenities: Paddock, Horses Allowed, Stable(s)
Improvement Assessed Value: $504,300
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Assessor

Building Information
Construction Materials: Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Patio(s), Porch(es)
Roof: Architectural Shingle
Structure Type: Detached
Other Structures: Run-in Shed, Barn/Stable, Shed Shop
Building Not Winterized

Exterior Information
Outbuilding(s), Play Equipment

Pool Information
Personal Pool
Concrete, In Ground

Lot Information
Lot Features: Partly Wooded, Rear Yard, Trees/Wooded, SideYard(s), Private, Poolside, Front Yard, Cleared
Tidal Water: No

Land Information
Land Assessed Value: $70,100

Farm Information
Agricultural District: AG

Above Grade Information
Finished Sq.Ft.: 5,563
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
Agricultural Tax Due: Yes
County Tax: $5,249
Tax Assessed Value: $560,867
Tax Year: 2021
Tax Annual Amount: $5,249

Assessments Information
Year Assessed: 2021

Lease Information
Lease Considered: No

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C, Programmable Thermostat, Zoned, Multi Units
Cooling Fuel: Electric
Forced Air, Programmable Thermostat
Heating Fuel: Propane - Owned
Hot Water: Propane
Sewer Septic: On Site Septic
Water Source: Private, Well
Municipal Trash: No

Location

School Information
Elementary School: CHURCH HILL
Middle Or Junior School: SUDLERSVILLE
High School: QUEEN ANNE'S COUNTY
School District Name: QUEEN ANNE'S 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
Outside City Limits
Directions: Route 213 Northbound, Right on Round Rop Road, Left On Pear Tree Road, House ON Left

Public facts

Beds: 5
Baths: 4.25
Sq. Ft.: 5,563
Stories: 3.0
Parking Spaces: 9
Basement: No
Accessible: Yes
Lot Size: 21.06 acres
Style: Single Family Residential
Year Built: 2005
Year Renovated: —
County: Kent County
APN: 07019092
HOA Dues: —
Garage: Yes
Features: Views, Pool

Home facts updated by owner on Jul 31, 2023

Around this home

Schools

Church Hill Elementary School

Public PreK-4 • Assigned • 5.6mi

5/10

Sudlersville Middle School

Public 5-8 • Assigned • 9.6mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 12.8mi

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

$1.11M – $1.34M

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New listings for sale in 21620

VIDEO TOUR

$38,200,000

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8184 Rock Hall Rd, Chestertown, MD 21620

(410) 778-3779

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302 S Mill St, Chestertown, MD 21620

(410) 778-0330

COMING SOON

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217 Edmore Rd, Chestertown, MD 21620

(410) 810-0010

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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

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COMING SOON

$304,000

3 beds2 baths1,232 sq ft

7464 Shortall St, Chestertown, MD 21620

(410) 476-2201

Home values near 265 Pear Tree Point Rd

Data from public records.

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

Address	Redfin Estimate
437 Pear Tree Point Rd, Chestertown, MD - Beds \| 2 Baths \| 1680 Sq. Ft.	$422,158
421 Pear Tree Point Rd, Chestertown, MD 2 Beds \| 1 Baths \| 997 Sq. Ft.	$308,980

Address	Redfin Estimate
456 Pear Tree Point Rd, Chestertown, MD 3 Beds \| 2 Baths \| 1834 Sq. Ft.	$860,176
441 Pear Tree Point Rd, Chestertown, MD - Beds \| 2 Baths \| 1680 Sq. Ft.	$352,316

Property information provided by BRIGHT MLS when last listed in 2021. This data may not show owner updates. 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 265 Pear Tree Point Rd

Tax history for 265 Pear Tree Point 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 265 Pear Tree Point Rd

More real estate resources