OFF MARKET

Off Market Dec 2018 for $328K

$544,499

Est. refi paymentEst. refi $2,578/mo

•

2,180

sq ft

1539 Chestnut Grove Rd, Winchester, VA 22603

About this home

Single-familyProperty Type

1995Year Built

5 acresLot Size

$250Est. Price/Sq.Ft.

3 car garageParking

Listed by Jennifer Egen • Move4Free Realty, LLC

•571-292-5377 (broker)

•giovanni@move4freerealty.com (broker)

Bought with Kathy Colville • Century 21 Redwood Realty

•703-790-1850 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #1002145938

Redfin Estimate

$544,499

$216K since sold in December 2018$9,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 18.6% higher than the average sale price ($459K) of 5 comparable homes.

SOLD JUN 10, 2026
$645,000
A
3 beds2.5 baths2,782 sq ft
294 Green Spring Dr, Winchester, VA 22603
SOLD AUG 3, 2026
$450,000
B
3 beds2 baths2,545 sq ft
432 Spring Valley Dr, Winchester, VA 22603
SOLD DEC 9, 2025
$519,000
C
3 beds3 baths1,624 sq ft
160 Country Squire Ln, Winchester, VA 22603
SOLD SEP 8, 2026
$360,000
D
3 beds2.5 baths2,373 sq ft
334 Overlook Dr, Cross Junction, VA 22625
SOLD JUN 25, 2026
$321,000
E
3 beds2 baths1,531 sq ft
106 Greenwood Ct, Cross Junction, VA 22625

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

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,244/mo

Redfin rental estimate

List your home for rent

Market trends in 22603, VA

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

98.5%

+0.2% MoM

Median sale price

$460K

$25K MoM

Avg. days on market

49d

7 days MoM

Recently sold homes

6 MoM

New listings for sale

$395,600
4 beds2 baths1,860 sq ft
178 Payne Rd, Winchester, VA 22603
(540) 259-4090
$625,000
4 beds3.5 baths2,768 sq ft
394 Old Baltimore Rd, Winchester, VA 22603
(540) 665-0360
$499,900
3 beds2 baths1,479 sq ft
1960 Siler Rd, Winchester, VA 22603
(540) 773-8475
COMING SOON
$289,900
3 beds3.5 baths1,906 sq ft
114 Tudor Dr, Winchester, VA 22603
(540) 665-0360
3D WALKTHROUGH
$1,100,000
5 beds5 baths5,525 sq ft
300 Clearview Dr, Clear Brook, VA 22624
(540) 686-7362
$675,000
2 beds1 bath1,540 sq ft
531 Cedar Grove Rd, Winchester, VA 22603
(540) 300-5700
OPEN SAT, 1PM TO 3PM
$549,900
4 beds3 baths2,208 sq ft
127 Mountain View Rd, Winchester, VA 22603
(540) 773-8475
$699,999
4 beds1.5 baths2,952 sq ft
3105 Apple Pie Ridge Rd, Winchester, VA 22603
(866) 825-7169
See all

Provided by Redfin

Sale history for 1539 Chestnut Grove Rd

Date

Event

Price

BRIGHT MLS #1002145938

Dec 19, 2018

Sold

$328,199

$151/sq ft

Nov 30, 2018

Contingent

—

Aug 23, 2018

Price Changed

$339,900

$156/sq ft

Aug 1, 2018

Listed

$349,900

$161/sq ft

MRIS #FV7478802

Sep 21, 2011

Delisted

—

Sep 2, 2011

Relisted

—

Aug 29, 2011

Delisted

—

Jun 3, 2011

Relisted

—

May 13, 2011

Delisted

—

Nov 12, 2010

Listed

BRIGHT MLS #1009270740

Sep 21, 2011

Listing Removed

—

Nov 12, 2010

Listed

$325,000

$149/sq ft

MRIS #FV7364836

Nov 2, 2010

Delisted

—

Jun 15, 2010

Listed

BRIGHT MLS #1009137886

Nov 2, 2010

Listing Removed

—

Jun 15, 2010

Listed

$349,500

$160/sq ft

Public Records

Oct 26, 2004

Sold

$299,700

$137/sq ft

Year

Property tax

Land + Additions

Assessment*

2026

$2,135 (+10.4%)

$101,000 + $301,800

$402,800

2025

$1,933 (+9.4%)

$101,000 + $301,800

$402,800

2024

$1,768

$82,500 + $264,100

$346,600

2023

$1,768 (+3.8%)

$82,500 + $264,100

$346,600

2022

$1,704

$74,500 + $204,800

$279,300

2021

$1,704 (+10.9%)

$74,500 + $204,800

$279,300

2020

$1,536

$74,500 + $177,300

$251,800

2019

$1,536 (+4.4%)

$74,500 + $177,300

$251,800

2018

$1,472 (−1.4%)

$74,500 + $177,300

$251,800

2017

$1,493 (+7.2%)

$74,900 + $166,400

$241,300

2016

$1,393 (+5.9%)

$74,900 + $173,900

$248,800

2014

$1,316

$62,200 + $162,800

$225,000

Tax history for 1539 Chestnut Grove Rd

Year

Property tax

Land + Additions

Assessment*

2026

$2,135 (+10.4%)

$101,000 + $301,800

$402,800

2025

$1,933 (+9.4%)

$101,000 + $301,800

$402,800

2024

$1,768

$82,500 + $264,100

$346,600

2023

$1,768 (+3.8%)

$82,500 + $264,100

$346,600

2022

$1,704

$74,500 + $204,800

$279,300

2021

$1,704 (+10.9%)

$74,500 + $204,800

$279,300

2020

$1,536

$74,500 + $177,300

$251,800

2019

$1,536 (+4.4%)

$74,500 + $177,300

$251,800

2018

$1,472 (−1.4%)

$74,500 + $177,300

$251,800

2017

$1,493 (+7.2%)

$74,900 + $166,400

$241,300

2016

$1,393 (+5.9%)

$74,900 + $173,900

$248,800

2014

$1,316

$62,200 + $162,800

$225,000

*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

2.5

Stories

Lot width

—

Lot depth

—

Lot size

5 Acres

Year renovated

2007

Sq. Ft.

2,776

Year built

1995

Style

Single Family Residential

County

Frederick County

APN

20 3 4

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2026.

Property details

Parking

Parking Information
# of Detached Garage Spaces: 3
Garage Features: Garage - Front Entry, Garage - Side Entry
# of Total Garage and Parking Spaces: 3
Has Garage
# of Garage Spaces: 3
Asphalt Driveway, Garage
Driveway, Detached Garage

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 3

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

Interior Information
Appliances: Washer/Dryer Hookups Only, Cooktop, Dishwasher, Dryer, Microwave, Oven - Double, Refrigerator, Trash Compactor, Washer, Water Conditioner - Owned
Door Features: Six Panel, French
Entry Location: Foyer
Interior Features: Attic, Dining Area, Kitchen - Country, Master Bath(s), Window Treatments, Recessed Lighting, Floor Plan - Traditional
Living Area Sq.Ft. Source: Estimated
Wall & Ceiling Types: Dry Wall, Wood Walls

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Kitchen, Family Room, Foyer, Bedroom 1, Sun/Florida Room, Laundry, Storage Room, Utility Room, Attic

Basement Information
Basement: Yes
Outside Entrance, Walkout Level, Fully Finished, Daylight, Full, Heated, Windows

Exterior

Property Information
Total Below Grade Sq. Ft.: 792
Irrigation Water Rights
Horse Amenities: Horses Allowed
Improvement Assessed Value: $170,100
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Estimated

Building Information
Construction Materials: Combination, Brick
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Porch(es)
Roof: Asphalt
Structure Type: Detached
Window Features: Double Pane, Screens
Other Structures: Shed

Exterior Information
Flood Lights, Satellite Dish
Fencing: Board, Invisible, Partially, Fully

Lot Information
Lot Features: Backs to Trees, Partly Wooded, Private, Landscaping
Tidal Water: No

Land Information
Land Assessed Value: $62,200

Above Grade Information
Finished Sq.Ft.: 1,388
Finished Sq.Ft. Source: Estimated

Below Grade Information
Finished Sq.Ft.: 792
Finished Sq.Ft. Source: Estimated

Financial

Tax Information
County Tax: $1,393.80
Tax Assessed Value: $232,300
Tax Year: 2017
Tax Annual Amount: $1,393.80

Assessments Information
Year Assessed: 2017

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C, Ceiling Fan(s), Heat Pump(s), Programmable Thermostat
Cooling Fuel: Electric
Central, Heat Pump(s), Programmable Thermostat
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Septic Exists
Water Source: Well

Location

Location Information
Directions: From Leesburg: Route 7 West to Winchester; 81N to Martinsburg; to Exit 317 (US11 to Winchester); Turn Left onto Martinsburg Pike (US 11); to VA 37South; to 522 to Winchester; Right onto 522N; Right onto Chestnut Grove Rd; SIGN ON PROPERTY

Public facts

Beds: 3
Baths: 2.5
Sq. Ft.: 2,776
Stories: 1.0
Lot Size: 5 acres
Style: Single Family Residential
Year Built: 1995
Year Renovated: 2007
County: Frederick County
APN: 20 3 4

Home facts updated by county records on Jul 13, 2026

Around this home

Schools

Gainesboro Elementary School

Public PreK-5 • Assigned • 2.4mi

2/10

Frederick County Middle School

Public 6-8 • Assigned • 2.6mi

2/10

James Wood High School

Public 9-12 • Assigned • 6.7mi

6/10

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

3/10 Fire Factor

0.15% chance of being in a wildfire in next 30 years

5/10 Heat Factor

7 days above 101° expected this year, 16 days in 30 years

2/10 Wind Factor

1% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winchester, VA • 22603

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 8.8 hours in June and 3.6 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

3.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$518,000 – $627,000

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

Nearby similar homes

NEW CONSTRUCTION

$959,000

3 beds2.5 baths2,000 sq ft

Light Rd, Winchester, VA 22603

(540) 665-0360

NEW CONSTRUCTIONVIDEO TOUR

$950,000

3 beds2.5 baths3,100 sq ft

Lot 13 Keval Gyan Way, Winchester, VA 22603

(540) 773-8475

FOR SALE BY OWNER

$134,400

2 beds1 bath784 sq ft

1107 Carpers Dr, Winchester, VA 22603

FOR SALE BY OWNER

$949,000

4 beds3 baths2,930 sq ft

969 Marple Rd, Winchester, VA 22603

NEW CONSTRUCTION

$899,900

3 beds2 baths2,488 sq ft

Lot 11 Keval Gyan Way, Winchester, VA 22603

(540) 773-8475

3D WALKTHROUGH

$399,900

3 beds2 baths1,176 sq ft

163 Margaret Ln, Winchester, VA 22603

(540) 348-4911

New listings for sale in 22603

$395,600

4 beds2 baths1,860 sq ft

178 Payne Rd, Winchester, VA 22603

(540) 259-4090

$625,000

4 beds3.5 baths2,768 sq ft

394 Old Baltimore Rd, Winchester, VA 22603

(540) 665-0360

$499,900

3 beds2 baths1,479 sq ft

1960 Siler Rd, Winchester, VA 22603

(540) 773-8475

COMING SOON

$289,900

3 beds3.5 baths1,906 sq ft

114 Tudor Dr, Winchester, VA 22603

(540) 665-0360

3D WALKTHROUGH

$1,100,000

5 beds5 baths5,525 sq ft

300 Clearview Dr, Clear Brook, VA 22624

(540) 686-7362

$675,000

2 beds1 bath1,540 sq ft

531 Cedar Grove Rd, Winchester, VA 22603

(540) 300-5700

OPEN SAT, 1PM TO 3PM

$549,900

4 beds3 baths2,208 sq ft

127 Mountain View Rd, Winchester, VA 22603

(540) 773-8475

$699,999

4 beds1.5 baths2,952 sq ft

3105 Apple Pie Ridge Rd, Winchester, VA 22603

(866) 825-7169

Home values near 1539 Chestnut Grove Rd

Data from public records.

Address	Redfin Estimate
1399 Chestnut Grove Rd, Winchester, VA 3 Beds \| 2 Baths \| 1680 Sq. Ft.	$436,110
1632 Chestnut Grove Rd, Winchester, VA 3 Beds \| 2.5 Baths \| 2164 Sq. Ft.	$436,714

Address	Redfin Estimate
1455 Chestnut Grove Rd, Winchester, VA 3 Beds \| 2 Baths \| 1512 Sq. Ft.	$495,248
1704 Chestnut Grove Rd, Winchester, VA 3 Beds \| 2 Baths \| 1794 Sq. Ft.	$479,096

Address	Redfin Estimate
1499 Chestnut Grove Rd, Winchester, VA 3 Beds \| 2.5 Baths \| 1826 Sq. Ft.	$481,535
1569 Chestnut Grove Rd, Winchester, VA 3 Beds \| 2.5 Baths \| 2335 Sq. Ft.	$571,140

Property information provided by BRIGHT MLS when last listed in 2018. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

22638 homes for sale
22601 homes for sale
22602 homes for sale
22603 homes for sale

Houses for rent in Winchester	Agents near me	Richmond, VA homes for sale	Winchester Housing Market
Houses for sale near me	Arlington, VA homes for sale	McLean, VA homes for sale
Land for sale near me	Alexandria, VA homes for sale	Chesapeake, VA homes for sale
Open Houses near me	Virginia Beach, VA homes for sale	Winchester Property Records
Condos for sale near me	Fairfax, VA homes for sale	VA New Listings

Martinsburg homes for sale
Front Royal homes for sale
Charles Town homes for sale

Historic District homes for sale
Old Town homes for sale
Kernstown homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 22603, VA

Sale history for 1539 Chestnut Grove Rd

Tax history for 1539 Chestnut Grove Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 22603

Home values near 1539 Chestnut Grove Rd

More real estate resources