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$279,000 -$11,000 (-3.79%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 1 Full Bath
  • 1,176 Sq. Ft.
  • Updated 3 days ago
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******Price Reduction****** 239 Chestnut Street is a charming rancher in the heart of Winchester. 2 bedrooms, 1 bath, a large rear deck, eat in kitchen, laundry room could be converted into a third bedroom. Building in the back yard could be used as storage or a 1 car garage. This is a solid starter or downsizing home convenient to shopping,schools and parks. A little TLC will go a long way "Come see the possibilities"

Full Property Details for 239 Chestnut St

General

  • Price: $279,000
  • Taxes: $2,011 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAFV2037798
  • Updated: 1/12/2026
  • Added to Site: 78 day(s) ago

Interior

  • Number of Rooms: 5
  • Rooms/Areas: Living Room, Kitchen, Laundry
  • Appliances: Built-In Microwave, Dishwasher, Dryer - Electric, Oven/Range - Electric, Refrigerator, Washer
  • Flooring: Hardwood, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

  • Total Bedrooms: 2
  • Bedrooms Main & Up: 2

Other Rooms

  • Laundry: Main Floor

Parking

  • Parking Type: Driveway, On Street

Location

  • County: FREDERICK
  • Driving Directions: Head north on Pleasant Valley, turn right on Woodstock at the red light, turn left onto Chestnut St. house will be on the left. Sign in front yard.
  • City Limits: Yes

School Information

  • School District: Frederick County Public Schools

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump - Gas BackUp
  • Heating Fuel: Natural Gas
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Ranch/Rambler
  • Structure Type: Detached
  • Construction: Aluminum Siding
  • Foundation: Block
  • Roof: Shingle
  • Walls/Ceilings: Dry Wall
  • Stories Description: Main
  • Square Feet: 1,176
  • Sq. Ft. Source: Assessor
  • Living Area: 1,176 Sq. Ft.
  • Finished Above Grnd: 1,176 Sq. Ft.
  • Year Built: 1976
  • Year Built Source: Assessor

Lot Features

  • Lot Size Source: Assessor
  • Zoning: MR

Financial Considerations

  • Price Per Sq. Ft.: $237.24
  • Assessment Year: 2025
  • City/TownTax: $2,011
  • City/TownTax Freq: Annually
  • County Tax Freq: Annually
  • Tax w/Assessment: $253,000
  • Tax Amount: $2,011
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1176

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 4A

Listed by Wildhawks Realty LLC, William R Wertz

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Listing agent

— 239 Chestnut St —

  • William R Wertz

    Wildhawks Realty LLC

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 239 Chestnut St

School District:Winchester City Public Schools
NameGradesDistance
Daniel Morgan Middle School
48 South Purcell Avenue, Winchester, VA 22601
7-80.3 mi
John Handley High School
425 Handley Boulevard, Winchester, VA 22601
9-121.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 239 Chestnut St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/12/2026
Price Reduced
$279,000
-3.79%
MLS
12/08/2025
Price Reduced
$290,000
-3.01%
MLS
10/29/2025
Listed
$299,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 239 Chestnut St

Year
Property Taxes
Change
Tax Assessment
Change
2024
100%
$253,000
12%
2024
-100%
$226,400
—
2023
$1,879
20%
$226,400
34%
2022
$1,567
—
$168,500
—
2021
$1,567
16%
$168,500
16%
2020
$1,346
—
$144,700
—
2018
$1,346
6%
$144,700
3%
2018
$1,273
11%
$139,900
—
2016
$1,143
—
$139,900
11%
2016
$1,143
—
$125,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Wildhawks Realty LLC, William R Wertz

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239 Chestnut Street, Winchester, VA 22601 (MLS# VAFV2037798) is a Single Family property with 2 bedrooms and 1 full bathroom. 239 Chestnut Street is currently listed for $279,000 and was received on October 29, 2025. Want to learn more about 239 Chestnut Street? Do you have questions about finding other Single Family real estate for sale in Winchester? You can browse all Winchester real estate or contact a Coldwell Banker agent to request more information.

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