239 Chestnut St

Winchester, VA 22601

$290,000
Price
2
Beds
1,176 Sq. Ft.
$247 / Sq. Ft.
1,176
Sq. Ft.
$247
per Sq. Ft.
a view of a brick house with a yard
a backyard of a house
a front view of house with yard
a front view of a house with a yard
a front view of a house with a yard
a view of a house with a yard
front view of a house with a yard
a kitchen with a sink stove and cabinets
a kitchen with a stove a refrigerator a sink a dining table and chairs with wooden floor
a kitchen with a refrigerator a stove a microwave and wooden cabinets
a kitchen with stainless steel appliances kitchen island granite countertop a dining table chairs and a refrigerator
a kitchen with a sink cabinets and window
a kitchen with a sink stove and refrigerator
a kitchen with stainless steel appliances granite countertop a sink stove and refrigerator
a bathroom with a sink toilet and a mirror
a bathroom with a sink a toilet and mirror
a bathroom with a sink and a mirror
a bedroom with a bed and a table
a bedroom with a bed and window
a bedroom with a bed a dresser with wooden floor
a view of a workspace with furniture and a window
a room with a window and chairs
a view of storage and utility room with washer and dryer
a bedroom with a bed and a chandelier
a living room with furniture and a flat screen tv
a living room with furniture and a flat screen tv
a living room with furniture a flat screen tv and a fireplace
a living room with furniture and wooden floor
a view of a house with a wooden deck
a view of a wooden deck with a yard
a view of a house with a yard
a view of a room with wooden walls
a view of a house with wooden fence
a view of a house with a yard

Description

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"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"
  1. Listed by William R Wertz • Wildhawks Realty LLC
    P: (540)-622-0211 randywertzrealtor@gmail.com

Property Details for 239 Chestnut Street

Tax ID Number
195-11-3A-4A
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Ranch/Rambler
Levels/Stories
1
Waterfront
No
LISTING UPDATED: 12/08/2025 09:37 AM

Property Details for 239 Chestnut Street

StatusActive
MLS #VAFV2037798
Days on Market48
Taxes$2,011 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1976
Lot Size0.00 AC / 0 SF
CountyWinchester Independent City

Location

Listing Courtesy of Wildhawks Realty LLC
Add your commute

Building Information for 239 Chestnut Street

Stories1Year Built1976Building Size-Lot Size0.00 AC / 0 SF

Payment Calculator

$1,601 per month

30 year fixed, 6.28% Interest

Principal and Interest

$1,433

Property Taxes

$168

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 239 Chestnut Street

Location
Location
  • In City Limits: Yes
  • School District Name: FREDERICK COUNTY PUBLIC SCHOOLS
  • School District County ID: 121140907577
  • SchoolDistrictSource: Listing Agent
  • County: FREDERICK
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: No
  • Navigable Water: No
  • Tidal Water: No
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $253,000
  • Year Assessed: 2025
  • County Tax: $0
  • Improvement Assessed Value: $194,500
  • City Town Tax: $2,011
  • Land Assessed Value: $58,500
  • Clean Green Assessed: No
  • Land Use Code: 100R
  • Historic: No
  • Zoning: MR
  • Tax Lot: 4A
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 2
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 1
Rooms
  • Room List: Living Room, Kitchen, Laundry
  • Stories: Main
Rooms Information
Room 1
  • Room Type: Living Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - HardWood
Room 2
  • Room Type: Kitchen
  • Room Level: Main
  • Room Exists: Yes
Room 3
  • Room Type: Laundry
  • Room Level: Main
  • Room Exists: Yes
Building Info
Building Info
  • Total Finished SQFT: 1,176.00
  • Total Finished SQFT Source: Assessor
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Parcel ID: 19874230
  • Ground Rent Exists: No
Parking
Parking
  • Type Of Parking: Driveway, On Street
Interior Features
Interior Features
  • Fireplace: No
  • Appliances: Built-In Microwave, Dishwasher, Dryer - Electric, Oven/Range - Electric, Refrigerator, Washer
  • Accessibility Features: None
  • Laundry Type: Main Floor
Exterior Features
Exterior Features
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump - Gas BackUp
  • Heating Fuel: Natural Gas
  • Hot Water: Electric
  • Water Source: Public
  • Sewer Septic: Public Sewer
Confidential Data
Listing Office
  • List Agent AOR: Massanutten Board of REALTORS

Property History for 239 Chestnut Street

DateEvent & SourcePriceAppreciation
Dec 8, 2025

Price Change

BRIGHT #VAFV2037798

$290,000—
Oct 29, 2025

Listed (Active)

BRIGHT #VAWI2009330

$299,000—
Dec 31, 2004

Closed

BRIGHT #VAWI102172

$165,000—
Dec 31, 2004

Pending

BRIGHT #VAWI102172

—
Dec 31, 2004

Listed (Active)

BRIGHT #VAWI102172

$165,000—
Dec 30, 2002

Closed

BRIGHT #VAWI103400

$100,000—
Dec 17, 2002

Pending

BRIGHT #VAWI103400

—
Nov 7, 2002

Listed (Active)

BRIGHT #VAWI103400

$115,000—
DateEvent & SourcePrice
12/08/2025

Price Change

BRIGHT #VAFV2037798

$290,000
10/29/2025

Listed (Active)

BRIGHT #VAWI2009330

$299,000
12/31/2004

Closed

BRIGHT #VAWI102172

$165,000
12/31/2004

Pending

BRIGHT #VAWI102172

—
12/31/2004

Listed (Active)

BRIGHT #VAWI102172

$165,000
12/30/2002

Closed

BRIGHT #VAWI103400

$100,000
12/17/2002

Pending

BRIGHT #VAWI103400

—
11/07/2002

Listed (Active)

BRIGHT #VAWI103400

$115,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 239 Chestnut Street

Taxable ValueLand$58,500Additions$194,500Total$253,000
Home Facts
Beds2Baths1Total Finished SqFt1,176 SqFtAbove Grade Finished SqFt1,176 SqFtStories1StyleSingle Family ResidenceYear Built1976Year Renovated1993ZoningMRCountyWINCHESTER CITYAPN195-11- - 3A- 4A

Schools near 239 Chestnut Street

This home is within Winchester City Public Schools.
Rating
School
Type
Grades
Distance
Daniel Morgan Intermediate School
Public - 5 to 6
Daniel Morgan Middle School
Public - 7 to 8
John Handley High School
Public - 9 to 12
John Kerr Elementary
Public - PK to 4
Rating
School
Distance
Daniel Morgan Intermediate School
Public5 to 6

Daniel Morgan Middle School
Public7 to 8

John Handley High School
Public9 to 12

John Kerr Elementary
PublicPK to 4

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 239 Chestnut Street, Winchester, VA 22601

239 Chestnut Street is a single family home for sale in Winchester, VA 22601. This property was listed for sale on October 29, 2025 by Wildhawks Realty LLC, it's currently listed at $290,000. It has been on the market for a total of 48 days and was last sold on December 31, 2004. This listing's school district is Winchester City Public Schools. Nearby schools include Daniel Morgan Intermediate School, Daniel Morgan Middle School and John Handley High School. 239 Chestnut Street is a 2-bed, 1-bath, 1,176 sqft single family home built in 1976.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Wildhawks Realty LLC

© 2025 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 12/08/2025 09:37 AM