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$181,000

  • Sold
  • Closed
  • Single Family
  • 2 Beds
  • 1 Full Bath
  • 1,134 Sq. Ft.
  • 2 Car Garage
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Great investor opportunity in the heart of Winchester! The LOWEST priced detached house within a 10-mile radius!! This 3-level home with a 2-car detached garage on a level treed lot is ideal for investors looking to fix and flip or fix and hold, with Shenandoah University only 3 miles away and Winchester Medical Center only 4 miles away. This detached 1933 front porch Cottage home on .20 acre lot sold strictly 'As-Is.' The house has one bedroom on the main level with a full bathroom, living room, and kitchen, plus a finished upper level with a 2nd large bedroom and an unfinished basement on public water and sewer with no HOA. Fabulous location just minutes to the historic city center and major commuting routes. Walking distance to historic Winchester shops, restaurants, and breweries. Close to Jim Barnett Park and the MSV hiking trails.

Full Property Details for 27 Jackson Ave

General

  • Sold For: $181,000
  • Taxes: $1,725 (2025)
  • Status: Closed
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWI2009294
  • Added to Site: 88 day(s) ago

Interior

  • Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Kitchen, Basement

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 2
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 1
  • Primary Bedroom: Primary Bedroom, Upper 1
  • Bedroom 1: Bedroom 2, Main

Other Rooms

  • Living Room: Living Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main

Exterior

  • Exterior Features: Street Lights
  • Porch/Patio/Deck: Porch(es)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Detached Garage, Off Street
  • Garage Description: Garage - Front Entry

Location

  • County: Winchester City
  • Development Name: Winchester City
  • Subdivision: Winchester City
  • Cross Streets: N Loudoun
  • Driving Directions: From DC/NOVA, take I-66 West to exit 6 onto US 340/US 522 North, continue onto Stonewall Jackson Hwy (US 522) to Millwood Pike/ US 17/50W then turn right onto Millwood Avenue to a right on S Cameron, then turn right onto N Loudoun St, then left on Jackson Avenue to 27 Jackson Avenue on the left.
  • City Limits: Yes

School Information

  • School District: Winchester City Public Schools
  • Elementary School: Virginia Avenue Charlotte Dehart
  • Middle School: Daniel Morgan
  • High School: John Handley

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Central
  • Heating Fuel: Oil
  • Water Heater: Electric

Utilities

  • Sewer: Public Septic
  • Water: Public

Structural Information

  • Architectural Info: Cottage
  • Architectural Style: Cottage
  • Structure Type: Detached
  • Construction: Combination
  • Basement: Yes
  • Basement Desc.: Interior Access
  • Foundation: Slab
  • Stories/Levels: 0
  • Stories Description: Main, Upper 1
  • Square Feet: 1,134
  • Sq. Ft. Source: Assessor
  • Living Area: 1,134 Sq. Ft.
  • Year Built: 1933
  • Year Built Source: Assessor
  • Property Condition: Major Rehab Needed

Lot Features

  • Property View: Garden/Lawn, Trees/Woods
  • Lot Size (Acres): 0.15
  • Lot Size (Sq. Ft.): 6,665
  • Lot Size Source: Assessor
  • Lot Features: Backs to Trees
  • Zoning: HR1
  • Lot Description: Backs to Trees

Financial Considerations

  • Price Per Sq. Ft.: $145.5
  • Assessment Year: 2025
  • City/TownTax: $1,725
  • City/TownTax Freq: Annually
  • County Tax Freq: Annually
  • Tax w/Assessment: $217,020
  • Tax Amount: $1,725
  • Tax Year: 2025
  • Terms: Standard Sale
  • Tax Total Finished Sq. Ft.: 1134

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 20A

Meet the listing agents

Meet the listing agents
— 27 Jackson Ave —

Get Pre-Approved Today

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 27 Jackson Ave

School District:Winchester City Public Schools
NameGradesDistance
Virginia Ave. Charlotte Dehart Elementary School
550 Virginia Avenue, Winchester, VA 22601
PK-40.9 mi
Daniel Morgan Middle School
48 South Purcell Avenue, Winchester, VA 22601
7-81.5 mi
John Handley High School
425 Handley Boulevard, Winchester, VA 22601
9-121.8 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 27 Jackson Ave

Date
Details
Price
Change
Source
11/14/2025
Sold
$181,000
9.7%
MLS
10/20/2025
Listed
$165,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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27 Jackson Avenue, Winchester, VA 22601 (MLS# VAWI2009294) is a Single Family property that was sold at $181,000 on November 14, 2025. This property was listed by Elizabeth Ide from our Woodbridge - Prince William County Office.Want to learn more about 27 Jackson Avenue? 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.