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.
Sold for $181,000
$181,000
27 Jackson Ave, Winchester, VA 22601
2beds
1,134sqft
Single Family Residence
Built in 1933
6,665 Square Feet Lot
$297,800 Zestimate®
$160/sqft
$2,018 Estimated rent
Home value
$297,800
$283,000 - $313,000
$2,018/mo
Zestimate® history
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$881/mo
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Zillow last checked:
Listing updated:
Listed by:
Beth Ide 703-217-0192,
Coldwell Banker Realty,
Co-Listing Agent: Ally Goldwater 571-991-0935,
Coldwell Banker Realty
Bought with:
Mikiala Whitacre, WVS210301588
ERA Oakcrest Realty, Inc.
Source: Bright MLS,MLS#: VAWI2009294
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
- Main level bathrooms: 1
- Main level bedrooms: 1
Rooms
- Room types: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Kitchen, Basement
Primary bedroom
- Level: Upper
Bedroom 2
- Level: Main
Basement
- Level: Lower
Dining room
- Level: Main
Kitchen
- Level: Main
Living room
- Level: Main
Heating
- Central, Oil
Cooling
- Central Air, Electric
Appliances
- Included: Electric Water Heater
Features
- Basement: Interior Entry
- Has fireplace: No
Interior area
- Total structure area: 1,134
- Total interior livable area: 1,134 sqft
- Finished area above ground: 1,134
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Detached, Off Street
- Garage spaces: 2
Accessibility
- Accessibility features: Doors - Swing In
Features
- Levels: Three
- Stories: 3
- Patio & porch: Porch
- Exterior features: Street Lights
- Pool features: None
- Has view: Yes
- View description: Garden, Trees/Woods
Lot
- Size: 6,665 Square Feet
- Features: Backs to Trees
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1340320A
- Zoning: HR1
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cottage
- Property subtype: Single Family Residence
Materials
- Combination
- Foundation: Slab
Condition
- Fixer
- New construction: No
- Year built: 1933
Utilities & green energy
- Sewer: Public Septic
- Water: Public
Community & HOA
Community
- Subdivision: Winchester City
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $160/sqft
- Tax assessed value: $217,020
- Annual tax amount: $1,725
- Date on market: 10/20/2025
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Price history
| Date | Event | Price |
|---|---|---|
| 5/8/2026 | Listing removed | $2,100$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 5/2/2026 | Listed for rent | $2,100$2/sqft |
Source: Zillow Rentals Report a problem | ||
| 3/25/2026 | Listing removed | $300,000$265/sqft |
Source:  Bright MLS #VAWI2009632 Report a problem | ||
| 3/9/2026 | Price change | $300,000-3.2%$265/sqft |
Source: Bright MLS #VAWI2009632 Report a problem | ||
| 2/15/2026 | Price change | $310,000-3.1%$273/sqft |
Source: Bright MLS #VAWI2009632 Report a problem | ||
| 12/27/2025 | Listed for sale | $320,000+76.8%$282/sqft |
Source: Bright MLS #VAWI2009632 Report a problem | ||
| 11/14/2025 | Sold | $181,000+9.7%$160/sqft |
Source: Bright MLS #VAWI2009294 Report a problem | ||
| 10/30/2025 | Contingent | $165,000$146/sqft |
Source: Bright MLS #VAWI2009294 Report a problem | ||
| 10/20/2025 | Listed for sale | $165,000$146/sqft |
Source: Bright MLS #VAWI2009294 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,725 +5.5% | $217,020 +10.2% |
| 2024 | $1,635 | $197,020 |
| 2023 | $1,635 +20.8% | $197,020 +35.3% |
| 2022 | $1,354 | $145,600 |
| 2021 | $1,354 +15.9% | $145,600 +13.4% |
| 2020 | $1,168 | $128,400 |
| 2019 | $1,168 | $128,400 |
| 2018 | $1,168 +11.9% | $128,400 |
| 2017 | $1,044 | $128,400 +11.9% |
| 2016 | $1,044 | $114,700 |
| 2015 | $1,044 -1% | $114,700 +3.3% |
| 2014 | $1,055 | $111,000 |
| 2013 | -- | $111,000 -5.5% |
| 2012 | -- | $117,500 |
| 2011 | -- | $117,500 -16.9% |
| 2010 | -- | $141,400 |
| 2009 | -- | $141,400 +4.5% |
| 2008 | -- | $135,300 |
| 2007 | -- | $135,300 +32.1% |
| 2006 | -- | $102,400 |
| 2005 | -- | $102,400 +27.8% |
| 2004 | -- | $80,100 |
| 2003 | -- | $80,100 +22.7% |
| 2002 | -- | $65,300 |
| 2001 | -- | $65,300 |
Find assessor info on the county website
Neighborhood: 22601
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Nearby schools
GreatSchools rating
- 3/10Virginia Ave. Charlotte Dehart Elementary SchoolGrades: PK-4Distance: 0.9 mi
- 4/10Daniel Morgan Middle SchoolGrades: 7-8Distance: 1.5 mi
- 3/10John Handley High SchoolGrades: 9-12Distance: 1.8 mi
Schools provided by the listing agent
- Elementary: Virginia Avenue Charlotte Dehart
- Middle: Daniel Morgan
- High: John Handley
- District: Winchester City Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$297,800
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$297,800
- Virginia
- Winchester City
- Winchester
- 22601
- 27 Jackson Ave
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