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$320,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 1 Full Bath
  • 1,134 Sq. Ft.
  • 2 Car Garage

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Open House: 1:00 PM - 3:00 PM

Sunday 1/18 1:00 PM - 3:00 PM

27 Jackson Avenue,Winchester, VA 22601

27 Jackson AvenueWinchesterVA22601

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Completely renovated and move-in ready, this charming 3 bedroom, 1 bath home is ideally located just minutes from downtown Winchester's shops, dining, and entertainment. Inside, you'll find beautiful hardwood floors throughout and a brand new kitchen and fully renovated bathroom. Major updates to the home include a new roof, new windows, new HVAC system, new hot water heater and new electric all installed in 2025. Outside there is an oversized garage with ample storage and a spacious backyard with privacy. A rare opportunity to own a turnkey home in a prime location - schedule your showing today!

Full Property Details for 27 Jackson Ave

General

  • Price: $320,000
  • Taxes: $1,725 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWI2009632
  • Updated: 12/27/2025
  • Added to Site: 20 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Living Room, Bedroom 2, Kitchen, Bedroom 1, Laundry, Loft, Bathroom 1
  • Interior Features: Bathroom - Tub Shower, Combination Kitchen/Dining, Entry Level Bedroom, Kitchen - Eat-In, Wood Floors
  • Appliances: Dishwasher, Refrigerator, Stove
  • Flooring: Hardwood

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 3
  • Bedrooms Upper: 1
  • Bedrooms Main & Up: 2

Other Rooms

  • Laundry: Hookup, Main Floor

Exterior

  • Exterior Features: Outbuilding(s)
  • Porch/Patio/Deck: Porch(es)

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Detached Garage, Driveway
  • Garage Description: Oversized

Location

  • County: WINCHESTER CITY
  • Subdivision: WINCHESTER CITY
  • Driving Directions: Take Martinsburg Pike into Winchester make a left and continue on Martinsburg Pike, in 1 mile turn right on Jackson Ave, home is on the left. Blue house with front porch and ERA Oakcrest sign in the front yard.

School Information

  • School District: Winchester City Public Schools

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Cottage
  • Structure Type: Detached
  • Construction: Combination
  • Basement: Yes
  • Basement Desc.: Interior Access, Unfinished
  • Foundation: Block
  • Roof: Shingle
  • Stories Description: Main, Upper 1
  • Square Feet: 1,134
  • Sq. Ft. Source: Assessor
  • Living Area: 1,134 Sq. Ft.
  • Finished Above Grnd: 1,134 Sq. Ft.
  • Year Built: 1933
  • Year Built Source: Estimated
  • Property Condition: Excellent

Additional Structures

  • Other Structures: Garage(s), Shed

Lot Features

  • Lot Size (Acres): 0.15
  • Lot Size (Sq. Ft.): 6,534
  • Lot Size Source: Estimated
  • Zoning: HR1
  • Lot Description: Rear Yard

Financial Considerations

  • Price Per Sq. Ft.: $282.19
  • Assessment Year: 2025
  • County Tax Freq: Annually
  • Tax w/Assessment: $217,020
  • Tax Amount: $1,725
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 1135

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 20A

Listed by ERA Oakcrest Realty, Inc., Mikiala Ann Whitacre

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Listing agent

— 27 Jackson Ave —

  • Mikiala Ann Whitacre

    ERA Oakcrest Realty, Inc.

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 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/27/2025
Listed
$320,000
76.8%
MLS
11/10/2025
Sold
$181,000
—
Public Record
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 27 Jackson Ave

Year
Property Taxes
Change
Tax Assessment
Change
2024
100%
$217,020
10%
2024
-100%
$197,020
—
2023
$1,635
21%
$197,020
35%
2022
$1,354
—
$145,600
—
2021
$1,354
13%
$145,600
13%
2020
$1,194
—
$128,400
—
2018
$1,194
2%
$128,400
—
2018
$1,168
12%
$128,400
—
2016
$1,044
—
$128,400
12%
2016
$1,044
—
$114,700
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 27 Jackson Ave

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by ERA Oakcrest Realty, Inc., Mikiala Ann Whitacre

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27 Jackson Avenue, Winchester, VA 22601 (MLS# VAWI2009632) is a Single Family property with 3 bedrooms and 1 full bathroom. 27 Jackson Avenue is currently listed for $320,000 and was received on December 27, 2025. 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.

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