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$269,000

  • For Sale
  • Under Contract
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,297 Sq. Ft.
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This Winchester City charmer is the perfect starter home, downsizing option, or investment opportunity. Thoughtfully updated with all the heavy lifting complete at the same time preserving the charm and character. Bedroom one is on the main floor with attached bathroom (complete with clawfoot tub!!) Upstairs you will find the sweetest loft perfect for home office, or reading nook...Second bedroom and full bath. (and a little surprise...Hint, Meow.) Roof, HVAC, Water heater and Stainless appliances replaced in 2019. Bring your green thumb or pets the rear yard is fenced in and will serve as your oasis in the city. Quiet evenings or morning coffee await. Walkable distance to Downtown Winchester's best restaurants and shops. Photos will be updated Saturday morning

Full Property Details for 939 Woodland Ave

General

  • Price: $269,000
  • Taxes: $1,744 (2025)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWI2010076
  • Updated: 3/10/2026
  • Added to Site: 28 day(s) ago

Interior

  • Interior Features: Entry Level Bedroom, Floor Plan - Traditional, Kitchen - Eat-In, Kitchen - Table Space, Primary Bath(s), Wood Floors
  • Appliances: Stove, Refrigerator, Stainless Steel Appliances, Washer/Dryer Stacked
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2
  • Upper Floor Baths: 1
  • Upper - Full Baths: 1
  • Main Floor Baths: 1
  • Main - Full Baths: 1

Bedrooms

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

Other Rooms

  • Laundry: Main Floor, Washer In Unit, Dryer In Unit

Exterior

  • Exterior Features: Exterior Lighting
  • Porch/Patio/Deck: Porch(es)

Parking

  • Parking Type: Driveway, Off Street

Location

  • County: WINCHESTER CITY
  • Subdivision: HARRIS ADDITION
  • Driving Directions: GPS works perfectly for this Winchester City Home
  • City Limits: Yes

School Information

  • School District: Winchester City Public Schools
  • High School: John Handley

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Natural Gas
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Cottage, Craftsman, Bungalow, Cape Cod
  • Structure Type: Detached
  • Construction: Stucco
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Outside Entrance, Unfinished
  • Foundation: Stone
  • Roof: Shingle
  • Walls/Ceilings: Dry Wall, Plaster Walls
  • Stories Description: Main, Upper 1
  • Square Feet: 1,297
  • Sq. Ft. Source: Estimated
  • Living Area: 897 Sq. Ft.
  • Finished Above Grnd: 897 Sq. Ft.
  • Year Built: 1940
  • Year Built Source: Assessor
  • Property Condition: Good, Very Good, Excellent

Additional Structures

  • Other Structures: Shed

Lot Features

  • Lot Size Source: Estimated
  • Zoning: MR
  • Lot Description: Front Yard, Rear Yard
  • Fencing (Description): Rear, Fully

Financial Considerations

  • Price Per Sq. Ft.: $299.89
  • Assessment Year: 2025
  • City/TownTax: $1,744
  • City/TownTax Freq: Annually
  • County Tax Freq: Annually
  • Tax w/Assessment: $219,400
  • Tax Amount: $1,744
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 897

Disclosures and Reports

  • Ownership: Fee Simple
  • Inclusions: stove, refrigerator, stackable washer/dryer
  • Lot Number: 113

Listed by Roberts Realty Group, LLC, Kristen Kerns

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Listing agent

— 939 Woodland Ave —

  • Kristen Kerns

    Roberts Realty Group, 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 939 Woodland Ave

School District:Winchester City Public Schools
NameGradesDistance
John Kerr Elementary
427 Meadow Branch Avenue, Winchester, VA 22601
PK-42.5 mi
Daniel Morgan Middle School
48 South Purcell Avenue, Winchester, VA 22601
7-80.4 mi
John Handley High School
425 Handley Boulevard, Winchester, VA 22601
9-121.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 939 Woodland Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/07/2026
Listed
$269,000
11.97%
MLS
5/18/2023
Sold
$240,250
—
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 939 Woodland Ave

Year
Property Taxes
Change
Tax Assessment
Change
2024
100%
$219,400
17%
2024
-100%
$186,800
—
2023
$1,550
21%
$186,800
35%
2022
$1,282
—
$137,900
—
2021
$1,282
12%
$137,900
12%
2020
$1,140
—
$122,600
—
2018
$1,140
5%
$122,600
3%
2018
$1,088
8%
$119,600
—
2016
$1,005
—
$119,600
8%
2016
$1,005
—
$110,400
—
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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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Roberts Realty Group, LLC, Kristen Kerns

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939 Woodland Avenue, Winchester, VA 22601 (MLS# VAWI2010076) is a Single Family property with 2 bedrooms and 2 full bathrooms. 939 Woodland Avenue is currently listed for $269,000 and was received on March 07, 2026. Want to learn more about 939 Woodland 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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