Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$269,000

  • For Sale
  • Under Contract
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,300 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
✨ Charming Winchester Home - Don't Let This One Slip Away! Welcome to this beautifully refreshed home in the heart of Winchester, offering exceptional value, versatility, and convenience. Thoughtfully updated throughout, this property is move-in ready while still leaving room to make it your own. Enjoy ample off-street parking for up to 8 cars with rear access from West Lane, fresh renovations, brand-new vinyl flooring on the main level, and a new upstairs deck - perfect for morning coffee or evening relaxation. Property Highlights: 🛏️ 3 spacious bedrooms filled with natural light 🛁 2 full bathrooms - one on each level, with main-level laundry for added convenience 🏡 Flexible main-level office or bonus room - ideal as a home office, guest room, or cozy reading nook 🌳 Fully fenced backyard perfect for entertaining, pets, or peaceful outdoor enjoyment 🪴 New upstairs deck offering additional outdoor living space 🚗 Rear-alley parking with entry from West Lane, providing privacy, convenience, and space for up to 8 vehicles Perfectly located near downtown Winchester, shops, dining, and commuter routes, this home combines charm, practicality, and potential - all at an unbeatable price. 📅 Don't miss this opportunity! Schedule your tour today!

Full Property Details for 423 Highland Ave

General

  • Price: $269,000
  • Taxes: $1,374 (2025)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: VAWI2009152
  • Updated: 12/19/2025
  • Added to Site: 74 day(s) ago

Interior

  • Rooms/Areas: Dining Room, Kitchen, Family Room, Laundry

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: 3
  • Bedrooms Upper: 3

Parking

  • Parking Type: On Street, Driveway, Alley

Location

  • County: WINCHESTER CITY
  • Subdivision: CITY
  • Driving Directions: From National Ave downtown Winchester take left on Gray ave, left on Grey ave, and left on Highland Ave
  • City Limits: Yes

School Information

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

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Baseboard - Electric
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public

Structural Information

  • Architectural Style: Traditional
  • Structure Type: Detached
  • Construction: Vinyl Siding
  • Foundation: Stone, Crawl Space
  • Stories Description: Main, Upper 1
  • Square Feet: 1,300
  • Sq. Ft. Source: Estimated
  • Living Area: 1,300 Sq. Ft.
  • Finished Above Grnd: 1,300 Sq. Ft.
  • Year Built: 1930
  • Year Built Source: Estimated

Lot Features

  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 3,746
  • Lot Size Source: Estimated
  • Zoning: HR1

Financial Considerations

  • Price Per Sq. Ft.: $206.92
  • Assessment Year: 2025
  • City/TownTax: $1,374
  • City/TownTax Freq: Monthly
  • Tax w/Assessment: $172,900
  • Tax Amount: $1,374
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Lot Number: 10

Listed by Samson Properties, Carlos da Rocha Soares Sr.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 423 Highland Ave —

  • Carlos da Rocha Soares Sr.

    Samson Properties

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 423 Highland Ave

School District:Winchester City Public Schools
NameGradesDistance
Virginia Ave. Charlotte Dehart Elementary School
550 Virginia Avenue, Winchester, VA 22601
PK-40.3 mi
Daniel Morgan Middle School
48 South Purcell Avenue, Winchester, VA 22601
7-80.8 mi
John Handley High School
425 Handley Boulevard, Winchester, VA 22601
9-121.2 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 423 Highland Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/24/2025
Price Reduced
$269,000
-1.82%
MLS
11/20/2025
Price Reduced
$274,000
-1.79%
MLS
11/17/2025
Price Reduced
$279,000
-3.46%
MLS
11/13/2025
Price Reduced
$289,000
-2.03%
MLS
11/04/2025
Listed
$295,000
65.73%
MLS
12/19/2022
Sold
$178,000
—
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 423 Highland Ave

Year
Property Taxes
Change
Tax Assessment
Change
2024
100%
$172,900
5%
2024
-100%
$164,100
—
2023
$1,362
34%
$164,100
50%
2022
$1,016
—
$109,200
—
2021
$1,016
21%
$109,200
21%
2020
$837
—
$90,000
—
2018
$837
22%
$90,000
19%
2018
$687
14%
$75,500
—
2016
$600
—
$75,500
15%
2016
$600
—
$65,900
—
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 423 Highland Ave

$
Down Payment
%
$
%

$
$

*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

Get Pre-Approved

Listed by Samson Properties, Carlos da Rocha Soares Sr.

Similar Properties near 423 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

208 Shenandoah Ave, Winchester, VA 22601 - Photo 1
$279,000

208 Shenandoah Ave  Winchester, VA 22601

  • Single Family
  • Active
  • 3
    Beds
  • 1
    Total Bath
  • 907
    Sq. Ft.
Listed by Colony Realty, Daniel J Whitacre
239 Chestnut St, Winchester, VA 22601 - Photo 1 Price Reduced
-$11,000 (-3.79%)
$279,000

239 Chestnut St  Winchester, VA 22601

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,176
    Sq. Ft.
Listed by Wildhawks Realty LLC, William R Wertz
204 Shenandoah Ave, Winchester, VA 22601 - Photo 1
$265,000

204 Shenandoah Ave  Winchester, VA 22601

  • Single Family
  • Active
  • 2
    Beds
  • 1
    Total Bath
  • 882
    Sq. Ft.
Listed by Keller Williams Realty, Janet M. Flaherty
177 Dicks Hollow Rd, Winchester, VA 22603 - Photo 1 Price Reduced
-$10,000 (-3.64%)
$265,000

177 Dicks Hollow Rd  Winchester, VA 22603

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 572
    Sq. Ft.
Listed by Cambridge Premier Realty, LLC., Amy Nichole Emerson-Kerns

Just Listed near 423 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

113 Timberlake Terrace, Stephens City, VA 22655 - Photo 1 Just Listed
$229,000

113 Timberlake Terrace  #2  Stephens City, VA 22655

  • Condo
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,054
    Sq. Ft.
Listed by MarketPlace REALTY, Kimberly D Hurst
120 Amelia Ave, Stephens City, VA 22655 - Photo 1 Just Listed
$425,000

120 Amelia Ave  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 3,192
    Sq. Ft.
Listed by Real Broker LLC, Mark S Francis
556 Garden Gate Dr, Stephens City, VA 22655 - Photo 1 Just Listed
$480,000

556 Garden Gate Dr  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,248
    Sq. Ft.
Listed by Samson Properties, Ann M. Conley
156 Willett Holw St, Stephens City, VA 22655 - Photo 1 Just Listed
$349,000

156 Willett Holw St  Stephens City, VA 22655

  • Townhouse
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,500
    Sq. Ft.
Listed by ERA Oakcrest Realty, Inc., James H Stafford III

Price Reduced near 423 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

106 Woodtop Ct, Stephens City, VA 22655 - Photo 1 Price Reduced
-$5,500 (-1.43%)
$379,500

106 Woodtop Ct  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,184
    Sq. Ft.
Listed by Thomas and Talbot Estate Properties, Inc., David W. Wilson
112 Jefferson Ct, Stephens City, VA 22655 - Photo 1 Price Reduced
-$3,000 (-0.71%)
$422,000

112 Jefferson Ct  Stephens City, VA 22655

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,682
    Sq. Ft.
Listed by ERA Oakcrest Realty, Inc., Tiffany J Hunter and ERA Oakcrest Realty, Inc., Tracie Clawson
64 Salem Church Rd, Boyce, VA 22620 - Photo 1 Price Reduced
-$160,000 (-13.91%)
$990,000

64 Salem Church Rd  Boyce, VA 22620

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,400
    Sq. Ft.
Listed by Thomas and Talbot Estate Properties, Inc., Anne W McIntosh and Thomas and Talbot Estate Properties, Inc., Maria Eldredge
64 Salem Church Rd, Boyce, VA 22620 - Photo 1 Price Reduced
-$160,000 (-13.91%)
$990,000

64 Salem Church Rd  Boyce, VA 22620

  • Farm Single-Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,400
    Sq. Ft.
Listed by Thomas and Talbot Estate Properties, Inc., Maria Eldredge

Recent Sales near 423 Highland Ave

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

320 Highland Ave, Winchester, VA 22601 - Photo 1 Sold
$266,000

320 Highland Ave  Winchester, VA 22601

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,313
    Sq. Ft.
Listed by Samson Properties, Heloisa P Amar
Sold by Keller Williams Realty, Richard L Guthrie and Keller Williams Realty, Phyllis Guthrie
621 Butler Ave, Winchester, VA 22601 - Photo 1 Sold
$300,000

621 Butler Ave  Winchester, VA 22601

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 1,803
    Sq. Ft.
Listed by RE/MAX Roots, Kaitlyn Behr
Sold by Five Star Real Estate, Justin Goodman
566 N Loudoun St, Winchester, VA 22601 - Photo 1 Sold
$277,000

566 N Loudoun St  Winchester, VA 22601

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 2,058
    Sq. Ft.
Listed by Colony Realty, Daniel J Whitacre
Sold by RE/MAX Gateway, Bailey Scot Cooper
525 E Cork St, Winchester, VA 22601 - Photo 1 Sold
$299,000

525 E Cork St  Winchester, VA 22601

  • Single Family
  • Closed
  • 2
    Beds
  • 1
    Total Bath
  • 858
    Sq. Ft.
Listed by Long & Foster Real Estate, Inc., Kimberly Anne Schroeder
Sold by RE/MAX Distinctive Real Estate, Sara E Duncan

423 Highland Avenue, Winchester, VA 22601 (MLS# VAWI2009152) is a Single Family property with 3 bedrooms and 2 full bathrooms. 423 Highland Avenue is currently listed for $269,000 and was received on November 04, 2025. Want to learn more about 423 Highland 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.

Tour this property