Charming Winchester Home Dont 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. Seller is motivated and offering $7,000 in closing cost assistance making this an incredible opportunity for qualified buyers!Enjoy ample off-street parking with rear-alley access, fresh renovations, brand-new vinyl flooring on the main level, and a new upstairs deckperfect 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 provides privacy and easy accessPerfectly located near downtown Winchester, shops, dining, and commuter routes, this home combines charm, practicality, and potential all at an unbeatable price. Dont miss this opportunity! Schedule your tour today and take advantage of the $7,000 closing cost incentive before its gone.
- VA
- Winchester
- 22601
- 423 HIGHLAND AVENUE
- MLS# VAWI2009152
- Date Listed11/04/2025
- Days on Realty 4 Days
- Bedrooms 3
- Bathrooms 2 Full baths
- Lot Size 0.09 acres (3,746 sq. ft)
- Sewer Public Sewer
- Subdivision CITY
- Property Type Single Family
- County WINCHESTER CITY
- Year Built 1930
- Water Public
- Square Feet 1,300 sq. ft
- Price Per Sq. Ft $226.92
Interior Features
- Appliances Electric Water Heater
- Cooling None
- Heating Electric, Baseboard
Exterior / Lot Features
- Roof -
- Lot Size Acres 0.09
- Lot Size SQFT 3,746.00
- Lot Features -
Directions
From National Ave downtown Winchester take left on Gray ave, left on Grey ave, and left on Highland Ave
Financial Considerations
- Tax Amount $1,374
- Terms Cash, Conventional, FHA, VA Loan
Nearby Schools
Source: School Digger
Virginia Ave. Charlotte Dehart Elementary School
Public • PK - 4 • Serves this home
0.73 mi
Distance
Daniel Morgan Intermediate School
Public • 5 - 6 • Serves this home
1.1 mi
Distance
Public • 9 - 12 • Serves this home
1.18 mi
Distance
Virginia Ave. Charlotte Dehart Elementary School
Public • PK - 4 • Serves this home
0.73 mi
Distance
Garland R. Quarles Elementary School
Public • PK - 4
2.02 mi
Distance
Frederick Douglass Elementary School
Public • PK - 4
4.17 mi
Distance
Public • PK - 4 • Serves this home
4.25 mi
Distance
Daniel Morgan Intermediate School
Public • 5 - 6 • Serves this home
1.1 mi
Distance
Public • 7 - 8
1.1 mi
Distance
Public • 9 - 12 • Serves this home
1.18 mi
Distance
Sales & Tax History
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 111 OLD DOMINION DRIVE | Listing | 3 | 3 | Sep 16, 2025 | $275,000 | Mar 21, 2024 | $346,882 |
| 106 RUGBY PLACE | Listing | 3 | 3 | Oct 21, 2025 | $359,000 | Mar 21, 2024 | $364,416 |
| 350 KERN STREET | Listing | 2 | 2 | Oct 21, 2025 | $224,900 | Mar 21, 2024 | $253,043 |
| 110 E GERMAIN STREET | Listing | 3 | 2 | Oct 21, 2025 | $314,900 | Jan 24, 2024 | $296,970 |
| 500 N BRADDOCK STREET | Listing | 4 | 2 | Oct 21, 2025 | $325,000 | Mar 21, 2024 | $385,133 |
| 100 SPAULDING DRIVE | Listing | 4 | 4 | Oct 21, 2025 | $330,000 | Mar 21, 2024 | $350,304 |
| 572 N LOUDOUN STREET | Listing | 3 | 1 | Oct 21, 2025 | $140,000 | Mar 21, 2024 | $124,795 |
| 424 MARION STREET | Listing | 4 | 2 | Oct 21, 2025 | $379,900 | Mar 21, 2024 | $378,833 |
| 510 S CAMERON STREET | Listing | 2 | 2 | Oct 21, 2025 | $265,000 | Mar 21, 2024 | $226,444 |
| 611 WATSON AVENUE | Listing | 3 | 2 | Oct 21, 2025 | $136,000 | Jan 24, 2024 | $225,175 |
Population & Environment
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | 30,038 | 28,575 | 28,589 | 335,858,263 |
| Population Density | 3,037 | 3,094 | 3,097 | 95 |
| People per Household | 2.4 | 2.4 | 2.4 | 2.6 |
| Median Age | 37.5 | 37.6 | 37.6 | 39.1 |
| Median Income | $61,466 | $61,643 | $61,653 | $66,222 |
| Average Income | $33,769 | $34,045 | $34,050 | $35,475 |
| Cost of Living Index | 75 | 75 | 75 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | 22.2°F | 22.2°F | 22.2°F | 22.6°F |
| July Avg. High Temp | 85°F | 85°F | 85°F | 86.2°F |
| Annual Precipitation | 36.4" | 36.4" | 36.4" | 38" |
79/100
Very Walkable
Walk Score ®
49/100
Bikable
Bike Score ®
Overview
Most errands can be accomplished on foot. It is possible to get on a bus. Minimal bike infrastructure.Walkability averages in the surrounding area
The average walkability score in the surrounding area is Walk Score: 16/100, Transit Score: 0/100, Bike Score: 25/100.
Property Change History
View Changes
Previous Description:
Updated Description:
Points of Interest near 423 HIGHLAND AVENUE, WINCHESTER, VA 22601
686 ft
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Frequently Asked Questions for 423 HIGHLAND AVENUE
Source: Realty.com
423 HIGHLAND AVENUE, WINCHESTER, VA 22601 is a Single Family 1,300 sq. ft. home listed for sale. Realty.com has 41 photos available of this 3 bed, 2 bath house, listed at $295,000. View sales and tax history, use our mortgage calculator and more on Realty.com
Realty.com has 41 photos of 423 HIGHLAND AVENUE.
Our records indicate that 423 HIGHLAND AVENUE was built in 1930.
The full address for this home is 423 HIGHLAND AVENUE, WINCHESTER, VA 22601.
423 HIGHLAND AVENUE has been listed on Realty.com since Tue November 04, 2025
Most errands can be accomplished on foot. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 16/100, Transit Score: 0/100, Bike Score: 25/100.
There are 3 schools assigned to this home. Check out the schools near 423 HIGHLAND AVENUE. Virginia Ave. Charlotte Dehart Elementary School (Grades: PK - 4), Daniel Morgan Intermediate School (Grades: 5 - 6), John Handley High School (Grades: 9 - 12)
Listing provided courtesy of:
Samson Properties
(tel: 540-348-4911)
Listing agent:
Carlos Soares
(tel: 540-532-2112)
(#3308841)
This content last refreshed on 2025-11-09 04:03:29. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 423 HIGHLAND AVENUE, WINCHESTER, VA 22601 : MLS# VAWI2009152