Search location…
553 Highland Ave photo 1
for sale
20 photos
1 / 20
553 Highland Ave photo 2
2 / 20
553 Highland Ave photo 3
3 / 20
553 Highland Ave photo 4
4 / 20
553 Highland Ave photo 5
5 / 20
553 Highland Ave photo 6
6 / 20
553 Highland Ave photo 7
7 / 20
553 Highland Ave photo 8
8 / 20
553 Highland Ave photo 9
9 / 20
553 Highland Ave photo 10
10 / 20
553 Highland Ave photo 11
11 / 20
553 Highland Ave photo 12
12 / 20
553 Highland Ave photo 13
13 / 20
553 Highland Ave photo 14
14 / 20
553 Highland Ave photo 15
15 / 20
553 Highland Ave photo 16
16 / 20
553 Highland Ave photo 17
17 / 20
553 Highland Ave photo 18
18 / 20
553 Highland Ave photo 19
19 / 20
553 Highland Ave photo 20
20 / 20

$299,999

3beds
|
2baths
|
1,362sqft
|
1921built
553 Highland Ave,Winchester, VA 22601

Est.$1,973/moCustomize payment

What's special

$220/sqft

Price per square foot

Built in 1921

105 years old

Overview

Awesome Colonial Revival just four blocks from Winchester's beloved walking mall! This 1921 charmer has been completely transformed with a total make-over you'll love. Brand new stainless steel appliances make cooking a joy, while fresh vinyl laminate flooring flows throughout for easy living. New LED fixtures brighten every room, and classy bathroom updates add that spa-like touch. Tucked away on a quiet one-way street, you get the best of both worlds - peaceful neighborhood living with downtown walkability, in an up and coming neighborhood. Three comfortable bedrooms and two full baths give ...

Listing updated: May 23, 2026 at 1:41 PM

Listed by:

Teri Domanski 540-687-8067, Your Home Sold Guaranteed Realty - East LLC

Source: Bright MLS · MLS #VAWI2009182Bright MLS

Property details

Cost estimate

Est. monthly payment

$1,774/mo
Principal & interest
$1,573
Property tax
$101
Home insurance (est.)
$100

Down payment

$60,00020% of list price
Adjust down payment20%
0%25%50%

Based on 20% down ($60,000), 6.85% interest rate, 30-year fixed. Insurance is an estimate. Actual costs may vary.

Rates provided by Mable Loans.

Customize scenario

Price history

DateEventPrice
May 22, 2026Price reduced$299,999($19,001)
Oct 3, 2025Listed for sale$319,000

Location

553 Highland Ave, Winchester, VA 22601

Nearby schools

VIRGINIA AVENUE CHARLOTTE DEHART

Elementary School

DANIEL MORGAN

Middle School

JOHN HANDLEY

High School

Recently sold nearby

Similar homes sold within 0.5 miles in the last 90 days.

This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

Nearby homes

$299,999

3 beds · 2 baths · 1,362 sqft

Bright MLS

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Samson Properties participates, and is provided by BRIGHT through a licensing agreement. © 2026 Bright MLS, All Rights Reserved. Information deemed reliable but not guaranteed. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Data last updated: 6/3/2026.