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Homes for Sale in Historic Downtown Winchester, Winchester, VA

1 active listing · 6 sold since 2020

1

For Sale

$817K

Median Sale Price

23

Median Days on Market

100.0%

Sold-to-List

$201

Price / Sq Ft

Newest homes for sale in Historic Downtown Winchester, Winchester, VA

See all 1 on the map

Historic Downtown Winchester, Winchester, VA home price trend

YearMedian Sale PriceHomes Sold
2025$817K2
2024$1.3M1
2023$1.4M1
2020$303K2

At the current trend, the median is modeled to reach about $1.4M in 2026 (estimate).

Cost to buy in Historic Downtown Winchester, Winchester, VA

At today's ~6.63% 30-year rate, the median $817K home in Historic Downtown Winchester, Winchester, VA runs about $5,274/mo with 20% down (principal & interest plus estimated taxes and insurance).

Estimate only — not a loan offer. Actual rate and payment depend on your profile.

Top agents in Historic Downtown Winchester, Winchester, VA

Most active agents by closed sales here over the past 18 months.

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Historic Downtown Winchester, Winchester, VA real estate FAQ

How many homes are for sale in Historic Downtown Winchester, Winchester, VA?

There is 1 home currently for sale in Historic Downtown Winchester, Winchester, VA.

How much do homes sell for in Historic Downtown Winchester, Winchester, VA?

The median sale price in Historic Downtown Winchester, Winchester, VA is $817K, based on 6 sales since 2020 (ranging from $246K to $1.4M).

How fast do homes sell in Historic Downtown Winchester, Winchester, VA?

Homes in Historic Downtown Winchester, Winchester, VA typically go under contract in about 23 days on market (median).

Do homes in Historic Downtown Winchester, Winchester, VA sell above asking?

Over the past 12 months, homes in Historic Downtown Winchester, Winchester, VA sold for an average of 100.0% of list price — at or above asking.

What is the price per square foot in Historic Downtown Winchester, Winchester, VA?

Homes in Historic Downtown Winchester, Winchester, VA have sold for a median of $201 per square foot since 2020.

Is the Historic Downtown Winchester, Winchester, VA housing market heating up or cooling down?

The median sale price in Historic Downtown Winchester, Winchester, VA has risen from $303K in 2020 to $817K in 2025. At the current trend, the median is on track for roughly $1.4M in 2026 (modeled estimate).

Who are the top real estate agents in Historic Downtown Winchester, Winchester, VA?

The most active agents in Historic Downtown Winchester, Winchester, VA over the past 18 months are: Charles Aaron Ridgeway (ERA Oakcrest Realty, Inc.) — 1 sale.