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Homes for Sale in City Of Winchester, Winchester, VA

4 active listings · 40 sold since 2020

4

For Sale

$305K

Median Sale Price

12

Median Days on Market

96.7%

Sold-to-List

$184

Price / Sq Ft

Newest homes for sale in City Of Winchester, Winchester, VA

See all 4 on the map

City Of Winchester, Winchester, VA home price trend

YearMedian Sale PriceHomes Sold
2026$825K1
2025$458K4
2024$359K5
2023$348K6
2022$250K7
2021$203K7
2020$265K10

At the current trend, the median is modeled to reach about $715K in 2027 (estimate).

Cost to buy in City Of Winchester, Winchester, VA

At today's ~6.63% 30-year rate, the median $305K home in City Of Winchester, Winchester, VA runs about $1,969/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 City Of Winchester, Winchester, VA

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

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City Of Winchester, Winchester, VA real estate FAQ

How many homes are for sale in City Of Winchester, Winchester, VA?

There are 4 homes currently for sale in City Of Winchester, Winchester, VA.

How much do homes sell for in City Of Winchester, Winchester, VA?

The median sale price in City Of Winchester, Winchester, VA is $305K, based on 40 sales since 2020 (ranging from $130K to $503K).

How fast do homes sell in City Of Winchester, Winchester, VA?

Homes in City Of Winchester, Winchester, VA typically go under contract in about 12 days on market (median).

Do homes in City Of Winchester, Winchester, VA sell above asking?

Over the past 12 months, homes in City Of Winchester, Winchester, VA sold for an average of 96.7% of list price — below asking.

What is the price per square foot in City Of Winchester, Winchester, VA?

Homes in City Of Winchester, Winchester, VA have sold for a median of $184 per square foot since 2020.

Is the City Of Winchester, Winchester, VA housing market heating up or cooling down?

The median sale price in City Of Winchester, Winchester, VA has risen from $265K in 2020 to $825K in 2026. At the current trend, the median is on track for roughly $715K in 2027 (modeled estimate).

Who are the top real estate agents in City Of Winchester, Winchester, VA?

The most active agents in City Of Winchester, Winchester, VA over the past 18 months are: Jeanne Mezzatesta (Colony Realty) — 2 sales; Roxanne B Watts (Coldwell Banker Realty) — 1 sale; Stuart A Wolk (ERA Oakcrest Realty, Inc.) — 1 sale.