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Homes for Sale in Winchester, VA

220 active listings · 4,984 sold since 2020

220

For Sale

$374K

Median Sale Price

11

Median Days on Market

98.8%

Sold-to-List

$187

Price / Sq Ft

Newest homes for sale in Winchester, VA

See all 220 on the map

Winchester, VA home price trend

YearMedian Sale PriceHomes Sold
2026$420K391
2025$420K695
2024$415K731
2023$392K641
2022$359K742
2021$330K880
2020$297K904

At the current trend, the median is modeled to reach about $463K in 2027 (estimate).

Cost to buy in Winchester, VA

At today's ~6.63% 30-year rate, the median $374K home in Winchester, VA runs about $2,414/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 Winchester, VA

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

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Winchester, VA real estate FAQ

How many homes are for sale in Winchester, VA?

There are 220 homes currently for sale in Winchester, VA.

How much do homes sell for in Winchester, VA?

The median sale price in Winchester, VA is $374K, based on 4,984 sales since 2020 (ranging from $181K to $740K).

How fast do homes sell in Winchester, VA?

Homes in Winchester, VA typically go under contract in about 11 days on market (median).

Do homes in Winchester, VA sell above asking?

Over the past 12 months, homes in Winchester, VA sold for an average of 98.8% of list price — below asking.

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

Homes in Winchester, VA have sold for a median of $187 per square foot since 2020.

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

The median sale price in Winchester, VA has risen from $297K in 2020 to $420K in 2026. At the current trend, the median is on track for roughly $463K in 2027 (modeled estimate).

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

The most active agents in Winchester, VA over the past 18 months are: James B Sears (D R Horton Realty of Virginia LLC) — 72 sales; Tracy M Jennings (D R Horton Realty of Virginia LLC) — 33 sales; Sheila R Pack (RE/MAX Roots) — 29 sales.

Neighborhoods & Subdivisions in Winchester, VA