house
1/17
$1,479/mo
$225,0003bd·2ba·1,526sf
369 Charles Street, Winchester, VA 22601
Listing Courtesy of ERA Oakcrest Realty, Inc.
Homes for Sale in Winchester City, Winchester, VA
2 active listings · 264 sold since 2020
2
For Sale
$297K
Median Sale Price
12
Median Days on Market
100.3%
Sold-to-List
$181
Price / Sq Ft
Newest homes for sale in Winchester City, Winchester, VA
See all 2 on the mapWinchester City, Winchester, VA home price trend
| Year | Median Sale Price | Homes Sold |
|---|---|---|
| 2026 | $356K | 14 |
| 2025 | $355K | 24 |
| 2024 | $326K | 46 |
| 2023 | $300K | 48 |
| 2022 | $267K | 29 |
| 2021 | $254K | 46 |
| 2020 | $245K | 57 |
At the current trend, the median is modeled to reach about $385K in 2027 (estimate).
Cost to buy in Winchester City, Winchester, VA
At today's ~6.75% 30-year rate, the median $297K home in Winchester City, Winchester, VA runs about $1,937/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 City, Winchester, VA
Most active agents by closed sales here over the past 18 months.
- Heloisa P AmarSamson Properties2 sales
- Lisa S GillERA Oakcrest Realty, Inc.2 sales
- Daniel J WhitacreColony Realty2 sales
- Aracely RiveraFirst Decision Realty LLC2 sales
- Meridee A PowarsLink Realty Services LLC2 sales
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Winchester City, Winchester, VA real estate FAQ
How many homes are for sale in Winchester City, Winchester, VA?
There are 2 homes currently for sale in Winchester City, Winchester, VA.
How much do homes sell for in Winchester City, Winchester, VA?
The median sale price in Winchester City, Winchester, VA is $297K, based on 264 sales since 2020 (ranging from $125K to $594K).
How fast do homes sell in Winchester City, Winchester, VA?
Homes in Winchester City, Winchester, VA typically go under contract in about 12 days on market (median).
Do homes in Winchester City, Winchester, VA sell above asking?
Over the past 12 months, homes in Winchester City, Winchester, VA sold for an average of 100.3% of list price — at or above asking.
What is the price per square foot in Winchester City, Winchester, VA?
Homes in Winchester City, Winchester, VA have sold for a median of $181 per square foot since 2020.
Is the Winchester City, Winchester, VA housing market heating up or cooling down?
The median sale price in Winchester City, Winchester, VA has risen from $245K in 2020 to $356K in 2026. At the current trend, the median is on track for roughly $385K in 2027 (modeled estimate).
Who are the top real estate agents in Winchester City, Winchester, VA?
The most active agents in Winchester City, Winchester, VA over the past 18 months are: Heloisa P Amar (Samson Properties) — 2 sales; Lisa S Gill (ERA Oakcrest Realty, Inc.) — 2 sales; Daniel J Whitacre (Colony Realty) — 2 sales.
