Top Realtors and Real Estate Agents in Winchester, VA
Rankings based on verified MLS transaction data. Last updated August 2026. No pay-to-play.
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Top Agent
$84.7M
All-Time Sales
$370K - $1.7M
Price Range
2
Sold in Winchester, VA
Top Agent$127.4M
All-Time Sales
$620K - $2.6M
Price Range
3
Sold in Winchester, VA
Top Agent
(15)
Carolyn Thompson
Real Estate Search and Sale, LLC
24 Years of experience
15+ Sales in the last 12 months
$67.1M
All-Time Sales
$290K - $1.1M
Price Range
1%
Negotiated Off List
Top Agent$33.1M
All-Time Sales
$210K - $750K
Price Range
2
Sold in Winchester, VA
Top Agent(33)
John Constant
Middleburg Real Estate/Atoka Properties
25 Years of experience
4+ Sales in the last 12 months
$52M
All-Time Sales
$510K - $1.6M
Price Range
3
Sold in Winchester, VA
Top AgentReviews not yet available
Nick Moore
Samson Properties
6 Years of experience
1+ Sales in the last 12 months
$20.5M
All-Time Sales
$430K - $1.4M
Price Range
5
Sold in Winchester, VA
Top Agent$19.9M
All-Time Sales
$260K - $1.6M
Price Range
2
Sold in Winchester, VA
Top AgentReviews not yet available
Ariel Guzman
RE/MAX Roots
4 Years of experience
9+ Sales in the last 12 months
$5.1M
All-Time Sales
$310K - $510K
Price Range
7
Sold in Winchester, VA
Top AgentReviews not yet available
Linda Wood
A New Century Realty
22 Years of experience
2+ Sales in the last 12 months
$2.6M
All-Time Sales
$170K - $800K
Price Range
2
Sold in Winchester, VA
Winchester Housing Market Trends
Homes in Winchester take a median 58 days to sell, go for 98.3% of asking, prices are down 6.1% from a year ago. Verified MLS market data through August 2026.
Market temperature
Balanced market
3.5 months of supply. Under 3 favors sellers, over 6 favors buyers.
What homes sell for
$374,742
median sale price
How fast they sell
58 days
median time on market
Supply and competition
3.5 months
of supply on the market
In Winchester