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
$530M
All-Time Sales
$370K - $26M
Price Range
4%
Negotiated Off List
Top Agent$420.9M
All-Time Sales
$470K - $11.6M
Price Range
11%
Negotiated Off List
Top Agent$309.1M
All-Time Sales
$390K - $2.4M
Price Range
3%
Negotiated Off List
Top Agent$224.2M
All-Time Sales
$370K - $1.3M
Price Range
1
Sold in Winchester, VA
Top Agent
(12)
Matias Leiva
Keller Williams Realty | ML Real Estate Group
9 Years of experience
192+ Sales in the last 12 months
$377.7M
All-Time Sales
$620K - $4M
Price Range
8
Sold in Winchester, VA
Top Agent$301.6M
All-Time Sales
$320K - $3M
Price Range
5%
Negotiated Off List
Top Agent$242.8M
All-Time Sales
$330K - $1.4M
Price Range
4%
Negotiated Off List
Top Agent(84)
Donald Winland
LPT Realty | Winland Real Estate
20 Years of experience
31+ Sales in the last 12 months
$249.9M
All-Time Sales
$340K - $1.6M
Price Range
3%
Negotiated Off List
Top Agent$354.2M
All-Time Sales
$390K - $1.8M
Price Range
1
Sold in Winchester, VA
Top Agent$326.3M
All-Time Sales
$590K - $4.5M
Price Range
4%
Negotiated Off List
Top Agent$101.1M
All-Time Sales
$200K - $1.1M
Price Range
5%
Negotiated Off List
Top Agent$201.1M
All-Time Sales
$300K - $1.8M
Price Range
2%
Negotiated Off List
Top Agent$196.3M
All-Time Sales
$360K - $4.3M
Price Range
3%
Negotiated Off List
Top Agent$265.7M
All-Time Sales
$500K - $2.1M
Price Range
2
Sold in Winchester, VA
Top Agent$297.4M
All-Time Sales
$590K - $3M
Price Range
5%
Negotiated Off List
Top Agent$153.8M
All-Time Sales
$340K - $1.2M
Price Range
2%
Negotiated Off List
Top Agent(16)
Kelly Gaitten
Berkshire Hathaway Home Services
35 Years of experience
25+ Sales in the last 12 months
$220.8M
All-Time Sales
$560K - $1.9M
Price Range
3
Sold in Winchester, VA
Top Agent$162.8M
All-Time Sales
$490K - $1.8M
Price Range
4%
Negotiated Off List
Top Agent$184.5M
All-Time Sales
$530K - $1.8M
Price Range
1
Sold in Winchester, VA
Top Agent(9)
Steve Bommarito
United Country Homeplace Properties
21 Years of experience
27+ Sales in the last 12 months
$46.2M
All-Time Sales
$110K - $1.1M
Price Range
2
Sold in Winchester, VA
Top Agent$190.3M
All-Time Sales
$570K - $3M
Price Range
4
Sold in Winchester, VA
Top Agent$126.1M
All-Time Sales
$420K - $1.3M
Price Range
3
Sold in Winchester, VA
Top Agent$49.1M
All-Time Sales
$470K - $1.4M
Price Range
1
Sold in Winchester, VA
Top Agent$98.8M
All-Time Sales
$410K - $2.4M
Price Range
5
Sold in Winchester, VA
Top Agent$80.3M
All-Time Sales
$240K - $1.4M
Price Range
3%
Negotiated Off List
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