Virginia • 25 Top Realtors • 2026 Rankings

Best Real Estate Agents in Winchester, Virginia

957
Transactions
$382M
Volume
25
Top Agents
RE/MAX Roots
Top Brokerage

Winchester, Virginia's historic downtown district and proximity to the Northern Virginia region make it an appealing market for homebuyers seeking small-town charm with metropolitan access. Our directory connects you with top local real estate professionals who have collectively closed 957 transactions worth $382 million, with RE/MAX Roots leading the market and individual agents driving the majority of sales volume.

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Winchester Real Estate Agents Ranked by Sales Volume

Finding the right agent is just the beginning.

Leslie Webb

Real Estate Agent

Long & Foster Real Estate

$29.79M
73 transactions
Individuals by Volume

Matt Roberts

Real Estate Agent

Redfin

$27.75M
43 transactions
Individuals by Volume

Bradley Comstock

Real Estate Agent

ERA OakCrest Realty, Inc.

$21.08M
47 transactions
Individuals by Volume

Rebecca Haughian

Real Estate Agent

Redfin

$15.33M
27 transactions
Individuals by Volume

Lisa Behr

Real Estate Agent

Coldwell Banker Premier

$12.18M
22 transactions
Individuals by Volume

Deborah Matthews

Real Estate Agent

ERA OakCrest Realty, Inc.

$11.90M
29 transactions
Individuals by Volume

Nicole Lewis

Real Estate Agent

Coldwell Banker Premier

$11.25M
30 transactions
Individuals by Volume

Laura White

Real Estate Agent

ERA OakCrest Realty, Inc.

$11.12M
23 transactions
Individuals by Volume

Justin Mistretta

Real Estate Agent

Berkshire Hathaway HomeServices PenFed Realty

$11.12M
29 transactions
Individuals by Volume

Julie Teets

Real Estate Agent

Long & Foster Real Estate

$10.71M
21 transactions
Individuals by Volume

Teresa Strohmeyer

Real Estate Agent

ERA OakCrest Realty, Inc.

$10.66M
30 transactions
Individuals by Volume

Wendy Conner

Real Estate Agent

Coldwell Banker Premier

$10.20M
22 transactions
Individuals by Volume

Debra Crosley

Real Estate Agent

Keller Williams Realty Alliance Group Leesburg

$10.16M
27 transactions
Individuals by Volume

Stuart Sinclair

Real Estate Agent

Coldwell Banker Premier

$10.04M
27 transactions
Individuals by Volume

Anna Fox

Real Estate Agent

NextHome Realty Select

$9.90M
38 transactions
Individuals by Volume

Kaitlyn Behr

Real Estate Agent

RE/MAX Roots

$9.74M
26 transactions
Individuals by Volume

Tracy Link

Real Estate Agent

Coldwell Banker Premier

$8.80M
26 transactions
Individuals by Volume

Bruce Elsey

Real Estate Agent

Long & Foster Real Estate

$7.41M
29 transactions
Individuals by Volume

Amanda Magana

Real Estate Agent

RE/MAX Roots

$5.61M
14 transactions
Individuals by Volume

Jennifer Sacco

Real Estate Agent

RE/MAX Roots

$4.21M
13 transactions
Individuals by Volume

Roxann Grimes Team

Real Estate Agent

RE/MAX Roots

$20.28M
50 transactions
Small Teams by Volume

Legacy Real Estate Group

Real Estate Agent

RE/MAX Roots

$17.88M
46 transactions
Small Teams by Volume

Ask4TeamEd LLC

Real Estate Agent

ERA OakCrest Realty, Inc.

$17.46M
39 transactions
Small Teams by Volume

Your Home Town Realtors

Real Estate Agent

RE/MAX Roots

$9.74M
26 transactions
Small Teams by Volume

Sheila Pack Team

Real Estate Agent

RE/MAX Roots

$68.02M
202 transactions
Medium Teams by Volume

Frequently Asked Questions

Who are the best real estate agents in Winchester, Virginia?

The best real estate agents in Winchester include Leslie Webb of Long & Foster Real Estate (73.1 transactions), Matt Roberts of Redfin (43 transactions), Bradley Comstock of ERA OakCrest Realty, Inc. (47 transactions), among others. Our directory tracks 25 top-performing agents ranked by verified sales volume and transaction history.

How do I find a good realtor near me in Winchester?

To find a top realtor in Winchester, compare their sales volume, transaction history, and client reviews. Our directory tracks 25 agents in Winchester—filter by specialty, review verified contact info, and reach out directly. Look for agents who specialize in your specific needs, whether buying, selling, or investing.

How can IonDocs help real estate agents in Winchester?

IonDocs analyzes property disclosure packages for homes in Winchester, Virginia in 60 seconds—work that typically takes agents 4–6 hours. Our AI catches costly surprises like pending HOA special assessments, permit issues, and structural discrepancies so Winchester agents can close more deals and spend less time on paperwork.

What are property disclosure packages and why do they matter?

Property disclosure packages are documents that sellers must provide to buyers in Virginia, revealing the property's condition, history, and any known issues. These packages often contain critical information about structural problems, pest damage, HOA finances, and legal issues. Missing a single detail can cost buyers tens of thousands of dollars—or kill a deal entirely.

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