Virginia • 44 Top Realtors • 2026 Rankings

Best Real Estate Agents in Chesapeake, Virginia

1,810
Transactions
$763M
Volume
44
Top Agents
Berkshire Hathaway HomeServices RW Towne Realty
Top Brokerage

Discover top-performing real estate agents in Chesapeake, Virginia, a thriving waterfront community known for its natural beauty, diverse neighborhoods, and strong maritime heritage. Our directory features the region's leading agents who collectively closed over 1,800 transactions valued at $763 million, with many specializing in the unique waterfront and suburban properties that define this dynamic coastal city.

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Chesapeake Real Estate Agents Ranked by Sales Volume

Finding the right agent is just the beginning.

Matthew Salway

Real Estate Agent

Iron Valley Real Estate Hampton Roads

$35.78M
107 transactions
Individuals by Volume

Julie Fish

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$25.48M
37 transactions
Individuals by Volume

September Lundeen

Real Estate Agent

Redfin

$18.56M
44 transactions
Individuals by Volume

Danielle Brinson

Real Estate Agent

Keller Williams Coastal Virginia Chesapeake

$17.10M
30 transactions
Individuals by Volume

Katie Burke

Real Estate Agent

Long & Foster Real Estate

$16.72M
40 transactions
Individuals by Volume

Andy Nelson

Real Estate Agent

Iron Valley Real Estate Hampton Roads - Chesapeake

$14.74M
49 transactions
Individuals by Volume

L. Ellen Drames

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$14.69M
31 transactions
Individuals by Volume

Matt Monaco

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$13.48M
23 transactions
Individuals by Volume

Nicole Glocker

Real Estate Agent

Iron Valley Real Estate Hampton Roads - Chesapeake

$13.27M
36 transactions
Individuals by Volume

Jason Harris

Real Estate Agent

Keller Williams Elite 757

$11.75M
42 transactions
Individuals by Volume

Evelyn Thomas

Real Estate Agent

CENTURY 21 Nachman Realty

$11.39M
25 transactions
Individuals by Volume

Tara Strauser

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$10.85M
34 transactions
Individuals by Volume

David Allison

Real Estate Agent

Atlantic Sotheby's International Realty

$10.76M
28 transactions
Individuals by Volume

John King

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$10.66M
23 transactions
Individuals by Volume

Jarrett Caldwell

Real Estate Agent

Keller Williams Coastal Virginia Chesapeake

$10.53M
28 transactions
Individuals by Volume

Christopher Wayne Prince

Real Estate Agent

Keller Williams Realty Town Center

$10.39M
18 transactions
Individuals by Volume

James Butler

Real Estate Agent

Iron Valley Real Estate Hampton Roads - Chesapeake

$10.21M
31 transactions
Individuals by Volume

Kelly Moran

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$9.67M
29 transactions
Individuals by Volume

Megan Elizabeth Messer

Real Estate Agent

Keller Williams Coastal Virginia Chesapeake

$9.49M
26 transactions
Individuals by Volume

Jasmine Feliu

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$9.25M
26 transactions
Individuals by Volume

Melinda Baldwin

Real Estate Agent

CENTURY 21 Nachman Realty

$8.94M
25 transactions
Individuals by Volume

Laura Blackwood

Real Estate Agent

CENTURY 21 Nachman Realty

$8.33M
26 transactions
Individuals by Volume

Paul Gitlin

Real Estate Agent

Redfin

$8.29M
22 transactions
Individuals by Volume

Kim Wilkins

Real Estate Agent

RE/MAX Ultra

$7.84M
23 transactions
Individuals by Volume

Melinda Swager

Real Estate Agent

NextHome Tidewater Realty

$7.72M
22 transactions
Individuals by Volume

Steven Hargrow

Real Estate Agent

NextHome SLH Real Estate Group

$6.75M
20 transactions
Individuals by Volume

Janay Richardson

Real Estate Agent

Keller Williams Coastal Virginia Chesapeake

$5.94M
26 transactions
Individuals by Volume

Reigne Brown

Real Estate Agent

RE/MAX Ultra

$4.76M
14 transactions
Individuals by Volume

Sherae Thompson

Real Estate Agent

Redfin

$2.59M
8 transactions
Individuals by Volume

Natalie Carrier

Real Estate Agent

Redfin

$2.44M
7 transactions
Individuals by Volume

The Thompson Team

Real Estate Agent

The Agency Coastal Virginia

$57.70M
115 transactions
Small Teams by Volume

Anna Paduhovich Team

Real Estate Agent

Keller Williams Coastal Virginia Chesapeake

$31.14M
77 transactions
Small Teams by Volume

Marable Realty Team

Real Estate Agent

Iron Valley Real Estate Hampton Roads - Chesapeake

$24.09M
44 transactions
Small Teams by Volume

The Yvonne Avila Team

Real Estate Agent

Iron Valley Real Estate Hampton Roads - Chesapeake

$23.52M
45 transactions
Small Teams by Volume

Bedsole Border Edge Team

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$22.36M
47 transactions
Small Teams by Volume

Rountree Team

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$20.77M
42 transactions
Small Teams by Volume

The Calderon Team

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$20.51M
42 transactions
Small Teams by Volume

Diane Keeley & Team

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$19.37M
31 transactions
Small Teams by Volume

The O Team

Real Estate Agent

Keller Williams Coastal Virginia Chesapeake

$17.93M
37 transactions
Small Teams by Volume

The Hollowell Group

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$16.75M
28 transactions
Small Teams by Volume

Mr Kempsville Team

Real Estate Agent

Iron Valley Real Estate Hampton Roads - Chesapeake

$16.62M
47 transactions
Small Teams by Volume

Katy & Co

Real Estate Agent

Keller Williams Coastal Virginia Chesapeake

$13.59M
47 transactions
Small Teams by Volume

The Ron Sawyer Team

Real Estate Agent

RE/MAX Prime

$84.94M
223 transactions
Large Teams by Volume

Wilkey Real Estate Team

Real Estate Agent

Berkshire Hathaway HomeServices RW Towne Realty

$45.53M
86 transactions
Large Teams by Volume

Frequently Asked Questions

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

The best real estate agents in Chesapeake include Matthew Salway of Iron Valley Real Estate Hampton Roads (107 transactions), Julie Fish of Berkshire Hathaway HomeServices RW Towne Realty (37 transactions), September Lundeen of Redfin (44 transactions), among others. Our directory tracks 44 top-performing agents ranked by verified sales volume and transaction history.

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

To find a top realtor in Chesapeake, compare their sales volume, transaction history, and client reviews. Our directory tracks 44 agents in Chesapeake—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 Chesapeake?

IonDocs analyzes property disclosure packages for homes in Chesapeake, 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 Chesapeake 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.

Buying in Chesapeake?

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Agent in Chesapeake?

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