How do I find a top real estate agent in Chestertown, MD?

The matching quiz is the fastest way — six questions about your timeline, budget, and what matters most, then you see the top three Chestertown agents based on your answers, and our team reviews your request, and after you confirm your email may connect you with them. You can also browse all Chestertown agents directly from this page.

How many agents does our Chestertown directory have?

It currently lists 38 agents in Chestertown, all sourced from license records. Agents on this page have closed at an average sale price of $468,438.

Who's the most active agent in Chestertown?

Erin Anderson of Chesapeake Real Estate Associates, LLC is one of the busiest agents in our Chestertown directory by recent transaction count. Use the matching quiz or browse the full list to compare.

How are Chestertown agents verified?

Every Chestertown agent profile is sourced directly from license records. An agent can claim their profile, and our team reviews and approves each claim; until then it's an unclaimed listing built purely from public license data.

Can I work with a Chestertown agent on both buying and selling?

Yes — the quiz lets you select more than one intent (e.g., selling your current Chestertown home + buying your next one). We'll match you with agents who can handle both sides of the transaction.

What does it cost to use Expert Agents Near Me in Chestertown?

Free for consumers. Always. And we never sell your contact information.

Home / States / Maryland / Chestertown

Top real estate agents in Chestertown, MD

38 agents listed

Match me with the top 3 in Chestertown Selling? See listing agents

Chestertown, MD is one of Maryland's real estate markets we cover, and our directory lists 38 agents here. Whether you're buying your first home, listing yours, refinancing, or sizing up an investment, the agent you pick should know Chestertown block by block.

Every Chestertown agent here is sourced from license records, and the busiest are closing at an average sale price of $468,438. Look for someone whose typical transaction matches your range.

The fastest way to find a fit is the matching quiz — answer six quick questions and you'll see the top three Chestertown agents for your situation. Our team reviews your request, and after you confirm your email we may connect you with them.

Real estate agents in Chestertown

Featured agents pay for placement. They are listed first where they serve and labeled Featured; everyone else is listed by sales volume.How placement works

Michael ONeill

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 21
Avg price: $802,182

Peter Heller

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 14
Avg price: $1,101,250

Hayley Norris

Unclaimed

Select Land & Homes, LLC

Chestertown, MD

Sales (12mo): 15
Avg price: $362,333

Richard Keaveney

Unclaimed

Cross Street Realtors LLC

Chestertown, MD

Sales (12mo): 9
Avg price: $720,000

Terri Kulp

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 20
Avg price: $561,436

Tinamarie Reamy

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 19
Avg price: $516,187

Erin Anderson

Unclaimed

Chesapeake Real Estate Associates, LLC

Chestertown, MD

Sales (12mo): 23
Avg price: $392,071

Joseph Ciganek

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 21
Avg price: $342,036

Kristina Hyland

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 21
Avg price: $408,000

Retha Arrabal

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 19
Avg price: $482,834

Maryn LeClair

Unclaimed

Chesapeake Real Estate Associates, LLC

Chestertown, MD

Sales (12mo): 19
Avg price: $353,912

Michele Palmer

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 16
Avg price: $317,833

Grace Crockett

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 11
Avg price: $398,333

Tracy Stone

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 5
Avg price: $467,500

Douglas Ashley

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 8
Avg price: $229,000

Mikeshia Lindsey

Unclaimed

Chesapeake Real Estate Associates, LLC

Chestertown, MD

Sales (12mo): 12
Avg price: $283,414

Lisa Raffetto

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 5
Avg price: $920,000

Brittany Lombardi

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 8
Avg price: $279,750

Sarah King

Unclaimed

Cross Street Realtors LLC

Chestertown, MD

Sales (12mo): 6
Avg price: $311,667

Andrew Meikle

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 7
Avg price: $350,550

Jennifer Mobley

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 5
Avg price: $463,800

Elisabeth Ostrander

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 4
Avg price: $600,000

Jody Baker

Unclaimed

Cross Street Realtors LLC

Chestertown, MD

Sales (12mo): 5
Avg price: $311,667

James Cronin

Unclaimed

Chesapeake Real Estate Associates, LLC

Chestertown, MD

Sales (12mo): 4
Avg price: $326,500

Nancy McGuire

Unclaimed

Maryland Heritage Properties

Chestertown, MD

Sales (12mo): 3
Avg price: $384,000

Lauren Cox

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 2
Avg price: $620,000

Debra Meikle

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 5
Avg price: $368,000

Robert Davis

Unclaimed

Davis Real Estate, Inc.

Chestertown, MD

Sales (12mo): 3
Avg price: $451,500

Heather Dolan

Unclaimed

Chesapeake Real Estate Associates, LLC

Chestertown, MD

Sales (12mo): 2
Avg price: $587,500

Francis Hickman

Unclaimed

Cross Street Realtors LLC

Chestertown, MD

Sales (12mo): 1
Avg price: $1,075,000

Vincenzo Assante Di Cupillo

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 1
Avg price: $925,000

Elizabeth Green

Unclaimed

Doug Ashley Realtors, LLC

Chestertown, MD

Sales (12mo): 3
Avg price: $237,450

Daniel Hercher

Unclaimed

Chesapeake Real Estate Associates, LLC

Chestertown, MD

Sales (12mo): 1
Avg price: $525,000

Charles Coates

Unclaimed

Select Land & Homes, LLC

Chestertown, MD

Sales (12mo): 1
Avg price: $339,950

Cheryl Hurt

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 1
Avg price: $320,000

Mary Fielding

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 1
Avg price: $295,000

Jo Edwards

Unclaimed

The Hogans Agency

Chestertown, MD

Sales (12mo): 1
Avg price: $290,000

Jyaire McCall

Unclaimed

Coldwell Banker Chesapeake Real Estate Company

Chestertown, MD

Sales (12mo): 1
Avg price: $80,000

Frequently asked questions about Chestertown real estate

Quick answers about how matching works in Chestertown and how to pick the right agent.

The matching quiz is the fastest way — six questions about your timeline, budget, and what matters most, then you see the top three Chestertown agents based on your answers, and our team reviews your request, and after you confirm your email may connect you with them. You can also browse all Chestertown agents directly from this page.