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Featured Agents in Chestertown, MD

Laurie Renshaw profile picture
Coldwell Banker Chesapeake

Laurie Renshaw

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42years of experience
400sales in the last 12 months
Prime Agent Badge
PRIME AGENT
Norman Lee Iii profile picture
Anne Arundel Properties

Norman Lee Iii

Completed Profile
1 review
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19years of experience
28sales in the last 12 months
500transactions all-time
Doug Ashley profile picture
Doug Ashley Realtors, Llc

Doug Ashley

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25years of experience

Compare 15 top-performing real estate agents in Chestertown, MD

Cr Realty

Chris Rosendale

1 review
Open 24 hours
Usually responds in 10 minutes
20 years of experience
102 sales in last 12 months
Serves Chestertown

About

I have been licensed and selling full time in the area for 17 years. For the past 17 years I have been one of the top selling agents in the area year after year.

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Achievements

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Top Centreville Agent 2025
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Top Company Agent 2025
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Top Sales Producer 2025

Top producer, Multimillion dollar club, top 5 realtors in bay area, Best of Eastern Shore Residential Brokerage (2017, 2018, 2019), Top residential realtor - Shore Update

Bachelor's Degree

Business Highlights

1031 Tax Exchange, Buyer Representative, Distressed Properties, Farm/Ranch
3rd generation Realtor/Broker/Owner/Realtor

Team Leader At Keller Williams

Toni Mcdowell

3 reviews
Open 9:00 AM - 5:00 PM
Usually responds in 1 hr
Prime Agent Badge
PRIME AGENT
21 years of experience
83 sales in last 12 months
Serves Chestertown

About

I have over 15 years in the business and my team has over 100 additional years of real estate expertise. The McDowell Team has sold over $400 million in homes this last 15 years. We are the top listing team out of our Annapolis Office for the last 7 years, We have listed over $250 million in homes during that time period. Our average days on market is 29 days (meaning your home might go under contract in less then 29 days). We average 98.4% of Sales Price to List Price, which compared to the local industry, you are 3.2% better working with us, than any other agent in the business.

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Achievements

Masters Club - $400 million in sales since 2005

Bachelor's Degree, University of Maryland
Business Management, 1978 - 1983

GRI, e-PRO

Business Highlights

1031 Tax Exchange, Buyer Representative, Condominiums, First Time Buyers
Boating along the Chesapeake Bay since early 70's, Very knowledgeable around the waterfronts.

Champion Realty, Inc.

Patsy Whiteley

32 years of experience
Serves Chestertown

About

Patsy Whiteley is a Real Estate Agent in Chestertown, MD with the brokerage Champion Realty, Inc.. Over the last 32 years we have tracked null MLS listings by Patsy.

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Achievements

High School Diploma

GRI, REALTOR®

Rosendale Realty

Tammy Rosendale

21 years of experience
Serves Chestertown

About

Tammy Rosendale is a Real Estate Agent in Chestertown, MD with the brokerage Rosendale Realty. Over the last 21 years we have tracked null MLS listings by Tammy.

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Achievements

High School Diploma

GRI, REALTOR®

Business Highlights

Lot/Land, Luxury Properties

Thyme Real Estate Co

Kimberly Simpson

Usually responds in 5 minutes
21 years of experience
568 transactions all-time
Serves Chestertown

About

I began my real estate career in 2003, the height of the housing market. Those days gave a false sense of the job, you’d stick a sign in the yard, & it would practically sell while you were doing it. By 2007 my business was on a trajectory of success. A bad auto accident knocked me out of work for many months. My best friend (now my right hand in business) sacrificially stepped in, helping me keep my business afloat. Through PT, & many doctor’s appointments, every day a struggle. The housing bubble burst when I was getting back on my feet. I had decide, switch careers or dig deeper? I was determined to stay in the business, I educated myself on foreclosures, distressed homes & short sales. I learned all the niches at all levels to broaden my experience for clients I worked for. But mainly in those tough years, I learned to listen & understand. I absorbed clients' stories, made it personal to help in any way I could. My business is about affecting lives & I do not take that lightly.

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Achievements

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Top Middletown Agent 2025
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Top Middletown Brokerage 2025
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Top Listing Agent 2025

Top producer, 100% club

Omega Real Estate School

REALTOR®

Business Highlights

1031 Tax Exchange, Buyer Representative, Distressed Properties, Farm/Ranch
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Chestertown Housing Market Report

Market Action Index

We are extensively tracking the housing market in Chestertown, MD. Here are the strongest factors contributing to this score:

Fewer sellers are listing their homes compared to last year
Houses are selling quickly compared to the amount on the market
83
seller's market
Buyer's Market
0102030405060708090100
Seller's Market
Real Time Market Profile

Median List Price

$395K

Per Square Foot

$244

Days on Market

121

Total Listings

41

Median List Price

Tue, Apr 14, 2026

Median List Price
1 Year

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