Top Real Estate Agents in Chestertown, MD

We analyze millions of home sales to find the best performing real estate agents & REALTORS® for your personalized needs.

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Find a Chestertown, MD Real Estate Agent Today.

HomeLight examines the transaction history for the 443 active Chestertown real estate agents to find the best ones. The top 3% of real estate agents in Chestertown get homes off the market in 62 days and sell for $34,341 more than the average.

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Top Chestertown REALTOR® Rankings

Top Agents List updated on July 17th, 2024
Jack Shoptaw snapshot

CENTURY 21 New Millennium

Jack Shoptaw assumed leadership of the Washington, D.C., branch of CENTURY 21 New Millennium in September 2016. CENTURY 21 New Millennium, consistently ranked among the top real estate organizations in the United States regardless of brand, has offices throughout Virginia, Maryland and the District of Columbia, offe...

Home Transactions


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Years of Experience


Vince Caropreso snapshot

Keller Williams Flagship Of Maryland

It Began with a Mission: Our mission is to deliver the dream of home ownership and to influence, impact, and improve the lives of those around us and our communities. Team Caropreso is passionate about Real Estate and our goal is to transform the Real Estate industry by producing extraordinary results to our clien...

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Average Price Point


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Gina White snapshot


We are a full service Brokerage. Specializing in Veteran and Active Military Relocation Home Sales and Rentals. First Time Home Buyers and Next Level Purchase is our primary business. Our Team will guide you through the process with ease. My personal goal is for each client to find a home that will enhance their fin...

Gina White's reviews

"She is an amazing person. I will do business with her all over again and I will recommend her to anyone. ..." see more reviews

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Average Price Point


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Stephanie Lehane snapshot

The Lehane Team at RE/MAX Eagle Realty

Stephanie is the BROKER/OWNER at RE/MAX Eagle Realty and Team Lead for The Lehane Team. Stephanie is a single family home expert. We have data on 642 of Stephanie’s transactions. Stephanie has worked with sellers 97% of the time, and has represented the buyer in 70 recorded transactions. Here’s a little about St...

Stephanie Lehane's reviews

"Ken was whom I worked with. He was Awesome, great knowledge knew what he was doing..." see more reviews

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Bob Frey snapshot

Exit Results Realty

Bob grew up in Reisterstown, MD and has lived his adult life in Baltimore, Howard and Carroll counties; this partly is why he has such an expansive knowledge of the Baltimore Metropolitan Marketplace. As a dedicated full time agent you will be sure to receive the best service possible, as Bob has a desire to help ot...

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Cornelia C snapshot

Long and Foster Real Estate

Cornelia C. Heckenbach, Associate Broker of the Long and Foster Real Estate St. Michaels office, was born and raised in Germany. She relocated to Talbot County in 1990. Cornelia is a dedicated full-time agent with notable expertise of the Talbot County, Maryland, Oxford, Easton and St Michaels real estate market, wh...

Home Transactions


Average Price Point


Years of Experience


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Dee Dee Miller snapshot

Long and Foster Real Estate Inc

Dee is a real estate agent with Long and Foster Real Estate Inc in Severna Park, Maryland and has been in the real estate business for 18 years. Dee has completed transactions in several areas including Severna Park, Arnold, Glen Burnie, Lake Shore, Cape St. Claire and Severn. HomeLight ranks Dee as one of the top 1...

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Robert McArtor snapshot

RE/MAX Components

Robert has been a licensed real estate agent in Maryland for 15 years and is currently with RE/MAX Components in Fallston. Robert's coverage area includes Joppatowne, Bel Air South, Bel Air North, Baltimore, Riverside and Havre de Grace. HomeLight ranks Robert as one of the top 1% of agents in Harford County for su...

Robert McArtor's reviews

"The dynamic Duo! I would not choose any other agent to sell my future home!..." see more reviews

Home Transactions


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Bevia Patrick snapshot

Keller Williams Flagship of Maryland

Bevia Patrick alongside her husband Jeffrey Patrick, has built a Veteran owned and operated team. This team is comprised of talented and experienced group of real estate professionals who have consistently produced top agents. With Bevia at the helm, Patrick Team Properties’ reputation of excellence and professional...

Bevia Patrick's reviews

"She was wonderful and knowledgeable...." see more reviews

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Erica Baker snapshot

TTR Sotheby's International Realty

As a lifelong resident of Maryland Erica Baker exceeds expertise knowledge for her local residential area. She is a local Realtor with a never-ending urge to go above and beyond what is expected in this ever changing real estate world. Real Estate to her is a lifestyle. With an exciting vision for Global Real Esta...

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Chestertown Top Real Estate Agents

How we select the best Chestertown agents

At HomeLight, our vision is a world where every real estate transaction is simple, certain, and satisfying.
We've analyzed transaction data of local real estate agents and REALTORS® across 6 distinct metrics to recommend a few of Chestertown's top Real Estate Agents.
Top Picks

Top real estate agents stats at a glance

HomeLight can match you with real estate agents in the top 3% of performers who, on average, sell 1.5x faster and for 155.7% more money.

Sale Price / List Price (%)

Days on Market

Lower is better

Homes Sold / Year

Find your perfect real estate agent in Chestertown, MD

Tools for sellers & buyers

Check out some of our other resources for Chestertown homeowners

Client FAQs

What does a top real estate agent do?

Top real estate agents have more local expertise, prepare in-depth market analyses, and have industry connections that you can’t find by yourself. They know your neighborhood like the back of their hand and use their market knowledge to sell your home faster than the average agent and for money.

What should you look for when interviewing a real estate agent in Chestertown?

When you sell a house, your real estate agent becomes your business partner, financial advisor, and emotional support system. It’s crucial to partner with someone you trust, so make sure you’re looking for an agent who can answer all of your questions with confidence during the interview. During this process, you want to get to know the agent’s business and find out how well they know the area. You’re listening for things that signal experience, expertise in your community, and workload. Selling a home takes an enormous amount of work, so you need an agent who’s got a plan for prep, pricing, and marketing and who is ready to roll up their sleeves to get the job done.

How important is it to hire a top real estate agent in Chestertown?

Our data shows that the top 5% of listing agents sell homes for as much as (+9%) more than the average real estate agent. A great agent makes a difference when you buy a house, too: We’ve found that the top 5% of buyer's agents on average save their clients 2.5% more on their home purchase. So, whether you’re in the market to find your dream home or sell your house at a great price, the right agent matters. We encourage you to connect with a top real estate agent if you’re buying or selling a home in Chestertown, MD.

When is the right time to hire a real estate agent in Chestertown?

The best window to contact an agent to sell your home is anywhere from three to six months in advance of your list date. When you start the search for an agent several months before hitting the market, there’s plenty of time to find the best agent, make key renovations, and market your home effectively, all of which are essential steps in selling your home for a great price. You can also hire an agent based on the best time to sell to take advantage of seasonal and cyclical trends in the market.

The right time to hire a real estate agent depends on the temperature of the housing market. For example, the best time to sell is in May. And since it takes around 3 months to close on a home, you should list in February. We recommend that you hire a real estate agent as soon as you're thinking of selling your home. Generally speaking, that's anywhere from 3 to 6 months prior to your desired move date.

What is the average real estate agent commission for agents in Chestertown?

While individual real estate agent commissions do vary, most real estate agents in Chestertown work for 6% of the home price.

Why should I use HomeLight to find a Chestertown real estate agent?

HomeLight analyzes all real estate agent in Chestertown to bring you custom, unbiased, data-driven recommendations. We use actual home sales transaction data to compare Chestertown real estate agent and will only introduce you to the top performing agents. They do not pay to advertise on our site and we do not pay to list them. To give you the best object recommendations, we consider things like: how fast a real estate agent sells, how many properties they work on, how much money they save or earn their clients, and what cities and neighborhoods they specialize in. You can trust that we’ll match you with the right agents for your needs.