We analyze top real estate agents in Chestertown and across the country to find you the most proven local agents, for free.
Agent Pronto analyzes transaction data, specialties, client reviews, and more to find the best agent for you. Updated for September 2025. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
Sell your home fast and for top dollar or find your dream home at the best possible price. Use our free service to find top agents you can trust.
We’ve helped over 500,000 home buyers and sellers find their ideal real estate agent.
“Realtor Kerry Foley is an exceptional agent. She is completely 'buttoned up' on every detail of the home buying process. She has every detailed piece of information at her fingertips and offers insightful advice about properties including condition, market comparisons and neighborhood insights.”
“My agent, Nisha Smithrick, was the ideal agent. We had tried to work with other Baltimore agents over the past year and they were terrible. Nisha was amazing from the get-go. She reached out immediately. She asked questions to understand our specific desires for my son's first home. She presented relevant listing within a day. She made herself available for appointments to fit our schedules. She showed us a great selection of homes. She followed up, gave her honest advice. She then was a great sounding board for creating an offer and negotiating with the seller. She was responsive and proactive through the whole process including to inspections and closing. She answered all our questions thoroughly and quickly. I highly recommend Nisha.”
“Donte Wade was a fantastic agent! My wife and I are first-time homebuyers needing to move to a city we didn't live in and couldn't visit, but Donte drove countless miles to have virutual viewings and helped provide local guidance on the various factors that were important to us. The most impactful thing that Donte did was provide a lot of insight and guidance during the negioation process to make sure that we were making our offer competitive and gave us the best chance of being successful. I will be recommending him to my family when they move into the area!”
“I loved John and Susan like they were my own family! Absolutely loved working with them! Communication was great and just the experience from start to finish was amazing! I would highly recommend John to anybody who needs a realtor! Words can't express nor describe what a wonderful experience I had working with John and Susan! They deserve the highest level of appreciation! Thank you for aligning me with them through my sale! The world needs more people like John and his sister Susan in the realtor community! Hugs to them!”
“Mary Ann understood what I wanted and found just the right home! I could not be happier with the price we paid. She helped get us a credit after the inspection showed plumbing issues. I would recommend her to anyone looking for a home.”
“This was my first home sale and Brittney made the entire process stress free! From first walk through to signing she was proactive and kept me in the loop. She always answered any questions I had and was extremely knowledgeable about the market and trends in the area. I highly recommend Brittney!!”
“This is our second time working with Tanya Cunningham and she continues to be incredible in all aspects of real estate transactions. She went above & beyond several times throughout our sale process to make it as easy on us as possible. I want to be like Tanya when I grow up. Would highly recommend to anyone in need.”
“Vicki was excellent. She handled every detail quickly, accurately, and professionally. She was available every time we needed to contact her. We were in Florida during the process of selling our home so Vicki had to handle all details and necessary actions without our help and she did. We are totally satisfied.”
“She was reliable, always prioritized us no matter the time or day. She made the home buying process significantly easier than I thought it would be.”
“Cathy was great to work with! She was very responsive and as soon as I placed my request, she contacted me and got things in motion. Thank you for all your help.”
“Matt Arnold is a superior agent. He helped me sell my home and buy my new home. Matt made the process happen quickly and seamlessly. I would highly recommend Matt to everyone.”
“Kelly was a pleasure to work with. She was very professional and helpful throughout this entire process. Kelly has always made herself available to any questions or concerns that I had. I would definitely recommend her to any future home buyers.”
“Lindsay Clark was excellent. She really listened to the needs of my family and responded with the right choices for us to look at. As we are not from the DC area, she also helped walk us through the closing process and was available to help when we were out of town. We will continue to use her for advice and recommendations.”
“Very easy and helpful.”
“Was paired with Vanita Adams and I couldn't have been more satisfied. She had great communication and knowledge. Very helpful and informative throughout the entire process.”
“Edward is hands down the best agent I have ever worked with and he went way above and beyond the call of duty, even helping me after closing with things. I cannot recommend him enough.”
“The service was awesome! I had no issues, unlike others that I've dealt with in the past. They were a huge mistake until I found Agent Pronto. The agent I worked with was excellent, professional. And to be honest, I am now able to call him a friend! ”
“My overall experience was well achieved and your Agent, Don Roberts, made my transition very smooth. Great Don went above and beyond to make sure all my questions were answered. He was always available to help me in any matter concerning my house. What a great person Don was, showing nothing but compassion and was very organized. I will rate Don Roberts as a five-star Realtor. Job well done. ”
“All my communications were prompt and very courteous. My agent, Mark Hewitson, couldn't have been more attentive or helpful from beginning to closing, even though my purchase was relatively modest.. Absolutely excellent service. I would recommend him completely.”
“Our experience with Greg Chamish was excellent. He was attentive, prompt, knowledgeable and very helpful. We highly recommend him to anyone looking to sell their home.”
Chestertown offers residents a welcoming, walkable community rich in history, with a vibrant arts and events scene, charming downtown, and easy access to parks, the river, and essential local services.
Chestertown hums with waterfront energy and centuries of history, where brick sidewalks meet the Chester River and everyday errands can include a coffee on the docks. The heartbeat of civic life is the Town of Chestertown, which hosts beloved traditions like First Fridays and a bustling farmers’ market. Education shapes the town’s rhythm, thanks to Washington College, whose campus brings lectures, gallery shows, and Shore-to-table research to town. On the water, the Sultana Education Foundation connects residents and students to the river through hands-on ecology and sailing programs, while the Garfield Center for the Arts lights up evenings with plays, concerts, and community workshops.
Nature lovers claim weekends at Eastern Neck National Wildlife Refuge for migrating waterfowl, quiet beaches, and miles of trails. Families appreciate the scale and support of Kent County Public Schools, with opportunities ranging from arts to STEM, and peace of mind comes from nearby care at UM Shore Medical Center at Chestertown. Housing options stretch from historic 18th-century residences to river-view cottages and modern builds, with marinas and parks never far from the front door.
Whether you’re drawn by a walkable historic district, a lively cultural calendar, or weekends spent paddling the Chester River, Chestertown offers an easygoing pace without sacrificing substance. If you’re ready to buy or sell here, Agent Pronto can quickly connect you with a trusted local real estate agent who knows the market and the community.
Within a few minutes, I was paired up with an awesome agent who really knew the local area and helped me find a great condo in a super tight market. It was daunting to think about how to find the right agent. Agent Pronto got me the right agent, pronto!
With over 2 million real estate agents across the U.S., it’s not easy deciding who to trust when buying or selling a home.
We’ve analyzed performance metrics, close rates, specialties, and client reviews of the top real estate agents in Chestertown to qualify the best agents for your specific needs.
We know that choosing the right real estate agent can be a stressful task. With Agent Pronto, it doesn’t have to be.
Agent Pronto works through troves of local and national housing data, client reviews, and agent performance metrics to find the top agents in Chestertown. But we don’t stop there.
Our Agent Specialists will take into account any special requests you have when searching for your real estate agent recommendation.
Need a great agent who speaks fluent Spanish and is a luxury condo expert in your neighborhood? No problem!
Tips and market insights to make your Chestertown real estate journey a success.
There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Chestertown. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Chestertown Realtor® or real estate agent today.
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