“Diane is a wonderful agent. She is very professional, courteous and knowledgeable agent. Recommend her as a excellent agent that goes above and beyond to get the job done.”
Pearson Smith Realty
- Agent Pronto
- Maryland
- Chestertown
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Compare top Chestertown real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for November 2026.*
*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.
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Learn more about what Chestertown has to offer.
Chestertown offers residents a historic, walkable town with a strong sense of community, vibrant arts and dining, excellent schools, and easy access to scenic waterways and outdoor recreation.
Chestertown sits along the Chester River, offering small-town scale with practical access to larger hubs like Annapolis and Wilmington. Residents appreciate its manageable traffic, walkable core, and a blend of historic streets and newer residential pockets that make daily life straightforward.
Downtown centers around Washington College, bringing cultural events, lectures, and athletics within minutes of most neighborhoods. The waterfront is a regular part of local routines, from strolls at Wilmer Park to seasonal riverfront festivals. Everyday errands are simple, with groceries, pharmacies, and healthcare close at hand, and regional shopping reachable by car.
Quality of life leans on community resources like the Kent County Public Library, the Garfield Center for the Arts, and youth programs through Kent County Parks and Recreation. Food options range from casual riverfront dining at Fish Whistle at the Granary to coffee meetups downtown, while nearby Rock Hall expands options for boating and marina access.
Whether you are weighing a move from Baltimore or relocating from another Kent County community like Galena, a local real estate agent who understands Chestertown’s streets, school zones, and zoning rules can remove guesswork and keep timelines on track. Agent Pronto connects both buyers and sellers with the right Chestertown expert so that each step of the process feels clear, coordinated, and far less stressful.
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“Samantha helped my son and daughter in law in an efficient and professional manner. She was patient for our first time home owners ending with then acquiring their dream home at a fair price. Thanks Sam”
Keller Williams Real Estate
“Karen was Great in every way, i am not to good with words i just would like to say, If i would buy another house i would go with Karen again 100%. Karen is professional, a great listener, We bought the house we wanted at the price we wanted .Thank you Karen again for all that you did for us.”
IN-VISION REALTY
“I had the distinct pleasure of assisting the buyers of one of Adam’s listings with their financing. While I typically have quite a bit of communication with the listing agent throughout a transaction, it is extremely rare that I come across an agent of Adam Murphy’s caliber. From the jump, Adam was responsive, personable, and extremely knowledgeable. He went above and beyond to work through the numbers and structure of the transaction to ensure his clients received the terms they needed, while also making sure my clients were taken care of and the transaction continued moving smoothly toward closing. As a lender, I have the unique perspective of working with hundreds of Realtors every year. That gives me the opportunity to see firsthand what separates a good agent from a truly exceptional one. The communication, problem solving, professionalism, and intangible skills Adam brings to the table are qualities I have encountered in very few agents throughout my career. Bottom line, if you are looking for someone to list your home or help you purchase your first or next one, you will be hard pressed to find a better agent than Adam. I would recommend him without hesitation.”
RE/MAX Realty Centre
“Vinny and his team were outstanding helping me sell my house and buy my new house in 2023. Thank you for a smooth transaction from selling to purchasing to moving. Highly recommend Vinny and his team.”
VS
RE/MAX
“Working with Jamie has been such an amazing experience! She is super attentive to what we wanted in a home and was wonderful at communication with her timely responses to our questions throughout the process! We found our very first home with her and are so excited to move in! My husband and I would most assuredly recommend her to anyone who wants the best in this field!”
Keller Williams Flagship
“I had an excellent experience working with Greg throughout my home buying journey. From the very beginning, Greg was patient, professional, knowledgeable, and always available to answer my many questions. I truly appreciated the long calls, detailed explanations, and guidance he provided throughout the process. He never made me feel like I was asking too many questions. Whenever I needed reassurance or clarification, Greg was there to help and make things easier to understand. Greg worked hard to help me find the right home. He took the time to understand what I was looking for, helped me identify the right property, guided me through making an offer, and supported me during the negotiations. I always felt that he had my best interests in mind. He also connected me with an excellent mortgage consultant and helped me navigate the many moving parts of buying a home. His communication, responsiveness, attention to detail, and willingness to go above and beyond made the entire process much less stressful. What stood out most was that Greg genuinely cared about helping me reach my goal. He did not just help me buy a house. He guided me through the entire journey and made me feel supported every step of the way. I am extremely grateful for everything Greg did for me. He is an outstanding real estate agent and a true professional. I highly recommend Greg to anyone looking to buy a home.”
Long & Foster Real Estate Long and Foster Real Estate
“We have moved and purchased several homes in the past 3 years. For our home in Delaware, we were very luck to find Dale. As we all know, the stress of finding a home and then moving can be overwhelming. This is where the professionalism, knowledge, and practical experiences of Dale took over. If he didn't have an answer (very rare) he would research and present the best solution. Without a doubt, Dale is the best Real Estate Partner that we have ever worked with in our home search. You and your Family will benefit working with Dale.”
Bayside Realty
“Tom's expertise as a Realtor proved invaluable throughout our home-buying journey. He demonstrated a comprehensive understanding of the market, patiently addressing every question and concern we raised. His diligent search and insightful guidance ultimately led us to the discovery of our ideal home, fulfilling our long-held aspirations and confirming his dedication to client satisfaction. Tom's professionalism and attentiveness made the entire process smooth and successful.”
Cummings and Co Realtors
“We couldn’t be more grateful for the incredible experience we had with Amy during the purchase of our first home. From day one, she was patient, knowledgeable, and truly invested in helping us find the perfect place. She guided us through every step of the process with clear communication and genuine care, making what could have been a stressful experience feel exciting and manageable. Highly recommend to anyone looking for a smooth, supportive home-buying journey.”
Chesapeake Real Estate Associates, LLC
“Anastasia was absolutely wonderful to work with. Her bubbly personality is why I kept her contact information over a year ago. Plus she was knowledgeable on the area I was interested in buying a condo. She responds quickly, follows through with things and helped to keep me on track during the whole process. She even goes out of her way to update the loan officer as things progress. We had a lot of laughs during the process. I feel like I started off with a nice realtor and ended up with a good friend. :)”
Cummings & Co Realtors
“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.”
Century 21 Gold Key Realty
“I just had to give Nicole Duncan of Crown Homes a 5-star review because of our wonderful experience with her! She sold us our new home as well as selling our old home. Nicole is very patient, answered all of our questions, and never got frazzled when there were hiccups along the way. Thank you, Nicole! She also went out of her way to get the correct repair people after the home inspection to make the sale of our old home go smoothly. She communicated with us promptly and found out any answers that she didn’t know. Nicole is a very pleasant person and a trust-worthy professional. We would not hesitate to refer her to our friends and family.”
REAL Broker, LLC
“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.”
Samson Properties
“Wendy did an amazing job to help sell my house. Was able to present my house in such a way that it sold faster than expected and for more than asking. Highly recommend Wendy for all your buying and selling needs.”
Long & Foster Real Estate Long & Foster
“Julie has been our Realtor 3 times now, and each time we walked away ecstatic and impressed with our experience. Her expertise shined in every negotiation. She will fight to make sure you get the best possible outcome in every scenario. What makes Julie standout from other realtors is that she TRULY cares about your best interests. She prioritizes your happiness over the business aspect of real estate (profits /etc.) When I describe her to family and friends, I tell them she’s like the Mama Bear of Real Estate. She’s the best!”
RE/MAX Vision
“Debbie is wonderful at what she does! She has years of experience and expertise, gives honest advice and looks out for her clients best interest! She is very responsive and flexible. She sold me my first home ten years ago and I just worked with her again to purchase my new home. 100% recommend her!”
SAMSON PROPERTIES
“Ms. Tamara is one of the Best Realtors in Maryland. She was very responsive to every question that I had, she's knowledgeable about what is good on the market and If you are looking for a stress-free experience, look no further because she will make your buying experience exceptional. Thank you for helping me find my home. You are Awesome!!!????”
Samson Broker Code 17807 -06
“Tracy was a wonderful agent. She is kind, hinest and extremely down to earth. For her, her job is truly to find you a home you love and is willing to work through the process with you honestly for as long as it takes. She helped me work through the struggles of closing with a calm demeanor and confidence. I couldn’t ask for a better agent!”
Long & Foster Real Estate Long and Foster Real Estate
“Joe was fantastic in helping sell our home and buying a new home. Both transaction were not simple and full of bumps that Joe was incredibly effective in helping us over. We relied heavily on him for so many things and he went above and beyond throughout the entire process. I can’t recommend him enough.”
Taylor Properties
Frequently Asked Questions
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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.
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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.
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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.
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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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