Professional Real Estate Agents in Chestertown, Maryland.

Looking for a property in Chestertown MD? We have the right real estate agent to help! We work with local communities & help you find the perfect property!

Situated on the coastline of the gorgeous Chester River, Chestertown is a relatively small town full of history and natural beauty. You won’t want to miss out on exploring what Chestertown, Maryland, has to offer you!

Art, Entertainment, and Culture

As the seat of Kent County, Chestertown is full of arts, entertainment, and cultural opportunities and events. To explore small-town Maryland culture, visit a selection of local shopping, restaurants serving delicious Maryland cuisine, and more. Stop by the farmer’s market to purchase locally made crafts and fresh produce, or consider trying one of the many waterfront restaurants. There’s something for everyone to enjoy!

Chestertown is a perfect place for history lovers. The Waterman’s Museum is open several days a week and has displays of historical photographs, boats, crabbing, fishing, and oystering. Additionally, the annual Chestertown Tea Party Festival celebrates the history of Chestertown. The festival includes a reenactment of Chestertown’s own tea party, a 5k run/walk, activities for children and adults, a Colonial Parade, and a tour of local historical sites.

In addition to its history, Chestertown is full of art and entertainment options! As one of the significant arts communities in the state, you can enjoy art shows, musicals, live music, and much more!

Sports, Parks, and Outdoor Recreation

Chestertown is located on the coast of the Chester River. The area embraces the natural beauty of the town. It’s home to estuarine habitats for local water wildlife. You’ll see amazing wildlife including sea and land birds, bass, perch, and other water and shore animals.

The town also has several beautiful parks. The parks offer outdoor recreation opportunities, playgrounds, and trails for hiking, biking, and walking. Or, if you’re looking to embrace all the Chester River has to offer you, Chestertown’s marina and waterfront offer you the chance to dock, sail, or explore by foot.


The Chestertown community has many educational opportunities to offer you or your family. The town itself has one public elementary school, H.H. Garnett Elementary School, and two nearby public elementary schools, Galena Elementary and Rock Hall Elementary. Kent County Middle School and High School are also located in Chestertown, as well as Washington College.

If you’re more interested in private schooling, there are three private schools and one special education school located in the town: Chester River Adventist, Chestertown Christian Academy, Kent School, and special education school Radcliffe Creek School.


Chestertown, with a population of 5,252, is a welcoming, warm community. Many describe Chestertown as the perfect place to raise a family, with most households being families. However, don’t shy away if you’re looking to move on your own! Chestertown, MD has lots of opportunities for non-family or single households.

You’ll find the place where you belong in Chestertown! Chestertown’s demographics are:

·        78.13% White

·        16.98% African American or Black

·        3.46% Asian or Pacific Islander

·        1.36% two or more races

·        0.08% other or unspecified race

Find Your New Home with the Sutton Team

Ready to move to beautiful Chestertown, Maryland? Get in touch with us today to find the property of your dreams!

People Said

Billy Sutton was great to work with on the purchase of our poultry farm. He provides a wealth of knowledge and we were completely blown away with how resourceful he was. Anytime an issue came up or we were worried about something, he had an answer. He is direct, kept us updated, and made it an enjoyable purchase.

Eddie P.April 27th, 2020

Billy contacted me one day and said he had found my way into the poultry business. I had never used a realtor before so this was all new to me. He was very helpful with every question I had. He made sure I was stress free every step of the way, always made sure I had everything done that needed to be so that we were always a step ahead, and always informed me of things to be done that I didn't know about. I would highly recommend using Bill Sutton as your realtor.

Dylan P.April 22nd, 2020

A very trustworthy and professional agent. I would definitely recommend him.

Brett D.March 9th, 2020

Billy was a fantastic realtor. Being a first time home buyer I was a little stressed and nervous, however, Billy made it stress free and was always wiling to come whenever I needed to show me a house, or answer a phone call to explain something to me. I would definitely recommend Billy to anyone that is buying a house, first time, or fifth time!

Patrick C.March 6th, 2020

It was great working with Billy, He is very dedicated to his clients and will go out of his way to satisfy your needs. So if your looking for a hard working realtor Billy is your guy!!!!!

David W.November 1st, 2019

If i could give 10 stars I would. Billy was a perfect fit for us. He is a true professional and was very understanding of our concerns. Billy was a great listener. He was with us the entire way. You can call him anytime with question and you will get a very prompt answer. We will definitely use Billy in the future with any real estate needs that might arise. You cannot go wrong with Billy.

Dave K.October 26th, 2019

I've heard horror stories over the years in regards to realtors, I guess those people didn't have the right realtor because Billy Sutton did an amazing job, I was looking at houses 2 1/2 hours apart and one way or another he would always show up full of energy and full of knowledge. It's been two years and we still communicate with one another and I recommend him 100%

Jorge V.October 9th, 2019

Billy was a pleasure to work with. He's knowledgeable, hard working, and sold my home quickly for a great price. I highly recommend!

Andrew M.October 2nd, 2019

Billy is a very knowledgeable real estate agent. If you have a home to sell, give him a call.

Patricia S.October 1st, 2019

Billy is incredibly knowledgeable in real estate and talked me through every step of the home buying process for my first home. I went into the process well informed and confident in my decision to buy, and would recommend Billy to anybody looking to purchase a home.

Nick M.September 29th, 2019

Lacey is an amazing person she listens to what you want in your dream home and takes the time to find the home that is perfect for you and your family. I totally recommend her to anyone.

Tanya C.April 17th, 2020

Lacey was a amazing realtor she worked tirelessly to find us a house that our family would love and she knocked it out of the park. Thank you so much for the hard work you put in.

Larry G.March 6th, 2020

I couldn't of asked for a better person helping us with our home! She's highly professional and made sure we found our dream home. Lacey always made time for us as clients and worked so hard to make everything go as smoothly as possible.

Stephanie D.March 5th, 2020

Lacey is amazing! She is so patient, understanding, honest and fair! She is everything you would want in a realtor but rarely find. The home buying and selling is a whole process that can be overwhelming and almost impossible if you don't have the right person on your side. She is so caring and pays attention to details you couldn't ask for anyone better to be there with you as you make such an important decision.

Cassi P.September 25th, 2019

I have known Lacey for over 15 years. She is one of the most detail oriented and hardworking people I know. I have watched her help people and over again!! I would recommend her to anyone!

Amanda B.September 25th, 2019

Get In Touch

Whether you’re selling or buying a home for the first time or the tenth time, we’re here to help the process go as smoothly and quickly as possible. Just let us know your real estate goals and we’ll make them happen.

We’d be happy to discuss your home for sale and answer any questions you may have about buying or selling homes in Maryland. Drop us a line or fill out the contact form today – we look forward to getting to know you!