Your Ultimate Guide to Buying a High-Quality Home in Chestertown

Your Ultimate Guide to Buying a High-Quality Home in Chestertown

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Welcome to Chestertown, a hidden gem nestled within Kent County, Maryland! If you're considering buying a home here, whether you're a first-time buyer, retiree, nature enthusiast, or simply seeking a change of scenery, you're in for a delightful journey. This guide is your comprehensive roadmap, crafted with love by your local real estate experts, Billy and Lacey Sutton. We’re here to navigate you through the charming streets of Chestertown to find your dream home.

Understanding the Chestertown Market

Chestertown’s real estate market offers a unique blend of historical homes, waterfront properties, and family-friendly neighborhoods. Let’s break down the key market analysis factors:

Active Listings

Chestertown has a diverse range of properties available. From colonial homes that echo the town's rich history to modern builds that cater to contemporary tastes, there’s something for everyone.

Median Listing Price

Compared to larger cities, Chestertown offers affordability without compromising on quality. The median listing price in Chestertown often presents a more attractive option than in surrounding areas, making it an excellent choice for those looking for value and character in their home.


One of the standout features of Chestertown is its affordability. While offering the quintessential small-town charm, the cost of living remains reasonable, making it an excellent choice for first-time buyers, retirees, and families alike. With various financing options available, owning a home in Chestertown is within reach for many.

Lifestyle in Chestertown

Let's dive into what makes Chestertown not just a place to live, but a lifestyle to embrace.

Historic Charm and Walkability

Chestertown is steeped in history, with its roots tracing back to the 18th century. The town’s historic district offers a picturesque setting, perfect for strolls and time travel through architecture. Imagine walking to local cafes, boutiques, and galleries from your front door. This walkability not only adds to the quality of life but also fosters a tight-knit community spirit.

Proximity to Nature

Nature enthusiasts will find Chestertown to be a sanctuary. Located by the Chester River and near several natural reserves, it offers easy access to water activities, hiking trails, and serene spots for picnics or meditation. The blend of convenience and access to nature makes Chestertown a haven for those looking to balance a peaceful lifestyle with the amenities of modern living.

Considerations for Your Lifestyle

Before diving into the home-buying process, it’s crucial to reflect on what matters most to you: Are you drawn to the hustle and bustle of downtown living, or do you prefer the tranquility of rural landscapes? Chestertown offers a diverse range of neighborhoods to suit every lifestyle, from vibrant urban areas to peaceful countryside retreats.

Think about your daily routine and how your new home can complement it. Whether you value walkability, community amenities, or proximity to nature, Chestertown has options that align with your lifestyle goals.

The 6-Step Home Buying Process in Chestertown

It's time to take a look at the six steps for buying a Chestertown home.

Step 1: Financial Preparation

Ensure your finances are in order. This includes checking your credit score, setting a budget, and getting pre-approved for a mortgage. Understanding your financial landscape upfront can make the entire process smoother.

Step 2: Define Your Must-Haves

List down your non-negotiables, from the number of bedrooms to specific features like a home office or a backyard. This clarity will streamline your search and help us find homes that match your dreams and needs.

Step 3: Partner with Local Experts

That's where we, Billy and Lacey Sutton, come in. With our deep understanding of Chestertown’s real estate market, we’re here to guide you every step of the way. From uncovering hidden gems to navigating negotiations, we're your allies.

Step 4: Explore and Visit Homes

Get ready to explore homes that fit your criteria. We’ll arrange showings and provide insights into the properties’ histories, neighborhoods, and potential. This is your chance to envision your life in each home.

Step 5: Making an Offer

When you've found "the one," we'll help you make a competitive offer, considering current market dynamics to ensure it stands out.

Step 6: Inspection and Closing

After your offer is accepted, a home inspection is crucial. We’ll be there to negotiate any necessary repairs or adjustments. Finally, we'll guide you through the closing process, where your dream home becomes a reality.

Additional Resources

In addition to working with trusted real estate professionals like us, there are several other resources available to homebuyers in Chestertown.

Local Government Websites: For zoning laws, future development plans, and community services.

Chestertown Forums and Social Media Groups: Engage with current residents to get a feel for the community spirit and insider tips.

Visit Chestertown: If possible, nothing beats experiencing the town firsthand. Spend a weekend exploring, dining, and talking to locals.

Real Estate Services in Chestertown

Chestertown offers a lifestyle filled with charm, community, and natural beauty. By considering your lifestyle expectations, being financially prepared, and partnering with local experts, you’re set for a successful home-buying journey in this enchanting town. Remember, buying a home here is more than a transaction; it’s a step into a life where every day feels like a little piece of history, nature, and community woven together.

Ready to find your dream home in Kent County? Our experts can help. Let’s embark on this adventure together. Welcome home to Chestertown, where your new life awaits.

Billy Sutton

Billy Sutton is a dynamic real estate professional at Coldwell Banker Chesapeake Real Estate in Chestertown, Maryland. With a deep-seated understanding of the local market, Billy has carved a niche in Kent and Queen Anne's counties, known for his exceptional negotiating skills, innovative marketing strategies, and problem-solving abilities. His expertise spans a wide range of properties, including residential homes, waterfront properties, and farmlands. Holding a Bachelor's degree in Agriculture, Billy brings a unique perspective to the agricultural real estate market. Outside of his professional life, he is an avid sports enthusiast and enjoys outdoor activities. His deep roots in the community and commitment to his clients make him a reliable and trusted advisor in the real estate sector.


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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 Chestertown real estate goals and we’ll make them happen.

We’d be happy to discuss your estate 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!