Chestertown Land for Sale

Chestertown Land for Sale

Welcome to Chestertown, Maryland – a hidden gem nestled in the heart of Kent County. This charming riverside town is steeped in history and brimming with small-town charm, making it an ideal place for those looking to escape the hustle and bustle of city life. Chestertown boasts picturesque streets lined with beautiful colonial architecture, vibrant local shops, and delightful eateries that reflect the town’s rich heritage and community spirit.

One of the most exciting aspects of Chestertown is the opportunity to invest in land for sale in this idyllic setting. Whether you’re dreaming of building your forever home, crafting a serene retreat, or developing a unique project, Chestertown offers a variety of parcels that cater to diverse needs and visions. With its lush landscapes and proximity to the Chester River, your new property can become a sanctuary where you can enjoy nature’s beauty and the tranquility of rural living.

Living in Chestertown means embracing a lifestyle filled with outdoor adventures, from kayaking on the river to walking along scenic trails. The community is known for its vibrant arts scene, with numerous galleries and cultural events that celebrate local talent. Plus, with its convenient location just a short drive from the Chesapeake Bay and major metropolitan areas, you can enjoy the best of both worlds – peaceful living with easy access to urban amenities.

Don’t miss your chance to be a part of this enchanting community. Explore the land for sale in Chestertown and discover the endless possibilities that await you in this charming corner of Maryland!

Newest Chestertown Land for Sale

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be sold with mls MDKE2006844

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the major traffic artery, Fairlee Rd, connecting to the surrounding areas.

Tonopah Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

Located in an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of different uses of the property and/or the lots for this project.

201 N Lynchburg St, Chestertown

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:40 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to all the attractions in Chestertown, Maryland. It offers easy access to major traffic arteries including Chestertown Road.

Towhee Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:25 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in Chestertown, Maryland within Kent County. Property is in close proximity to all the attractions in Chestertown, Maryland. Property is vacant. The area provides easy access to the major traffic artery Chestertown Road.

Beltram Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:35 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to all the attractions in Chestertown, Maryland. It offers easy access to major traffic arteries including Chestertown Road.

Fish Hatchery Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

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Joseph Ciganek

As an Eastern Shore Realtor, I know that a real estate transaction is built on trust. I pride myself on my honesty and integrity in providing the highest quality representation for my clients. I have spent my entire life in Chestertown and on the Chesapeake Bay and have a deep respect and understanding for why life here is so special. You can rely on my deep knowledge of the eastern shore and its waterways when buying a home. As an Eastern Shore native, full-time Realtor and licensed Attorney, I have the skill set to help you navigate any real estate transaction; waterfront, farms, commercial, you name it. Buying or selling real estate requires an experienced and trustworthy advocate. Let me be your guide. Growing up on the banks of the Chester River, I was fortunate enough to enjoy everything the Chesapeake Bay has to offer, whether crabbing, fishing or just about every water-sport you can think of. After graduating from Washington College with a B.A. in Economics and Finance, I attended University of Baltimore School of Law. Working full time and going to school at night, I graduated cum laude and proceeded to clerk for the Honorable Harris P. Murphy, Circuit Court of Kent County, Md. That’s when I decided to make a drastic career shift to practicing full time as a Realtor in 2021. Since then I have enjoyed showing others why life on the shore really is the land of pleasant living. Outside of real estate, I enjoy getting exercise with my black lab, playing pickleball, soccer and racing the historic log canoe sail boats up and down the Chesapeake Bay.

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