Chestertown Land for Sale

Chestertown Land for Sale

Welcome to Chestertown, Maryland – a charming riverside community that beautifully blends history with modern living. Nestled in the heart of Kent County, Chestertown is celebrated for its rich heritage, picturesque landscapes, and vibrant arts scene. This quaint town, with its cobblestone streets and historic buildings, invites you to explore its unique shops, delightful eateries, and thriving cultural events.

If you’re looking for land for sale in this enchanting area, you’re in luck! Chestertown offers a variety of parcels that cater to diverse needs, whether you’re dreaming of building your forever home, investing in a getaway retreat, or developing a new project. With its scenic views of the Chester River and proximity to the Chesapeake Bay, the available land provides a serene backdrop for your vision to come to life.

Imagine waking up to the gentle sounds of nature, enjoying leisurely strolls along the waterfront, or indulging in local festivals that celebrate the community’s vibrant spirit. Chestertown is not just a place to live; it’s a lifestyle that embraces the beauty of the outdoors and the warmth of small-town charm.

Don’t miss your chance to be a part of this idyllic community. With land for sale in Chestertown, you can create your own slice of paradise in a town where history meets opportunity. Contact us today to explore the possibilities and discover why Chestertown is the perfect place to call home!

Newest Chestertown Land for Sale

$300,000
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
$3,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/4/2026, 10:00 AM. Bidding ends 9/4/2026, 10:00 AM. 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
$750,000
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
$5,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/4/2026, 10:00 AM. Bidding ends 9/8/2026, 1:45 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
$5,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/4/2026, 10:00 AM. Bidding ends 9/8/2026, 1:30 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
$5,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 9/4/2026, 10:00 AM. Bidding ends 9/8/2026, 1:40 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.

Fish Hatchery Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124
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