Chestertown Land for Sale

Welcome to Chestertown, Maryland—a charming town nestled in the heart of Kent County, where history and natural beauty intertwine seamlessly. This picturesque riverside community, with its rich colonial heritage, offers a delightful blend of quaint small-town charm and vibrant cultural experiences. Founded in the 1700s, Chestertown boasts beautifully preserved architecture, captivating waterfront views, and a welcoming atmosphere that makes it a perfect place to call home.

As you explore the enchanting streets of Chestertown, you’ll find an array of local shops, galleries, and eateries that reflect the town’s artistic spirit and culinary diversity. The town is also home to Washington College, which enriches the community with academic vigor and hosts numerous events throughout the year, fostering a lively social scene.

For those looking to invest in land, Chestertown offers an exciting opportunity. With parcels of land available for sale, you can embrace the chance to build your dream home or develop a unique project in this idyllic setting. Imagine waking up to the sounds of nature, with the Chesapeake Bay just a stone’s throw away, providing endless opportunities for outdoor activities such as boating, fishing, and hiking.

Whether you are seeking a peaceful retreat or a vibrant community, Chestertown is an ideal location. With its stunning landscapes, rich history, and welcoming residents, it’s no wonder that this charming town is a hidden gem in Maryland. Explore the available land for sale and take the first step toward creating your own piece of paradise in Chestertown!

Newest Chestertown Land for Sale

Sandpiper Rd, Chestertown $4,500

Recreational lot- access community amenities, bird watch, garden, make a trail, firewood, etc. Not buildable unless the county adds public sewer in the future. RVs are no...

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

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

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

Courtesy of RE/MAX Associates-Hockessin

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

305 Roosevelt Dr, Chestertown $60,000

Nice cleared building lot in an established community. Public water and sewer available. Property recently acquired through tax sale foreclosure, recording is in process....

Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

Fairlee Rd, Chestertown $75,000

Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed ...

Courtesy of RE/MAX Chesapeake

Listing courtesy of RE/MAX Chesapeake. Contact:

8886 Georgetown Rd, Chestertown $69,900 ▼

Discover the possibilities on this beautiful 4+ acre parcel. Recently surveyed, with water and sewer allocations paid, a value exceeding $16,000! This property offers a ...

Courtesy of Samson Properties

Listing courtesy of Samson Properties. Contact: 4433178125

23741 L Rd, Chestertown $15,000

Discover the potential of this 1-acre wooded parcel, offering a peaceful setting with mature trees and plenty of privacy. Buyer to verify all information and perform all ...

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

Map 36 Parcel 80 Watertower Rd, Chestertown image

Map 36 Parcel 80 Watertower Rd, Chestertown $55,000

Discover the potential of this open .69-acre lot in Fairlee! Whether you’re looking to build your dream home, create a weekend retreat, or invest in future development, t...

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Sandy Bottom Rd, Chestertown $49,000 ▼

Escape to the peace and quiet of the countryside with this beautiful private wooded 2-acre lot, tucked away down a secluded gravel lane. Offering a perfect blend of matur...

Courtesy of Village Real Estate Company LLC

Listing courtesy of Village Real Estate Company LLC. Contact:

Cogar Rd, Chestertown $3,000

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, 12:50 PM. The ...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

Haacke Drive Lot 3, Chestertown $225,000

This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for ...

Courtesy of Select Land & Homes, LLC

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

Scheeler Road Lot 2, Chestertown $250,000

This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for...

Courtesy of Select Land & Homes, LLC

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

Tonopah Rd, Chestertown $3,000

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 l...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124