Chestertown Real Estate

Chestertown Real Estate

Welcome to Chestertown, Maryland – a charming riverside town that beautifully blends history, community, and natural beauty. Nestled along the banks of the Chester River, Chestertown is a hidden gem that offers residents a unique lifestyle steeped in rich heritage and vibrant culture.

As you stroll through the picturesque streets, you'll be captivated by the well-preserved 18th-century architecture and the warm, welcoming atmosphere that defines this quaint subdivision. Chestertown is not just a place to live; it’s a place to thrive. With a variety of local shops, art galleries, and cozy cafes, the town is a hub for creativity and small-town charm.

Outdoor enthusiasts will find plenty to love here, with opportunities for kayaking, fishing, and hiking just moments away. The nearby parks and waterfront areas provide the perfect backdrop for family picnics, leisurely walks, or simply soaking in the stunning sunsets over the river.

Education is a priority in Chestertown, with excellent schools that focus on nurturing young minds and preparing them for a bright future. Additionally, the community hosts a range of events throughout the year, from farmers' markets to art festivals, fostering a strong sense of belonging among residents.

Whether you’re looking for a peaceful retreat or a vibrant community to call home, Chestertown offers a perfect blend of both. Discover the charm and warmth of this delightful subdivision, where history meets modern living, and make it your new home today!

Newest Listings in Chestertown

$675,000
5 Beds ⋅ 3 Baths
Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor living. Complete with a 2-car garage.

212 Washington Ave, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$1,195,000
2 Beds ⋅ 1 Baths
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$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 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:45 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
$750,000
2 Baths
Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

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 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:15 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 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 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:00 AM. 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 9/24/2026 @ 10:00 AM. Bidding ends 9/28/2026 @ 9:10 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 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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