Chestertown Real Estate

Chestertown Real Estate

Welcome to Chestertown, Maryland – a charming riverside town that perfectly blends historical charm with modern living. Nestled in Kent County, this vibrant community is steeped in rich history and offers a picturesque setting along the banks of the Chester River. With its cobblestone streets, colonial architecture, and welcoming atmosphere, Chestertown is a hidden gem that captivates residents and visitors alike.

This quaint subdivision is known for its tight-knit community, where neighbors become friends and local businesses thrive. Stroll through the historic downtown area, and you’ll discover an array of boutique shops, art galleries, and delightful eateries that celebrate the area’s culinary heritage. The Chestertown Farmers Market, held every Saturday, showcases fresh produce, artisanal goods, and local crafts, making it a perfect spot to connect with the community.

Outdoor enthusiasts will find plenty to love in Chestertown. The surrounding natural beauty offers ample opportunities for kayaking, fishing, and hiking. Explore the scenic trails along the river or enjoy a peaceful afternoon at Wilmer Park, where families gather for picnics and events throughout the year.

Education is a priority in Chestertown, with access to quality schools and a commitment to fostering a supportive learning environment. The town is also home to Washington College, which adds a youthful energy and cultural vibrancy to the community.

Whether you are seeking a serene place to call home or a vibrant community filled with history and charm, Chestertown is an ideal choice. Embrace the unique lifestyle this enchanting town has to offer, where every day feels like a step back in time, yet with all the conveniences of modern living.

Newest Listings in Chestertown

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:

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:

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 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

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

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

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

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

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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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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