Chestertown Homes for Sale

Chestertown Homes for Sale

Welcome to Chestertown, Maryland – a charming riverside community that beautifully blends historic charm with modern conveniences. Nestled along the picturesque Chester River, this quaint town offers a unique lifestyle that attracts both families and retirees alike. With its rich history dating back to the 18th century, Chestertown is adorned with beautifully preserved colonial architecture, inviting shops, and vibrant local art scenes, making it a delightful place to call home.

The heart of Chestertown is its lively downtown area, where residents can enjoy a variety of local restaurants, boutiques, and cultural events throughout the year. The town is also known for its annual festivals, including the renowned Chestertown Tea Party Festival, which celebrates the town's revolutionary spirit and community pride.

If you’re considering a move to Chestertown, you’ll be pleased to know that a variety of homes for sale are available, catering to diverse tastes and budgets. From charming historic homes with character to modern new constructions, Chestertown offers something for everyone. Many properties boast beautiful views of the river or are just a short walk from local parks and recreational areas, perfect for outdoor enthusiasts and families.

With a strong sense of community and a welcoming atmosphere, Chestertown is not just a place to live but a place to thrive. Whether you’re looking for a peaceful retreat or an active lifestyle, the homes for sale in Chestertown provide an excellent opportunity to embrace the best of Maryland living. Discover your dream home in this enchanting town and experience the warmth and charm that Chestertown has to offer!

Newest Chestertown Homes for Sale

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:

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

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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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