Antique and Classic Boats for Sale in Chestertown

Antique and Classic boats in Chestertown, MD offer a unique opportunity to own a piece of maritime history on the scenic Chester River. Whether you seek pristine new models or well-maintained used vessels, our listings feature top-quality options perfect for leisurely cruises or regattas. With peak season approaching, these sought-after boats sell quickly—don’t miss your chance to secure a timeless classic. If you can’t find the perfect boat in Chestertown, check nearby cities like Rock Hall or Easton for additional listings. Act now to enjoy the rich boating culture of Maryland’s Eastern Shore.