Nestled in the water-access community of Chesapeake Landing, this charming Cape Cod-style home offers a perfect blend of classic character and modern comfort. With over 2,100 square feet of finished living space, the home features four spacious bedrooms and three full bathrooms, ideal for flexible living arrangements. Inside, you'll find a freshly painted bright and open layout with beautiful bamboo flooring, a thoughtfully designed kitchen with durable Meganite countertops, brand new stainless steel appliances, and updated mechanical systems including a high-efficiency water heater and forced-air heat pump for year-round comfort. The main level provides easy access with a bedroom and full bath, offering convenience for guests or multi-generational living. Outside, the property has been enhanced with fresh landscaping and a brand-new gravel driveway, creating an inviting first impression. The private deck overlooks nearly an acre of serene, wooded surroundings, offering a peaceful retreat. Residents of Chesapeake Landing enjoy access to community water privileges, including a boat ramp and dock-perfect for those who love to spend time on the water. With no town taxes, a low annual HOA fee, and just a short drive to historic downtown Chestertown, this home is a wonderful opportunity to enjoy the best of Eastern Shore living.