This classic 1931 Cape Cod farmhouse with a fully self-sufficient guest house offers timeless charm, privacy, and year-round comfort on a large corner lot. Tucked away on a quiet, tree-lined street in central Chester, the property is surrounded by mature trees, lush perennial gardens, and elevated views offering a serene and peaceful retreat in one of Nova Scotia’s most beloved seaside communities. The main home features approximately 2,500 sq. ft. of refined living space, including three spacious bedrooms on the second floor and a top-floor primary suite with a private balcony and sweeping views. This bright, versatile space could also serve as a studio, office, or playroom, easily adapting to your lifestyle. Interior highlights include refinished hardwood floors, a large wood-burning brick fireplace, compass rose inlay, wood ceiling accents, and generous natural light from oversized double-hung windows. A flagstone path leads to the covered wrap-around porch with skylights -perfect for peaceful mornings or relaxed evening entertaining. Two insulated sunrooms from east and west additions provide year-round connection to the outdoors, while the bright open-concept kitchen offers French doors leading to a private, sheltered deck. A dry, walkout basement with ample storage ensure the home is as functional as it is welcoming. The detached guest house with carport was once a carriage house, thoughtfully converted in the late 1980s into a fully self-contained suite with a kitchenette, full bathroom, and separate power meter. Original wood beams remain exposed, lending warmth and historic charm to the space—ideal for hosting guests, accommodating extended family, working remotely, or generating rental income. Just a short stroll from Chester’s yacht club, the Boat Yard, cafés, and boutiques—this is a rare opportunity to own a legacy property on an oversized, estate-style lot in one of Nova Scotia’s most picturesque and tightly held coastal villages.