Income-Generating Historic Estate in Canaan, NY - Dual Homes, Proven Rental History, Prime Location Investor's Dream in the Berkshires Gateway: This exceptional two-home estate in Canaan, NY presents a rare opportunity to own income-producing property in a highly desirable location.This is the first time this meticulously maintained estate has been offered for sale (in over 40yrs) Live in one home and rent the other, or leverage both for short- or long-term rental income. Ideal for investors, multi-generational living, or a combination of personal use and passive income. Property 1 - Knoll Rock: A meticulously restored 1700s post-and-beam farmhouse on 2.79 acres with a strong short-term rental track record. Featuring 4 bedrooms, 4 stylish bathrooms, and 2 fully renovated kitchens, the home is designed with flexibility in mind—perfect for hosting multiple guests or dividing the space for dual rental use. Original chestnut beams and wide-plank floors create a warm, historic atmosphere, while modern updates ensure comfort and convenience. Outdoor amenities include a covered porch, stone patio, and access to nearby Queechy Lake, a seasonal draw for renters and guests. Property 2 - The Miller Cottage: A beautifully updated 1890 farmhouse on 7.9 acres with 3 bedrooms, 2 bathrooms, and a self-contained guest house (with kitchenette and bath). The Miller Cottage house boasts a modern kitchen, cozy wood stove, wide-plank flooring, and a first-floor primary suite with private deck access. A spacious barn provides additional storage or potential event/rental space. The scenic grounds include open meadows and mature trees, appealing to nature-loving tenants and travelers. Prime Location with Year-Round Appeal: Just 10 minutes from Tanglewood in Lenox, MA and centrally located between the Berkshires and Hudson Valley, this property is only 2.5 hours from NYC and 2 hours from Boston. Its accessibility and cultural surroundings make it a consistent draw for vacationers, weekenders, and seasonal renters. Why This Property Stands Out: Two separately livable, income-ready homes Proven rental history and dual-kitchen flexibility Guest house and barn for added income or expansion High-demand area for tourism and seasonal rentals Ideal for 1031 exchange, Airbnb, or family compound use. Turnkey opportunity with built-in revenue streams—this historic Canaan estate is not just a home, but a smart investment in location, flexibility, and long-term value.