Welcome to 37 Michigan Street, a meticulously cared-for, turnkey four-unit multi-family property offering incredible versatility, robust cash flow, and complete flexibility. The unit mix features a spacious four-bedroom open-concept layout that is ideal for an owner-occupant or high-yield rental income, complemented by one two-bedroom apartment and two one-bedroom apartments for a total of eight bedrooms across the entire building. High-quality infrastructure provides rare peace of mind, highlighted by a dependable Buderus furnace, durable metal roof, separate electric meters for each apartment, a coin-op laundry room, and a sprawling, private back yard. Situated on 8.9 wooded acres, the property boasts valuable standing timber and unlimited potential for future expansion or development with town approval. Nestled in charming Winchester, owners and tenants enjoy a vibrant Monadnock Region lifestyle with local craft tasting rooms, historic covered bridges, and peaceful paddling on the Ashuelot River. Outdoor enthusiasts will appreciate being just minutes from the 13,300-acre Pisgah State Park for hiking, mountain biking, and trail exploration, all while commuting with quick drives to Keene, Massachusetts, and Vermont. Whether you choose to house-hack by living virtually rent-free in the flagship four-bedroom home or expand your investment portfolio with an income-generating property, this presents a rare blend of charm, turnkey quality, and immediate upside.