A rare opportunity to own a truly versatile property in sought-after South Natick, featuring two residential dwellings plus a detached garage/barn. Offering exceptional flexibility for homeowners, extended family, guests, or rental potential, this unique property combines character, functionality, and thoughtful updates. The main residence offers 4 bedrooms and 3 bathrooms, including a newly added upstairs full bathroom (2020), along with a remodeled kitchen (2025), new furnace (2025), new siding (2021), and a partially finished basement with fireplace providing bonus living or recreational space. The home is also partially powered by an owned 36-panel solar array, offering an additional energy-efficient feature. A charming separate cottage provides 2 additional bedrooms and living space, making it ideal for guests, extended family, a home office, or potential rental income. Mini-split heating and cooling was added in 2023 to supplement the existing oil heat. Set in a desirable location with convenient access to Natick Center, South Natick Village, local restaurants, major routes, beautiful gardens, and scenic trails, the property offers both convenience and the charm and tranquility of South Natick. With two distinct residences, a detached garage/barn, extensive recent improvements, and a flexible layout, this is a unique opportunity to create a home that adapts to your needs while offering potential for additional income or multigenerational living.