Two homes under one roof on a level 0.65-acre corner lot just off Main Street! Owned by the same family for decades, this classic c.1890 two-family offers 2,974 sq ft and rare flexibility. Unit 1 features 3 bedrooms, 1.5 baths, a bright bay-windowed living room, a dining room with a decorative ceiling, an updated white kitchen, and laundry. Unit 2 offers 2 bedrooms, a full bath, living room, family room, and eat-in kitchen. Each unit lives on two levels, like a home of its own. Enjoy screened porches, a deck, perennial gardens, and a yard with room to play, grow, and gather. Ideal for multigenerational living, owner-occupying one unit while rent from the other helps offset your mortgage, or adding a solid investment to your portfolio. Full basement, vinyl siding, parking for 4, and a lake/pond beach within a mile. Two-families like this rarely come to market in Upton. Schedule your showing today!