Welcome to 142 Pleasant St! This spacious two-family home offers 5 bedrooms, 2.5 baths, and a versatile layout. Recent updates include refinished hardwood floors, new interior paint throughout, restored carpentry, updated light fixtures, and major electrical improvements. The kitchen features new quartz countertops and new appliances, while bathroom updates include new vanities and toilets. The third level includes a bonus room and bedroom, providing even more usable space. A two-level garage adds another unique feature, with a second floor, its own egress, and plenty of possibilities. Unit 2 is located on the second floor including 1 bedroom, living room, updated bathroom and updated kitchen with quartz countertops. Conveniently located near the center of Winchendon, with shops, dining, and local amenities nearby, along with the North Central Pathway, Whitney Pond, and Lake Dennison State Recreation Area. This property has character, thoughtful updates, flexible space, and plenty of potential for its next owner.