Nestled on one of Medway's picturesque New England roads, this beautifully maintained property combines warmth, space, and versatility. Framed by a classic stone wall, the main home offers approx 2,200 square feet of living space, including four bedrooms and one full bathroom upstairs; and an eat-in kitchen, living room, family room, laundry room, and 3/4 bathroom on the first floor. A standout feature is the additional 676-square-foot bonus space above the garage with a separate entrance, kitchenette, and 3/4 bathroom - ideal for a guest room, home office, recreation room, craft room, or potential future ADU. Outside, enjoy your private oasis featuring an in-ground swimming pool, hot tub, and plenty of space for entertaining and outdoor activities. Additional highlights include a two-car garage and a convenient location close to shopping, Route 109, Interstate 495, Medway's Choate Park, and Holliston's Stoddard Park on beautiful Lake Winthrop.