Fantastic two-family home tucked at the end of a cul-de-sac in Winter Hill, steps to the Gilman Square Green Line T Station and close to Somerville High School, the Public Library, Community Bike Path, and Union Square. Owner-occupied for 30 years by an artist and carpenter, the property blends original character with thoughtful updates. The upper unit at 28 Gilman Terrace spans the second and third floors and features a renovated kitchen with stainless steel appliances, marble countertops, solid-wood cabinetry, peninsula seating for four, and adjacent laundry. The main level also offers a formal dining room, a spacious living room with a wood-burning fireplace featuring a hand-carved original mantel and a soapstone hearth, a renovated full bathroom, and one bedroom. The third floor includes three additional bedrooms and a full bathroom with a clawfoot tub.The first-floor rental at 26 Gilman Terrace offers a living room, dining room, one bedroom, a full tiled bathroom, and a renovated eat-in kitchen with stainless steel appliances, oak cabinetry, granite countertops, recessed lighting, and parquet flooring.Both units have central air conditioning and access to a full unfinished basement with laundry, built-in shelving, and ample storage. Exterior features include Hardie Plank siding, Azek trim, an architectural-shingle roof, and new front porches. A detached one-car garage currently used for storage/workshop space qualifies for ADU conversion, with driveway parking in front. A charming side yard features a slate patio and a garden area. A rare opportunity to own a character-filled two-family property in a highly accessible Winter Hill location. Solar system for Unit 2 only.