This charming colonial in prime flats location is full of surprises! Showcasing a stunning rear 3 story addition duplex with walls of windows & 4 rooms! Use as the primary, home office, art studio or let your children enjoy this unique space~ The first floor offers a classic layout with an expanded updated kitchen & family area open to gorgeous deck overlooking the beacon hill style yard featuring a quaint patio/ entertaining space. Formal living & dining w three-season porch perfect for relaxing. Upstairs, the primary suite feels like a retreat with skylights, cathedral ceiling, loft, and private balcony. Three bedrooms and a study on 2 share a bath, with flexible space on the third floor featuring a loft and two rooms. Outside, the deck and patio create a private oasis with tranquil views. 2 separate garages. Conveniently located in the Flats location near Wedgemere Station and Winchester’s vibrant downtown, this home delivers space, character & Ambrose elementary just up the hill!