Set within Brookline's prestigious Chestnut Hill North Historic District, this exceptional Shingle-style residence was built from the ground up and completed in 2008, and captures the character of its historic surroundings while offering the livability and infrastructure of a newer home. Offering 4,015 finished square feet (plus additional unfinished area in the lower level), 6 bedrooms, and 5.5 baths, 23 Circuit Road features a thoughtful floor plan that lives well beyond its footprint. Gracious proportions, abundant natural light, and beautifully crafted interiors create an inviting atmosphere that is both refined and comfortable. The main level offers elegant entertaining rooms, two wood burning fireplaces, a guest bedroom or study with en-suite bath, and an expansive kitchen and family room with french doors that expand the living area outside. Upstairs, the second floor comprises 4 bedrooms, including a stunning primary bedroom with dual walk-in closets and en-suite bath with 15-ft vaulted ceilings, and a laundry room. The top floor offers flexibility with a second family/media room, 6th bedroom, office area, and full bath. An additional 1,600+ square feet of unfinished lower-level space offers extraordinary future potential. Outside, mature landscaping surrounds a spacious and private level yard with two bluestone terraces and an oversized detached two-car garage. Ideally situated along a picturesque, tree-lined street near acclaimed schools, including Brimmer and May, this is a rare opportunity to enjoy the architectural distinction of historic Chestnut Hill without the compromises of an older home. No open houses -- private showings by request.