Welcome to 171 Judd Hill Road, a stunning custom built home with high end finishes throughout, nestled in the quiet beauty of Middlebury CT. Built in 2015, this immaculately maintained 5 bed, 4 bath home offers thoughtful design, with a separate in-law suite plus additional 400 SF of unfinished basement for extra storage. The main level features hardwood floors, a sun-filled two-story foyer and great room with fireplace, formal dining room and open-concept eat-in kitchen. The main level primary suite includes a walk-in closet, full bath, and a separate office - perfect for remote work (or can be used as a 2nd closet). A 2nd bedroom with full bath also on main floor. Upstairs are 2 bedrooms, 1 full bath, plus versatile bonus room ideal as a media space or 6th bedroom. Downstairs, a fully soundproofed 1 bed apartment with ensuite bathroom, full kitchen, laundry, fireplace, and home gym offers endless options for multigenerational living, guest space, or an income-producing rental. Enjoy long views from the back deck and bonus features like a well-organized laundry/mudroom and second fridge & freezer in the garage. Set in a quiet neighborhood with access to top-rated public & private schools, Lake Quassapaug, parks, trails, and just minutes to I-84 and Middlebury's town center. A rare find in one of New Haven County's most welcoming communities.