106 Chatham Road Rare compound in coveted Harwich where multigenerational living converges across main house, guest house, pool and grounds - the setting for timeless summers and iconic entertaining year after year. Custom developed by Whitcomb Building and Remodeling, the main residence features an open concept floor plan connecting dining, living, and a chef's kitchen with ease -- warm, considered, and built for how people actually live. The first floor includes a primary suite with spa-caliber bath and walk-in closet. Upstairs, two bedrooms and a bonus room with custom built-ins round out a layout that works for everyone. The lower level impresses with soaring ceilings, wet bar, and full bath. The antique guest house, rooted in the 1800s, pairs new systems, white oak floors, and a custom kitchen with original exposed beams in the vaulted ceiling. A penthouse-style bedroom and private patio complete the retreat. Matching Pella windows and siding, cobblestone driveways, and and dramatic boulder retaining walls unite both homes. A Shoreline heated pool with surrounding patio and gas fire pit anchors the grounds. Singular in Harwich. Properties like this simply don't come around twice.