A rare offering on the shores of Little Pleasant Bay, 40 Toms Hollow is a generational waterfront estate encompassing four acres of upland with an expansive shoreline, private sandy beach, and iconic boathouse. A winding shell drive leads through a serene coastal landscape to a timeless center-entrance Colonial, where soaring ceilings and panoramic bay views set the tone. The cathedral-ceilinged great room, with pass-through hearth, forms the heart of the home--flanked by a custom kitchen and gracious dining area, perfectly sited for beautiful vistas. A first-floor primary suite offers privacy and comfort, while private guest quarters provide flexibility for extended stays. The finished walkout lower level adds generous space for recreation, gatherings, or overflow guests--all opening to a lush backyard and lawn that invites gatherings, play, and the potential for a pool. Outside, a vast stretch of shoreline allows for easy beach access and mooring rights invite endless boating adventures. The historic boathouse--brimming with potential--anchors the property in authentic Cape Cod tradition. This is a rare legacy estate where nature and coastal elegance live in quiet harmony.