Little Pleasant Bay Waterfront Estate

A rare offering on the shores of Little Pleasant Bay, 40 Toms Hollow is a generational waterfront estate encompassing four acres of wooded upland with an expansive shoreline, private sandy beach, and iconic boathouse on Cape Cod’s largest estuary. 

A winding shell drive leads through a serene coastal landscape to a timeless center-entrance Colonial built in 1999, 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 or additional rental income. 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—with power, plumbing, and potential—anchors the property in authentic Cape Cod tradition. With strong rental history, thoughtful updates, and room for future vision, this is a rare legacy estate where natural beauty and coastal elegance live in quiet harmony.