Home of the Week: Exclusive Waterfront Estate on Little Pleasant Bay

Address: 40 Toms Hollow Lane, Orleans, MA
Price: $5,900,000
Area: 4,000 square feet
Bedrooms: 6
Bathrooms: 7

For more information: Tony Guthrie & Alfred Schofield, Guthrie Schofield Group

Discover one of Cape Cod’s most exceptional waterfront properties at 40 Toms Hollow, a private four-acre estate nestled along the pristine shores of Little Pleasant Bay. With its expansive frontage, secluded sandy beach, and historic boathouse, this rare offering presents an unparalleled opportunity to own a legacy property on Cape Cod’s largest estuary. A picturesque shell drive winds through mature coastal woodlands, arriving at a classic center-entrance Colonial home built in 1999.

Inside, the residence exudes timeless elegance with vaulted ceilings, walls of glass showcasing sweeping bay views, and a sunlit great room with a striking double-sided fireplace. The open layout connects seamlessly to a custom chef’s kitchen and spacious dining area, all oriented toward the water for stunning vistas throughout the day. The main level includes a private primary suite, thoughtfully designed for comfort and seclusion. Upstairs, additional guest accommodations offer flexibility for multigenerational living or potential vacation rental income. A fully finished walkout lower level adds valuable space for entertaining, recreation, or overflow guests—opening to a lush, landscaped yard with room to add a pool.

Step outside to your own private stretch of shoreline, where beach access and mooring rights create the perfect launch point for sailing, kayaking, or exploring the bay. The iconic boathouse, equipped with power and plumbing, offers endless possibilities—from waterside entertaining to studio or guest space—all rooted in authentic Cape Cod character.

Whether you’re seeking a private retreat, a smart investment, or a long-term family compound, 40 Toms Hollow delivers the best of Cape Cod waterfront living.

See the full listing here.