40 Toms Hollow Lane, Orleans, MA 02653

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$5,900,000

bedrooms

bathrooms

square feet

4,000

Acreage

3.84

Open Houses

Apr 3

year built

1999

Full Baths

Half Baths

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A rare offering on the shores of Little Pleasant Bay, 40 Tom's Hollow is a generational waterfront estate encompassing nearly four acres of bucolic landscape with an expansive shoreline, private sandy beach, and iconic boathouse. A winding drive leads through a serene coastal setting 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 positioned to capture the beauty beyond. A first-floor primary suite offers privacy and comfort, while separate guest quarters provide flexibility for extended stays. The finished walkout lower level adds space for recreation, gatherings, or overflow guests—all opening to a lawn that invites entertaining and the potential for a pool. Outside, a wide stretch of shoreline allows for private beach access, and mooring rights open the door to water-sport 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.

Location
Subdivision	-
County	Barnstable
Elementary School	-
Middle School	-
High School	-

Driving directions

Open houses

Apr

Thursday

10AM — 12PM

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MLS number: 22501262

Listing agent: Guthrie Schofield Group

Listing broker: Robert Paul Properties, Inc. (508) 863-4663

Copyright © 2025 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. [source]

Last update: Wednesday, April 2 2025 at 5:57 p.m. EDT

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