40 Toms Hollow Lane, Orleans, MA 02653

Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
#1#2#3
40 Toms Hollow Lane,Orleans, MA 02653
$5,900,000
  • 6 Beds
  • 7 Baths
  • 4,000 sq. ft.
  • Single family
  • Active
Listed by:guthrie schofield group
Office:berkshire hathaway homeservices robert paul properties
MLS#:73352932
Source:MLSPIN

Price summary

  • Price:$5,900,000
  • Price per sq. ft.:$1,475

About this home

A rare offering on the shores of Little Pleasant Bay, 40 Tom's Hollow is a generational waterfront estate encompassing four acres with a private sandy beach and iconic boathouse. A winding drive leads to a timeless Colonial with soaring ceilings and panoramic bay views. The cathedral-ceilinged great room, with pass-through hearth, forms the heart of the home—flanked by a custom kitchen and gracious dining area. A first-floor primary suite offers comfort and privacy, while guest quarters provide flexibility for extended stays. The finished walkout lower level adds space for recreation or overflow guests, opening to a lush lawn with potential for a pool. A broad shoreline allows for private beach access, while mooring rights invite boating adventures. The historic boathouse—brimming with potential—anchors the property in classic Cape Cod tradition. A true legacy estate where nature and coastal elegance meet in quiet harmony.

Contact an agent

contact an agent

Yes, I would like more information from BHGRE®. Please use and/or share my information with an BHGRE affiliated agent to contact me about my real estate needs. By clicking Send message, I agree an BHGRE affiliated agent may contact me by phone or text message including by automated means about real estate services, and that I can access real estate services without providing my phone number. I acknowledge that I have read and agree to theTerms of useandPrivacy notice

Home facts

  • Year built:1999
  • Listing Id #:73352932
  • Updated:August 14, 2025 at 10:28 AM

Rooms and interior

  • Bedrooms:6
  • Total bathrooms:7
  • Full bathrooms:6
  • Half bathrooms:1
  • Living area:4,000 sq. ft.

Heating and cooling

  • Cooling:Central Air
  • Heating:Central

Structure and exterior

  • Year built:1999
  • Building area:4,000 sq. ft.
  • Lot area:3.84 Acres

Utilities

  • Water:Public
  • Sewer:Private Sewer

Finances and disclosures

  • Price:$5,900,000
  • Price per sq. ft.:$1,475
  • Tax amount:$33,210 (2024)
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

New listings near 40 Toms Hollow Lane