REQUEST A TOUR If you would like to see this home without being there in person, select the "Virtual Tour" option and your agent will contact you to discuss available opportunities.

In-PersonVirtual Tour

Thu

Apr

Fri

Apr

Sat

Apr

John Stringfellow

homes@capecodstar.com +1(508) 319-9101

$ 5,900,000

Est. payment -/mo

Save

Open 4/3 10AM-12PM

40 Toms Hollow Lane Orleans, MA 02653

6 Beds

7 Baths

4,000 SqFt

OPEN HOUSE

Thu Apr 03, 10:00am - 12:00pm

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 4,000 sqft

Price per Sqft $1,475

MLS Listing ID 22501262

Style Colonial

Bedrooms 6

Full Baths 6

Half Baths 1

HOA Y/N No

Abv Grd Liv Area 4,000

Originating Board Cape Cod & Islands API

Year Built 1999

Annual Tax Amount $33,210

Tax Year 2024

Lot Size 3.840 Acres

Acres 3.84

Property Sub-Type Single Family Residence

Property Description

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

State MA

County Barnstable

Zoning 1010

Direction From Quanset Road, take a right onto Ellerslie Rd, then right onto Tom's Hollow. When road splits initially stay to the left and then right to 40. House has white stone driveway.

Body of Water Little Pleasant Bay

Rooms

Basement Finished, Walk-Out Access

Interior

Interior Features Sound System

Heating Forced Air

Cooling Central Air

Flooring Carpet

Fireplace No

Exterior

Exterior Feature Outdoor Shower

Garage Spaces 3.0

Waterfront Description Bay

View Y/N Yes

Water Access Desc Bay/Harbor

View Bay/Harbor

Roof Type Shingle

Street Surface Unimproved

Garage Yes

Private Pool No

Building

Faces From Quanset Road, take a right onto Ellerslie Rd, then right onto Tom's Hollow. When road splits initially stay to the left and then right to 40. House has white stone driveway.

Story 2

Foundation Poured

Sewer Private Sewer

Water Well

Level or Stories 2

Structure Type Shingle Siding

New Construction No

Schools

Elementary Schools Nauset

Middle Schools Nauset

High Schools Nauset

School District Nauset

Others

Tax ID 82130

Special Listing Condition None

Listed by Berkshire Hathaway HomeServices Robert Paul Properties

+1(508) 319-9101

homes@capecodstar.com

Brewster, MA, 02631, USA