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40 Toms Hollow Lane, Orleans, MA 02653

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For Sale

$5,900,000

6 beds • 6 baths • 1 half baths • 4,000 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • $1,475.00
    Price per square foot

  • 21-30 Years Old
    Age

Explore this Property

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.
MLS# 22501262

Courtesy Of Robert Paul Properties, Inc.

(508) 945-5553

Property Features

  • Age
    21-30 Years Old
  • Amenities
    Water Front
  • Architecture Style
    Other
  • Floor Covering
    Carpet
  • Heating System
    Forced Air
  • Lot Size
    3.84 Acres
  • View Type
    Harbor

Map and Directions

Directions to 40 Toms Hollow Lane, Orleans, MA 02653

Home seller CENTURY 21 North East

Get to know the neighborhood. A local affiliated CENTURY 21 office will help you set up tours, give advice, and negotiate with sellers.

CENTURY 21 North East

(800) 844-7653
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Calculators provided for estimating purposes only. Consult with your lender to determine precise payment requirements.

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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. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data powered by Attom Data Solutions. Copyright© 2025. Information deemed reliable but not guaranteed.

This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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