$3,495,000

645 S Orleans Road, Orleans, MA 02653

  • 7 beds |
  • 7 baths |
  • 3,548 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1945
  • Property Lot Size Icon0.25acre lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $985/sqft
  • Property List Date Icon Listed 5 months ago

Property Description

For the first time in generations, this extraordinary Pleasant Bay compound—featuring the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''—is offered as a rare, legacy waterfront estate. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation potential. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. ''Topside'' offers 5 bedrooms and 4.5 baths with timeless coastal character and spaces designed for gathering, while the ''Boathouse'' sits just above the shoreline, featuring 2 bedrooms, 1 bathroom, and its own deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn offer a blend of intimacy and scale. With a strong rental history and immense potential for expansion or personalization, this is a lifestyle property that invites multigenerational living, savvy investment, or a private retreat. A once-in-a-lifetime opportunity to own one of Cape Cod's most storied waterfront settings.

Listing Status:
Active
Date Added:
October 23, 2025 at 05:00AM
Listing Office:
Berkshire Hathaway HomeServices Robert Paul Properties : 508-945-5553
Listing Agent:
Guthrie Schofield Group : 774-487-8554
MLS ID:
22502226
  • Appliances: Water Heater
  • Basement: Bulkhead AccessPartial
  • Flooring: WoodTile
  • A/C: None
  • Heating: Oil
  • General: GardenPrivate Yard
  • Roofing: Asphalt
  • General: Vinyl Siding2BlockCrawl Space
  • Originating MLS: Cape Cod & Islands Association of REALTORS®
  • County: Barnstable
  • Zoning: 96-23-0
  • Water: Public
  • Sewer: Private Sewer
  • Source: Cape Cod & Islands Association of REALTORS®

This listing courtesy of Guthrie Schofield Group, Berkshire Hathaway HomeServices Robert Paul Properties

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

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Location

Schools Nearby

O

Orleans Elementary School

46 Eldredge Pkwy, Orleans, MA, 02653

Grades KG-5

3.40 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.