$2,700,000

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 $761/sqft
  • Property List Date Icon Listed 1 year ago

Property Description

For the first time in generations, this landmark Pleasant Bay compound--anchored by the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. 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. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, ''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 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!

Listing Status:
Active
Date Added:
March 23, 2026
Data Last Updated:
July 31, 2026 at 2:37AM
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: Partial
  • Flooring: WoodTile
  • A/C: None
  • Heating: Oil
  • General: Garden
  • Roofing: Asphalt
  • General: Vinyl Siding2
  • Originating MLS: Cape Cod & Islands Association of REALTORS®
  • County: Barnstable
  • Zoning: 96-23-0
  • Water: Public
  • 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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