$2,700,000

645 S Orleans, Orleans, MA 02653

  • 7 beds |
  • 7 baths |
  • 3,549 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1930
  • Property Lot Size Icon0.25acre lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $761/sqft
  • Property List Date Icon Listed 11 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 estate. With a deep-water dock, moorings, and direct bay access, it delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy 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 charm and inviting gathering spaces. The "Boathouse," perched just above the shoreline, features 2 bedrooms, 1 bath, and a private deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn complete the experience. With strong rental history and exceptional potential for personalization or expansion, this lifestyle property invites multigenerational enjoyment, investment, or retreat—an iconic opportunity in one of Cape Cod’s most storied settings.

Listing Status:
Active
Date Added:
May 12, 2025
Data Last Updated:
April 29, 2026 at 11:08PM
Listing Office:
Berkshire Hathaway HomeServices Robert Paul Properties : 508-945-5553
Listing Agent:
Guthrie Schofield Group : 508-246-3236
MLS ID:
73373131
  • A/C: Window Unit(s)
  • Heating: Baseboard
  • Fireplace: FireplaceFireplaces: 2
  • Style: Antique
  • Parking: Parking spaces: 4
  • General: Block
  • Originating MLS: MLS Property Information Network
  • County: Barnstable
  • Zoning: 96-23-02365906
  • View: Scenic View(s)View
  • Water: Public
  • Sewer: Private Sewer
  • Source: MLS Property Information Network

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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