645 S Orleans

Location & Nearby

HThis property

• A
  🏖️ South Orleans Beach

  0.15 mi
• B
  ⛳ Wequassett Resort and Golf Club

  0.94 mi
• C
  🍽️ Outer Bar & Grille

  0.99 mi
• D
  🍽️ LiBAYtion

  0.99 mi
• E
  ⛳ Cape Cod National Golf Club

  1.15 mi
• F
  🌲 Pleasant Bay Woodlands

  1.28 mi
• G
  ⚓ Pleasant Bay Marina

  1.53 mi
• H
  🏖️ Jacknife Beach

  1.72 mi

About this property

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.

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