Luxury Real Estate Group Boston > Orleans > 645 S Orleans

LRG Boston

(617) 233-5800

355 Boylston St

Boston, Ma 02116

645 S Orleans

Orleans, MA

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.

offered at

$3,950,000

  • Listing ID: 73373131
  • Bedrooms: 7
  • Full Baths: 6
  • Half Baths: 1
  • Living Area: 3,549 sqft Convert
  • Lot Size: 10,890 sqft Convert
  • Acres: 0.25

Additional Details

Type: Single Family, Single Family Residence

Zip Code: 02653

Parking

Parking Spaces: 4

Rooms and Dimensions

Total Rooms: 12

Contact: LRG Boston at (617) 233-5800

LRGBOSTON.COM

355 Boylston St. Boston, MA 02116

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