645 S Orleans, Orleans, MA 02653

Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
645 S Orleans,Orleans, MA 02653
$3,495,000
  • 7 Beds
  • 7 Baths
  • 3,549 sq. ft.
  • Single family
  • Active
Listed by: guthrie schofield group, alfred schofield
Office: berkshire hathaway homeservices robert paul properties
MLS#:73373131
Source:MLSPIN

Price summary

  • Price:$3,495,000
  • Price per sq. ft.:$984.78

About this home

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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Home facts

  • Year built:1930
  • Listing ID #:73373131
  • Updated:November 15, 2025 at 11:44 AM

Rooms and interior

  • Bedrooms:7
  • Total bathrooms:7
  • Full bathrooms:6
  • Half bathrooms:1
  • Living area:3,549 sq. ft.

Heating and cooling

  • Cooling:Window Unit(s)
  • Heating:Baseboard

Structure and exterior

  • Year built:1930
  • Building area:3,549 sq. ft.
  • Lot area:0.25 Acres

Utilities

  • Water:Public
  • Sewer:Private Sewer

Finances and disclosures

  • Price:$3,495,000
  • Price per sq. ft.:$984.78
  • Tax amount:$9,500 (2024)
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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