645 S Orleans Road, Orleans, MA 02653

Orleans
Local realty services provided by:Better Homes and Gardens Real Estate The Shanahan Group
645 S Orleans Road,Orleans, MA 02653
$2,700,000
  • 7 Beds
  • 7 Baths
  • 3,548 sq. ft.
  • Single family
  • Active
Listed by: guthrie schofield group
Office: berkshire hathaway homeservices robert paul properties
MLS#:22502226
Source:CAPECOD

Price summary

  • Price:$2,700,000
  • Price per sq. ft.:$760.99

About this home

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...

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Home facts

  • Year built:1945
  • Listing ID #:22502226
  • Added:467 day(s) ago
  • Updated:August 22, 2026 at 02:57 PM

Rooms and interior

  • Bedrooms:7
  • Total bathrooms:7
  • Rooms Total:12
  • Basement Description:Bulkhead Access, Partial
  • Living area:3,548 sq. ft.

Structure and exterior

  • Year built:1945
  • Building area:3,548 sq. ft.
  • Lot area:0.25 Acres
  • Exterior Features:Garden

Finances and disclosures

  • Price:$2,700,000
  • Price per sq. ft.:$760.99
  • Tax amount:$10,740
MLS LogoDisclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Coldwell Banker Realty include the name of the listing broker. Neither the listing company nor Better Homes and Gardens Real Estate The Shanahan Group shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

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