645 S Orleans Road, Orleans, MA 02653

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 extraordinary Pleasant Bay compound--featuring the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, legacy waterfront estate. 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 potential. Both homes enjoy sweeping 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 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 rental history and immense potential for expansion or personalization, this is a lifestyle property that invites multigenerational living,

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Home facts

  • Year built:1945
  • Listing ID #:22502226
  • Added:276 day(s) ago
  • Updated:February 10, 2026 at 03:24 PM

Rooms and interior

  • Bedrooms:7
  • Total bathrooms:7
  • Full bathrooms:6
  • Living area:3,548 sq. ft.

Heating and cooling

  • Heating:Hot Water

Structure and exterior

  • Roof:Asphalt
  • Year built:1945
  • Building area:3,548 sq. ft.
  • Lot area:0.25 Acres

Schools

  • Middle school:Nauset
  • Elementary school:Nauset

Utilities

  • Sewer:Private Sewer

Finances and disclosures

  • Price:$2,700,000
  • Price per sq. ft.:$760.99
  • Tax amount:$10,740 (2026)
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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