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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.

More Info

Basic Information

  • Bedrooms7
  • Mls StatusActive
  • Bathroom7
  • Parcel Number 2365906

Location

  • Address645 S Orleans
  • Building Number645
  • CountyBarnstable
  • StateMA
  • StreetS Orleans
  • TownOrleans
  • Zip02653

Property Information

  • Square Feet3,549
  • Building Area Source Public Records
  • Living Area 3,549
  • Lot Size Square Feet 10,890
  • Lot Size Units Acres
  • View YN Yes

Other

  • Date Listed05/12/2025
  • Farm Land Area Units Square Feet
  • View Count5

Tax Information

  • Tax Assessed Value $1,757,800
  • Tax Year 2026
  • Taxes$10,740

Basic Information

  • List Price$2,700,000
  • MLS Number73373131
  • Modification Date05/16/2026
  • Property SubTypeSingle Family Residence

Property

  • Acreage0.25

Utilities

  • Cooling Window Unit(s)
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Baseboard
  • Sewer Private Sewer
  • Water Source Public

Parking

  • Parking Spaces4

Rooms

  • Bathrooms Total Decimal 6.5
  • Full Bath6
  • Half Baths1

Building

  • Building Area Units Square Feet
  • FireplaceYes
  • Fireplaces Total 2
  • FoundationBlock
  • Property StyleAntique
  • Rooms12
  • Year Built1930
  • Year Built Details Approximate
  • Year Built Source Public Records

Water Body

  • Miles to Beach0.1
  • WaterfrontYes
  • Waterfront Features Waterfront, Ocean, Bay, Harbor, Dock/Mooring, Frontage, Deep Water Access, Direct Access, Private, Beach Access, Bay, Harbor, Direct Access, Frontage,0 to 1/10 Mile To Beach

Map Location

Listed by Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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. MLSPIN 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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