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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

Tax Information

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

Parking

  • Parking Spaces4

Rooms

  • Bathrooms Total Decimal 6.5
  • Full Bath6
  • Half Baths1

Basic Information

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

Location

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

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

Property

  • Acreage0.25

Utilities

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

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

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

Legal

  • Zoning96-23-0

Other

  • Date Listed05/12/2025
  • Farm Land Area Units Square Feet
  • View Count6

Map Location

Driving Directions

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

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