1. Massachusetts
  2. Orleans
  3. 645 S Orleans
$3,950,000

645 S Orleans, Orleans, MA 02653

  • 7 beds |
  • 7 baths |
  • 3,549 sqft
  • Property Icon Single-Family Home
  • Property Year Built Icon Built in 1930
  • Property Lot Size Icon0.25acre lot
  • Property Parking Icon —— car garage
  • Property Price Per Square Feet Icon $1,113/sqft
  • Property List Date Icon Listed 1 month ago

Property Description

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.

Listing Status:
Active
Listing Office:
Berkshire Hathaway HomeServices Robert Paul Properties : 508-945-5553
Listing Agent:
Guthrie Schofield Group : 508-246-3236
MLS ID:
73373131
  • A/C: Window Unit(s)
  • Heating: Baseboard
  • Fireplace: FireplaceFireplaces: 2

This listing courtesy of Guthrie Schofield Group, Berkshire Hathaway HomeServices Robert Paul Properties

Monthly Payment

$Est. Payment
  • Principal & Interest $
  • Property Taxes $
  • Home Insurance $
  • VA Funding Fee $

Ready to Start a VA Loan?

Get Started Veterans United Home LoansNMLS #1907  †
Get Prequalified »
Interest rates used in the VA mortgage calculator are shown for illustrative purposes only. Your rate may differ based on a variety of factors, including your credit score and the current market conditions. To get your personalized interest rate, start your quote online.

Location

Schools Nearby

O

Orleans Elementary School

46 Eldredge Pkwy, Orleans, MA, 02653

Grades KG-5

3.40 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.