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645 S Orleans Road, Orleans, MA 02653

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For Sale

$3,950,000

7 beds • 6 baths • 1 half baths • 3,548 sqft

Estimated Payment

$      /mo. †

APR for 30 years

Change Loan Terms

  • Single Family Detached
    Property type

  • $1,113.30
    Price per square foot

  • Over 50 Years Old
    Age

Explore this Property

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, savvy investment, or a private retreat. A once-in-a-lifetime opportunity to own one of Cape Cod's most storied waterfront settings.
MLS# 22502226

Courtesy Of Robert Paul Properties, Inc.

(508) 945-5553

Property Features

  • Age
    Over 50 Years Old
  • Amenities
    Garden, Water Front
  • Architecture Style
    Other
  • Exterior Type
    Vinyl Siding
  • Floor Covering
    Tile, Wood
  • Lot Size
    0.25 Acres
  • Roof Type
    Asphalt

Map and Directions

Directions to 645 S Orleans Road, Orleans, MA 02653

Home seller CENTURY 21 North East

Get to know the neighborhood. A local affiliated CENTURY 21 office will help you set up tours, give advice, and negotiate with sellers.

CENTURY 21 North East

(800) 844-7653
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Monthly Payment Breakdown

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Calculators provided for estimating purposes only. Consult with your lender to determine precise payment requirements.

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Copyright © 2025 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data powered by Attom Data Solutions. Copyright© 2025. Information deemed reliable but not guaranteed.

This information is provided for general informational purposes only and should not be relied on in making any home-buying decisions. School information does not guarantee enrollment. Contact a local real estate professional or the school district(s) for current information on schools. This information is not intended for use in determining a person's eligibility to attend a school or to use or benefit from other city, town or local services.

† Based on a 30-year fixed rate of 3.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Interest rates are also subject to credit and property approval based on secondary market guidelines. The rates shown are based on average rates for our best qualified customers. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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