645 S Orleans Orleans Orleans MA 02653 MLS #73373131

645 S Orleans Orleans
Orleans, MA, 02653
$3,950,000
7 Beds
6.5 Baths
3,549 SqFt
0.25 Acres
$3,950,000
645 S Orleans Orleans
Orleans, MA, 02653
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.

Property Details

Price:
$3,950,000
MLS #:
73373131
Status:
Active
Beds:
7
Baths:
6.5
Address:
645 S Orleans Orleans
Type:
Single Family
Subtype:
Single Family Residence
City:
Orleans
Listed Date:
May 12, 2025
State:
MA
Finished Sq Ft:
3,549
Total Sq Ft:
3,549
ZIP:
02653
Lot Size:
10,890 sqft / 0.25 acres (approx)
Year Built:
1930

Schools

Interior

Bathrooms
6 Full Bathrooms, 1 Half Bathroom
Cooling
Window Unit(s)
Fireplaces Total
2
Heating
Baseboard

Exterior

Architectural Style
Antique
Parking Spots
4

Financial

Tax Year
2024
Taxes
$9,500
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Marie Andrews

Marie Andrews

Realtor®, Broker/Owner, GBREB, Notary Public

Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…

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Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
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645 S Orleans Orleans
Orleans, MA