$2,700,000
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:
$2,700,000
MLS #:
73373131
Status:
Active
Beds:
7
Baths:
6.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
May 12, 2025
Finished Sq Ft:
3,549
Total Sq Ft:
3,549
Lot Size:
10,890 sqft / 0.25 acres (approx)
Year Built:
1930
Schools
Interior
Above Grade Finished Area
3549
Bathrooms
6 Full Bathrooms, 1 Half Bathroom
Cooling
Window Unit(s)
Fireplaces Total
2
Heating
Baseboard
Exterior
Architectural Style
Antique
Open Parking Spaces
4
Parking Spots
4
Parking Total
4
View
Scenic View(s)
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
Financial
Tax Year
2026
Taxes
$10,740
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…
More About MarieMortgage Calculator
Map
Current real estate data for Single Family in Orleans as of May 04, 2026
36
Single Family Listed
156
Avg DOM
707
Avg $ / SqFt
$2,224,075
Avg List Price
Community
- Address645 S Orleans Orleans Orleans MA
- CityOrleans
- CountyBarnstable
- Zip Code02653
Similar Listings Nearby
Property Summary
- 645 S Orleans Orleans Orleans MA is a Single Family for sale in Orleans, MA, 02653. It is listed for $2,700,000 and features 7 beds, 7 baths, and has approximately 3,549 square feet of living space, and was originally constructed in 1930. The current price per square foot is $761. The average price per square foot for Single Family listings in Orleans is $707. The average listing price for Single Family in Orleans is $2,224,075. To schedule a showing of MLS#73373131 at 645 S Orleans Orleans in Orleans, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
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.
645 S Orleans Orleans
Orleans, MA