645 S Orleans Road, Orleans, MA 02653 (MLS# 22502226)
645 S Orleans Road, Orleans, MA 02653
$3,495,000
Property Type:
Residential
Bedrooms:
7
Baths:
7
Square Footage:
3,548
Lot Size (sq. ft.):
10,890
Status:
Active
Current Price:
$3,495,000
List Date:
11/13/2025
Last Modified:
1/14/2026
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 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.
More Information MLS# 22502226
Contract Info
List Price/SqFt: 985.06
Status: Active
Original List Price: 3950000
List Price: $3,495,000
Current Price: $3,495,000
List Date: 2025-05-12
Legal and Taxes
Town: Orleans
Village: Orleans
Estimated Annual Taxes: 10740
Building Assessments: 955700
Other Assessments: 120600
Total Assessment: 1757800
Title Reference - Book: 33292
Title Reference - Page: 185
Flood Ins Required: Yes: verify w/insurance agent
Lead Base Paint: Unknown
Mass Use Code: 10 - Multiple Use Property
Nitrogen Sensitive Area: Yes
Street #: 645
Pre Direction: S
Street Name: Orleans
Street Suffix: Road
County: Barnstable
State: MA
Zip Code: 02653
Tax ID: 96-23-0
Tax Year: 2026
General Property Info
Region: Lower Cape
School District: Nauset
Zoning: R
Property Sub-Type: Single Family Residence
Renovated: No
Stories: 2
Total Rooms: 12
Field Card SqFt: 671
Additional Finished Space: 2877
Additional SqFt Source: Public Records
Basement: Yes
Baths - Half: 1
Association: No
Private Dock: Yes
Private Pool: No
Lot Size SqFt: 10890
Leased Land: No
Lot Size Source: Field Card
Acres: 0.25
Garage: No
Year Round: Yes
Separate Living Qtrs: Yes
Golf Course Front: No
Golf Course View: No
Waterfront: Yes
Water Body: Little Pleasant Bay
Waterfront Type: Bay/Harbor
Water Body Type: Salt
Water Access Type: Private
Waterview: Yes
Water Body View: Little Pleasant Bay
Waterview Type: Bay/Harbor
Property Includes Recording Devices: No
Year Built: 1945
Total Finished Space: 3548
Bedrooms - Total: 7
Baths - Full: 6
Baths - Total: 7
Remarks & Misc
Public Remarks: 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.
Directions to Property: Use GPS - On South Orleans Road, property is on the right. Main house is on the right of property, boathouse to left.
Street Description
Paved: 1
Public: 1
Special Listing Cond
None: 1
Year Built Desc
Approximate: 1
Basement Description
Bulkhead Access: 1
Partial: 1
Architectural Style
Antique: 1
Foundation Details
Block: 1
Crawl Space: 1
Private Dock Description
Deep Water: 1
Floating: 1
Platform: 1
Floors
Tile: 1
Wood: 1
Sewer
Private Sewer: 1
Roof Description
Asphalt: 1
Siding Description
Vinyl Siding: 1
Heating
Hot Water: 1
Cooling
None: 1
Fuel Type
Oil: 1
Water
Public: 1
Hot Water
Water Heater: 1
Hot Water Source
Electric: 1
Living Room
Fireplace: Wood Burning
Kitchen
Fireplace: Wood Burning
Exterior Features
Garden: 1
Private Yard: 1
Property Features
Street Description: Paved; Public
Special Listing Cond: None
Architectural Style: Antique
Year Built Desc: Approximate
Basement Description: Bulkhead Access; Partial
Foundation Details: Block; Crawl Space
Floors: Tile; Wood
Private Dock Description: Deep Water; Floating; Platform
Exterior Features: Garden; Private Yard
Roof Description: Asphalt
Siding Description: Vinyl Siding
Sewer: Private Sewer
Heating: Hot Water
Cooling: None
Fuel Type: Oil
Water: Public
Hot Water: Water Heater
Hot Water Source: Electric
Lead Paint Disclosure ›
Listing Office:
Berkshire Hathaway HomeServices Robert Paul Properties
Listing Agent:
Guthrie Schofield Group
Last Updated: January - 14 - 2026
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