645 S Orleans Road
Orleans, MA 02653
- 7 beds
- 7 baths
- 3,548 sqft
- 10,890 sqft lot
- $1,113 per sqft
- 1945 build
- – on site
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.
Last checked:
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Checking…
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Last updated May 13, 2025
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MLS# 22502226 —
The Building
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Year Built:1945
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New Construction:false
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Roof:Asphalt
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Foundation Details:Block
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Stories:2
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Basement:Bulkhead Access
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Exterior Features:Garden
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Building Area Units:Square Feet
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Building Area Total:3548
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Below Grade Finished Area Units:Square Feet
Interior
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Kitchen Description:Fireplace(s): Wood Burning
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Rooms Total:12
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Living Room Description:Fireplace(s): Wood Burning
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Fireplace:false
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Fireplace Features:Wood Burning
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Flooring:Wood
Room Dimensions
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Living Area Units:Square Feet
Location
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Directions:Use GPS - On South Orleans Road, property is on the right. Main house is on the right of property, boathouse to left.
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Coordinates:-69.991148, 41.732431
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Latitude:41.732431
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Longitude:-69.991148
The Property
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Property Type:Residential
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Property Subtype:Single Family Residence
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Property Condition:Approximate
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Property Attached:false
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Parcel Number:96230
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Lot Size Acres:0.25
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Lot Size SqFt:10890
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Lot Size Area:0.25
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Lot Size Units:Acres
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Lot Size Source:Field Card
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Zoning:R
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Waterview:Bay/Harbor
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Waterfront:true
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Water Body Name:Little Pleasant Bay
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Private Dock Description:Deep Water,Platform,Floating
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Road Frontage Type:Public
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Road Surface Type:Paved
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Land Lease:false
Listing Agent
- Contact info:
- Agent phone:
- (774) 487-8554
- Office phone:
- (508) 945-5553
Taxes
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Tax Year:2025
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Tax Annual Amount:10215
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Tax Assessed Value:1637100
Beds
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Bedrooms Total:7
Baths
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Total Baths:6.5
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Total Baths:7
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Full Baths:6
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Half Baths:1
The Listing
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Home Warranty:false
Heating & Cooling
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Heating:Hot Water
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Heating:true
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Cooling:None
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Cooling:false
Utilities
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Sewer:Private Sewer
Appliances
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Appliances:Electric Water Heater
Schools
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Elementary School District:Nauset
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Middle Or Junior School District:Nauset
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High School District:Nauset
The Community
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Association:false
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Pool Private:false
Parking
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Garage:false
Monthly cost estimate
Asking price
$3,950,000
| Expense | Monthly cost |
|---|---|
|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$21,151
|
| Taxes | $851 |
| Insurance | $1,086 |
| Utilities | $375 See report |
| Total | $23,463/mo.* |
| *This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
| Date | Event | Source | Price | % Change |
|---|---|---|---|---|
|
5/12/25
May 12, 2025
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Listed / Active | CCI | $3,950,000 |
