645 S Orleans Rd

Orleans, MA 02653

$3,495,000
Price
7
Beds
3,548 Sq. Ft.
$985 / Sq. Ft.
3,548
Sq. Ft.
$985
per Sq. Ft.
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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...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.
  1. Listed by Guthrie Schofield Group • Berkshire Hathaway HomeServices Robert Paul Properties

Property Details for 645 South Orleans Road

Village
Orleans
School District
Nauset
Style
Antique
Waterfront Type
Bay/Harbor
Waterview Type
Bay/Harbor
Waterfront
Yes
Waterview
Yes
FEMA 100 Yr Flood Plain
VE
LISTING UPDATED: 11/13/2025 03:04 PM

Property Details for 645 South Orleans Road

StatusActive
MLS #22502226
Days on Market225
Taxes$10,215 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Single Family Residence
Year Built1945
Lot Size0.25 AC / 10,890 SF
CountyBarnstable County

Location

Listing Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties, Guthrie Schofield Group
Add your commute

Building Information for 645 South Orleans Road

Stories2Year Built1945Building Size-Lot Size0.25 AC / 10,890 SF

Payment Calculator

$18,121 per month

30 year fixed, 6.28% Interest

Principal and Interest

$17,270

Property Taxes

$851

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 645 South Orleans Road

Summary
Location and General Information
  • 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.
  • Title Reference - Book: 33292
  • SqFt Source: Public Records
  • Region: Lower Cape
  • County: Barnstable
  • City Postal ID: 02653
  • Street Number: 645
  • Water Body Name: Little Pleasant Bay
  • MLSAreaMajor: Orleans
  • General Property Info:Water Body: Little Pleasant Bay
Parking
  • Garage: No
Taxes and HOA Information
  • Tax Year: 2025
  • Association: No
  • Annual Assoc Fee: $0
  • AssociationYN: No
  • Annual Taxes: $10,215
Virtual Tour
  • Virtual Tour YN: No
Property
Lot Information
  • Zoning: R
  • Tax ID: 96-23-0
  • Lot Size Source: Field Card
  • TopographyLot Desc:View: Scenic View(s)
  • Land Use: 10 - Multiple Use Property
  • Lot Size Square Feet: 10890
  • Sqft Total: 3548
  • Field Card SqFt: 671
  • Additional Finished Space: 2877
  • Lot Size Units: Acres
  • Living Area: 3549.0
  • General Property Info:Leased Land: No
Property and Assessments
  • Total Assessment: $1,637,100
  • Land Assessments: $631,000
  • Building Assessments: $885,600
  • Other Assessments: $120,500
  • Renovated: No
  • Flood Ins Required: Yes: verify w/insurance agent
  • Lead Base Paint: Unknown
  • Year Round: Yes
  • Landlord Pays:Sewer: Private Sewerage
  • Landlord Pays:Hot Water: Yes
  • Year Built Desc:Approximate: Yes
  • Property Type: Residential, Single Family Residence
  • Property Subtypes: Single Family Residence
  • Year Built Numeric: 1945
  • Construction Materials: Vinyl Siding
  • Property Type: Residential
  • Property Attached: No
  • Senior Community: No
Utilities
  • Cooling: None
  • Fuel Type:Oil: Yes
  • Hot Water:Tank: Yes
  • Sewer:Private Sewer: Yes
  • Water:Town Water: Yes
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Exterior Features: Private Yard, Garden
  • Private Dock: Yes
  • Private Dock Description: Deep Water, Electric, Floating, Platform
  • Foundation: Crawl Space, Block
  • Roof Description: Asphalt
  • Siding Description:Vinyl/Aluminum: Yes
  • Private Pool YN: No
Interior Features
  • Basement Description:Bulkhead Access: Yes
  • Basement Description:Partial: Yes
  • Floors: Wood, Tile
  • Heating: Oil
  • Basement: Yes
  • Fireplace: Yes
  • Sep Living Qtrs Info: Beds: 0
  • Total Rooms: 12
  • Baths Total: 7
  • Baths Full: 6
  • Baths Half: 1
  • Bedrooms Total: 7
  • Total Floor Plans Count: 0
  • RoomsTotal: 12
  • Bathrooms Total (Decimal): 6.50
  • Bathrooms Total (Notational): 6.10
  • Cooling: No
  • Heating: Yes
  • Stories: 2
  • General Property Info:Stories: 2
Living Room
  • Living Room:Fireplace: Wood Burning
Kitchen
  • Kitchen:Fireplace: Wood Burning
Rental
Rental Information
  • Owner Pays: Hot Water

Property History for 645 South Orleans Road

DateEvent & SourcePriceAppreciation
May 12, 2025

Listed (Active)

MLS PIN #73373131

$3,950,000—
May 12, 2025

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22502226

$3,950,000—
Mar 24, 2025

Expired

Cape Cod & Islands Multiple Listing Service #22404734

$2,995,000—
Sep 26, 2024

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22404734

$2,995,000—
DateEvent & SourcePrice
05/12/2025

Listed (Active)

MLS PIN #73373131

$3,950,000
05/12/2025

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22502226

$3,950,000
03/24/2025

Expired

Cape Cod & Islands Multiple Listing Service #22404734

$2,995,000
09/26/2024

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22404734

$2,995,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 645 South Orleans Road

Taxable ValueLand$631,000Additions$1,006,100Total$1,637,100
Tax Record2025$10,216 ($851 / month)
Home Facts
Baths1Total Finished SqFt1,154 SqFtAbove Grade Finished SqFt1,154 SqFtStories1Lot Size10,890 SqFtStyleMulti-Family Dwelling (2-4)Year Built1945Year Renovated1987ZoningRCountyBARNSTABLEAPNORLE M:096.0 B:0023 L:0000.0

Schools near 645 South Orleans Road

This home is within Orleans School District.
Rating
School
Type
Grades
Distance
Orleans Elementary School
Public - K to 5
Nauset Regional Middle School
Public - 6 to 8
Nauset Regional High School
Public - 9 to 12
Rating
School
Distance
Orleans Elementary School
PublicK to 5

Nauset Regional Middle School
Public6 to 8

Nauset Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 645 South Orleans Road, Orleans, MA 02653

645 South Orleans Road is a single family home for sale in Orleans, MA 02653. This property was listed for sale on May 12, 2025 by Berkshire Hathaway HomeServices Robert Paul Properties, it's currently listed at $3,495,000. This listing's school districts are Orleans School District, Nauset School District. Nearby schools include Orleans Elementary School, Nauset Regional Middle School and Nauset Regional High School. 645 South Orleans Road is a 7-bed, 7-bath, 3,548 sqft single family home built in 1945.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Berkshire Hathaway HomeServices Robert Paul Properties, Guthrie Schofield Group

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Compass includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. Neither the listing firm nor Compass shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.