645 South Orleans Road

DJI_20240812115202_0062_D
DJI_20240812114659_0035_D
DJI_20240812114606_0033_D (1)
31
DJI_20240812120137_0128_D
DJI_20240812120006_0116_D
DJI_20240812115032_0049_D
33
2
6
7
8
9
10
11
12
13
14
15
16
17
21
23
22
18
19
20
20.1
20.2
24
25
36
9L4A6795
9L4A6798
9L4A6804
9L4A6816
9L4A6818
9L4A6822
9L4A6827
9L4A6830
9L4A6835
9L4A6839
9L4A6841
9L4A6847
9L4A6850
9L4A6854
27
28
29
35
37
38
3
DJI_20250701004157_0856_D
DJI_20250701004419_0861_D
DJI_20250701021554_0914_D
DJI_20250701004127_0854_D
Active
$2,700,000
7 beds3,548 sqft
645 S Orleans Rd, Orleans, MA 02653
Est: $15,309/moGet pre-approved
Single FamilyProperty Type
0.25 acresLot Size
1945Year Built
$761/sq ftPrice per sq ft

Description

For the first time in generations, this landmark Pleasant Bay compound--anchored by the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. 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. Both homes enjoy sweeping 270-degree views across the water to Eastward...For the first time in generations, this landmark Pleasant Bay compound--anchored by the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, generational waterfront estate, a site long cherished by those who have called it home. 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. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. Thoughtfully sited by its original architect to capture the light and water at every turn, ''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 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!
496 days on Market
  • Listed by: Guthrie Schofield Group • Berkshire Hathaway HomeServices Robert Paul Properties
Last updated: 07/21/2026 01:33 PM • Source: Cape Cod & Islands Multiple Listing Service, MLS#: 22502226

See It First™ on Compass

Find homes before they're listed on other real estate sites.

Start your search

Location

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

Payment Calculator

Get preapproved with Rocket Mortgage1

$15,309 per month

30 year fixed, 7.03% Interest

Principal and Interest

$14,414

Property Taxes

$895

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 645 South Orleans Road

Property Details
  • Taxes: $10,740 / year
  • MLS Type: Single Family / Single Family Residence
  • County: Barnstable County
  • 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
  • Town: Orleans
Building Information
  • Stories: 2
  • Year Built: 1945
  • Lot Size: 0.25 AC / 10,890 SF
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: 2026
  • Association: No
  • Annual Assoc Fee: $0
  • AssociationYN: No
  • Annual Taxes: $10,740
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: $1,757,800
  • Land Assessments: $681,500
  • Building Assessments: $955,700
  • Other Assessments: $120,600
  • 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)

Cape Cod & Islands Multiple Listing Service #22502226

$3,950,000—
May 12, 2025

Listed (Active)

MLS PIN #73373131

$3,950,000—
Mar 24, 2025

Expired

Cape Cod & Islands Multiple Listing Service #22404734

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

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22502226

$3,950,000
05/12/2025

Listed (Active)

MLS PIN #73373131

$3,950,000
03/24/2025

Expired

Cape Cod & Islands Multiple Listing Service #22404734

$2,995,000

For completeness, we 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.

Similar Homes

New listings in 02653

$499,000 | 45 West Road, Unit 4G, Orleans, MA 02653
1/50
New

$499,000

2
Bedrooms
2
Bathrooms
1,349
Square Feet

45 West Road, Unit 4G, Orleans, MA 02653

$1,149,000 | 3 Carver Road, Orleans, MA 02653
1/23
Listed By Compass

$1,149,000

2
Bedrooms
1
Bathrooms
1,080
Square Feet
0.29
Acres

3 Carver Road, Orleans, MA 02653

$326,000 | 190 Route 6A, Unit 4B, Orleans, MA 02653
1/33

$326,000

2
Bedrooms
1
Bathrooms
750
Square Feet

190 Route 6A, Unit 4B, Orleans, MA 02653

$1,050,000 | 27 Sturbridge Drive, Orleans, MA 02653
1/79

$1,050,000

4
Bedrooms
3
Bathrooms
2,076
Square Feet
0.65
Acres

27 Sturbridge Drive, Orleans, MA 02653

$3,650,000 | 18 Cole Place, Orleans, MA 02653
1/10

$3,650,000

4
Bedrooms
5
Bathrooms
3,746
Square Feet
0.46
Acres

18 Cole Place, Orleans, MA 02653

an aerial view of a house with swimming pool a yard and outdoor seating
1/65
Listed By Compass

$1,800,000

4
Bedrooms
3
Bathrooms
3,069
Square Feet
0.48
Acres

7 Hofe Road, Orleans, MA 02653

a living room with furniture and a fireplace
1/42

$1,175,000

3
Bedrooms
4
Bathrooms
1,840
Square Feet

5 Barley Neck Road, Orleans, MA 02653

$747,300 | 7 Carman Lane, Orleans, MA 02653
1/36
Virtual Tour

$747,300

3
Bedrooms
2
Bathrooms
2,005
Square Feet
1.28
Acres

7 Carman Lane, Orleans, MA 02653

$935,000 | 9 Wesquansett Road, Orleans, MA 02653
1/34

$935,000

4
Bedrooms
2
Bathrooms
1,972
Square Feet
0.52
Acres

9 Wesquansett Road, Orleans, MA 02653

Explore Nearby Homes

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 $2,700,000. 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 any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim 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 seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make 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 and its related brokerages 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 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.