645 S Orleans, Orleans MA 02653
Orleans, MA 02653
$3,950,000
$2,700,000
Est. $14,748/month
About this home
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 to own one of Cape Cod's most storied, landmark waterfront settings.
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Property History
Market Insights
1
Price Changes
22.7%
Price Range
Property Timeline
Back On Market
Mar 23, 2026
Active
Pending Sale
Mar 8, 2026
Offer accepted, sale pending
Price Reduced
Jan 31, 2026
$2,700,000
$795,000
(-22.75%)
From $3,495,000 to $2,700,000 (-22.8%)
Listed for Sale
May 12, 2025
$3,495,000
Original listing
Agent: Guthrie Schofield Group
Office: Berkshire Hathaway HomeServices Robert Paul Properties
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 03/23/2026 | • Back On Market | - | - | - | Active |
| 03/08/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 01/31/2026 | ↓ Price Reduced | $2,700,000 | $795,000 | - | From $3,495,000 to $2,700,000 (-22.8%) |
| 05/12/2025 | 🏠 Listed for Sale | $3,495,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $10,740 | $1,757,800 |
Financial Details
Annual Property Tax
$10,740
Tax Year 2026
Assessed Value
$1,757,800
Facts & Features
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
1930
Living Area
3,549 sq ft
Lot Size
0.25 acres
Bedrooms
7
Full Baths
6
Half Baths
1
Total Rooms
12
Interior
Heating
Baseboard
Cooling
Window Unit(s)
Flooring
None
Appliances
None
Fireplace
None
Fireplaces
2
Basement
None
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Antique
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Features
None
Total Spaces
4
Utilities
Electric
None
Water
Public
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$10,740
Assessed Value
$1,757,800
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Barnstable
Total market time (incl. prior listings)
421 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1930
Bedrooms
7
Full Bathrooms
6
Half Bathrooms
1
Living Area
3,549 sq ft
Total Rooms
12
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,549 sq ft above grade
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Interior Features:
Windows:
Basement:
Laundry:
Security:
Construction & Materials
Style:
Antique
Year Built:
1930
Structure Type:
Exterior Materials:
Roof:
Foundation:
Block
Heating, Cooling & Utilities
Heating:
Baseboard
Cooling:
Window Unit(s)
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Road Surface:
Parking & Garage
Total Parking Spaces:
4
Parking Features:
Special Features
Fireplaces:
2
Fireplace Type:
Waterfront:
Yes
Waterfront Type:
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
View:
Yes
View Type:
Scenic View(s)
Community Amenities:
Nearby Schools
School District
Nauset School District local
B
School Safety
2024-25
4.1%
Above Average
4.1%
Suspensions
0.7%
In-School
1.4% below state avg
Elementary Schools
3 schools
The Laurel School
3.1 mi
Grades PK-05
Cape Cod Christian Academy
3.1 mi
Grades K-08
A+
Orleans Elementary School
3.4 mi
|
#65 of 824
|
Score: 61.4
Improved 140 spots from last year
+3.2 above state avg
149 students
Moderate
Rising School
Grades K-05
Middle Schools
3 schools
B-
Cape Cod Lighthouse Charter School
2.3 mi
|
#190 of 352
|
Score: 41.4
Improved 90 spots from last year
-16.8 below state avg
251 students
Less Diverse
Rising School
Grades 06-08
B+
Monomoy Regional Middle School
2.8 mi
|
#117 of 352
|
Score: 47.5
Dropped 36 spots from last year
-10.7 below state avg
395 students
Moderate
Grades 05-07
B+
Nauset Regional Middle School
4.2 mi
|
#130 of 352
|
Score: 46.3
Dropped 13 spots from last year
-11.9 below state avg
455 students
Moderate
Grades 06-08
High Schools
2 schools
B+
Cape Cod Regional Vocational Technical High School
4.5 mi
|
#116 of 346
|
Score: 59.1
Same rank as last year
+0.9 above state avg
682 students
Moderate
15 sports
• 956 athletes
High Graduation Rate
Career Tech Programs
College Ready Curriculum
Strong Athletics
Grades 09-12
B-
Monomoy Regional High School
4.7 mi
|
#205 of 346
|
Score: 51.2
Dropped 30 spots from last year
-7 below state avg
738 students
Moderate
17 sports
• 1,050 athletes
College Ready Curriculum
Strong Athletics
Grades 08-12
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Monthly Payment Breakdown
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Property Tax
$895
Homeowners Insurance
$200
PMI (if <20% down)
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Loan Summary
Total of 360 payments
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
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Location
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Neighborhood
645 S Orleans, Orleans MA 02653
Orleans, MA 02653
Listing Information
Listing Agent
Guthrie Schofield Group
Listing Office
Berkshire Hathaway HomeServices Robert Paul Properties
Office Phone
508-945-5553
Agent MLS ID
TM359164
Office MLS ID
AN6519
Listing Data Updated
Jul 21, 2026 1:50 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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