645 S Orleans Road, Orleans, MA 02653
What's special
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!
- 469 days |
- 1,934 |
- 69 |
Travel times
Aerial
Decks & Dock
Grounds
Main House | Foyer
Main House | Family Room
Main House | Dining Room
Main House | Kitchen
Main House | Living Room
Main House | Sunroom
Main House | Bedroom
Main House | Bedroom
Main House | Bedroom
Main House | Bedroom
Main House | Bunk Room
Boat House | Living Room
Boat House | Kitchen
Boat House | Bedroom
Boat House | Bedroom
Boat House | Workshop
Zillow last checked:
Listing updated:
Guthrie Schofield Group 774-487-8554,
Berkshire Hathaway HomeServices Robert Paul Properties
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 7
- Full bathrooms: 6
- 1/2 bathrooms: 1
Kitchen
- Description: Fireplace(s): Wood Burning
Living room
- Description: Fireplace(s): Wood Burning
Heating
- Hot Water
Cooling
- None
Appliances
- Included: Electric Water Heater
Features
- Flooring: Wood, Tile
- Basement: Bulkhead Access,Partial,Crawl Space
- Has fireplace: No
- Fireplace features: Wood Burning
Interior area
- Total structure area: 3,548
- Total interior livable area: 3,548 sqft
Property
Features
- Stories: 2
- Exterior features: Garden
- Has view: Yes
- Has water view: Yes
- Water view: Bay/Harbor
- On waterfront: Yes
- Body of water: Little Pleasant Bay
Lot
- Size: 0.25 Acres
Details
- Parcel number: 96230
- Zoning: R
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Antique
- Property subtype: Single Family Residence
Materials
- Foundation: Block
- Roof: Asphalt
Condition
- Approximate
- New construction: No
- Year built: 1945
Utilities & green energy
- Sewer: Private Sewer
Community & HOA
HOA
- Has HOA: No
Location
- Region: Orleans
Financial & listing details
- Price per square foot: $761/sqft
- Tax assessed value: $1,757,800
- Annual tax amount: $10,740
- Date on market: 5/12/2025
- Cumulative days on market: 635 days
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 3/23/2026 | Listed for sale | $2,700,000$761/sqft |
Source:  CCIMLS #22502226 Report a problem | ||
| 3/9/2026 | Pending sale | $2,700,000$761/sqft |
Source: CCIMLS #22502226 Report a problem | ||
| 1/31/2026 | Price change | $2,700,000-22.7%$761/sqft |
Source: CCIMLS #22502226 Report a problem | ||
| 9/4/2025 | Price change | $3,495,000-11.5%$985/sqft |
Source: CCIMLS #22502226 Report a problem | ||
| 5/12/2025 | Listed for sale | $3,950,000+31.9%$1,113/sqft |
Source: CCIMLS #22502226 Report a problem | ||
| 3/25/2025 | Listing removed | $2,995,000$844/sqft |
Source: MLS PIN #73295426 Report a problem | ||
| 9/26/2024 | Listed for sale | $2,995,000$844/sqft |
Source: MLS PIN #73295426 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,216 +2.7% | $1,637,100 +5.5% |
| 2024 | $9,950 +10% | $1,552,300 +6.9% |
| 2023 | $9,047 +10.9% | $1,452,200 +39.5% |
| 2022 | $8,159 | $1,040,700 |
| 2021 | $8,159 +4.6% | $1,040,700 +0.9% |
| 2020 | $7,797 +1% | $1,031,400 -1.1% |
| 2019 | $7,720 +14.7% | $1,043,200 +2.8% |
| 2018 | $6,730 +6.8% | $1,015,100 +2% |
| 2017 | $6,302 -14.1% | $995,600 -12.3% |
| 2016 | $7,336 +2.8% | $1,135,600 +2.1% |
| 2015 | $7,138 +3.5% | $1,111,900 |
| 2014 | $6,894 +1.6% | $1,111,900 |
| 2013 | $6,783 +3.8% | $1,111,900 +0.5% |
| 2012 | $6,536 +6.1% | $1,106,000 |
| 2011 | $6,160 +2.8% | $1,106,000 -4.9% |
| 2010 | $5,992 +4.7% | $1,163,500 -0.8% |
| 2009 | $5,722 +9.9% | $1,172,600 +1.8% |
| 2008 | $5,207 +10.7% | $1,152,100 +4.6% |
| 2007 | $4,703 -0.9% | $1,101,400 -3.5% |
| 2006 | $4,748 +15.7% | $1,141,300 +22.1% |
| 2005 | $4,104 -6.5% | $934,900 -6.1% |
| 2004 | $4,391 +9.7% | $995,700 +27.4% |
| 2003 | $4,001 +3.7% | $781,500 +32.4% |
| 2001 | $3,859 | $590,100 |
Find assessor info on the county website
Monthly payment
Estimated market value
Not available
Estimated sales range
Not available
$5,448/mo
Climate risks
Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.