645 S Orleans, Orleans, MA 02653
Barnstable County
Key Facts
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 estate. With a deep-water dock, moorings, and direct bay access, it delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy 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 charm and inviting gathering spaces. The "Boathouse," perched just above the shoreline, features 2 bedrooms, 1 bath, and a private deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn complete the experience. With strong rental history and exceptional potential for personalization or expansion, this lifestyle property invites multigenerational enjoyment, investment, or retreat—an iconic opportunity in one of Cape Cod’s most storied settings.
Property Information
Property Type
Residential
Sub-Type
Single Family Residence
Style
Antique
Year Built
1930
Living Area
3,549 sq ft
Lot Size
0.25 acres
Parking Spaces
4
Zoning
96-23-0
Days on Market
355
MLS® Listing#
73373131
Property Features
Cooling
Heating
Lot Features
Foundation
Sewer
Water Source
Financial Details
HOA
None
Annual Taxes
$10,740
Tax year 2026
Assessed Value
$1,757,800
Parcel Number
2365906
Directions
On S Orleans Road, heading North, turn right. Main House is on the right of driveway.
Affordability Calculator
$540,000
Estimated monthly payment
$14,371/mo
Principal $2,160,000 · Est. interest $3,013,392 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in Orleans, MA
- $1,000,000
- Median Listing Price
- 86
- Median Days on Market
- 2,432
- Median Sq Ft
- $622
- Median Price / Sq Ft
- 56
- Active Listings
- This home’s price is 170% above the area median.
- Its price per sq ft is 22% above the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in Orleans, MA.
Location
Points of Interest in Orleans, MA
Showing the Orleans area map.
Nearby Schools
Cape Cod Lighthouse Charter School
Secondary · 2.2 mi away
A Child's Wonderland
School · 2.5 mi away
Chatham High School
Secondary · 2.8 mi away
The Laurel School
Elementary · 3.1 mi away
Cape Cod Lighthouse Charter School
School · 3.2 mi away
Rocking Unicorn
Elementary · 3.3 mi away
Nauset Public Schools
School · 3.4 mi away
Orleans Elementary
Elementary · 3.4 mi away
Chatham Elementary School
Elementary · 3.5 mi away
Nauset Regional Middle School
Secondary · 3.6 mi away
Stony Brook Elementary School
Elementary · 4.3 mi away
Eddy Elementary
Elementary · 4.5 mi away
Cape Cod Region Vocational Technical
Secondary · 4.6 mi away
Monomoy Regional High School
Secondary · 4.9 mi away
Harwichport Tennis Association
School · 5.7 mi away
Harwich Elementary School
Elementary · 5.8 mi away
Harwich Middle School
Elementary · 5.8 mi away
Penny Lane Day School
School · 6.2 mi away
Holy Trinity School
School · 7.1 mi away
Eastham Elementary
Elementary · 7.6 mi away
Commute Calculator
Nearby Homes
Similar Homes Nearby
Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 88 Route 6a, Orleans, MA | $1,900,000 | 6 | 7 | 3,843 |
| 88 Route 6A, Orleans, MA | $1,900,000 | 6 | 7 | 3,843 |
| 645 S Orleans Road, Orleans, MA | $2,700,000 | 7 | 7 | 3,548 |
| 17 Gosnold Road, Orleans, MA | $3,495,000 | 6 | 5 | 3,820 |
| 17 Gosnold Road, Orleans, MA | $3,495,000 | 6 | 5 | 3,820 |
Moving Cost Estimate
EXIT Agents in Orleans
Listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties - 5089455553
Presented by: Guthrie Schofield Group