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Sheena Ruggirello

sheena.ruggirellos@gmail.com +1(860) 222-4734

$2,700,000

Est. payment - /mo

7 Beds

6.5 Baths

3,549 SqFt

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UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 3,549 sqft

Price per Sqft $760

MLS Listing ID 73373131

Style Antique

Bedrooms 7

Full Baths 6

Half Baths 1

HOA Y/N false

Year Built 1930

Annual Tax Amount $10,740

Tax Year 2026

Lot Size 10,890 Sqft

Acres 0.25

Property Sub-Type Single Family Residence

Property 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 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.

Location

State MA

County Barnstable

Zoning 96-23-0

Direction On S Orleans Road, heading North, turn right. Main House is on the right of driveway.

Interior

Heating Baseboard

Cooling Window Unit(s)

Fireplaces Number 2

Exterior

Waterfront Description 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 Y/N Yes

View Scenic View(s)

Total Parking Spaces 4

Garage No

Building

Foundation Block

Sewer Private Sewer

Water Public

Architectural Style Antique

Others

Senior Community false

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Listed by Berkshire Hathaway HomeServices Robert Paul Properties

Nearby School & Business

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Sheena Ruggirello

+1(860) 222-4734

Agent | License ID: CN234452

Agent License ID: CN234452

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645 S Orleans Orleans, MA 02653

Sheena Ruggirello

Key Details

Location

Interior

Exterior

Building

Others

Nearby School & Business

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