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John Stringfellow

homes@capecodstar.com +1(508) 319-9101

$ 3,950,000

Est. payment -/mo

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645 S Orleans Road Orleans, MA 02653

7 Beds

7 Baths

3,548 SqFt

UPDATED:

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 3,548 sqft

Price per Sqft $1,113

MLS Listing ID 22502226

Bedrooms 7

Full Baths 6

Half Baths 1

HOA Y/N No

Abv Grd Liv Area 3,548

Originating Board Cape Cod & Islands API

Year Built 1945

Annual Tax Amount $10,215

Tax Year 2025

Lot Size 10,890 Sqft

Acres 0.25

Property Sub-Type Single Family Residence

Property 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 waterfront estate. 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 potential. Both homes enjoy sweeping 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 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 immense 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 waterfront settings.

Location

State MA

County Barnstable

Zoning R

Direction Use GPS - On South Orleans Road, property is on the right. Main house is on the right of property, boathouse to left.

Body of Water Little Pleasant Bay

Rooms

Basement Bulkhead Access, Partial, Crawl Space

Interior

Heating Hot Water

Cooling None

Flooring Wood, Tile

Fireplaces Type Wood Burning

Fireplace No

Appliance Electric Water Heater

Exterior

Exterior Feature Garden

View Y/N Yes

Water Access Desc Bay/Harbor

View Bay/Harbor

Roof Type Asphalt

Street Surface Paved

Garage No

Private Pool No

Building

Faces Use GPS - On South Orleans Road, property is on the right. Main house is on the right of property, boathouse to left.

Story 2

Foundation Block

Sewer Private Sewer

Level or Stories 2

New Construction No

Schools

Elementary Schools Nauset

Middle Schools Nauset

High Schools Nauset

School District Nauset

Others

Tax ID 96230

Special Listing Condition None

Listed by Berkshire Hathaway HomeServices Robert Paul Properties

+1(508) 319-9101

homes@capecodstar.com

Brewster, MA, 02631, USA