About This Home

This 7-bedroom, 7-bathroom single family at 645 S Orleans Road in Orleans, MA is listed for $2,700,000 ($761 per sqft). Built in 1945, the home offers 3,548 sqft of living space on a 0.25 acres lot.

Key Features

  • Built in 1945
  • 0.25 acre lot
  • 2 stories
  • Waterfront

Property Details

2 stories
6 full, 1 half
1945

Amenities

WaterfrontView
Listing 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.

Monthly Cost Estimate

$14,440/mo

20% down · 6.5% · 30 years

Principal$1,953
Interest$11,700
Insurance$788

Estimates only. Actual payments may vary.

Location

645 S Orleans Road

Orleans, MA 02653

Features & Amenities

Exterior Features

Private YardGarden

Property Details

Flooring

TileWood

Construction

Vinyl Siding

Views

Harbor

Heating

Oil

Appliances

Water Heater

Questions & Answers

This 7-bedroom, 7-bathroom single family at 645 S Orleans Road is listed at $2,700,000 ($761/sqft). The estimated monthly payment is $14,441 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1945, 0.25 acre lot, 2 stories, Waterfront. Exterior Features: Private Yard, Garden.

This property is listed by Guthrie Schofield Group and can be reached at 7744878554.

GG

Guthrie Schofield Group

Agent at Berkshire Hathaway HomeServices Robert Paul Properties

(774) 487-8554

Listed by Berkshire Hathaway HomeServices Robert Paul Properties · View on Broker Site

MLS# 22502226· Source: listhub· 417 days on market

Copyright © 2026 Cape Cod & Islands Association of REALTORS®, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

645 S Orleans Road, Orleans, MA 02653

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