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Tony Guthrie
Tony Guthrie
Robert Paul Properties
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735 Bay Road

Duxbury, Massachusetts 02332, United States

5Bedroom(s)
6Bathroom(s)
71,438.40Sqft
$3,950,000

735 Bay Road

Duxbury, Massachusetts 02332, United States

5Bedroom(s)
6Bathroom(s)
71,438.40Sqft
Rooted in Duxburys maritime heritage yet designed for modern coastal living, this exceptional 5,073-square-foot estate pairs architectural elegance with resort-style amenities. Sited on 1.63 acres just two doors from the Bay Farm Trails, the five-bedroom, six-bath residence offers sweeping views of Duxbury Bay and the waters beyond.
$3,950,000

645 S Orleans Road

Orleans, Massachusetts 02653, United States

7Bedroom(s)
7Bathroom(s)
10,890Sqft
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.
$3,950,000

645 S Orleans Rd

Orleans, Massachusetts 02653, United States

7Bedroom(s)
7Bathroom(s)
10,890Sqft
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.
$3,950,000

645 S Orleans Rd #Main House

Orleans, Massachusetts 02653, United States

5Bedroom(s)
5Bathroom(s)
Topside is a rare offering in an iconic waterfront setting, showcasing unparalleled 270-degree vistas of Little Pleasant Bay. Designed with distinctive charm, the upper-level bunk room opens to a deck reminiscent of a ship, granting sweeping views across the water to Eastward Ho, Chatham Yacht Club, and the Atlantic beyond. This enchanting home features 5 bedrooms, 4.
$2,995,000

645 S Orleans Road

Orleans, Massachusetts 02653, United States

5Bedroom(s)
5Bathroom(s)
10,890Sqft
Topside is a rare offering in an iconic waterfront setting, showcasing unparalleled 270-degree vistas of Pleasant Bay. Designed with distinctive charm, the upper-level bunk room opens to a deck reminiscent of a ship, granting sweeping views across the water to Eastward Ho, Chatham Yacht Club, and the Atlantic beyond. This enchanting home features 5 bedrooms, 4.
$2,995,000

104 Seapine Road

Chatham, Massachusetts 02650, United States

3Bedroom(s)
3Bathroom(s)
19,166.40Sqft
With views of Crows Pond from every room, this North Chatham residence offers a front-row seat to one of the areas most coveted settings. Tucked within the exclusive Harbor Coves Association, it combines sweeping vistas with direct access to a private association beach just steps away. Built in 1999 by von Thaden Builders, the 3-bedroom, 2.
$2,750,000

104 Seapine Road

North Chatham, Massachusetts 02650, United States

3Bedroom(s)
3Bathroom(s)
19,166.40Sqft
With views of Crows Pond from every room, this North Chatham residence offers a front-row seat to one of the areas most coveted settings. Set within the exclusive Harbor Coves Association, this home combines sweeping water vistas with direct access to a private association beach just steps away. Built in 1999 by noted local firm von Thaden Builders, the 3-bedroom, 2.
$2,750,000

193 Quanset Road

Orleans, Massachusetts 02653, United States

4Bedroom(s)
3Bathroom(s)
54,450Sqft
Set along one of Orleans most scenic and protected saltwater corridors, this waterfront retreat captures the essence of coastal living - calm, connected, and deeply restorative. The setting is remarkably private, with elevated views, natural light, and direct access to the water for kayaking, paddleboarding, or launching into Pleasant Bay - one of Cape Cods premier boating destinations.
$2,699,999

193 Quanset Road

Orleans, Massachusetts 02653, United States

4Bedroom(s)
3Bathroom(s)
54,450Sqft
Set along one of Orleans most scenic and protected saltwater corridors, this waterfront retreat captures the essence of coastal living--calm, connected, and deeply restorative. The setting is remarkably private, with elevated views, stunning natural light, and direct access to the water for kayaking, paddleboarding, or launching into Pleasant Bay--one of Cape Cods premier boating destinations.
$2,699,999

25 Menekish Ln

Chatham, Massachusetts 02633, United States

4Bedroom(s)
4Bathroom(s)
22,215.60Sqft
Tucked away on a private lane in North Chatham, 25 Menekish Lane offers a rare blend of privacy and proximity just steps from Cow Yard Beach, Chatham Bars Inn, the Fish Pier, and Main Street. Built in 2006, the nearly 4,000 sq ft home blends timeless Cape charm with modern ease: soaring ceilings, abundant natural light, and a flowing floor plan ideal for entertaining.
$2,500,000

25 Menekish Lane

Chatham, Massachusetts 02633, United States

4Bedroom(s)
4Bathroom(s)
22,215.60Sqft
Tucked away on a private lane in North Chatham, 25 Menekish Lane offers a rare blend of seclusion and proximity--steps from Cow Yard Beach, Chatham Bars Inn, the Fish Pier, and Main Street.
$2,500,000
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