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110 Quanset Rd, Orleans
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 73588050 MLS
With its distinctive proportions, inviting south-facing porch, and period detailing, this antique home has an unmistakable sense of character and presence. The L-shaped design and architectural details reflect the craftsmanship of another era, while later additions speak to the home's evolution over time. There is something especially appealing about a property that feels both rooted in its history and ready for its next chapter.Known as the Mayo Home, the property also reflects the area's longstanding connection to the water, including a sailing camp that once operated nearby. Set on generous grounds, the property offers a wonderful sense of space and privacy, with plenty of opportunity to enjoy both the land and the home's unique architectural character.Just beyond the property, Twinnings Pond Trail provides a nearby opportunity to explore the natural beauty of the area, while a public town landing just down the street offers convenient access to the water.A rare opportunity to own an antique home with architectural distinction, generous acreage, and a strong sense of place, this special property is ready to be thoughtfully enjoyed and carried forward for generations to come.

110 Quanset Rd, Orleans

Listing courtesy of Listing Agent: Hayley Nickerson from Listing Office: William Raveis Real Estate & Homes Services.
332 S Orleans Road, Orleans
$1,149,000
4 Beds ⋅ 3 Baths ⋅ 73491792 MLS
A local gem, this property invites you to embrace the quintessential Cape Cod lifestyle. Tucked back from the road, it features an expansive front yard, a detached barn, and a main house surrounded by a large private, level backyard--perfect for outdoor gatherings or exploring nearby conservation trails. Inside, sunlight floods through windows and skylights, illuminating beautiful wide-planked wood floors that radiate timeless charm. The kitchen opens to a cozy sitting area, ideal for conversations as meals are prepared, while the dining room with backyard views and slider access is made for entertaining. A spacious living room with a fireplace and adjacent bedroom and full bathroom offer comfort and convenience. Upstairs, there are two bedrooms, an office (via a back staircase), and a balcony that places you in a peaceful natural setting. Need more space? The newly constructed post-and-beam barn with garage offers potential guest accommodation. A separate shed provides extra storage.

332 S Orleans Road, Orleans

Listing courtesy of Listing Agent: Sandra Tanco from Listing Office: Kinlin Grover Compass.
645 S Orleans, Orleans
$2,700,000
7 Beds ⋅ 7 Baths ⋅ 73373131 MLS
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.

645 S Orleans, Orleans

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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