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$1,775,000
3 Beds ⋅ 3 Baths ⋅ 73547863 MLS
Beautiful Waterviews: Experience the quintessential Cape Cod lifestyle in this beautifully renovated antique home, where timeless charm meets modern comfort. The updated kitchen and beautifully remodeled baths blend seamlessly with the home's original character, while stunning fir floors add warmth and elegance throughout. Enjoy picturesque views of sparkling, saltwater Paw Wah Pond and Pleasant Bay beyond. Designed for both relaxation and entertaining, the home features a spectacular great room perfect for gatherings, a welcoming front porch, and a private patio overlooking the natural surroundings. Set at the end of quiet Namequoit Road, this exceptional property is surrounded by conservation land and natural beauty, with trails leading to the beach steps away. Additional highlights include a detached one-car garage, storage shed, outdoor shower, fire pit, and the peaceful privacy that makes this a truly special Cape Cod retreat.

152 Namequoit, Orleans

Listing courtesy of Listing Agent: Leighton Team from Listing Office: Keller Williams Realty.
$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.
$4,999,000
4 Beds ⋅ 3 Baths ⋅ 73434698 MLS
Own a coveted East Orleans property with a private deep-water dock on a sprawling 2.62 acres, just 2.6 miles from Nauset Beach. This estate, surrounded by water, features rolling meadows and mature trees. The 3,867 sq ft residence blends timeless charm with modern comforts. Located on Lucy's Point Peninsula, it's perfect for a family compound or riverfront retreat. Inside, enjoy wide plank pine floors, decorative fireplaces, and historic moldings. The layout offers open spaces and privacy, with four bedrooms, three bathrooms, and diverse living areas. The primary ensuite is a private wing with a sitting area and walk-in closet. The kitchen setup is ideal for culinary creativity. Entertain or relax in the nostalgic ambiance. A newer roof, heating, and AC ensure comfort. Outdoors, a versatile barn/boathouse offers recreational possibilities. Whether seeking tranquility or lively gatherings, 66 Tides End Lane welcomes you with grace and beauty.

66 Tides End Ln, Orleans

Listing courtesy of Listing Agent: Cape Cod Power of Two from Listing Office: Compass.
$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: .

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