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Discover Low-Key Luxury at The Roundtree:
Your Serene Escape in the Hamptons


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In the world of exclusive getaways, where opulence often takes center stage, finding a place of understated elegance and tranquility can be a true rarity. Nestled within the charming hamlet of Amagansett, between the bustling East Hampton and iconic Montauk, lies The Roundtree—a hidden gem just a two-and-a-half-hour drive from the vibrant heart of New York City. With only 13 meticulously designed rooms and an idyllic setting on two acres of beautifully landscaped grounds, The Roundtree offers a retreat that redefines luxury in the Hamptons.

The property seamlessly embodies the classic Hamptons charm, with shingle-style exteriors, hydrangea-lined walkways, and a design that pays homage to Amagansett’s agricultural heritage—a heritage to which this property itself once belonged, as a working farm.

At the heart of The Roundtree is the sprawling and immaculately manicured Great Lawn, adorned with white umbrellas, plush sun loungers, and an array of lawn games, including the ever-popular cornhole. As the sun sets, guests gather around a cozy fire pit for nightcaps and stargazing, forging a sense of community that truly makes you feel like an Amagansett resident, even if it’s just for a night, a week, or however long your stay.

Amagansett, with its small main street and limited number of shops and restaurants, offers a refreshingly quaint alternative to its bustling neighbors, East Hampton and Southampton. Here, you can leisurely explore local favorites like Amber Waves, a combination farm market and café, savor delectable meals at Il Buco al Mare, and enjoy live performances at the old-school music venue, Talkhouse. The Roundtree’s resident Experiences Director creates bespoke excursions for guests, such as private beach bonfires and guided tours, ensuring an immersive experience of this charming hamlet.

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The Roundtree boasts an impressive array of accommodation options. From eight rooms and suites housed within a beautifully restored 100-year-old barn to five freestanding cottages and two multi-bedroom houses, there’s something for everyone. The ultra-private Beach House, just a five-minute drive from the property and minutes from the beach, offers a sublime retreat for families and groups of friends. Each room has its own entrance, enhancing the sense of privacy that defines The Roundtree.

Step inside, and you’ll feel like you’ve entered the pages of a stylish magazine. The interiors exude understated refinement with a natural color palette and sleek furnishings. Wide-plank hardwood floors pay homage to the property’s heritage, while the in-room amenities cater to contemporary tastes, featuring Grown Alchemist bath products, Frette linens, Nespresso machines, and complimentary minibars stocked with local delights, such as Tom’s Perfect 10 granola and South Fork Bakery brownies.

At The Roundtree, serenity takes precedence over spectacle. Many guests prefer to unwind by their cottage or on the Great Lawn, enveloped in a peacefully congenial atmosphere. Complimentary pastries and cookies, along with an indulgent ice cream happy hour, cater to both young and older guests. In the summer, guests receive beach passes to the beautiful Amagansett Beach, while fall and winter offer opportunities for private tours of LongHouse Reserve, hikes in Montauk’s walking dunes, and visits to Jackson Pollock’s East Hampton home and studio.

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Checking in at The Roundtree feels like staying with that effortlessly stylish friend who knows all the seasonal hotspots but prefers the simple pleasures of life. Enjoy a serene afternoon of reading in the shade of a maple tree, embark on a leisurely bike ride culminating in a private beach excursion, indulge in a late-afternoon in-room massage followed by a glass of local Wölffer Estate Vineyard rosé, and cap off your evening by a flickering fire pit, complete with S’mores and awe-inspiring stargazing.

The Roundtree goes above and beyond to cater to its youngest guests by arranging a Lemonade Stand on Main Street, with all proceeds benefiting the Animal Rescue Fund (ARF) of the Hamptons. And for those who can’t bear to part with their four-legged friends, The Roundtree is a pet-friendly haven that welcomes your furry companions with open arms.

Located just a few miles from The Roundtree and minutes from Amagansett Beach, The Beach House stands out as the largest accommodation on offer. With four bedrooms and an open-floorplan layout, it’s a favorite among families and groups of friends. The property, once the residence of Tony-winning playwright Neil Simon, boasts a full kitchen, a gas fireplace, a dining area, a spacious living room, and a sizable backyard for BBQs and the quintessential Hamptons outdoor shower experience.

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For special events, The Roundtree can host weddings and other celebrations for up to 250 guests, requiring a full takeover of the property to ensure an exclusive and unforgettable experience.

Escape to The Roundtree in Amagansett, where low-key luxury and timeless elegance converge in a serene setting that beckons you to savor life’s simple pleasures. Rates start at $495 in the quieter seasons, making this luxurious retreat an attainable oasis in the heart of the Hamptons.

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