Fifteen Rooms on Land That Has Been Occupied Since the 1600s

On Main Street in Amagansett, a wood-shingled building sits on two manicured acres with the quiet authority of a place that knows it was here first. The property dates to the 1600s, when one of the hamlet’s original founding families settled the land. Today it is the Roundtree Amagansett, a 15-room boutique hotel that opened in June 2020 (during a global pandemic, which is either the worst or the best timing in hospitality history, depending on your philosophy of risk). Sylvia Wong, the hotel’s owner and creator, would likely argue it was the best. She would be right.

The Roundtree represents a new model of Hamptons hospitality, one that is closer to what Aman does in Bali than what the traditional East End hotel has ever attempted. Fifteen rooms. Five standalone cottages (one over 250 years old). Matouk towels. Frette sheets. Commissioned artwork throughout. Bicycle rentals. A daily manager’s reception. Continental breakfast included. The design language is quiet luxury in the most literal sense: everything signals taste, nothing signals volume. For the West Village couple who books Aman Tokyo for their anniversary and wants something comparable within driving distance of Manhattan, the Roundtree is the answer they didn’t know existed.

Sylvia Wong: From Paul Weiss to Pillow Menus

The Roundtree’s origin story begins not in hospitality but in corporate law. Sylvia Wong started her career at Paul, Weiss, Rifkind, Wharton & Garrison, one of New York’s most prestigious law firms, specializing in mergers and acquisitions, financing, and corporate transactions. Subsequently, she moved to IBM, where she eventually led the global ethics and compliance program for the company’s 380,000 employees across 175 countries. From 2009 to 2012, she served as General Counsel of IBM’s Growth Markets Unit, a $20 billion business spanning Asia, Latin America, Russia, Eastern Europe, the Middle East, and Africa.

The Pivot to Hospitality

Wong’s transition from corporate law to hotel ownership was driven by a lifetime of travel. After decades of staying in hotels around the world, she developed a specific vision for what a small luxury property could be. In 2019, she acquired the former Gansett Green Manor, a stalwart wedding venue on Main Street in Amagansett, for $6.175 million. The property sat on a serene two-acre farmstead that dated to the 1600s, when one of the first four European families to settle Amagansett made their home there. Wong saw what others had missed: not a tired wedding venue, but the bones of a boutique hotel with 300 years of soul already built in.

After six months of renovations, the Roundtree opened its doors on June 1, 2020. On opening night, there was not a single reservation. Nobody was traveling. The pandemic had shuttered the hospitality industry worldwide. Still, Wong opened anyway. However, within weeks the logic of her timing became clear. Wealthy New Yorkers, fleeing the city for the Hamptons in unprecedented numbers, desperately needed places to stay. A boutique hotel with acres of outdoor space, private cottages, and no crowding was exactly what the moment demanded. By summer’s end, the Roundtree was fully booked.

The Property: What Fifteen Rooms Looks Like

The Roundtree occupies two acres on Main Street, steps from Amagansett Square, a ten-minute walk from the beach, and within strolling distance of every restaurant in the hamlet. The main house is a shingle-style structure close to 125 years old, containing eight guest rooms. Five standalone cottages, including one constructed over 250 years ago, are scattered across the grounds. A restored 100-year-old barn anchors the property’s communal spaces.

The Design Philosophy

Wong’s approach to design was guided by a single principle: the hotel should feel like a sophisticated extension of home. Modern furnishings blend with natural materials. Commissioned artwork populates the walls rather than generic prints. Bespoke amenities (Matouk towels, Frette sheets) replace the anonymous white linens of chain hotels. The grounds feature hydrangea-lined gravel paths, lush gardens, and enough green space to make the property feel significantly larger than its two acres. Certainly, there is no lobby in the conventional sense. Instead, guests arrive to a gravel driveway and a building that looks, from the sidewalk, like a beautiful family home. That resemblance is intentional. Wong designed the Roundtree to feel like arriving at a friend’s country house, not checking into a hotel.

For the Tribeca design consultant who has stayed at Soho House properties around the world and finds them increasingly predictable, the Roundtree registers as something different. It is not a brand. It is a place. The distinction matters in hospitality the way it matters in restaurants: a place has a soul, and a brand has a manual. Wong built a place.

The Roundtree in Context: Amagansett’s Hotel Scarcity

One of the Roundtree’s greatest assets is also one of Amagansett’s most defining features: the near-total absence of hotel inventory. Southampton has multiple hotel options. Sag Harbor has Baron’s Cove and the American Hotel. Bridgehampton has Topping Rose House. East Hampton Village has a handful of inns. Amagansett, by contrast, has the Roundtree, the Sea Crest Resort (a beachfront motel), the Windward Shores, and the Reform Club (a newer addition with suites and cottages). Altogether, that is essentially the entire inventory for a hamlet that draws thousands of visitors every summer.

Scarcity as Strategy

This scarcity is not a market failure. It is a feature. Amagansett’s lack of hotels means that most visitors are renters, and the rental market creates a different kind of visitor than the hotel market does. Specifically, renters unpack. They shop at Amber Waves, learn the coffee line at Jack’s Stir Brew, and develop routines. After two or three rental summers, many transition from visitor to buyer. The rental-to-purchase pipeline is real, and it is one of the primary engines of Amagansett’s real estate market.

The Roundtree occupies a unique position within this landscape. It serves the visitor who hasn’t yet committed to a rental (perhaps they’re testing the hamlet for the first time) and the visitor who has aged out of rental logistics (they want someone else to make the bed). In either case, the Roundtree functions as a gateway. A weekend at Wong’s hotel is frequently the first chapter in a longer Amagansett story. Indeed, real estate brokers in the hamlet have learned to treat Roundtree guests as pre-qualified leads.

The Nolita brand strategist books the Roundtree for a weekend in late May.
She has never been to Amagansett. East Hampton six times, but never here.
Arrival is Friday at 4 p.m. Gravel driveway. Hydrangeas. A building that looks like a house.
Saturday: the beach, Il Buco al Mare, Amber Waves.
Sunday: rental listings for July.
The following March: purchase listings for everything.
The Roundtree didn’t sell her Amagansett. It introduced them.
Introductions, when done correctly, are permanent.

The Competitive Landscape: Roundtree vs the Hamptons Hotel Market

In the broader Hamptons hotel market, the Roundtree occupies a lane that barely existed before Wong created it. Topping Rose House in Bridgehampton operates as a full-service luxury hotel with a Jean-Georges restaurant, a spa, and event programming. Baron’s Cove in Sag Harbor offers waterfront rooms with marina views and a social atmosphere. The Baker House 1650 in East Hampton provides historic bed-and-breakfast charm. Certainly, each is excellent. None is what the Roundtree is.

The Boutique Difference

What separates the Roundtree is scale and intent. Fifteen rooms means the hotel never feels crowded. The grounds are large enough that guests can find solitude on the property itself. There is no restaurant competing for attention (Wong directs guests to Amagansett’s own dining scene, which is, as our restaurant guide details, more than sufficient). There is no spa generating foot traffic. Instead, the Roundtree offers spa services on request, delivered in the privacy of your room or cottage. The model is subtraction rather than addition: Wong removed everything a luxury hotel doesn’t strictly need and kept everything it does.

Compare that philosophy to the trend in Hamptons hospitality, which generally favors more: more restaurants, more programming, more amenities, more reasons for guests to spend money on-property. The Roundtree’s approach assumes the opposite. It assumes the guest is here for Amagansett, not for the hotel. Consequently, the hotel’s job is to make Amagansett more accessible, not to compete with it. This is an unusually confident bet for a hospitality business, and it has paid off. The Roundtree has won multiple awards and earned coverage in publications from Avenue Magazine to Fodor’s to Indagare.

Practical Information

The Roundtree is located on Main Street in Amagansett, steps from Amagansett Square. Naturally, rates vary by season. Peak summer weekends (late June through Labor Day) command premium pricing consistent with the boutique luxury category. Shoulder season (May, September, October) offers more availability and lower rates, and many Amagansett regulars argue the shoulder months are the best time to visit. Amenities include complimentary continental breakfast, free Wi-Fi, bicycle rentals, beach umbrellas and towels, a daily manager’s reception, and self-parking. The hotel is pet-friendly. Reservations can be made at theroundtreehotels.com.

For the person deciding between the Roundtree and a rental, the calculation is straightforward. If you want to test Amagansett without committing to a full summer rental, the Roundtree is your entry point. If you want the hotel experience without the hotel scale, the Roundtree is your permanent answer. Either way, you’re sleeping on land that has been occupied since the 1600s. Few hotels in America can make that claim. Fewer still make it this quietly.

Where the Conversation Continues

Social Life Magazine has covered Hamptons hospitality for 23 years. Five summer issues, 25,000 copies each, distributed in the hotels, restaurants, and shops from Westhampton to Montauk. When a new hotel opens on the East End, we’re the publication that places it in context.

If your hospitality brand serves the Amagansett visitor (boutique hotels, luxury rentals, design, wellness, concierge services), a feature in Social Life Magazine puts you at the point of arrival. Learn more at sociallifemagazine.com/submit-a-paid-feature.

Polo Hamptons 2026 returns to Bridgehampton on July 18 and July 25. BMW North America sponsors. Christie Brinkley hosts. Reservations at polohamptons.com.

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The Roundtree has 15 rooms on land from the 1600s. Sylvia Wong opened it during a pandemic with zero reservations. Sometimes the quietest bets are the ones that compound.