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Thomas Osborne acquired the property between 1650 and 1660 from Robert Bond, not long after arriving from Connecticut. He established a tannery that passed through six generations of Osborne tanners. William L.H. Osborn built the main structure in 1840. His son Burnett ran the hotel for over 32 years before retiring. The 1938 hurricane severely damaged the building when a tree crashed into the main structure. Reconstruction gave the porch its current sturdier appeal.<\/p>\n
The Swedish Interlude<\/h3>\n
Swedish-American hotelier Jenny Ljungberg purchased the property in 2008 and transformed it into a Scandinavian-centric oasis. Rooms were named after famous Nordic personalities: the Hans Christian Andersen room, the Eliel and Eero Saarinen studio, the Alfred Nobel cottage. Red bicycles became the hotel’s signature\u2014guests could be spotted pedaling throughout East Hampton. The restaurant served Swedish cuisine. Morning yoga appeared on the schedule. For sixteen years, The Maidstone cultivated a devoted following through this distinctly Northern European sensibility.<\/p>\n
Then came the sale. In April 2023, LDV Hospitality partnered with Irwin Simon and Mayank Dwivedi of ISMD to acquire the property for over $12 million. The new ownership promised something different: Italian luxury paired with the culinary excellence that made Scarpetta a three-star New York Times restaurant. The transformation took a year. The hotel reopened in June 2024 with an entirely new identity\u2014but the same bones that have anchored Main Street for nearly two centuries.<\/p>\n
The LDV Hospitality Vision<\/h2>\n
John Meadow founded LDV Hospitality in 2008 with the opening of Scarpetta, which quickly earned three stars from the New York Times and a James Beard Foundation “Best New Restaurant” nomination. The company name stands for “La Dolce Vita”\u2014the good life\u2014reflecting Meadow’s belief that every restaurant should channel joy and warmth. From Scarpetta’s flagship on Madison Avenue, LDV expanded to American Cut steakhouses, Dolce Italian, and restaurants spanning nine cities across five countries. System-wide sales exceeded $100 million in 2024.<\/p>\n
“It has always been a dream of mine to transition into the hotel space,” Meadow explains. “I’ve witnessed firsthand the allure and charm of The Maidstone Hotel, as it has been a beacon in the community for many years.” The acquisition represented LDV’s first full hotel operation\u2014a chance to extend the hospitality philosophy beyond restaurants into complete guest experiences.<\/p>\n
Designer Poonam Khanna’s Refresh<\/h3>\n
Designer Poonam Khanna of The Unionworks led the cosmetic refresh, aiming to honor the building’s history while introducing contemporary luxury. “Refreshed guest room interiors are rooted in a natural palette, reflecting the timeless beauty of the Hamptons\u2014earthy sand tones, warm amber and soft peaches that call to mind varying hues from the coastline,” she describes. “We want to honor its spirit and soul while adding a more contemporary and luxurious hospitality experience for East Hampton’s most discerning guests.”<\/p>\n
Guest hallways feature woven carpet runners and bold abstract paintings, evoking an art collector’s seaside home. Rotating exhibitions celebrate La Dolce Vita through September. The lobby renovation introduced board games and transportive elements. Retail space now houses curated selections from Giuliva Heritage, YOLO Journal, and WM Brown. Fashion pop-ups\u2014like this season’s S\u00e9zane shopping experience\u2014activate the hotel’s backyard throughout summer.<\/p>\n
The Restaurant Experience<\/h2>\n
Open year-round, the restaurant currently offers aperitivo, lunch, brunch, and dinner. Chef Jorge Espinoza\u2014who oversees operational excellence for The Maidstone, Scarpetta, and Dolce Italian within LDV’s portfolio\u2014crafted a menu evoking quintessential Italian charm while honoring the Hamptons’ coastal culture. Seasonal produce, local catch, and bold elevated ingredients define every dish.<\/p>\n Start with cocktails. The Maidstone Spritz combines Tanqueray Ten, St. Germain, Prosecco, and pink grapefruit for an elevated twist on a classic. The Lychee Sgroppino, with Ketel One and lychee pur\u00e9e, offers a sweet summer tribute. Zero-proof options like the Ginger Highball satisfy those seeking refreshment without alcohol. The bar itself invites lingering\u2014three fireplaces create intimate gathering spaces throughout the lounge.<\/p>\n The scallop crudo arrives as delicate slices layered with white asparagus vinaigrette and caviar. Charred zucchini salad features Castelrosso cheese and citrusy jus over grilled squash. Long Island oysters from nearby Peconic Bay anchor the raw bar alongside little necks, shrimp cocktail, octopus ceviche, and Alaskan king crab. Mouth-watering crudos demonstrate the kitchen’s reverence for pristine seafood.<\/p>\n Pasta follows Scarpetta’s philosophy: simple preparations executed flawlessly. The signature spaghetti\u2014fresh pasta made daily, enrobed in an emulsion of tomatoes, garlic, basil-infused olive oil, and a non-traditional touch of butter\u2014sells over 50,000 orders yearly at Scarpetta’s New York flagship alone. That same technique, that same reverence for fundamental Italian cuisine, now defines The Maidstone’s pasta program. Homemade pastas paired with seasonal ingredients showcase what devotion to craft can achieve.<\/p>\n The Maidstone’s reinvention reflects broader trends reshaping luxury hospitality. According to industry analysis<\/a>, boutique hotels are capturing travelers who seek unique experiences that chains cannot replicate. “Why waste a visit at a chain when you can develop a lifelong memory somewhere unique and fun\u2014and showcase it on social media?” observes one hospitality expert. In 2025, boutique hotels are solidifying their position as the preferred choice for travelers seeking originality, story, and soul.<\/p>\n The global boutique hotel market reached approximately $94 billion in 2024, with projections suggesting growth to $130 billion by 2029. This expansion reflects changing consumer preferences: travelers increasingly prioritize distinctive, personalized accommodations over standardized offerings. According to luxury hospitality research<\/a>, the sector promises a compound annual growth rate of 11.5% through 2032, with major investments flowing into properties that combine heritage with innovation.<\/p>\n Modern luxury emphasizes experiential and wellness-focused travel, with trends like “quiet luxury” prioritizing substance and sustainability. The Maidstone embodies this shift. Complimentary bikes allow guests to explore East Hampton at their own pace. The beach sits just five minutes away by cruiser. Daily breakfast, in-room GRD hair tools, and the outdoor lawn and patio create a complete experience beyond mere accommodation.<\/p>\n Designer pop-ups in the backyard\u2014like S\u00e9zane’s shopping experience\u2014blur the line between hotel stay and lifestyle curation. The retail space stocks carefully selected items that guests might actually want rather than generic hotel merchandise. This integration of shopping, dining, and lodging reflects hospitality’s evolution toward comprehensive lifestyle experiences rather than transactional overnight stays.<\/p>\n The Maidstone offers 16 guest quarters in the main house and three standalone cottages. Rooms embrace minimalist-meets-vintage style sensibility, creating cozy refinement that feels more like staying at a sophisticated friend’s guesthouse than a traditional hotel. Private cottages separate from the main building feature their own entrances, wood-burning fireplaces, and private bluestone patios.<\/p>\n The individualized d\u00e9cor means no two rooms feel identical. Spaces tend toward the smaller side, while suites offer seating areas and additional room. The overall effect suggests careful curation rather than mass production\u2014every piece of furniture, every artwork, every fabric selected for this specific space in this specific building. The antebellum Greek Revival architecture provides bones; the contemporary touches provide personality.<\/p>\n The Maidstone occupies 207 Main Street in East Hampton Village, directly across from South End Cemetery, which dates to the 1600s. Town Pond provides scenic views from certain rooms. East Hampton’s galleries, shops, theaters, and restaurants spread within a five-minute walk. The beach requires a 15-minute walk or five-minute drive. Sag Harbor sits 15 minutes away by car; Montauk takes 25 minutes; Southampton requires closer to 30.<\/p>\n The position near East Hampton’s center means guests access everything without needing cars. The Hampton Jitney stops nearby; the LIRR East Hampton station connects to Manhattan. This walkability distinguishes The Maidstone from more isolated Hamptons properties. You can stroll to dinner at the hotel restaurant, then wander to Main Street shopping, then return for nightcaps by the fireplace without ever searching for parking.<\/p>\n Chef Jorge Espinoza brings deep experience within LDV’s system to The Maidstone. His tenure at Scarpetta taught him the philosophy that defines LDV restaurants: treating simple ingredients with profound respect, executing fundamentals flawlessly, creating dishes that feel simultaneously humble and elevated. The famous spaghetti exemplifies this approach\u2014the most basic peasant dish transformed through technique and sourcing into something people travel across cities to taste.<\/p>\n Scarpetta’s spaghetti sells upward of 50,000 orders per year at the New York flagship alone. The dish earned legendary status through its commitment to freshness: pasta made daily, California plum tomatoes or quality substitutes, basil-garlic infused olive oil steeping until flavors concentrate, butter added at the end for luxurious texture. “That spaghetti personifies the restaurant and us as a group of people as a whole,” Meadow notes. “Simple, amplified, elegant, goodness.”<\/p>\n The Maidstone maintains a chef’s garden on the property, supplying herbs and vegetables to the kitchen during growing season. When the garden can’t provide, the kitchen sources organic ingredients from local producers\u2014the Hamptons’ agricultural heritage making farm-to-table sourcing practical rather than performative. Oysters come from nearby Peconic Bay. Fish arrives from local waters. The seasonal menu shifts with what’s actually available rather than what sounds marketable.<\/p>\n The wine cellar holds more than 300 bins from around the world. A resident sommelier assists with meal pairings, guiding guests through Italian selections that complement the cuisine’s regional specificity while offering global options for those seeking variety. The bar program extends beyond cocktails into craft beer and carefully curated spirits.<\/p>\n The restaurant at The Maidstone serves dinner Wednesday through Sunday from 5:30 PM. Weekend hours extend until 10 PM on Fridays and Saturdays; weeknights close at 9 PM. The bar operates Monday through Thursday and Sunday from 5 to 9 PM; Friday and Saturday service runs noon to 10 PM. Summer brings aperitivo and lunch service. Reservations are strongly recommended, particularly on weekends and during summer season.<\/p>\n The 52-seat dining room fills quickly. A relaxing bar and lounge with three fireplaces offers additional seating for those preferring informal atmosphere. The bright and airy sunroom overlooks Main Street, Town Pond, and the hotel grounds. The outdoor garden provides dining and lounge seating during warm months\u2014perhaps the most magical space, where string lights and landscaping create European ambiance under Hamptons skies.<\/p>\n The raw bar provides an excellent starting point\u2014Long Island oysters, octopus ceviche, the tower combining multiple preparations. Scallop crudo demonstrates the kitchen’s precision with raw seafood. For pasta, anything on the menu honors Scarpetta’s legacy, but the spaghetti with tomato and basil remains the signature experience. Entr\u00e9es feature grilled seasonal produce alongside sumptuous cuts of meat and fresh local catch.<\/p>\n The Maidstone Spritz makes an ideal aperitivo. Dessert shouldn’t be skipped\u2014the sticky toffee date cake earns particular praise. Sunday brunch offers an alternative entry point for those who can’t secure dinner reservations. The breakfast buffet\u2014smoked fish, ham, cheese, yogurt, fruit, butter croissants, coffee, juice\u2014can be enjoyed in the restaurant, adjacent lounge, garden, or light-soaked sunroom.<\/p>\n Italian restaurants proliferate across the Hamptons. Hotel restaurants, too, compete for attention. But few combine the pedigree of a major metropolitan restaurant group with the intimacy of a 19-room historic inn. The Maidstone exists in a category of one: a property whose restaurant could succeed anywhere, choosing to operate within a building whose history predates the Civil War.<\/p>\n The LDV acquisition brought resources and expertise that independent operations cannot match. Chef training follows Scarpetta standards. Service philosophy reflects decades of Manhattan hospitality refinement. Yet the setting remains genuinely intimate\u2014a dining room where regulars develop relationships with staff, where the owner’s vision translates directly into guest experience, where you feel welcomed rather than processed.<\/p>\n This balance defines what the Hamptons’ best restaurants should offer: world-class execution in settings that feel personal rather than corporate, ambitious cuisine in buildings that connect to actual history, experiences worth the premium prices without pretension that undermines enjoyment. The Maidstone achieves all of this, establishing itself as one of the East End’s essential dining destinations.<\/p>\n Feature Article Ideas \/ Advertising \/ Brand Partnership Inquiries<\/strong> Polo Hamptons Tickets, Cabanas & Brand Sponsorships<\/strong> Join Our Email List<\/strong> Social Life Magazine Print Subscription<\/strong> Support Our Work – Donate $5<\/strong> Best Hamptons Hotels 2026<\/a><\/p>\n![\"Breakfast](\"https:\/\/social-life-magazine.s3.amazonaws.com\/~sociall1\/wp-content\/uploads\/2025\/11\/28020505\/Screenshot-2025-11-28-020422.png\")
The Menu Philosophy<\/h3>\n
Understanding the Boutique Hotel Renaissance<\/h2>\n
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The Experience Economy<\/h3>\n
The 19 Rooms That Define Hamptons Elegance<\/h2>\n
Location Advantages<\/h3>\n
The Chef Behind the Vision<\/h2>\n
Farm-to-Table Commitment<\/h3>\n
Practical Information for Dining<\/h2>\n
What to Order<\/h3>\n
Why The Maidstone Matters to Hamptons Dining<\/h2>\n
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