Luxury Homes In Long Island

$16,750,000
5 Beds 6 Baths 1023552 MLS
Robinwood is one of Millbrook’s distinguished country estates, where timeless architecture, exceptional craftsmanship, and breathtaking natural beauty come together across 90+ magnificent acres. Built in 1935, the estate has been entrusted to just two families. The first created and preserved its historic grandeur and the second lovingly and meticulously restored it with an exquisite eye to every detail. The result is a home of remarkable character that honors its heritage while offering every convenience. Robinwood is a profoundly private world all its own while also just minutes from the village. Spacious, light-filled rooms harmoniously flow one to the next. French doors throughout the main level offer a seamless connection between the elegant interiors and the landscape. A gracious gallery hall extends from the front entrance through the heart of the home. Every element has been thoughtfully considered, including brass radiator fittings, an exquisitely carved library mantel, and finely crafted millwork throughout the home. Designed for both grand entertaining and comfortable daily living, the residence offers formal living and dining rooms, a richly wood-paneled music room, and a soaring sunroom with three walls of windows. The gracious eat-in kitchen with its adjoining butler’s pantry is as functional as it is beautiful. The main residence offers five generously proportioned en suite bedrooms, including a magnificent primary suite with a private sitting room, dressing room, and fireplace. Robinwood is designed as a true compound. Two separate guest houses, each with a full kitchen and bath, provide exceptional accommodations for guests or staff. A private office suite with its own kitchen and bath, additional guest accommodations, and a spacious game room further enhance the estate’s versatility for entertaining, multigenerational living, or working from home. The magnificent grounds are as thoughtfully composed as the residence itself. A wraparound bluestone terrace captures sweeping Catskill views, while the pool house opens fully on one side, creating an effortless indoor-outdoor entertaining experience. Beautifully curated gardens, rolling lawns, multiple barns and outbuildings, an outdoor riding ring, and a three-stall stable with tack room complete an exceptional country property equally suited for equestrian pursuits, recreation, or quiet retreat. Robinwood is a rare legacy estate whose beauty, craftsmanship, and extraordinary setting will endure for generations to come.

482 Overlook Road, Millbrook

$21,000,000
5 Beds 7 Baths 1040841 MLS
There are beautiful homes in the Hudson Valley, and then there are properties that seem to occupy a world entirely their own. Set at one of the most extraordinary vantage points in the region, this exceptional contemporary estate presides over 135 private acres with sweeping, unobstructed views across the Hudson Valley to the Catskill Mountains. The sense of scale is remarkable: open sky, rolling land, distant mountains, and complete privacy in every direction—yet Hudson and Great Barrington are each only 25 minutes away. The residence was designed around this landscape; dramatic walls of glass frame the Catskills throughout the house, while soaring ceilings and expansive, open living spaces give the interiors a sense of volume without sacrificing warmth. Living, dining, and kitchen spaces unfold effortlessly toward the terrace and infinity pool, where the water appears to disappear into the mountains beyond. The entire home lives on a single level, an increasingly rare luxury at this scale. Two primary suites and three additional ensuite bedrooms create five beautifully private bedroom suites, equally suited to intimate everyday living or a house full of family and friends. Throughout, the architecture is sophisticated but restrained, allowing the extraordinary setting to remain the focus. And the house is only the beginning. The estate encompasses 135 acres of lawns, fields, woods, and private trails, creating a property that can be experienced as much as admired. A large, crystal-clear swimming pond offers an idyllic counterpoint to the infinity pool. Miles of trails wind through the acreage for riding, hiking, and exploring, while a barn and riding arena establish the property as a true equestrian retreat. A separate two-bedroom cottage provides charming guest accommodations, while a carriage house with its own apartment creates additional flexibility for guests, staff, an office, or studio. What ultimately distinguishes this property, however, is something photographs and specifications can only begin to convey: the feeling of being here. Morning light moving across 135 private acres. Long afternoons by the pond. Horses on the trails. Dinner overlooking the mountains. And, each evening, the sun setting behind the Catskills from an infinity pool seemingly suspended above the Hudson Valley. It is extraordinarily private without being isolated, grand without being ostentatious, and remarkably complete without feeling overdone. Properties of this caliber are exceedingly difficult to create—and even harder to find. Just 25 minutes from the restaurants, galleries, shops, and cultural life, this is not simply a country house. It is one of those rare places that makes leaving the city feel like arriving somewhere else entirely.

21 Schoolhouse Road, Hillsdale

$15,995,000
8 Beds 13 Baths 1036802 MLS
The Bluffs at Premium Point represents a once-in-a-generation opportunity to acquire one of the most significant waterfront estates on Long Island Sound in the award-winning Mamaroneck school district. Set on 1.3 acres at the crest of Premium Point’s coveted 24-hour guard-gated peninsula, this newly completed residence commands extraordinary 360-degree views across the Sound and Premium Mill Pond. One of the enclave’s landmark “Big Four” properties, it offers an irreplaceable combination of scale, privacy, elevation, water frontage and proximity to Manhattan. Built by Cum Laude Group, one of Westchester’s premier luxury builders, the residence reflects an uncompromising commitment to craftsmanship, materials and execution. Portions of the original stone estate remain within its footprint, while a new slate roof, copper gutters, and entirely new systems, finishes and surfaces bring modern refinement and full builder warranty. More than 13,000 square feet of beautifully finished living space unfolds across multiple elevator-served levels, with eight bedrooms, 10 full and three half baths, a heated and cooled three-car garage, pool house/guest suite and dedicated fitness level. Walls of glass, expansive Marvin windows, high ceilings, white oak floors, sculptural stairways and custom millwork frame sweeping water views from nearly every principal room. The main level is anchored by a dual-island chef’s kitchen with custom white oak cabinetry, dramatic marble surfaces, Wolf and Sub-Zero appliances, two Bosch dishwashers, extensive pantry storage and a sunlit breakfast bay overlooking the Sound. A separate butler’s pantry with wine refrigeration connects to the formal dining room, while the living and family rooms open through multiple sets of glass doors to expansive bluestone terraces and uninterrupted water views. The primary suite is a private retreat with panoramic Sound views, gas fireplace, two boutique-scale walk-in closets and a spa bath with steam shower, freestanding tub, and marble finishes. Additional ensuite bedrooms, a flexible office/guest suite, second-floor laundry, third-floor recreation room and private guest accommodations provide exceptional versatility for entertaining and extended stays. Outdoors, professionally landscaped architecture, a Belgian-block motor court, broad waterfront terraces, pool and spa, private neighborhood beach access, boat slips and a covered outdoor kitchen with Lynx appliances create a complete setting for waterfront living. The separate two-story pool house adds a guest suite, pool bath, dedicated laundry and dramatic custom gym. Infrastructure is equally impressive, including seven-zone high-efficiency HVAC, radiant heat in select areas, Lutron RadioRA 3 lighting, Sonos audio, commercial-grade network/WiFi, 400-amp electrical service, upgraded water and gas service, fire sprinklers, and whole-house generator. Rarely does an offering combine this caliber of construction, architectural finish, waterfront presence and privacy within a short commute to New York City. The collaboration of an irreplaceable Premium Point setting with the craftsmanship of Cum Laude Group elevates The Bluffs beyond even the exceptional. It is a legacy property in one of Westchester’s most tightly held enclaves, created for a buyer who recognizes that true luxury is ultimately defined by what cannot be duplicated. For those with the ability to choose among the finest homes in the world, this is the kind of property that stands apart not simply for its quality, but because opportunities of this caliber on this setting are seldom available at any price.

104 Premium Point, Mamaroneck

$24,995,000
9 Beds 13 Baths 1045735 MLS
Set along one of the most coveted stretches of Sagaponack South, just moments from the ocean, **493 Sagaponack Main Street is now complete**, presenting a rare opportunity to own a newly constructed estate in the Hamptons’ most exclusive and highest-priced zip code. Sited on 1.9 meticulously designed acres, this 11,369-square-foot residence has been thoughtfully conceived as a seamless blend of classic Hamptons architecture and modern luxury living, where every detail—from scale to finish—feels both timeless and forward. Arriving through a gracious drive, the home reveals a commanding yet elegant presence, with expansive windows and refined cedar-shingle craftsmanship that invite natural light throughout. Inside, a flowing floor plan unfolds across three levels, offering nine bedrooms—including a junior suite on the first level and a private primary suite upstairs—alongside eleven full and three half baths. Designed for both grand entertaining and intimate living, the interiors are complemented by an elevator servicing all levels, as well as a full suite of lifestyle amenities including a golf simulator with lounge area, a state-of-the-art gym, and a spa retreat featuring a large sauna, steam shower, and outdoor plunge pool. Outdoors, the estate transforms into a private resort. A 20×60 heated gunite pool and spa anchor the grounds, accompanied by a beautifully appointed pool house and expansive lounging areas that capture the essence of Hamptons summer living. The sunken tennis court adds another layer of recreation, while curated landscaping frames multiple entertaining zones—from al fresco dining terraces to quiet garden moments—creating a sense of privacy and serenity rarely found this close to the beach. As the day transitions to evening, the property takes on an entirely new character—warm interior lighting glows through oversized windows, landscape lighting softly defines the grounds, and the estate becomes a true showcase of architectural elegance. Whether hosting under the stars or enjoying a quiet weekend escape, every moment here is elevated. **Now fully completed and ready to be experienced,** 493 Sagaponack Main Street is more than a home—it is a statement property, delivering extraordinary scale, an exceptional location, and the rarity of brand-new construction in a market where opportunities of this caliber are nearly nonexistent. For the discerning buyer seeking immediate access to the Hamptons lifestyle at its highest level, this is an address that defines Sagaponack living.

493 Sagg Main Street, Sagaponack

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.