luxury houses for sale Orient, United States

This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

Experience a rare combination of privacy, architecture, open water, and resort-like amenities at 66 Gardiners Bay Drive, an exceptional waterfront offering on Shelter Island. Set against sweeping views of Gardiners Bay, the property features a private beach, expansive lawns and gardens, and a spectacular gunite pool positioned directly along the water. The main residence was designed by renowned architect Andrew Geller, whose distinctive modernist vision is reflected in the home's thoughtful relationship to its extraordinary setting. The five-bedroom residence features five en-suite bathrooms, an open living and kitchen floor plan, and walls of windows that bring in abundant natural light while capturing panoramic Bay views. Both the main residence and guest house underwent a comprehensive renovation in 2022, with every aspect carefully considered. The renovation encompassed the kitchen, all bathrooms, major systems, and numerous other elements of both properties. Nothing was overlooked, with an emphasis throughout on quality, craftsmanship, and the finest materials and fixtures. Outdoor living is at the heart of the property. A generous deck, fully equipped outdoor kitchen, waterside lounge, and gunite pool create an exceptional setting for entertaining or simply enjoying the beauty of the Bay. The property also benefits from a grandfathered irrigation system, helping maintain lush green lawns and established gardens throughout the summer-an especially valuable amenity for a waterfront property of this scale. A beautifully renovated two-bedroom, three-bath guest house provides exceptional accommodations for family and guests, while maintaining privacy from the main residence and enjoying its own stunning water views. A full, newly refinished basement in the main house adds further living and recreational space. What makes 66 Gardiners Bay Drive particularly compelling is the remarkable breadth of what is offered in one property: privacy, expansive lawns and gardens, a private beach, sweeping open-water views, a waterside pool, sophisticated outdoor entertaining spaces, a renowned architectural pedigree, a beautifully renovated guest house, and a comprehensive renovation already completed. Rarely at this price point can one find so much on the water. The combination of setting, amenities, privacy, architectural significance, and turnkey condition makes 66 Gardiners Bay Drive a truly unique and compelling Shelter Island offering.

Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the lens of effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island’s premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.

Set on a well-proportioned acre in one of Shelter Island’s most sought-after neighborhoods, this 1850s farmhouse offers charm, generous living space, and an exceptional location. The main level features a spacious living room with a wood-burning fireplace, a dining room with a second wood-burning fireplace, and a bright sunroom. The open kitchen offers two exterior doors leading to side porches, providing an inviting connection to the outdoors and an ideal setting for entertaining. Upstairs are five generously sized bedrooms and three full bathrooms. A full basement and attic provide ample storage and utility space. Just a stone’s throw from Coecles Harbor Marina, this property presents an opportunity to enjoy the tranquility of Shelter Island.

This is a Once in a Lifetime Opportunity. Some properties can be reproduced, this one cannot. Built in 1914 by industrialist Samuel Hird and later lovingly stewarded by cosmetics magnate Bob Ruttenberg, this extraordinary Shelter Island Estate is a surviving expression of a more gracious era when great waterfront homes were created with scale, permanence and a sense of place rarely possible today. Set on 1.5 acres with approximately 245 feet of waterfront and a separate .12-acre waterfront parcel with private dock, the approximately 4,500-square-foot residence commands sweeping western views across Dering Harbor. Mature grounds, covered porches and a heated gunite pool with spa create the privacy and romance of a true country estate. The property provides ultimate privacy, a secluded oasis sheltered from the world outside. A three-car garage and pool cabana with changing rooms, both retaining historic details, further enhance the property, with the garage and cabana offering the opportunity to be thoughtfully refreshed or reimagined. Inside the home, beautifully proportioned rooms unfold toward the water. Expansive windows, French doors and multiple wood burning fireplaces give the house warmth and character, while gracious living and dining rooms, an inviting kitchen with butler's pantry, intimate den and generous bedroom accommodations make the home equally suited to relaxed living and elegant entertaining. The primary suite is a private retreat with its own sitting room or office, fireplace and ensuite bath. Upper-level guest rooms capture elevated harbor views, allowing the water to remain a constant presence throughout the house. The opportunity extends well beyond the waterfront estate itself. The residence, waterfront grounds, garage, pool and private dock are now offered at $15,995,000, together with a right of first refusal to purchase 3.2+ additional buildable acres. For those who envision a larger compound, the additional acreage may be acquired with the estate for a total offering of $17,995,000, creating the rare possibility for a substantial guest residence, tennis, or expanded gardens and recreation. Few waterfront properties offer the opportunity to acquire an estate of this character today while also preserving the ability to substantially expand its scale for the future. This is more than waterfront real estate, it is an opportunity to live with the grandeur and graciousness of the Gilded Age, with the comforts of modern life. Proudly presenting 6 Harbor Lane, what is a century in the making, impossible to recreate, and a once-in-a-lifetime opportunity to become its next steward.

A rare opportunity to own an early 20th-century Adirondack-style cottage in Greenport, ideally situated just 0.12 miles from a beautiful Sound beach and only one mile from the heart of Greenport Village. This charming cottage showcases many of the home’s original details starting with a screened-in front porch spanning the full width of the façade, creating a welcoming indoor/outdoor retreat. Inside, the open floor plan includes a living/dining room with a wood-burning stove, an eat-in kitchen, full bath, laundry, and access to a rear deck. The second floor offers a cozy loft-style bedroom. Two additional accessory structures — each equipped with electricity and water, and one including a bedroom — offer flexible space for guests, a home office, studio, or creative workspace. Surrounded by trees creating privacy and offering open vineyard views, this distinctive cottage compound captures the relaxed character and timeless appeal of the North Fork.

What stands out about this home is how established and inviting it already feels. Mature trees and thoughtful landscaping surround the property, creating a beautiful setting from the moment you arrive. The covered front porch is a perfect place to sit and take in the changing colors of spring and summer, including the striking blue blossoms of the mature Vitex that become a highlight of the landscape each season.Inside, the home has an easy, open flow with wood floors, a spacious hallway leading to the bedrooms, and a living room and kitchen that connect naturally for everyday living and entertaining. Just off the garage, the laundry room and mudroom create a practical drop zone for shoes, bags, beach gear and everything else that helps keep the main living spaces organized.The fenced backyard has its own personality, with an outdoor fire pit, established vegetable gardens, a huge fig tree and an additional garden shed for tools, bikes and outdoor storage. It is the kind of yard that already feels lived in, cared for and ready to enjoy.Location adds another layer to the lifestyle. Iconic 67 Steps Beach is within walking distance at the end of Sound Rd for minutes away for those incredible sunsets over Long Island Sound, while Greenport's coffee shops, restaurants and village destinations are close enough that grabbing your morning coffee does not always have to involve getting in the car.It is a home that combines comfortable everyday living with gardens, outdoor spaces and one of the things that makes Greenport so special: the ability to enjoy the beach, the village and the North Fork lifestyle right outside your door,

This charming cape is situated in Greenport, just minutes from Greenport Village and Beaches. The home has 4 bedrooms, 2 full bathrooms, and approximately 1500 sq ft. The eat-in kitchen has granite countertops and an awesome backsplash. The basement is unfinished with bilco doors. There is a fenced backyard and 1 car garage. The home currently has tenants, who will be leaving.

Welcome to 90 Caiola Court, nestled within the highly sought-after waterfront community of Rock Cove Estates in the charming hamlet of Greenport. Built in 2007 and impeccably maintained, this Post Modern residence makes an immediate impression with its mature specimen landscaping, manicured grounds, and timeless curb appeal. Step inside to a grand, light-filled foyer featuring soaring ceilings, an elegant open staircase, and an inviting sense of scale that sets the tone for the home's thoughtfully designed interior. The main level offers an exceptional layout for both everyday living and entertaining, featuring a formal dining room, gracious living room, and an inviting media room anchored by a classic wood-burning fireplace. At the heart of the home, the spacious eat-in kitchen is appointed with abundant cabinetry, generous counter space, and a highly functional layout designed to accommodate everything from casual everyday meals to large-scale gatherings. Just beyond, a private home office overlooks the rear grounds, providing a peaceful and inspiring workspace. Occupying nearly 900 square feet, the second-floor primary suite serves as a true private retreat, complete with dual custom walk-in closets and a luxurious spa-inspired bath featuring double vanities, a walk-in shower, and a Jacuzzi soaking tub. Three additional guest bedrooms and a well-appointed full hallway bathroom complete the upper level, providing comfortable accommodations for family and guests alike. Another huge bonus is the expansive unfinished basement with 8' ceilings and walk-out egress already in place, making this ripe for another fully finished space which would add approximately 1400 additional sqft. Perfectly positioned within one of Greenport's most desirable beach communities, residents enjoy private access to the Rock Cove Estates association beach while remaining just minutes from the vibrant shops, acclaimed restaurants, marinas, and waterfront attractions of Greenport Village, as well as the renowned wineries, farm stands, and scenic beauty that define the North Fork lifestyle.

Welcome to 550 Madison Avenue in Greenport, a thoughtfully designed New Construction farmhouse that feels comfortable from the moment you arrive. The covered front porch is more than an architectural detail. There is actually room for a chair and side table, creating the perfect spot for a quiet morning coffee. Inside, wide 6-inch oak floors connect the bright, open living spaces. The powder room is conveniently located near the front entrance, but it is tucked far enough away from the open living room, dining area, and kitchen to give everyone a little privacy when the house is full. The custom kitchen design brings together the features buyers keep asking for, including a paneled refrigerator, a full pantry closet, open shelving, generous cabinetry, and a kitchen sink positioned beneath a window overlooking the backyard. Even doing the dishes comes with a view of the established maple trees. A full glass slider in the dining area fills the back of the home with natural light and creates an easy connection to the outdoor entertaining spaces and grill. The backyard views can also be enjoyed from the living room, making the surrounding landscape feel like part of the interior design. Upstairs, the primary bedroom features a peaceful en-suite bathroom with distinctive tile flooring and calm, carefully selected finishes. Even the first-floor powder room has beautiful wallpaper, adding personality and making this New Construction home feel intentional rather than predictable. The fully fenced backyard is surrounded by established maple trees, creating a quiet and private setting that feels like a hidden corner of Greenport. The newly installed stone patio includes an outdoor cushioned conversation area, a separate outdoor dining patio, and a dedicated fire pit for evenings under the trees. There is also room to explore the possibility of adding a pool without making the yard feel crowded. The location brings the North Fork lifestyle within easy reach. The Greenport LIRR station and Hampton Jitney stop are approximately half a mile away for convenient transportation to New York City. Aldo’s Coffee is about a three-minute bike ride or a ten-minute walk, with Greenport Village shops, restaurants, waterfront destinations, and local beaches all close enough to enjoy without always getting back into the car. New Construction, a custom kitchen, paneled appliances, wide oak floors, en-suite bathrooms, a fenced backyard, mature trees, outdoor entertaining spaces, and easy access to Greenport Village. This might be the one you have been waiting for. You really need to come see it. In the evening it sparks with fireflies to capture summer vibes in Greenport Village.

This 2024 constructed 5,800-square-foot modern waterfront residence, built by Fountainhead Construction Inc., offers 250 feet of sandy beach and extraordinary panoramic water views. 180 degrees of sweeping water views from Crab Creek to North Haven Point and across Great Peconic Bay, with 250 feet of sandy beach along the shoreline. Walls of glass in the kitchen, dining area, living room, and select bedrooms frame the remarkable water views and glowing sunsets, creating a seamless connection between indoors and out. Step onto the waterfront patio or terrace to experience the setting even more fully. The sleek five-bedroom home includes six full baths and two half baths, with sophisticated finishes and amenities throughout, including 10-foot doors, a kitchen with custom Italian cabinetry and natural stone countertops, a fireplace, media room, and heated waterside pool. Set on 2.12 secluded acres, this exceptional property offers a rare opportunity for refined waterfront living

Shelter Island Ranch style home with 3 bedrooms and 2 bathrooms. Situated close to town and easy access to all beaches and either ferry this adorable home is currently configured as a 2 bedroom (large oversize primary bedroom with sliders to deck, guest bedroom, 2 newly renovated bathrooms, kitchen with new appliances, open living and dining area has stone surround fireplace and sliders to deck area. The lower level has finished space, laundry area, and doors to steps to access pool area. Large attic space and a separate garage with second level storage space.

Welcome to 12 Clinton Avenue, a distinguished waterfront estate nestled in the heart of Shelter Island Heights, NY. This remarkable property spans 1.5 acres along the serene Dering Harbor, offering an unparalleled lifestyle marked by elegance and tranquility. With 10,000 square feet of meticulously designed living space, this gated estate presents a rare opportunity to own a piece of paradise. The residence boasts seven spacious bedrooms and six and a half luxurious bathrooms, each adorned with high-end finishes and extensive use of natural marble. The grandeur of the home is immediately apparent upon entering the soaring great room, which doubles as a library, complete with a massive fireplace that serves as the focal point. The walnut flooring throughout adds warmth and sophistication to the expansive layout. The kitchen is a chef's dream, featuring a vast prep area and top-of-the-line appliances, seamlessly connected to a formal dining room perfect for hosting intimate gatherings. The screened-in porch, equipped with storm shutters, offers breathtaking views of the harbor, creating an ideal space for relaxation and entertainment. Outdoor amenities are equally impressive, including a private dock, a water-side gym, and a pool with an automatic cover. The magical landscaping enhances the property's allure, while the garden and irrigation system with a cistern ensure year-round beauty. The block paver driveway leads to a two-car garage, providing ample parking and storage. For those seeking leisure and community engagement, the estate offers access to community tennis courts and a beach club. The village lifestyle is serene, with no need for a car to access local restaurants, shops, coffee bars, and the post office, all within walking distance. Additional features include a bar, sauna, and an office room lined with bookcases offering stunning water views. The entry foyer sets the tone for the home's elegance, while the extensive use of luxury finishes throughout ensures a sophisticated living experience. This property is a testament to refined living, combining privacy, luxury, and convenience in one of New York's most coveted locations. Don't miss the opportunity to own this exceptional estate, where every detail has been thoughtfully curated to provide an unmatched living experience.

Rare opportunity to own a charming early-1900s Victorian farmhouse in the historic Heights. Set on a quiet road, this inviting home features an extra-large yard perfect for entertaining and a welcoming wraparound porch ideal for relaxing summer evenings. Inside, the home boasts a spacious living room with a wood-burning fireplace, a gracious parlor, formal dining room, and a first-floor bedroom with a full bath. Upstairs are two additional bedrooms and another full bath. A full basement provides ample storage and utility space. Just a stone’s throw from downtown shopping, restaurants, and all that the Heights has to offer, this is a rare find in one of Shelter Island’s most sought-after neighborhoods.

Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Island! Tennis courts directly across the street and backyard view of rolling land, minutes to the beach and a few steps to restaurants and gallery.

Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unparalleled escape from the ordinary. Step onto the property and be captivated by the charm of covered porches and a heated pool, inviting you to relax and soak in the picturesque vistas. Whether you're enjoying a quiet morning coffee or hosting unforgettable gatherings, this waterfront oasis provides the perfect backdrop for every occasion. Don't miss this opportunity to own a piece of paradise in Mashomack Preserve.

Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a beautifully landscaped yard with deck perfect for relaxing, entertaining, or summer gatherings. A wonderful opportunity to enjoy easy island living in a move-in-ready home.

Discover a rare and compelling offering on Shelter Island where historic character and modern sophistication exist in perfect harmony. 7 Stearns Point Road presents a unique opportunity to live expansively-either as a private family compound or as an owner-occupied five-bedroom Bed & Breakfast. The residence is set on 0.70 acres in the heart of Shelter Island Heights, just moments from Crescent Beach and Sunset Beach. Spanning approximately 5,838 square feet, with an additional 2,588-square-foot full-height basement, the home seamlessly blends timeless architectural details with contemporary comfort. Arranged across two distinct structures connected by a covered breezeway, the property's nine bedrooms and nine bathrooms are thoughtfully distributed between the original Annex-offering seven bedrooms-and a recently completed extension featuring two additional ensuite bedrooms. The new wing is further distinguished by a dramatic double-height living area and a dedicated wellness room, equally suited for private residential use or boutique hospitality. Generous entertaining spaces include two living rooms and a well-equipped kitchen designed to accommodate both intimate gatherings and larger-scale hosting. Outdoors, the grounds evoke a private resort atmosphere, featuring a heated 40' x 18' gunite pool, mature landscaping, and multiple areas for relaxation and entertaining. Two separate driveways provide added convenience and privacy for owners and guests alike. With zoning and approvals allowing for an owner-occupied five-bedroom Bed & Breakfast, along with the benefit of an existing liquor license for guest use, the property offers a rare level of versatility. Whether envisioned as a legacy family retreat, a refined island escape, or a boutique hospitality venture, the possibilities are both flexible and compelling.