luxury real estate 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.

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 in the wonderful North Fork beach community of Summit Estates, this spacious 3 bedroom, 2-bath cedar shake expanded ranch is ideal with its single-story living design and large yard ~ perfect for a pool and poolhouse. The Community beach, park, and dock are down an elegant private lane to a community parking lot and a magical paved trail. So handy to easily transport your beach and boat equipment from car to beach and boat! Close to Island’s End Golf Course, wineries, and the transportation hub and shopping/dining in the historic seaport Village of Greenport. A lovely North Fork retreat!

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.

Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 1,000 square feet and features soaring vaulted ceilings with decorative cross beams and an open-concept Great Room seamlessly connecting the kitchen, dining, and living areas. Three generously sized bedrooms, a full bathroom, and an in-unit washer and dryer complete the space. The main-level residence offers a similar layout with approximately 1,300 square feet of living space. Highlights include three bedrooms, one full bathroom, a spacious kitchen with vaulted ceilings, and an additional 300 square feet of living area, providing added flexibility and room to spread out. Outside, the property is equally impressive, with meticulously maintained landscaping, a newly installed crushed-stone driveway with Belgian block edging, a large rear lawn, full irrigation, and a charming front porch. A substantial 600-square-foot, two-car garage and additional storage shed further enhance the property's functionality. Whether you're an investor seeking a ready-made income-producing property or an end user looking to offset carrying costs with rental income, 430 First Street presents a compelling opportunity in the heart of Greenport Village. Located just two blocks from Greenport's vibrant business district, the property offers convenient access to public transportation, shops, restaurants, grocery stores, local farm stands, parks, and beaches—all while providing the space, condition, and versatility that make this a truly special offering.

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.

Opportunity knocks! This rare farmhouse style cottage rests on an expansive double lot on the edge of Greenport Village and is prime to be revamped. Featuring 1700sqft of interior space, a large block foundation with full basement throughout most of the footprint, a 12x22 detached garage and a yard that will allow your imagination to run wild. Walk into town, walk to 5th and 6th street beaches and easy access to all that the North Fork has to offer.

Dating back to the original 1871 layout of the Shelter Island Grove and Camp Meeting Association, Spring Garden Avenue is celebrated for its organic, rolling streetscapes and preserved 19th-century architecture. 5 Spring Garden Avenue is an authentic 1880 Victorian residence that embodies the classic style of the era, from its steeply pitched rooflines to its expansive exterior woodwork. The interior layout is expansive and true to its vintage, characterized by distinctive octagonal rooms on both the first and second floors. With five bedrooms, a sprawling third-floor attic loft, and a substantial footprint of covered decks and porches, the home offers a generous canvas within a historic setting. A significant structural update was completed in 2008, replacing the older foundation with a new poured concrete basement and structural footings, alongside the installation of a new roof. Featuring full access to the Shelter Island Heights Association tennis courts and beach club, this property represents an authentic piece of island history.

Set along the quiet shoreline of Pipers Cove Bay in Shelter Island Heights, this west-facing waterfront retreat is tucked at the end of a private drive and has been thoughtfully reimagined by Heiberg Cummings, whose signature approach to layered design transforms the home into something both sophisticated and deeply connected to its surroundings. Every room on both levels is oriented toward the water, creating a constant dialogue between the interiors and the landscape beyond. Natural textures, a restrained palette, and carefully considered details allow the landscape to remain the focal point. The house unfolds around the view with a central wood-burning fireplace anchoring the open living room, kitchen and dining space. Glass doors open onto a series of waterfront decks, blurring the line between indoors and out and offering a front-row seat to the island's spectacular western sunsets. The primary suite occupies the main level, complete with an en-suite bath and private waterfront terrace. Downstairs, two bedrooms and a full bath are complemented by a generous waterfront den and library, creating an inviting second living space with uninterrupted views across the cove. On the opposite side of the den, a shaded terrace offers another quiet place to read, relax, or escape the afternoon sun. Outside, the property reveals itself one destination at a time. Multiple outdoor living spaces, perfect for hosting summer dinners on the terrace overlooking the water, or sunset cocktails in the private beach garden with two fire pits and a lantern lit dining area. Fully equipped beach bar , integrated outdoor sound system disappears into the landscape. Mooring rights for a vessel up to 40 feet make it easy to explore the surrounding waters before returning home for sunset. Private, thoughtfully designed, and deeply connected to the water, this is a home that captures the quieter side of the East End, where mornings begin on the beach, afternoons are spent on the water, and each day ends with the sun setting over Pipers Cove Bay. Residents also enjoy access to the Shelter Island Heights community tennis courts, while the Ferry, Marie Eiffel Market, Leon 1909, and the Heights' shops and waterfront are all just a short distance away, placing some of the island's favorite destinations within close proximity.

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.

Experience the pinnacle of refined living in this completely reimagined home, boasting a comprehensive renovation and redesign led by a professional interior designer. Every square inch has been thoughtfully curated, starting with the custom front door featuring openable screened sidelights that welcome you inside. Premium oak hardwood flooring flows seamlessly throughout the main living areas, grounding the home in natural warmth and elegance. The heart of the home, the great room and large kitchen, is an entertainer's dream, featuring gas fireplace, a dry bar with a wine fridge, premium lighting and plumbing fixtures, quartz countertops and custom window treatments including blinds and valances. First floor also includes a light filled den and separate office space for working at home. Retreat to the spectacular owner’s suite, a true sanctuary defined by architectural ceilings with shiplap details and a custom walk-in closet. The en-suite bathroom is clad in Italian marble and featuring premium fixtures. Indulge in the luxury of radiant floor heating—which extends into the large, curbless spa shower with its sleek infinity drain. Your guests are treated to equal luxury; guest baths feature premium fixtures and their own radiant floor heating. The guest bedrooms offer cozy carpeting and custom woodworking with the twin room featuring blackout and light-filtering shades for perfect rest. Behind the walls, the home is just as impressive. A whole-house water softening and purification system, smart irrigation system, and 2-zone heat/AC with smart thermostats ensure comfort and peace of mind. This is more than a renovation; it is a complete lifestyle upgrade. Located close to the heart of downtown Greenport Village and its bayfront beaches and transportation hub.

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.