luxury properties 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.

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.

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.

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.

A masterful blend of timeless character and elevated modern luxury, this designer-renovated Shelter Island residence delivers a curated living experience across more than an acre of lush, private grounds. Every space has been thoughtfully reimagined with bespoke finishes, high-end materials, and a refined aesthetic that feels both effortless and elegant. Step inside to sun-filled interiors with clean lines, wide-plank flooring, and a seamless flow ideal for year-round living and entertaining. The designer kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, and a sophisticated palette that complements the home's heritage. The adjacent dining and living spaces offer an inviting atmosphere, with natural light and tasteful detailing enhancing every moment. Five beautifully appointed bedrooms and three spa-inspired bathrooms provide comfort and privacy for guests or full-time residents. Each room reflects a balance of luxury and warmth, from serene color schemes to thoughtfully selected fixtures and finishes. A luxurious primary suite includes a spa-style bathroom and walk-in closet, creating a private retreat within the home. Outdoors, resort-style living comes to life. A heated gunite pool, expansive bluestone patio, and multiple lounging and dining areas create a truly elevated summer retreat. Manicured gardens, mature landscaping, and a serene pond offer tranquil views and exceptional privacy, while the acre+ setting provides ample space for recreation, entertaining, or simply enjoying the natural beauty of Shelter Island. The property also includes an outdoor kitchen, fire pit, and multiple shaded seating areas, perfect for alfresco dining and gatherings. Additional amenities include a state-of-the-art HVAC system, smart home features, and ample storage throughout. The property's layout and orientation maximize natural light, cross-ventilation, and the surrounding scenic vistas. Located moments from beaches, Mashomack Preserve, South Ferry, marinas, and local restaurants, this home captures the essence of Shelter Island living-quiet, refined, and effortlessly connected to the best of the East End. Move-in ready and finished to a designer standard, this is a rare opportunity to own one of Shelter Island's most sophisticated and lifestyle-driven offerings, where every detail has been curated for comfort, elegance, and timeless appeal.

Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes from the South Fork. An amply equipped open kitchen pours out into the windowed dining area, with a fully screened in, covered porch just adjacent. The formal living room, complete with fireplace is spacious yet inviting. The en suite first floor primary is bright and beautiful. Upstairs are three more bedrooms and two baths, plus an open landing area, perfect for a study, at the top of the stairs. Add the two car garage and this home is a perfect fit for the Shelter Island lifestyle.

Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony, Salt Restaurant, and the Island Boatyard Marina. Originally built in 1960, the main residence features a spacious open-plan living and dining area with a cozy fireplace, a formal dining room, and a sunroom off the kitchen-perfect for relaxing or entertaining. There's plenty of potential here to update or expand with your own design vision. The property also includes a separate, partially completed renovated 1-bedroom cottage, complete with a legal kitchen, spacious bathroom, and inviting living area-ideal for guests, extended family, or as a rental income opportunity. A detached 2-car garage and ample outdoor space, including room for a pool, complete this rare offering in one of the area's most desirable locations. Owned solar panels provide significant energy savings with little to no ongoing cost. Don't miss your chance to enjoy the peaceful living just minutes from local favorites and the charm of the surrounding community. The sauna, lap pool in the basement are not being represented. This home is being sold As Is.

Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the relaxed waterfront lifestyle. Designed for both entertaining and everyday enjoyment, the property features two private docks ideal for boating, paddleboarding, and kayaking, along with a spacious waterside deck overlooking the sparkling water. The first floor has a large waterfront room that opens directly onto the deck, complemented by 4 generously sized bedrooms and 4 full bathrooms. Upstairs, soaring cathedral ceilings frame an open-concept great room encompassing the living, dining, and kitchen areas. Walls of glass capture stunning panoramic water views, creating a light-filled and inviting gathering space. Privately situated off the great room, the expansive primary suite offers a large walk-in closet and a spa-inspired bathroom. Completing the property is a detached 2-car garage with a finished upper level, providing the perfect space for recreation, a home office, artist’s studio, or additional guest accommodations. A rare opportunity to enjoy waterfront living with private docks, beach access, tennis, and some of Shelter Island’s most captivating water views.

This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. A large, inviting living room with a wood-burning fireplace provides a comfortable gathering space year-round. Just off the kitchen, sliding French doors open to a covered three-season room/screened porch with a vaulted ceiling, creating a seamless indoor-outdoor flow and easy access to the backyard—ideal for barbecuing and relaxing. The home includes three generously sized bedrooms and two and a half baths, all set on a .44-acre lot. Additional highlights include an outdoor shower, a partial basement with finished space for added flexibility, an attached two-car garage, and a detached 1.5-car garage offering additional storage or workspace. A wonderful opportunity to enjoy the charm and tranquility of Shelter Island living.

Wonderful remodeled home located in secluded Silver Beach on West Neck Bay. With water on 2 sides of this lovely estate, enjoy the water views from all rooms. 5 Bedrooms, 6 baths, finished lower level and open rooms, this is a wonderful home to enjoy for the summer or year round. The large open kitchen with high-end appliances opens to a massive dining room overlooking the rolling yard down to the water. The primary bedroom on the second floor features a full bath and two very large walk in closets and French doors out the a balcony. Just off the primary bedroom is one of two laundry areas and 2 guest suites all en-suite. On the main level is an en-suite guest bedroom, library with fireplace, open kitchen and dining room, another full bath for the pool area and a living room with an additional laundry just off the service entrance. This lovely home features a veranda with a pool, detached garage, partially finished lower level and an expansive yard and deep water dock. A wonderful home with exquisite views and room for everyone.

Some properties are simply irreplaceable. This is one of them. Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island Shingle beach house sits on a level acre along one of the Island's most coveted stretches of waterfront - 190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour. Deceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. Two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Mature landscaping on all sides for privacy. The expansive side lawn - often mistaken for a separate lot - offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow. A chance to own a piece of Shelter Island's story.

Between the shoreline and the fairways is where you'll find Stonegate Estates at Cameron Court, Old Lyme's newest luxury development conveniently set close to White Sands beach. Embrace upscale living in these carefully crafted custom homes. The Ashton is the first offering and framing is complete. This home has a flexible floor plan, open flow, and smart design. A total of 8 lots remain available, including select premium lots overlooking the Black Hall Golf Course. Other plans available, whether you're looking to build your perfect home style, from one-level ranch to farmhouse to colonial design. Enjoy this opportunity to bring your design dreams to life! Old Lyme has award winning schools, a deep appreciation for the arts and activities for the woods or water! Conveniently set 2 hours from Boston and NYC.

A rare opportunity to own an historic house with land that runs between Union and Jefferson Streets allowing for a south-facing light, room for a large garden and swimming pool is listed for sale. Included are permitted plans plans for a substantial addition on one of the largest residential parcels within this location of Sag Harbor Village. A three-quarter (.75 acre) site with mature landscaping and perimeter evergreens all makes for a securing a rare jewel in this convenient and central location and moments from the best of what Sag Harbor has to offer for one of the best lifestyle experiences on the East End.

Wake up to endless views of the Peconic Bay — sunlight glimmering off the water, birds gliding over the nearby nature preserve, and the calm rhythm of the deep-water inlet just beyond your deck. This sweet beach cottage captures everything that makes summer on the North Fork unforgettable. With 3 comfortable bedrooms, 2 baths, and an open, easy-flow layout connecting the living, dining, kitchen, and entertainment nook, it’s made for barefoot mornings and breezy afternoons with friends. Step outside to a spacious wraparound deck and 130 feet of pristine waterfront — perfect for soaking in the sun, launching a kayak, or simply taking in the view. Secluded yet steps to the private sandy association beach, this is a rare slice of coastal paradise where summer never really ends.

Enjoy exclusive Beach Rights and ultimate coastal living in the highly desirable Chapman Beach community! Just steps from the sand, this bright and airy 3-bedroom, 1-bath seasonal cottage is the ultimate shoreline escape you've been waiting for. Inside, 828 square feet of sun-drenched living space is perfectly optimized for relaxed, carefree seaside vibes. Tucked away on a private lot along a quiet road, your outdoor oasis features a generous deck ready for summer BBQs, an expansive yard for lawn games, and a dedicated shed to stow your surfboards and beach gear. Ready for your personal touch! Just moments from the Connecticut Shoreline's finest dining, marinas, and boutique shopping, this rare gem is the timeless summer escape you've been waiting for.

Occupying a premier position on Hither Lane-widely regarded as one of the most beautiful and private streets in the Hamptons-the estate enjoys exceptional walkability. Three ocean beaches, The Maidstone Club, village restaurants, shopping, coffee, golf, and The Jitney are all within easy reach, allowing residents to avoid summer traffic entirely-an uncommon and highly valued advantage in East Hampton. Privately gated and approached via a long, tree-lined allée, the property unfolds behind custom steel entry gates into a fully enclosed landscape of mature plantings, offering a remarkable degree of privacy, security, and quiet. Architecture & Design Spanning approximately 8,000 square feet, the residence presents a refined architectural dialogue between classic Hamptons craftsmanship and contemporary design. Traditional detailing is executed with precision, while modern elements introduce lightness, scale, and understated sophistication. Natural materials, bespoke millwork, and tailored finishes define the interiors. Glass curtain walls, soaring ceilings, and carefully proportioned volumes create a seamless flow that supports both elegant entertaining and relaxed daily living. Interiors The main level is open yet thoughtfully structured, allowing each space to feel distinct while flowing effortlessly from one to the next. The formal living room draws inspiration from London's finest hotels, with lacquered wood-paneled walls, integrated architectural lighting, a custom wet bar, and a gas fireplace framed in Italian quartzite. The dining room is anchored by illuminated Italian stone wall panels, floating glass shelving, and refined custom detailing. The kitchen features bespoke Poliform/Varenna cabinetry, Wolf and Miele appliances, a butler's pantry, and an adjacent lounge designed for informal gathering. An expansive upstairs media room spanning over 30 feet includes a projection theater, wet bar, full bath, and motorized blackout shades-ideal for relaxed evenings or entertaining on a larger scale. Primary Suite & Guest Accommodations: The main-floor primary suite offers a serene retreat, complete with a private sculpture garden, sitting area, and spa-inspired bath featuring heated stone floors, double vanities, and a glass-enclosed shower. Two custom walk-in closets and motorized window treatments complete the space. Five additional bedroom suites, each with en-suite baths and generous closets, provide exceptional comfort and privacy for family and guests. Outdoor Living: The exterior program unfolds across three distinct outdoor pavilions, designed for year-round enjoyment. A heated glass-roof atrium connects the main residence to an outdoor dining pavilion via sliding glass walls. The primary outdoor living pavilion features 14-foot ceilings, a custom summer kitchen, wood-burning fireplace, and a dramatic infinity-edge heated saltwater spa. Motorized retractable screens allow seamless transition between open-air and enclosed comfort. The pool pavilion includes a full bath, outdoor shower, and a generously scaled gunite pool, with the sound of ocean waves audible on summer evenings. Technology & Amenities: The estate is fully integrated with app-based smart systems controlling security, gates, climate, lighting, audio/video, pool and spa, window treatments, and irrigation-allowing effortless management whether in residence or abroad. Additional amenities include a gym, wine room, sauna, cedar closets, a heated two-and-a-half-car garage, Lutron lighting, custom architectural LED systems, and comprehensive audio throughout the home and outdoor spaces. Furnishings & Art (Available Upon Request) Custom couture furnishings and a curated modern art collection, including pieces by Alexander McQueen, Patricia Urquiola, Jasper Morrison, Charlotte Perriand, Marcel Wanders, Hermès, and others-are available.

Welcome to 145 Baldwin Place, a spacious and inviting 5 bedroom Colonial set on two private acres in the heart of Cutchogue. A sun-filled foyer with cathedral ceilings creates an impressive first impression, leading to thoughtfully designed spacious living spaces ideal for both everyday living and entertaining. The center of the home is the expansive open concept kitchen with a seamless flow into living and dining areas. Upstairs, the private primary suite serves as a true retreat with vaulted ceilings, generous closet space and a spacious ensuite bathroom. Four additional bedrooms provide generous space and flexibility throughout the home. Set on two private acres, the property offers a beautifully landscaped setting along with plenty of open space for recreation, a pool or outdoor entertaining. Located just moments from the pristine beaches of the Peconic Bay, residents can enjoy swimming, kayaking, paddleboarding, and unforgettable sunsets. Nearby farmstands, vineyards, waterfront dining, and charming village shops complete the quintessential North Fork lifestyle. Whether you are seeking year round residence or a weekend escape, this home offers space, privacy and the best of North Fork living.

Located in one of the most beautiful and private neighborhoods of Southampton North This spacious and beautiful gabled traditional was custom built by Farrell Building Co. Impeccably maintained, the 6,300+/- sq. ft. home on an acre landscaped for privacy offers six en-suite bedrooms, eight full baths, state-of-the-art kitchen, and a location convenient to Southampton, Sag Harbor, and Bridgehampton, with ocean and bay beaches minutes away. Gracious, light-filled living areas include a living room with fireplace, coffered ceiling and French doors to an expansive rear deck, formal dining room, and eat-in kitchen with island seating, breakfast area, and glass doors to the deck. The bright, airy master suite has vaulted ceilings in the bedroom with a sitting area, a private balcony overlooking the unlimited reserve and a luxurious bath. In the finished lower level find a theater, sauna and billiards room. Outdoors relax or entertain on the sunny deck or spacious covered porch with outdoor fireplace; enjoy the heated gunite pool and spa.

Experience the essence of Essex village living in this distinguished historic home. Perfectly positioned in the heart of the village, 17 Scholes Lane is a master class in period charm and modern amenities offering a peaceful, sun-drenched retreat where 18th-century soul blends seamlessly with high-end, contemporary finishes. Thoughtfully renovated to prioritize water view, light and flow. At its center is the airy chef's kitchen, a striking space featuring, architectural drama, soaring vaulted ceilings and oversized windows that bathe the room in natural light and maximize the expansive water view. Exquisite finishes, custom cabinetry anchored by a natural stone island, and designer details like premium Waterworks fixtures provide a polished, timeless touch. Throughout the home, the character of 1784 is vibrantly alive. You'll find original paneling, wide-plank flooring, and period doors with their authentic hardware. The first-floor primary suite offers a private sanctuary of modern luxury. The ensuite bathroom is a work of art, featuring marble-tiled floors and walls paired with elegant Waterworks appointments. Adding to the old-world charm are the three working wood burning fireplaces. One is centered in the Living Room which features a floor to ceiling bow picture window capturing the ever-changing, picturesque water view and nature.

This Amagansett beach house is a true work of art, blending timeless design with the natural beauty of its oceanfront setting. Located just moments from the sand and framed by flowering dunes, it immerses you in the sights and sounds of coastal living. Enjoy breathtaking panoramic ocean views from the expansive rooftop deck. The oversized designer kitchen flows seamlessly into a bright, open living space with radiant heat flooring and a fireplace, perfect for entertaining or relaxed gatherings. The entire top floor is dedicated to a private master retreat, complete with its own deck, hot tub, and outdoor shower for the ultimate sanctuary experience. Two additional bedrooms with two full bathrooms are conveniently located on the first floor, providing comfort and privacy for family and guests. Rare for the area, the home also includes an underground garage, offering both security and ease of access. Nestled in a quiet beachfront enclave, this home offers unmatched tranquility, modern luxury, and a front-row seat to the ocean's beauty.

A rare and unparalleled opportunity to acquire an iconic c.1900 property set atop a gentle rise at the head of Main Street in historic Essex Village. This substantial, professionally maintained building is comprised of two legal condominium units, and offers unmatched flexibility with its APPROVED MIXED RETAIL/OFFICE/RESIDENTIAL USE status. Potential to create your own custom Essex village pied-a-terre with an income-producing component, or to convert this current office building into your full-time Essex home. Solid and well maintained, the building is currently divided into two condominium units. Unit 'A' consists of 1,200 SF on the first floor. Unit 'B' comprises 1,977 SF on the second level and 1,083 SF on the third level. Features include first class mechanical systems, kitchen, and a spacious second level room overlooking Main and Pratt Street with glimpses of the CT river. A terrace and private rear yard are accessed from the second level. The location is spectacular. Enjoy a commanding presence, and commanding views, of the heart of Essex village. Adjacent to shops, restaurants, yacht clubs, marinas, and artist galleries.

A rare and highly coveted estate parcel in bucolic Sagaponack South just half a mile from the Atlantic Ocean. This perfectly proportioned 2.2 acre building site enjoys a premier setting at Town Line Road and Hedges Lane, directly across from a 15 acre conservation easement - an area of preserved scenic beauty that enhances the natural openness and enduring value of the property. Create a distinguished legacy estate on one of the largest parcels in Sagaponack South with the potential for extraordinary development, with allowances for 32,000+ SF of lot coverage and the opportunity to construct an 11,000+/- SF residence across three levels with amble room for pool, pool house, a north-south facing tennis court and expansive front, rear and side lawns. This exceptional double-wide parcel ensures privacy and flexibility making it a truly unique canvas with no clearing restrictions. Sagaponack stands among the most prestigious and sought-after zip codes in the United States, renowned for its natural beauty, exclusivity and legacy of estate properties.

Signature building in Essex Village. Originally the EE Dickinson corporate offices; grandfathered use in a residential zone. Reimagine this amazing space, water views, Essex Village, .78 acres of land, large footprint. Rare opportunity to own a cherished piece of Essex history