luxury houses with terrace for sale Southold, United States

Step behind the hedges. Founders Landing, Southold. Private park-like .63 acre. Custom Arts & Crafts influenced home. Bay beaches, marina, restaurants, shopping & transportation all just a stone's throw away. Exquisitely landscaped. Gracious front porch. Large foyer with a one-of-a-kind staircase with crafted newel posts. Vaulted ceilings, large windows w/ transoms and an openness that invites nature inside. Imposing brick wood-burning fireplace. Custom kitchen, dining room w/ tray ceiling. French doors lead to sunroom w/ west, south & north exposures. 1st fl master suite.. Beautiful fenced backyard w/ brick patio & specimen plantings. Plenty of room for the pool of your dreams. Whole house generator. Meticulously maintained and move-in ready. Adjacent .64 acre property also available. Call for details. Your family compound might just be in sight.

Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries, beaches, and all attractions on the North Fork. This meticulously maintained single-level home features 4 bedrooms and 3 bathrooms, offering a versatile floor plan designed for comfortable living and entertaining. The private primary en-suite includes a beautifully updated bath with elegant tile work and soaking tub. Two additional guest bedrooms and updated hall bath provide ample accommodations, while a separate wing with its own private entrance offers endless possibilities. Ideal as a home office, guest quarters, or a secondary primary suite, this space includes a sitting room, bedroom, and full bath with a handicap-accessible shower. The spacious, light-filled kitchen is designed for both everyday living and entertaining. Featuring an abundance of cabinetry, expansive counter space, and an efficient layout, the kitchen offers plenty of room for meal preparation and storage. The open design flows into the dining area and living room, creating an inviting atmosphere for casual gatherings or larger celebrations. The dining area offers sliding doors leading to a large deck overlooking the scenic grounds, the perfect setting for outdoor dining, relaxing, or entertaining. The full basement with outside entrance offers endless possibilities for expansion of the living space if desired. Every detail of this residence reflects exceptional care and pride of ownership. Beautifully maintained, the home presents with the feel and quality of new construction. A rare opportunity to own a pristine country retreat with room for a pool, where privacy, natural beauty, and convenience come together in perfect harmony.

Cutchogue Farmstead. Ideal North Fork location. This property includes the home, a 2600 sf barn with horse stalls, water and electric, outbuildings, and 4.5 acres of vines planted in Merlot, Sauvignon Blanc and Riesling varietals. This 1800's restored farmhouse is set on 17.5 acres of level, fertile land. Development rights are intact offering not only agricultural potential but also subdivision and other options. The farmstead's manageable land size is suitable for an eco-friendly, entry level enterprise and also offers additional acreage to an established owner looking to increase crop production. The 3BR, 2 BA farmhouse has a lovely, covered porch with a Western exposure, great for afternoon get-togethers. A patio with a pergola overlooks the planted vines. Opportunity abounds in this 17.5-acre, development rights intact property in Cutchogue, the sunniest place in New York State. REALLY! Central, accessible North Fork location. Bring your concept to life here.

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

An extraordinary offering on the Peconic Bay, this refined Cedar Beach waterfront estate presents over 200 feet of direct, sun drenched, south facing shoreline and beach with a protected, private dock deep enough for a mid twenty ft boat, a truly rare combination of attributes to find on the North Fork. Thoughtfully designed to embrace its breathtaking setting, the house is set on a double lot whose southern exposure also produces the luxuries of southerly breezes and a true, useable and enjoyable beach not encumbered by prolific rocks or muck. The home itself is defined by soaring cathedral ceilings, sun-drenched interiors, and elegant entertaining spaces that seamlessly transition to expansive waterside terraces overlooking endless bay views and spectacular sunsets. Private ensuite accommodations and beautifully curated living spaces evoke a sense of understated coastal sophistication. Complementing the property, a separate waterfront parcel directly across the street features a newly refurbished private dock with direct bay access, offering an exceptional opportunity for boating, fishing, quick trips to Shelter Island, Sag Harbor, the Hamptons and other beautiful East End destinations. A exceptional and rare North Fork lifestyle centered around the beach, sun and water.

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.

Welcome home to this four bedroom two and and half bath expanded ranch style-home in the coveted Highland Estates section of Cutchogue. Set of .92 acres offering effortless indoor-outdoor living. The open concept kitchen offers both Silestone and Butcher block countertops with modern floating shelves and ample cabinetry. The first floor primary suite provides a private retreat with easy access to the primary bath with tub. An inviting indoor-outdoor atrium sun-room creates the perfect space for relaxation and entertaining. The family room has a wood burning fireplace to cozy up to on those cold winter days. Two additional upper level bedrooms and full bath complete the upper level. Step outside to your own backyard oasis featuring a salt-water in-ground pool, outdoor cabana and lush landscaping. Multiple seating areas include a fire-pit, and separate grilling area. The out-door lighting provides a tranquil atmosphere allowing for to entertaining into the evening, all designed to provide a peaceful setting right in the comfort of your home. A rare opportunity to own your own slice of paradise, close to beaches, restaurants and wineries. Priced to sell House is being sold as is. .

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.

Presenting a rare opportunity in the tiny village of New Suffolk. This slice of paradise is situated on the easterly side of West Creek along Grathwohl Road. This move in ready home is an oasis, consisting of the main house, beautifully appointed inground pool, pool house, outdoor kitchen and offered with this amazing property is a private guest cottage that can be used as overflow for family and friends or as an income generator. In the main house, you will find high end finishes and a true chefs kitchen (Wolf, Sub Zero etc). A finished game room below, three bedrooms on the second floor including the primary suite. The guest house, also tastefully cozy with two bedrooms, one on the main level, another on the second. Living room, eat-in kitchen, laundry and dry basement. Together, this offering represents in many ways the essence of the North Fork with its beauty, privacy and location. This is an exceptional opportunity.

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.

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

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.

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,

Romance, Elegance and Timeless beauty over 38 acres on bucolic Oregon Road, you couldn't ask for anything more! 36 acres of DRS land which includes 30 planted acres of grape vines, deer fencing and bird netting, irrigation in place for an additional 2-3 acres of planting and a potential wine tasting area. The updated vintage farmhouse rests on 2 acres of DRI land and features 3 bedrooms, 2 bathrooms, sun drenched open floor plan, eat-in-kitchen, dining area, sitting area with reading nook, living room with a fireplace. Step outside and enjoy lush landscape surrounding the pool, outdoor shower and vineyard views! Surrounded by award winning North Fork wineries, restaurants, farm stands, boating & great shopping.

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 shingled 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. Maturenlandscaping on all sides for privacy. The expansive side lawn is often mistaken for a separate lot and 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.nA chance to own a piece of Shelter Island's story.

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.

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

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 1.6 acres with approximately 245 feet of waterfront with a private deep water 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.

Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef’s kitchen with a casual dining area, and a screened porch perfect for long summer evenings. A remarkable addition completed in 2005 is the approximately 1,300-square-foot artist’s atelier, featuring radiant-heated floors and an upper-level primary suite that opens onto a spacious rooftop deck. A detached guest cottage adds another dimension to the property, offering independent accommodations with a large bedroom, full bath, kitchen, living room, and its own garden and lawn. A charming outbuilding provides yet another opportunity, whether envisioned as a reading nook or hobby space. With its blend of historic architecture, dedicated studio space, separate guest quarters, and generous grounds, the property invites a variety of possibilities, including the potential for a swimming pool. Equally suited to relaxed summer gatherings or comfortable year-round living, this is a distinctive island sanctuary with room to create something truly your own.

Your search is over. If you've been looking for that rare blend of modern design and stunning sound front sunsets, look no further. This incredible Res4-Build on the Long Island Sound is located within one of Mattituck's most coveted locations. Step inside and you are greeted by sundrenched interiors and walls of glass framing those endless water views from every angle. Expansive room for guests with an open layout, 4 bedrooms, 5 baths and a huge finished basement with tons of natural light and incredible space. Grill waterside, overlooking your Gunite pool. The rooftop deck and the putting green offer moments of quiet or playtime! This sexy Sound Front stunner is a must see!

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.

The one you've been waiting for. Welcome to your private retreat in the heart of Mattituck. This spacious 3-bedroom, 2 updated bath sprawling ranch is nestled in a quiet, sought-after neighborhood and offers the perfect blend of comfort, charm, and outdoor beauty. Step inside to find a large, sun-filled eat-in kitchen—ideal for gathering with family and friends. The warm and inviting family room features a classic wood-burning fireplace, creating the perfect ambiance for cozy fall and winter evenings. Outside, escape to your own backyard oasis. Enjoy lush gardens, mature landscaping, and a sparkling pool—perfect for relaxing summer days or entertaining guests in style. Whether you're lounging poolside or sipping coffee on the patio out front surrounded by nature, this home delivers peace and privacy. With plenty of room for all and a layout designed for easy living, this home is perfect for year-round living or a seasonal getaway. Don’t miss this rare opportunity to own a slice of North Fork serenity!

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.