luxury real estate for sale Southold, United States

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

A great business and/or investment opportunity awaits! Once a popular Southold holistic/chiropractic office with separate living quarters and then a childcare facility and apartment, this adaptable split-level property is awaiting its next creativite live-in business venture! Located on a beautiful .83 acre, this property fronts the high visibility County Road 48/North Road and backs up to scenic preserved farmland. The ground floor has a large waiting room, offices with sinks, and a half bath. The 2nd floor is a spacious 2-bedroom 1 bath rental apartment that could also be used as the business owner's home. Its Limited Business Zoning offers many opportunities including professional office, retail operation, custom workshop, garden shop/nursery, restaurant, dog and cat care facility, repair shop, etc.

Coveted Maple Lane setting in the heart of Southold Village with easy access to all Southold Village amenities and LIRR ~ This recently transformed shingled Craftsman Style residence offers 4 bedrooms, 3.5 baths, timeless architectural character, exceptional private outdoor living, and a truly special North Fork lifestyle. Beautifully landscaped with specimen plantings, the property is designed for relaxed year-round or seasonal enjoyment. Outdoor amenities include a new heated 16 x 32 inground saltwater pool, hot tub, outdoor shower, and gracious covered porches at both the front and rear of the home. Classic Craftsman details enhance the curb appeal, including Arts & Crafts-style columns on river rock bases, double-dipped cedar shingles, a custom garage door, and a signature Craftsman front door. Inside, the main level offers an inviting open layout with wood floors throughout. The spacious living room features a wood-burning fireplace, while the eat-in kitchen, dining room, and window-filled den provide warm, functional spaces for everyday living and entertaining. Both the kitchen and den open directly to the rear covered porches, creating an easy flow for indoor-outdoor living. The first floor also includes two bedrooms, one full bath, one half bath, and a mudroom/laundry room. Distinctive interior details include oak trim around the windows and doors, as well as a beautiful staircase with a one-of-a-kind custom newel post. Upstairs, the primary suite serves as a private retreat with a generous sitting and office area, two-sided gas fireplace, sauna, and a fabulous tiled bath with spacious walk-in shower. A newly added junior primary suite, completed in 2026, adds comfort, privacy, and flexibility for guests or extended stays. Just a few doors from the edge of charming Southold Village, the Southold Historical Society and close to Founders Landing Bay Beach and Park, this exceptional home offers easy access to the marina, restaurants, shops, wineries and NYC transportation. This is a rare Southold Village offering with remarkable character, amenities, and the superior North Fork location you have been looking for.

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.

Southold – Goose Creek- Located along a quiet private lane leading to Goose Creek Beach, this beautifully crafted and completely renovated cedar shingled two story home offers the perfect blend of charm, privacy, and North Fork living. The first floor features an open, sun filled layout highlighted by a spacious living room with a wood burning stove, a bright and airy kitchen with an expansive dining area framed by walls of windows, and a dining area with doors opening to the pool and patio. A first floor sitting room with an adjacent full bath provides a flexible space that can be easily converted into a first floor primary en-suite. Upstairs, the generous primary en-suite offers creek views, accompanied by two additional guest bedrooms and a full guest bath. Privacy surrounds the heated saltwater in ground pool and patio, creating a peaceful retreat for relaxation or entertaining. This exceptional property captures the essence of the North Fork lifestyle — a short stroll to beautiful Goose Creek Bay beach, yet tucked away in a quiet, coveted location. With creek access you can launch a kayak or paddleboard and enjoy the serene waters of Goose Creek. f you are interested in a "real" North Fork experience, this house checks off all the boxes. Restaurants, shopping, farm stands, wineries, breweries, boating... you name it. It's all right there.

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.

Rare opportunity to own this stunning 13.85 acres bay front parcel with over 450ft of secluded beach. This property boasts a depth of over 1000ft, creating a huge blank canvas to design your dream legacy estate. Offering scenic trails, serene ponds, and glorious sunrises. The perfect place to build your dream home and weave your everlasting story.

.38-acre wooded level lot in a private and natural setting. Ideally located near Paradise Point, Cedar Beach, Southold shops, vineyards, farmstands and Greenport Brewery. This is a triangle shape lot with 258ft of frontage on N Bayview Rd and 178ft/182ft deep on each side. A rare opportunity to create your own coastal retreat in one of the North Fork’s most desirable neighborhoods. No preliminary work has been done with the DOH, Planning Board, or building dept at this time. Please don't walk property without your agent present.

Extraordinary North Fork Bayfront Estate on a Private Peninsula on Paradise Point, Southold- Welcome to one of Southold's most exceptional waterfront offerings, a spectacular bayfront estate set on a private 1.6-acre peninsula within the coveted Paradise Point community. Surrounded by water on three sides and boasting an extraordinary 335 feet of Bayfront shoreline and private dock in a protected boat basin, this remarkable property captures sweeping panoramic views across Southold Bay to Shelter Island and beyond. Approached by a circular drive framed by mature specimen plantings and meticulously landscaped grounds, the residence immediately impresses with its timeless Nantucket-inspired architecture and commanding waterfront presence. Encompassing approximately 5,100 square feet, the home offers 4 bedrooms and 3.5 baths thoughtfully designed to maximize light, space, and breathtaking water vistas from nearly every room. A grand two-story foyer welcomes you with a dramatic sightline through the home to the open bay beyond. Soaring ceilings, expansive living spaces, and walls of windows create an atmosphere of elegance and tranquility. The open-concept main level features a gracious living room with a wood-burning fireplace, a waterfront sitting room with a gas fireplace, and an office alcove. The expansive chef's kitchen is designed for both entertaining and daily living, featuring stainless steel appliances, granite countertops, and captivating views of the bay and heated waterside pool. Casual dining overlooks the water, while the formal dining room enjoys picturesque views of the protected boat basin. The first floor also includes a bayside en-suite primary bedroom, laundry room, and powder room. Upstairs, the luxurious primary suite and private sitting room offer unrivaled views over the boat basin and open bay. Two additional oversized guest bedrooms, each with water views, share a full bath, while the open landing provides yet another spectacular vantage point. Additional amenities include an elevator to all three level, whole house generator, spacious walkout basement ready for customization, 2-car garage and a heated waterfront pool. Rarely does a property combine such privacy, waterfront frontage, boating access, and panoramic views in one extraordinary setting. This is a once-in-a-generation opportunity to own a signature North Fork estate with dock and waterside pool. A truly exceptional waterfront retreat unlike any other.

Location is everything. Privately set on 2.1 secluded acres, this stylish and charming farmhouse style home is approached by a long winding drive that reveals a striking 1,000-square-foot post-and-beam barn before opening to sweeping views of the property's picturesque grounds. Thoughtfully maintained and rich in character, the home offers a traditional floor plan complemented by hardwood flooring throughout and a substantial wood-burning fireplace that anchors the main living space. The kitchen has been tastefully updated with a gas range and generous peninsula seating, flowing seamlessly into a dining area overlooking the manicured landscape and seasonal water views beyond. Upstairs, four well-proportioned bedrooms include three guest bedrooms served by a full hall bath, while the sun-filled primary suite offers a private retreat overlooking the property, also offering those peek-a-boo winter water-views. A rare opportunity to enjoy privacy, acreage, and timeless North Fork charm in an exceptional setting w/ ample room an in-ground pool or equestrian activities. This is the country house on the North Fork you've searching for!

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.

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.

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.

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best 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. .

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.

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.

This quiet community known as Long View acres is the perfect place to build your Shelter Island dream home. Located just minutes from Bootleggers Alley Beach which is known for their spectacular sunsets. This .58-acre vacant lot backs up to historic Westmoreland Farms creating a beautiful backyard views.

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.

Tucked away in the coveted waterfront hamlet of New Suffolk, this charming move-in ready ranch captures the easygoing spirit of North Fork living. Warm hardwood floors run throughout the home, where an inviting living and dining area flows effortlessly into a bright, sun-filled kitchen overlooking the backyard gardens. The layout offers two comfortable guest bedrooms, a full hall bath, and a private primary suite with its own full bath, walk-in closet, and laundry area. Outside, the property feels peaceful and established, with lush green lawns, thoughtfully maintained garden beds, and a vegetable garden tucked along the rear of the yard. Just moments from the beloved New Suffolk beach, local favorites like Minnow and Legends Restaurant, and Shagwong Marina, the location places you right in the heart of one of the North Fork’s most cherished waterfront communities. Whether envisioned as a quiet weekend escape or a year-round home, life in New Suffolk offers a timeless coastal charm that never goes out of style.

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.

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.

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.