433 properties for sale in Southold

The pinnacle of Luxury Living In the historic heart of Sag Harbor — a village shaped by its storied whaling past and now celebrated for its cultural sophistication — Residence A stands as a singular architectural statement along one of the most coveted stretches of waterfront. Commanding approximately 250 feet of prime frontage on the harbor, this exceptional estate is far more than a home; it is a four-level masterwork of glass, stone, and light, created for a global buyer seeking complete privacy, effortless luxury, and direct nautical access. This extraordinary property is the result of a visionary collaboration between J. Bialsky of Bialsky Premiere Design & Development and the internationally acclaimed Hollander Design Landscape Architects. Together, they have crafted a residence that exists in perfect harmony with the Peconic Bay — a seamless dialogue between architecture, landscape, and water. Every line is intentional, every perspective framed, and every material selected to en

Introducing a one-of-a-kind opportunity to own a legacy estate south of the highway in Bridgehampton's farm country-120 Halsey Lane. This newly constructed, fully custom 14,267-square-foot residence is set on 2.5 lush acres and promises the pinnacle of Hamptons living. Newly Completed and Move in Ready, this architectural masterpiece will offer 9 bedrooms, 11 full bathrooms, and 3 half baths, designed to seamlessly blend modern luxury with timeless shingle-style elegance. Step inside to soaring spaces and grand proportions-an awe-inspiring 26' tall great room sets the tone for the rest of the home. Every inch of the layout has been thoughtfully curated: two true primary suites, one conveniently located on the main level and the other as a second-floor sanctuary complete with a private deck. From the oversized 3-car garage to the two elegant staircases and private elevator, no detail is overlooked. The lower level is an entertainer's dream featuring an 11' ceiling height, a golf simulat

Set on 6.2 private acres, Cabin in the Woods is a distinctive architectural residence designed by renowned architect Jasmit Singh Rangr of Rangr Studio. With dramatic cantilevered forms, clean architectural lines, natural wood, and expansive glass, the award-winning design balances a striking modern aesthetic with inviting interiors that embrace the tranquil setting. An elongated infinity-edge gunite pool appears to extend into the forest, while a tennis court, spa, and separate structure housing a gym complete the property's impressive outdoor amenities. The 5-bedroom, 4.5-bathroom residence features refined modernist interiors that pair natural materials with understated elegance. At the heart of the home, an open kitchen, dining area, and great room with a fireplace connect to two screened porches and overlook the deck, oversized pool, and surrounding landscape through expansive walls of glass. One screened porch features a fireplace, while the other offers a built-in grill, creatin

This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail, featuring an open floor plan with elegant white oak and porcelain tile flooring, stone countertops, and premium Thermador appliances throughout. Expansive living spaces are designed to embrace the surrounding views, while the second level covered deck offers the perfect setting for unwinding against a picturesque bay backdrop. Additional amenities include a heated gunite pool, radiant heat, wet bar, fireplace, pantry, and other thoughtful features that enhance everyday living. Ideally situated in Shelter Island, the property provides a peaceful retreat with convenient access to local amenities, beaches

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

Stylish modern house with 3 bedrooms, 1 Full Bathroom and half bathroom. Ready full finished basement and Summer perfect yard with brick and stone, easy to upkeep yard. Ample driveway for approximate 8 cars. This unique house is close to best tennis courts and convivence shops. Blessed with the close by 4 mile hiking trails of Tuckahoe Woods Preserve

Beautifully maintained and updated 3-bedroom, 2.5-bath condominium in the desirable Southampton Commons community. This light-filled two-story residence features an open floor plan with spacious living and dining areas, an updated eat-in kitchen with granite countertops, stainless steel appliances, and a bay window. The sun-filled living room offers a wood-burning fireplace and access to a private patio surrounded by mature landscaping. The first floor also includes a powder room, laundry area, and additional storage space. Upstairs, the primary suite features multiple closets and an updated en-suite bath with double vanities and a walk-in shower. Two additional bedrooms share an updated full bath. A skylight provides abundant natural light throughout the second level. Community amenities include heated swimming pools, clubhouse with fitness facilities, tennis courts, pickleball courts, golf practice area, and bocce courts. Conveniently located near Southampton Village, ocean beaches,

Step into the timeless charm of this adorable 1950s beach cottage, where character meets coastal living. This inviting one bedroom, one bath home features soaring high ceilings that create a bright, airy feel and make the space live larger than its footprint. Perfectly situated in a highly desirable location, you're just moments from the beach, local shops, restaurants, and everything that makes coastal living so special. Whether you're looking for a weekend getaway, full time residence or investment opportunity, this cottage offers endless possibilities

Discover chic style and easy living in this beautifully renovated turn-key home, nestled within Sag Harbor Village's prestigious waterfront community. Every detail of this residence has been meticulously considered for maximum enjoyment. The upper level welcomes you with an airy and open floor plan, bathed in natural light. A chic modern chef's kitchen awaits, flowing into a sun-filled great room. Perfect for entertaining. This level also features two bedrooms and a newly renovated bathroom complete with a luxurious soaking tub and spa shower. Downstairs is an inviting retreat, offering a comfortable bedroom, another pristine bathroom, and a versatile bonus room. Gather in the recreation/media room or cozy up by the fireplace, and enjoy the seamless transition outdoors via full walk-out sliders to the yard and bluestone patio. A dedicated laundry area adds to the convenience. Step outside to your private paradise. Off the kitchen, a second-story deck provides elevated views of the mani

Set along the water on one of Sag Harbor Village's most storied streets, this exceptional Captain's Row estate unfolds across nearly. 60 +/. Acres of beautifully landscaped grounds. Built circa 1850, this beautifully restored and renovated Greek Revival Sag Harbor waterfront home sits directly on Main Street with frontage on Otter Pond and views toward Upper Sag Harbor Cove. Mature trees, rolling lawns, hydrangeas and established gardens surround the residence, pool and spa, and multiple structures, creating a private waterfront setting just moments from the center of the Village. Expanded with architect Anthony Vermandois, the 2,670 +/-SF residence offers four bedrooms, five full baths and one-half bath, complemented by a separate 406 +/-SF studio and a 157 +/-SF pool house. A gracious covered front porch welcomes you into the home, where original wide-plank wood floors, period architectural details and seven working fireplaces lend warmth and a sense of history throughout. The main l

Huge potential. This turn of the 20th century gem was the residence of a single family through generations since its inception! A Queen Anne style house with its classic front gable and massive covered front porch invokes grandeur of times past as it sits prominently on prestigious Lumber Lane. Much of the original detail has been maintained including millwork, windows, doors, staircase, siding, structure, and the bones of this grand dame appear of high integrity. Collectors often favor a little patina over a flurry of modifications de jour. Such is the case with this roughly 2,100 sf residence, currently configured as two-family home, offering 4 bedrooms, 2 baths, 2 kitchens, 8’8” first floor and 8’4” second floor ceiling heights. In addition, the “1/2 story” attic with four dormers adorned with large leaded glass windows facing in each direction of the compass can stir one’s imagination of what it could become. 119 Lumber Ln located in the heart of Bridgehampton is a short distance f

Nestled on a quiet corner lot in the heart of Sag Harbor Village, this beautifully designed 3-bedroom with potential for a 4th bedroom, 3.5-bath home offers the perfect blend of luxury, comfort, and coastal charm. Thoughtfully crafted with an open floor plan and soaring 9-foot ceilings, the home is centered around a dramatic living room open to above, complete with a wood-burning fireplace and gas hookup option for added convenience. The first-floor primary suite is a private retreat featuring direct access to the expansive mahogany deck and a spa-inspired bath with an antique clawfoot tub, oversized walk-in steam shower, marble bench seating, and multiple body sprays. The chef’s kitchen flows seamlessly into the living and dining areas, creating an ideal space for entertaining and everyday living. Upstairs, a loft overlooking the main living space adds architectural interest and flexibility, while two additional bedrooms share a spacious bath with full tub. A cozy reading nook and add

Welcome to 9 Marsden Street in Sag Harbor Village. With a historic aesthetic and sophistication for modern living, this BJC Custom Builders residence sits on approximately 0.8 acre-an exceptionally generous setting in Sag Harbor Village. Offered fully furnished, thoughtfully curated, and professionally designed, the home encompasses approximately 7,000 square feet across three levels. A custom Ciuffo chef's kitchen anchors the living spaces, complemented by a gracious great room, formal dining and a separate, private family room. A main-floor primary bedroom offers flexibility, while five upstairs bedrooms include an expansive primary suite featuring a private balcony, fireplace, and spa-inspired bath. The lower level abounds with an expansive rec room and showcase bar with exquisite finish. A gym with wellness and 2 guest rooms complete. Outside, the park-like grounds create a setting for entertaining and relaxation, with an oversized pool, spa, and pool cabana with fireplace, wet bar

An Exceptional opportunity at 115 Huntington Crossway to create a custom Hamptons residence in one of Bridgehampton's increasingly sought-after pockets. Situated on approximately half an acre, this R-20 zoned property presents compelling potential for builders, investors, or end users looking to design and build a new construction home in a location experiencing significant redevelopment and new-construction activity. The property is improved with an existing 3-bedroom, 2-bath residence along with a full basement, however the true opportunity lies in the land and its potential for redevelopment. Huntington Crossway has become an increasingly attractive destination for new construction, with multiple properties in the immediate area being acquired, redeveloped, and transformed into luxury new-construction residences. Ideally located between Bridgehampton and Sag Harbor, the property offers convenient access to Bridgehampton Village, Sag Harbor's Main Street, world-class dining, shopping

Builder owned, beautifully renovated Townhome. When you enter this beautifully renovated and immaculate 2,904+/. Sq. ft. (2000 above ground 900 below ground) 3 level townhome with three bedrooms and three full baths, which is extremely rare for Southampton with this much space, you will be thoroughly delighted. It is bright, welcoming and very tastefully finished and appointed. Health conscious buyers will also appreciate the whole house water filter. The first floor serves as a great room, including a bright living room with gas fireplace, open dining, and an upgraded eat-in kitchen featuring stainless steel appliances, quartz countertops and backsplash, with seating at a quartz counter height peninsula. The ample dining area has a door leading to the spacious patio, hot tub and garage. The outdoor space is roomy enough for dining al fresco, relaxing and cooking, and it's landscaped for privacy and has a wonderful spa. Whether you are outside or indoors, this is a wonderful entertaini

Discover a rare opportunity to own a contemporary home in the heart of Water Mill, NY, set on a beautifully landscaped 0.50± acre property with room for expansion. This stylish 3 bedroom, 2 bath home offers soaring ceilings and an open, light-filled layout ideal for both year-round living and Hamptons summer entertaining. The main level features a well appointed kitchen, spacious den with a wood burning fireplace, laundry room, full bathroom, and two bedrooms-one with sliding glass doors leading to the back deck, creating seamless indoor-outdoor living. The primary suite occupies the upper level, complete with a soaking tub, dual shower, walk in closet, and a versatile flex space ideal for a home office, gym, or lounge area. Additional highlights include a two car garage with high ceilings and a full basement with an egress window. Architectural plans are already in place to finish the approximately 1,200 sq ft lower level and add an additional bedroom & bathroom. A brand new heated gu

Experience elevated Hamptons living in this newly constructed custom estate on a private 0.75-acre flag lot in one of Southampton's most desirable locations. Thoughtfully designed with over 7,500 square feet across three finished levels, this 8-bedroom, 7 full and 2 half bath residence seamlessly blends timeless craftsmanship with cutting-edge technology, creating the ultimate luxury retreat. A dramatic custom floating staircase welcomes you into light-filled living spaces finished with wide-plank white oak flooring, bespoke millwork, designer stonework, and curated architectural details throughout. The chef's kitchen is appointed with a premium Sub-Zero/Wolf appliance package, while multiple entertaining areas flow effortlessly to the expansive outdoor living spaces. The home features three gas fireplaces, a fully integrated Savant smart home system, Lutron lighting, whole-home audio, a dedicated home theater with a Sony 4K laser projector and 130-inch screen, Origin Acoustics surroun

Just completed and set on 1.63 acres in the heart of Bridgehampton, this brand-new estate at 225 Norris Lane delivers the ultimate Hamptons lifestyle—where modern luxury, scale, and resort-level amenities converge across 10,000 square feet of meticulously crafted living space. A long, private approach opens to a classic yet refined exterior, wrapped in cedar shingles and framed by manicured grounds. Inside, soaring ceilings and walls of glass flood the home with natural light, creating an effortless flow between formal entertaining spaces and relaxed everyday living. Wide-plank oak floors, custom millwork, and curated designer finishes set the tone throughout. The chef’s kitchen is a true showpiece—anchored by a substantial center island, marble slab backsplash, custom cabinetry, and top-tier appliances—seamlessly opening to the great room and outdoor entertaining areas. Oversized sliding glass doors lead to a covered patio and expansive backyard, blurring the line between indoor and o

Approved to be built for 3,843 square feet new residential single-family home in Sag Harbor Village Suffolk County Department of Health for septic system and Sag Harbor Village Architectural Review Board approved plans. Designed by renowned Hamptons architect Peter Cook, 69 Hillside Drive has an enviable location and inspired design ready to deliver the best of luxury living in the Hamptons. Just moments from Main Street and with a short walking distance to private Nineveh Beach access, this prime property offers both convenience and coastal charm with a chic contemporary style home boasting 3,843 +/. Sq. ft. (Including the fully finished lower level), 5 bedrooms, 5 full baths and 2 half baths, 10'x'20 in ground pool and pool house. Enter an elegant open-concept floor plan with large windows that beam light from the rear grounds. The main level includes a large eat-in kitchen, dedicated dining space, large great room, and first-floor ensuite jr. Primary. Ready for entertaining and ever

Introducing a one-of-a-kind opportunity to own a legacy estate south of the highway in Bridgehampton’s farm country—120 Halsey Lane. This newly constructed, fully custom 14,267-square-foot residence is set on 2.5 lush acres and promises the pinnacle of Hamptons living. Newly Completed and Move in Ready, this architectural masterpiece offers 9 bedrooms, 11 full bathrooms, and 3 half baths, designed to seamlessly blend modern luxury with timeless shingle-style elegance. Step inside to soaring spaces and grand proportions—an awe-inspiring 26’ tall great room sets the tone for the rest of the home. Every inch of the layout has been thoughtfully curated: two true primary suites, one conveniently located on the main level and the other as a second-floor sanctuary complete with a private deck. From the oversized 3-car garage to the two elegant staircases and private elevator, no detail is overlooked. The lower level is an entertainer’s dream featuring an 11’ ceiling height, a golf simulator,

The Cotswolds meets the Hamptons in this extraordinary property, gracefully set on a secluded acre in the coveted Hamptons Farm Estates section of Bridgehampton. Rich in character and timeless elegance, this exceptional home seamlessly blends old-world craftsmanship with refined Hamptons luxury. The beautifully appointed four-bedroom, three-full and one-half bath residence is designed for effortless living and sophisticated entertaining. At its center is a spectacular chef's kitchen featuring new premium appliances, including a Wolf six-burner range with griddle, double wall ovens, two dishwashers, a large farmhouse sink, an additional prep sink, and a wine refrigerator. A stunning marble center island is complemented by elegant soapstone perimeter countertops, creating a kitchen that is as beautiful as it is functional. Throughout the main level, rich reclaimed wood flooring from Gibraltar lends warmth, history, and an unmistakable sense of authenticity. The inviting living room is an

This 8-bedroom, 9.5-bath, industrial modern barn built and designed by celebrity lifestyle restaurateur William Jack Degel, is located on 1.83 acres in Watermill's pristine horse country. The outdoor oasis features a 2,000 square feet covered outdoor living space with a full kitchen, fridge, pantry, bar, lounge, fireplace, and dining area. A private vineyard named FORCYNTHIA showcases Wolffer grapes and picnic tables. Adjacent is the 50’ long by 20’ wide gunite saltwater pool, 10 by 10 raised spa, a sunken all-weather pickleball sports court, 700 hedges 1,200 seasonal flowering perennials, 12 flowering trees, and 300 privacy trees. Additional highlights include remote control window treatments, 5/8 Gypsum wallboard and ceilings, LED lighting, central vac, an all-natural aromatherapy system, solar panels, Toto/Kohler bathroom fixtures, and full smart home automation through Control4, custom vanities, and a 20 kW Kohler generator. The first floor of the home features the state-of-the-art

Built by one of the Hamptons' most respected builders and refined by an award-winning Manhattan design firm, this masterfully crafted, just-completed residence sets a new standard for Hamptons living. Set along a private access road, the property offers sweeping open-field reserve views that feel worlds away — yet convenient to farm stands, village shops, restaurants, and world-class beaches. Spanning nearly 10,000 square feet across three impeccably finished levels served by a private elevator, the estate offers eight bedrooms, ten full baths, and two half baths — striking an ideal balance between grand-scale entertaining and intimate serenity. A dramatic double-height foyer floods the entrance with natural light, while exquisite millwork and graceful architectural detail set a warm, welcoming tone throughout. The living room features oak ceiling beams and a finely finished double-sided fireplace that opens to an inviting den. Glass doors line the rear of the home, where the beautiful

Discover the possibilities with this 3-bedroom, 2-bath ranch on nearly an acre at the end of a quiet cul-de-sac in Jamesport. Offered by its original owner, this property offers privacy, generous outdoor space, and a peaceful natural setting. Inside, enjoy an open layout with cathedral ceilings and skylights, plus a full basement and attached garage. Convenient to North Fork wineries, beaches, farm stands, restaurants, and shopping, this is a rare opportunity to own a spacious property in a sought-after location and create a home that reflects your vision

Set in the peaceful North Sea area of Southampton, with access on both Big Fresh Pond Road and Beechwood Drive and minutes from the vibrant village of Sag Harbor, this property offers a rare opportunity to create a private retreat in a naturally beautiful setting. Surrounded by tranquil landscapes, mature greenery, and the serene waters of Big Fresh Pond, the property offers a wonderful sense of privacy while remaining close to the beaches, restaurants, shops, and all that both Sag Harbor and Southampton Village has to offer. The existing structure is ready for renovation. The ideal opportunity to make it your own! With its sought-after setting, generous grounds, and access to the water, this property presents a rare development chance to create a truly unique Hamptons abode. Whether envisioned as a private compound, weekend escape, or custom-designed retreat, this could be your chance to bring your ideal home vision to one of Southampton's most desirable and increasingly coveted areas

Water Mill Opportunity. Customize Your Dream Hamptons Retreat! An exceptional opportunity to create your own Hamptons retreat in the coveted hamlet of Water Mill. Home is being sold as is and buyer is to assume completion of the property and all permits. This three-bedroom, two-bathroom residence offers a head start on your vision, with the exterior completed and a swimming pool already in place. The interior remains unfinished, presenting a rare opportunity for the next owner to customize the living spaces, finishes, and details to their personal taste. With the groundwork already established, this property offers the potential to transform an existing structure into a personalized getaway or year-round residence. Enjoy the appeal of Water Mill and the opportunity to bring your vision to life in one of the Hamptons' most desirable locations

Set on. 97 acres in Sag Harbor, this three-bedroom, two-bathroom home offers more than 2,500 square feet of space surrounded by immaculate gardens and beautifully maintained grounds. Enjoy room to relax, entertain, and take in the peaceful setting-all in a sought-after Sag Harbor location

Welcome to this exceptional Hamptons retreat in Southamptons North Sea area, set on just shy of two private, beautifully landscaped acres. Mature landscaping creates a serene and secluded setting for the oversized saline pool, surrounded by approximately 60 feet of mahogany decking and a poolside gazeboperfect for entertaining, relaxing, and enjoying the outdoors.Inside, the open-concept layout features soaring ceilings, gleaming hardwood floors, and abundant natural light. The living room, anchored by a gas-burning fireplace, offers a warm and inviting space to unwind, while the first floor includes two guest bedrooms with a full bath and a charming family room tucked into a quiet corner of the home.At the heart of the home, the well-appointed kitchen combines style and function with premium appliances, custom cabinetry, granite countertops, and a generous island with ample seating and storage. The elegant formal dining area is equally suited to intimate family dinners or larger gathe

Shelter Island Waterfront with Dock. A rare opportunity to own waterfront in Silver Beach, one of Shelter Island’s most beautiful and sought-after enclaves. Set directly on the tranquil Silver Beach lagoon, this four-bedroom, 2.5-bath home offers approximately 2,289 square feet on a private. 76-acre property with approximately 102 feet of waterfront frontage—all just a five-minute walk to beautiful Silver Beach. The home has a distinctive character, combining comfortable interiors, hardwood floors and an abundance of natural light with wonderful water and landscape views from both levels. The kitchen and baths are fully functional and well maintained, while the home’s more traditional finishes offer an opportunity for a new owner to update and personalize the style over time. The waterfront setting is the true centerpiece. An expansive lawn framed by mature trees leads to the canal and an approximately 20-foot grandfathered dock with water and electric, creating direct access for boati

Welcome to 8 Railroad Avenue, a haven of comfort and convenience nestled in the heart of Jamesport. This 2-bedroom, 2-bathroom residence boasts a new roof, siding, and gutters, promising a worry-free living experience. The secluded backyard is a personal oasis, complete with a pool featuring a new lining and energy-efficient pump. A gazebo and Trex deck offer the perfect spots for relaxation, while the 1500 square foot putting green, pickleball court, and basketball court invite fun and games. This is not a land lease. Just a stone's throw away, you'll find a picturesque marina, tennis courts, and a stunning sugar sand beach. The North Fork region, renowned for its wineries, fresh produce, and diverse dining options, is right at your doorstep. With its low taxes, this home is a smart investment in a lifestyle of leisure and pleasure. Whether you're a beach lover, a sports enthusiast, or someone who enjoys the finer things in life, 8 Railroad Avenue is a place where every day feels like