433 properties for sale in Southold

A beautifully preserved 19th-century Victorian home set in the heart of Orient Village. The large screened three-season porch opens onto a picturesque rear garden, perfect for entertaining. A detached garage, recently renovated with heat, A/C, and EV charging — currently an art studio, but fully functional as a garage with intact new garage doors. The first-floor features custom cabinetry, a formal dining room, original radiators, a powder room, and the screened porch. Upstairs are two bedrooms and a full bath. Both the front and rear gardens have been professionally landscaped. Just steps from the post office, Country Store, yacht club, marina, and bay and sound beaches

Quintessential North Fork Farmhouse and Barns on 23 acres. These two properties, with tremendous potential, consist of a 2 bedroom, 1 bath home with unfinished second floor that is awaiting its new improvements. A detached 2 car garage and two barns (30' x 60') & (28' x 60') open up to 21.8 acres of pristine farmland. The house and barns sit on 1.84 acres (1000-115-. 1) while the adjacent DRS farmland sits on 1.84 acres (1000-115-. 2). Sold as is. An adjacent property consisting of a 4 bedroom cape home on. 25 acre is also for sale MLS# 1073-

A pristine condition waterfront home completed in 2013 featuring a private deep water dock, exceptional westerly views of Deep Hole Creek and picture perfect sunsets. A spectacular waterfront property designed for relaxation and endless adventure. Boaters and water enthusiasts will love the private bulkhead and substantial deep-water dock, perfect for launching your boat for day trips or jump on your kayaks, wave runners and paddleboards right from your backyard. Climb aboard your boat and enjoy quick access to the Great Peconic Bay, allowing you to skip the traffic and cruise directly to world-class destinations like the Hamptons, Shelter Island, and Greenport. Every detail of this outdoor oasis maximizes your enjoyment, featuring a covered porch with ceiling fans, a spacious patio ideal for entertaining, and a built-in gas grill for outdoor cooking. After a day on the water, unwind in the luxurious hot tub or rinse off under the refreshing outdoor shower. Inside, an open-concept floo

There are houses with water views, and then there are houses where the water is the whole point. Located in a waterfront beach community with tennis and pickleball, 380 The Strand delivers the rare North Fork combination of waterfront, an elegant renovation, community amenities, and a setting that feels quietly removed from the world-while still being exactly where you want to be. Picture perfect with the kind of wide-open sunset views that make dinner plans feel beside the point. Lovingly reimagined and offered turnkey, it has the ease of a summer house with the finish and comfort to make it very hard to leave in September. The interiors are fresh, warm, and thoughtfully done-nothing fussy, nothing to'fix'. Just arrive, unpack, and settle into the rhythm of the North Fork. A garage adds welcome practicality, while the property offers room for a pool should one feel inclined to make a very good thing even better

Welcome to this special North Fork retreat, set on a quiet, private road in East Marion. Rebuilt from the foundation in 2005 in a timeless New England transitional style, this thoughtfully designed home offers generous spaces for everyday living, entertaining, and enjoying the seasons. A gracious, double-height entry with a handsome staircase welcomes you into the expansive first floor, where red oak floors and custom crown molding add warmth and classic detail. The open yet comfortably defined layout includes a living room with surround sound and a gas fireplace, an eat-in kitchen with solid wood cabinetry, Silestone countertops, and a gas range, a spacious and flexible dining room, home office, full bath, and a convenient mudroom with half bath and direct access to the two-car garage. Multiple doors open to the raised deck, patio, and pool, creating an easy connection between indoor and outdoor living. Upstairs, a long hall leads to three generously sized bedrooms, a full hall bath,

Perfectly positioned in the sought-after Fairway Farms community, this spacious 3,200-square-foot residence enjoys peaceful views overlooking the golf course while offering the best of North Fork living. Set on a beautifully landscaped 0.93-acre property, this home is just minutes from the charming hamlet of New Suffolk, Pequash Beach, vineyards, marinas, farm stands, and acclaimed restaurants. Designed for both comfortable everyday living and effortless entertaining, the home features five bedrooms, four full bathrooms, hardwood floors throughout, two fireplaces, an inviting eat-in kitchen, and a formal dining room. Bathed in natural light, the expansive enclosed porch offers a bright and inviting space to relax, dine, or entertain while taking in the tranquil views of the surrounding grounds and picturesque golf course. With walls of windows and an airy, open feel, it serves as a seamless extension of the home's living space and is sure to become a favorite gathering space. Step outs

Life on the North Fork doesn't get better than this! Set along the Long Island Sound in one of Southold's most desirable locations, this chic waterfront escape offers sweeping water views, sensational sunsets, and effortless coastal living. Renovated in 2016 and completely move-in ready, the home blends sophisticated style with relaxed comfort, creating the perfect setting for both entertaining and quiet moments by the sea. Thoughtful upgrades include radiant floor heating, ducted heating and cooling with remote access, marble countertops, updated mirrors and light fixtures, keyless entry, Sonos speakers, and a beautifully appointed chef's kitchen. The primary suite includes a gorgeous bathroom, featuring a sculptural egg-shaped soaking tub perfectly positioned to capture the sunset views, separate shower and double sinks. The primary also has an office nook, and custom walk-in closet. Outdoor living is at the heart of the property. An expansive sun deck provides ample space for dining

Welcome to this beautifully expanded three-bedroom, three-bath ranch set on a spacious. 82-acre lot, in prime Mattituck location offering comfort, privacy, and an exceptional array of amenities. The home features an extra-large first floor primary en-suite bedroom with walk-in closet plus a junior en-suite bedroom, providing flexible accommodations for family and guests. Hardwood floors throughout and all of the bathrooms and kitchen have been recently updated. The eat-in kitchen is equipped with GE Profile stainless steel appliances and elegant quartzite countertops. The inviting living room or dining room, however you want to use it features a wood burning fireplace with insert, creating a warm and welcoming atmosphere. Relax in the heated and air-conditioned four-season sunroom, with radiant heat flooring which is also featured in all bathrooms. Central air conditioning provides additional comfort throughout the home. Large garage with epoxy floors, provides room for your vehicles a

Located in the heart of Orient Village, across the street from the Yacht Club and near all Village amenities, this fully updated nineteenth-century home features a wrap-around front porch, original hardwood floors, three bedrooms, first & second floor full baths, and a large eat-in kitchen with original pantry. The home has a front and rear staircase and a glass pocket door between the living room and formal dining room. A pathway leads through the rear garden to a two-story accessory structure of approximately 1,714 square feet, currently used as an artist's studio and art storage. The grounds are professionally landscaped with mature plantings, a dining patio, and multiple seating areas. Rarely does a property this unique come to market in Orient Village, the crown jewel of the North Fork

What caught my attention at 216 Monsell Place is how much of the original Greenport farmhouse feeling is still here, but the house has evolved into a layout that works really well today. You start with that wide wraparound porch. I can immediately picture sitting out there with coffee in the morning or having a drink at the end of the day. Then you walk inside and the pine floors, wood-burning fireplace and natural character remind you why these older North Fork homes are so appealing in the first place. The kitchen feels fresh and updated with new appliances, but what I really noticed was the light. There is a full-glass door at the side entrance, and in the afternoon the sunlight comes right into the kitchen. It gives the room a completely different feel and connects it visually with the backyard. Upstairs, there are three bedrooms, and one of them has some really interesting ceiling details that you just don't expect until you walk into the room. There are built-in closets, a second

Huge Price adjustment! Bring your contractor and ideas. To 1520 Meday Avenue, a rare mid-century modern ranch built in 1977 and ideally located in the heart of Mattituck on Long Island’s coveted North Fork. Offering 5 bedrooms and 4 full bathrooms, this expansive residence combines classic architectural character with exceptional scale, privacy, and resort-style outdoor living on a shy half acre. Originally 2 combined lots. Designed around a striking central courtyard, the home is oriented to maximize natural light and views from nearly every room, creating a seamless connection between indoor and outdoor spaces. At the heart of the property lies a private in-ground pool, beautifully positioned within the courtyard and surrounded by a putting green—transforming the entire center of the home into a one-of-a-kind private retreat. Inside, the home features a spacious living room with fireplace, an open-concept kitchen, and a large dining room that together create an easy, flowing layout i

Just One Block from Peconic Bay | Coastal Ranch in Coveted Fleet’s Neck Beach A rare opportunity to own a home just one block from the sandy shoreline of Pequash Beach, with access to the beautiful stretch of coastline extending to private Fleet’s Neck Beach in Cutchogue. Set within one of the North Fork’s most desirable beach communities, this coastal ranch offers the perfect setting to embrace the best of waterfront living. Enjoy a lifestyle defined by sun, sand and the sea, with a new playground, lifeguard-protected swimming, boat dockage at Shagwong Marina, and seasonal sailboat races adding to the charm of this special community. Privately situated on a quiet corner lot, the property offers a spacious yard with plenty of room to create your own outdoor oasis, including the possibility of a future pool. Inside, a generous eat-in kitchen opens to a sunroom, while a formal dining room provides an inviting setting for entertaining. The cozy coastal living room is filled with natural l

Full of character, this historic farmhouse pairs the warmth of an older home with the comfort and functionality of a comprehensive renovation. The four-bedroom, three-bath residence has a welcoming, easygoing feel, with a layout that works equally well for everyday living and entertaining. A gracious wrap-around porch sets the tone, offering an inviting setting at all hours. Inside, sun-filled living spaces feature hardwood floors, a beautifully appointed kitchen with a large island, and a cozy living room. A first-floor bedroom and full bath provide added flexibility. Upstairs, the primary suite includes a private bath, while two additional bedrooms share a third full bath. Ideally situated moments from Mattituck Inlet and Love Lane's shops, restaurants, and amenities, the property offers charm, authenticity, and the ease of modern living

A home defined by a natural, organic aesthetic, meticulously restored with an appreciation for simplicity, texture, and timeless materials. The result is a residence that feels both refined and deeply connected to its surroundings, with mature landscaping offering privacy and a quiet retreat. Well-proportioned rooms and incredible natural light create an airy sense of space, while carefully preserved exposed beams, wide-plank pine floors, and beadboard detailing lend warmth and architectural character. The kitchen centers on a generous custom-made island, an AGA range, and a farmhouse sink, while the dining room is anchored by a sunny bay window and decorative plaster medallion. A cozy home office sits alongside a large living room at the west end of the first floor. Upstairs, a vaulted top-floor bedroom offers a private escape, complemented by two additional bedrooms. A full basement offers additional flexibility. Just a few blocks from the heart of Greenport Village and 5th Street Be

A rare and exceptional offering in the heart of Greenport—one of the only duplex-style properties of its kind on the North Fork—this fully turnkey property delivers a unique combination of lifestyle, flexibility, and proven income potential. Located within Greenport Village and offering approximately 3,376 square feet of living space, this back-to-back duplex features two fully independent, two-story residences, each with its own full basement, central air conditioning, and private living areas as well as two electric panels, two meters, two propane tanks and separate basements. Built approximately 7 years ago, the property offers the advantages of newer construction, including modern systems, efficient design, and low-maintenance living. The front residence offers 4 bedrooms and 2.5 baths, highlighted by a welcoming covered front porch, fireplace, and a full basement with 8-foot ceilings—ideal for expansion, recreation, or storage. The rear residence features 3 bedrooms and 2.5 baths,

Welcome to the heart of North Fork wine country! Located in a desirable Cutchogue neighborhood, this inviting 3-bedroom, 2.5-bath home offers the perfect opportunity to enjoy the best of North Fork living. Just a short walk to Cutchogue Hamlet, you'll love the convenience of nearby restaurants, farm stands, wineries, vineyards, beaches, golf, and boating. A beautiful mahogany front porch creates a warm and welcoming first impression, while side and rear stone patios provide wonderful spaces for outdoor entertaining, relaxing, and enjoying the peaceful surroundings. The spacious backyard offers plenty of room for a pool, garden, or creating your own outdoor oasis. Whether you're looking for a year-round residence, weekend retreat, or a place to enjoy the North Fork lifestyle, this property presents a wonderful opportunity in a sought-after location. Come experience all that Cutchogue has to offer!

Welcome to 402 5th Street, a 4 bedroom, 2 full bathroom historic Victorian located in the heart of west Dublin on a double lot, with plenty of room for an in-ground pool and just 3 blocks to a sandy bay beach. The home is also zoned to be converted to a 2-family dwelling. The residence offers original wide plank flooring, a large back deck and private back yard with a large shed. On the first floor, a side entrance leads to a formal kitchen, dining room, den or reading area and living room with a colossal fireplace. The second floor primary bedroom has a cathedral ceiling with skylights and plentiful amounts of natural light. There are three additional bedrooms, a full bathroom and separate exterior staircase leading to the second floor. The home is located a few blocks from the heart of Greenport Village

Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-century modern residence offers an extraordinary combination of waterfront, privacy, architectural character, and artistic location. Held in the same family for more than 50 years, the over 4000-square-foot home is set on two private acres overlooking the natural beauty of Great Pond. Expansive light-filled rooms, walls of glass and bold architectural lines create a residence that feels as compelling today as it was when first conceived. Mature landscaping, an inground pool, abundant wildlife and magnificent sunsets all contribute to the architectural composition. These features enhance the sense of retreat and home, while two beautiful Long Island Sound beaches—Kenney’s and McCabe’s—are just moments away. A true North Fork treasure, equal parts architectural time capsule and North Fork, grab this opportunity before it's

Some houses make an impression before you even reach the front door. Pulling up the gravel driveway, with that beautiful stone wall and the home’s striking architectural presence, you already want to see what’s inside. What caught my attention first were the windows. Their oversized proportions bring in wonderful natural light throughout the day, showing off the restored pine floors, original millwork and window seats. Wood-burning fireplaces give the living spaces a welcoming feel, and the screened porch off the second living room is one of those places where you can picture an afternoon turning into an evening. The four levels give this home a layout worth exploring. On the lower level, the den has glass sliders that bring in daylight and open to a garden path leading to the pool and patio. The second and third floors hold the bedrooms, with intriguing possibilities for thoughtfully reworking the layout to incorporate bedrooms with ensuite baths. Walking through, you start imagining

Welcome to 1175 9th Street in Greenport—a two-story, four-bedroom, three-and-a-half-bath with a full, finished basement with exterior staircase. The home is filled with natural light and hardwood floors throughout the main living spaces. The first floor offers an open living area with a wood-burning fireplace that flows into a spacious eat-in kitchen with a large island and sliding glass doors to the a secluded and private rear yard. Just off the entry, a formal dining room connects to the kitchen, and a hallway includes a conveniently placed half bath and pantry. Upstairs are four bedrooms, including a primary suite with an ensuite bath, plus a second full bathroom. In the winter months, two of the bedrooms enjoy views of the bay. The finished full basement adds flexible bonus space with a full bathroom, a dedicated laundry area with washer and dryer, and a walk-out staircase to the exterior side yard. Less than a half mile to 5th and 6th Street beach, park and dock and roughly three-

North Fork. Cutchogue. Create your ideal North Fork retreat in an extraordinary natural setting. This single story, four-bedroom home sits along the tranquil edge of West Creek in Cutchogue, offering the rare potential for water views and a front row seat to the area’s ever changing local wildlife. Whether you envision a thoughtful renovation or a completely new design, the property provides a canvas in one of the North Fork's desirable locations. Down the road, a 10' wide neighborhood only right-of-way leads to a 33' portion of a Bay beach. Sweeping vistas make every visit unforgettable. The New Suffolk Beach is only moments from your doorstep, and the North Fork Country Club sits just steps away, adding to the exceptional lifestyle this setting affords

Beautifully Upgraded Ranch with Exceptional Garage & Setting in Mattituck Welcome to this well-maintained 3-bedroom, 2-bath Ranch-style home, set on a rise in a desirable Mattituck setting with peaceful easterly views. The home is in excellent condition and features numerous recent upgrades, offering a comfortable blend of classic Ranch-style living and modern improvements. A large deck extends the living space outdoors, providing an ideal spot for relaxing, entertaining, or enjoying the tranquil views and natural surroundings on this half acre of property, the electric is supplemented by owned solar panels offering substantial savings to electric bill. One of the property’s standout features is the oversized detached 24'x32' 4+car garage, complete with heat, electric, 768 sq. Ft. —a rare and highly versatile amenity. Whether you need substantial space for vehicles, hobbies, a workshop, storage, or recreational equipment, this garage offers tremendous flexibility. Situated on a slightl

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

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

Highlights: Vintage 1963 home on 1.25 private acres. 4 bedrooms | 2.5 baths. Spacious, functional floor plan with endless potential. Formal living room plus separate den. Eat-in kitchen. Office/flex space on both the first and second floors. Abundant storage throughout. Full basement. Plenty of room for a pool (subject to permits). Close to local beache Built in 1963, this vintage home presents a rare opportunity to bring your vision to life. Set on a beautiful 1.25-acre parcel, the home features a generous and thoughtfully designed layout with four bedrooms, two-and-a-half baths, formal living and dining spaces, a separate den, an eat-in kitchen, and flexible office areas on both the first and second floors. Original details add character, while the spacious floor plan provides an exceptional foundation for renovation, restoration, or a complete reimagining. With ample room for a pool and possibilities both inside and out, this is a property where vision, design, and location come tog

Home Complete! Professional Photos Coming Soon. Exceptional new construction by well-known local builder set on. 42 acres with approximately 4,600 sq. Ft. offering 7 bedrooms and 6½ baths. Sophisticated design features include 10’ ceilings, 4” white oak floors, European windows, Cortizo doors, architectural roof, and Hardie Plank siding. Designer kitchen with Taj Mahal quartzite countertops, waterfall island, custom cabinetry, butler’s pantry, Thermador appliances, XO hood and wine refrigerator. Luxurious first-floor junior en suite and stunning second-floor primary suite with spa-like wet room, soaking tub, walk-in closet and mahogany balcony. Living room with gas fireplace, finished lower level, heated 18’ x 36’ in-ground pool, irrigation and professional landscaping. Detached two-car garage with overhead storage. A new construction offering space, style and sought after amenities. Close to 67 Steps Beach and moments from all that Greenport has to offer

Ready to Move In.New Construction Luxury Southold Home completed October 2026. Nestled in the prestigious Wildberry Fields, this new home blends coastal elegance with peaceful North Fork country living. Features 5,100+ SF of living space on 3 levels with 4 Bedrooms and 4.5 Bathrooms plus a bonus room/office over your attached 3 car garage. This stunning home has everything including a Giant front wrap-around-porch, heated saltwater 18x36 pool, outdoor shower and both first and second level primary bedrooms with ensuite baths. Every bedroom has large walk-in-closets. All high-end finishes were used throughout including Natural Alaskan Cedar Siding, Anderson 400 Series Windows, Luxury Appliances and Quartz Countertops, Wide Plank Natural White Oak Floors, Gas Fireplace, Custom Glass Shower Doors throughout, and more. Full Finished Basement with 9.5’ ceilings, Outside entrance to the lower level, full lower level bathroom, built in wine fridge, and luxury oversized double glass doors lead

Welcome to 275 Main Bayview in Southold, a warm and inviting home close to all the North Fork has to offer. This delightful Cape-style home boasts 3 spacious bedrooms, including a unique loft bedroom upstairs, and 2 bathrooms. Step inside and be greeted by a welcoming living room, complete with a cozy fireplace to warm those chilly nights. The expansive kitchen offers ample room for culinary adventures and leads conveniently into a dedicated laundry/mud room. Step outside to a serene back patio, perfect for dining or a morning cup of coffee. The backyard is a private haven, with an open view, surrounded by impressive rock walls at both the entrance and rear. This outdoor space is a testament to the beauty of nature, offering a peaceful retreat. The home's central location is a true highlight. You're just a stone's throw away from a variety of shops, wineries, restaurants, and beaches. As part of the Southold Town park district, you'll enjoy access to the picturesque Founders and South