437 properties for sale in Southold

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

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

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

Built in 2020, this 4-bedroom, 3.5-bath cedar-shingle home in East Marion pairs modern construction with extensive outdoor amenities, protected farmland views, and the Peconic Bay at the end of the street. Designed by landscape architects Marshall & Paetzel, the resort-style backyard features a 15x40 heated gunite pool with an electric cover and fiber-optic lighting, complemented by a private 5x15 hot tub with a soothing fountain and fully irrigated Zen garden. The custom poolside cabana offers motorized screens, a half bath, a bar with a sink, ice maker, and refrigerator, plus an outdoor shower that is served by its own tankless water heater. A 20x40 foot marble patio brings the outdoor entertaining space together with a built-in DCS grill and dedicated dining and lounging areas. Inside, a vaulted entry opens to the main level, where the dining room flows into the chef’s kitchen with an oversized island, Viking range, Sub-Zero refrigerator, Miele dishwasher, and wine refrigerator. The

Beautifully renovated ranch set on a manicured acre in a prime Mattituck location. This well-appointed 4-bedroom, 3-bath home offers a spacious and versatile layout, including a bonus room ideal for a home office and more! Two separate living rooms, each with its own fireplace, provide warm and inviting spaces for relaxing and entertaining. The eat-in kitchen features granite countertops and opens to a separate dining area, while the primary bedroom includes a private ensuite bath. Sliding doors lead to a beautiful outdoor oasis with covered patio and a heated, saltwater gunite plunge pool, surrounded by pristine gardens and mature landscaping. The legally finished lower level expands the living space with plenty of room for a playroom, media room, recreation area, and more. Ideally located near Love Lane shops and restaurants, amazing bay beaches, wineries, farm stands, and all that the North Fork has to offer, this turnkey Mattituck home offers the perfect combination of comfort and

Two legal residential single family homes, one exceptional mattituck opportunity. Discover a hard to find North Fork property offering two well-maintained residences on one lot. With an incredible 1,729 square foot three bedroom, two bath main house and a separate 500 square foot beautiful one bedroom, one bath house/cottage, this versatile offering provides options for personal enjoyment and rental income. Live in one residence and rent the other, or rent both out at the same time as an investment. Separate electric meters. The 1480 Factory Avenue house features a comfortable living room, a dedicated office, and an eat-in kitchen. Two bedrooms and a full bath are conveniently located on the first floor, with the third bedroom and second bath upstairs. Includes two spacious walk in closets. Central air conditioning adds comfort, while a large, full basement with good ceiling height and interior access offers valuable storage and utility space. The 1470 Factory Avenue custom architectur

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 tha

Built in 1910, this classic Greenport Village farmhouse offers something that is becoming increasingly hard to find in the Village by having an extra wide, extra deep lot with the space to truly create the backyard lifestyle you have been wanting. With an outdoor fireplace under the stars, long summer dinners, gardens, entertaining space, and afternoons spent soaking up the sun before heading down to 6th Street Beach at the end of the road to cool off with the breeze off the water. Inside, the home retains original woodwork and that inviting farmhouse feel. With a surprisingly adaptable floor plan this house has an open layout. The front living room flows through the dining room and into the large farmhouse kitchen, creating a direct sightline all the way to the backyard. Morning light fills the kitchen, which opens naturally to the outdoor space and makes the yard a great space for outdoor dinners after having lunch at the beach. A generously sized bedroom on the main floor is in dema

Welcome to a truly unique North Fork opportunity in the heart of Mattituck! This special property offers a charming 2-bedroom, 2-bath main residence along with a separate seasonal 2-bedroom, 1-bath cottage—perfect for guests, extended family, or additional seasonal possibilities. Enjoy access to a private dock, making it easy to embrace the best of waterfront living and spend your days out on the water. Ideally situated near Mattituck’s renowned vineyards, farm stands, beaches, restaurants, and all that the North Fork has to offer. Whether you’re searching for a year-round residence, weekend escape, or a property with incredible versatility, this one offers a rare combination of location, lifestyle, and opportunity. LB Not responsible for Info contained in the listing buyer must verify all info

Meticulously restored Craftsman on coveted Orchard Street in the heart of Orient Village. The private 0.55-acre lot offers an 18x40 heated in-ground pool, an original two-car garage and an outbuilding. A covered front porch opens to a welcoming foyer, which flows into a living room with a wood-burning fireplace and on to the dining room and eat-in kitchen. A mud room with laundry and a powder room complete the first floor. Upstairs is a primary suite with full bath and two additional bedrooms sharing a second full bath. Stroll to the village shops, country store, post office and yacht club, and enjoy the breezes off Orient Harbor

What surprised me is the option to consider a 2.7% assumable mortgage, a ownership member of the 2.5 acre beach and an updated home with updates and charm. The first thing I noticed about this house was actually the side entrance. There’s this casual mudroom entry with pieces of driftwood collected from the beach tucked around the railings, and it immediately gives the house that relaxed coastal cottage feeling. Inside, the morning light is probably one of my favorite things. The corner dining nook has windows on both sides, so the sunlight just pours into the room. From there, everything connects. The dining area opens visually to the kitchen, where the sink sits under a window looking out toward the outdoor dining table, and the living room is right there too. You can literally be cooking, sitting at the table or relaxing on the sofa and still see the TV. It’s a really comfortable layout for everyday living. The two bedrooms are nicely separated into the sleeping side of the house wi

This very well maintained 4 bedroom, 2 full bath home with detached 1+ car garage is set on a serene. 33 acre parcel that backs up to preserved land. A large bonus room upstairs with sink would make the perfect studio, hobby room or play room. Bay access with views of Shelter Island and the famous'Bug Light' lighthouse is located just. 4 mile at the end of Shipyard Lane. Close to all that the area has to offer. Vineyards, restaurants, quaint villages, golf and more. This home is the perfect North Fork getaway!

Top Location, very private contemporary home with panoramic vineyards and bay beach— Welcome to The Vineyard House nestled between Peconic Bay Vineyard and East Creek—one of Cutchogue’s most coveted coastal enclaves—where 1541 Stillwater Avenue offers an exceptional opportunity to own in a high-value North Fork location. A short stroll leads to Fleet's Neck and Pequash Beach, one of the finest stretches of bay shoreline on the North Fork. This transitional contemporary 4-bedroom, 3-full bath residence has been meticulously updated and is ideally positioned on a beautiful secluded property just shy of one acre, featuring stunning vineyard views, relaxing sunsets and room for a pool. The highly desirable layout features a skylit sunroom surrounded by nature, perfect for relaxation. The open floor plan features a spacious formal living room and library, with room for a piano, custom built in bookshelves and hardwood floors. A central dining room area leads to a separate den with a brick w

Tucked away on one of the most coveted streets in Greenport Village, 216 Broad Street is a classic two-bedroom farmhouse just waiting for its next chapter to begin. If you’ve been dreaming of a creative project where you can build equity and put your personal stamp on a piece of North Fork history, this is the'diamond in the rough' you’ve been searching for. Stepping inside, you’re greeted by the warmth of original wood floors and the kind of architectural character that simply can't be replicated in new builds. The layout feels cozy yet functional, featuring a large pantry that offers incredible potential for a custom culinary space. Out front, the adorable porch is the perfect spot to sit with a morning coffee and soak in the breeze, while the expansive, private backyard serves as your own secret garden. The property even includes an accessory building—a blank canvas waiting for your imagination to turn it into a studio, workshop, or a unique garden retreat. Opportunities like this i

Introducing an exceptional opportunity to own a truly turnkey, fully restored farmhouse-style two-family home in a prime Greenport Village location. 430 First Street features two meticulously updated residences, each offering three bedrooms, one full bathroom, and thoughtfully designed living spaces. The upper-level residence encompasses approximately 850 square feet and features soaring vaulted ceilings with decorative cross beams and an open-concept Great Room seamlessly connecting the kitchen, dining, and living areas. Three generously sized bedrooms, a full bathroom, and an in-unit washer and dryer complete the space. The main-level residence offers a similar layout with approximately 870 square feet of living space. Highlights include three bedrooms, one full bathroom, a spacious kitchen with vaulted ceilings, and separated living room, providing added flexibility and room to spread out. Outside, the property is equally impressive, with meticulously maintained landscaping, a newly

Charming updated Soundfront beach house! This home is what dreams are made of. Steps away is a plush, powder white sandy path leading to a serene private beach where panoramic vistas and mesmerizing sunsets will sweep you off your feet. Offering approximately 1,600 sq. Ft. of living space, the first level boasts an eat-in-kitchen, living room with fireplace to cozy up to during those brisk fall evenings, access to a 110 sq. Ft. screened-in porch. Perfect for enjoying your morning coffee, a family room/dining area with soaring pitched ceilings, a full bath, laundry room and a bonus room that is currently used as a bedroom. Two additional bedrooms are located on the second floor. Both with water views. There is also a new HVAC system in place. A multitude of opportunities await. This property is also offered as a compound. See 3645 Soundview Ave

Welcome home to an unparalleled North Fork retreat located on over 2 acres, nestled at the end of a winding stone driveway. This striking new construction farmhouse perfectly blends sophisticated craftsmanship with the casual elegance of coastal country living. Spanning approximately 3,000 square feet, the open layout features four spacious bedrooms and 4.5 beautifully appointed bathrooms. Designed for ultimate flexibility, the home boasts two luxurious primary suites—one conveniently located on the first floor and a second on the upper level. The full basement with direct outside access, offers an ideal canvas for a custom home gym, media room, or a private wine cellar. The home’s impressive exterior design seamlessly gives way to an outdoor entertainment oasis. Hidden behind a lush border of mature trees, the sprawling, professionally landscaped grounds feature a heated saltwater pool and a dedicated chiminea area for cozy evening gatherings. You can spend your days relaxing under th

Welcome home to this four-bedroom two and and half bath expanded ranch style-home in the coveted Highland Estates section of Cutchogue. This corner property is set on 0.92 acres of flat landscaped property, which offers effortless indoor and outdoor living. The open concept kitchen has both Silestone and Butcher block countertops with modern floating shelves, ample cabinetry, white tiled backsplash and adequate prep space. 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 generates the perfect space for relaxation and entertaining. There is a large family room, complete vaulted ceilings and a wood burning fireplace. Two additional upper level bedrooms and a full bathroom with walk in shower with glass surround, 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-pi

Introducing Bay Breeze Veranda, a one-of-a-kind luxury custom build set within a coveted coastal enclave in one of the North Fork’s most desirable and high-value communities. Privately positioned on a shy one-acre corner lot in Cutchogue, this exceptional 5-bedroom, 6-bath residence captures the essence of refined coastal living with extraordinary attention to craftsmanship, scale, and design. From the moment you arrive, Bay Breeze Veranda makes a statement. Thoughtfully conceived for both sophisticated entertaining and effortless everyday living, the home blends timeless architectural character with elevated modern amenities and an unmistakable sense of place. The spacious interiors are filled with natural light and designed to create a seamless connection between indoors and out. Generous living spaces, beautifully appointed finishes, and custom details throughout reflect the quality and individuality of this exceptional residence. At the heart of the home, an upscale chef kitchen fe

South of the Boulevard! Location, location, location. Just 370 feet from a beautiful sandy private bay beach. This 3 bedroom, 2 bath split entry/high ranch home, awaiting your vision, boasts a heated in-ground pool, walk out basement and large outdoor shower. A seasonally lifeguarded beach with park area and playground is right around the corner. Located close to a Jitney stop, wineries, boating, restaurants, golf and shopping, this would make the perfect north fork beach getaway. Come and see the big potential in this home!

Charming 2-bedroom, 1-bath home in desirable Cutchogue, featuring an attached 2-car garage and room for a pool. A wonderful opportunity to make it your own, with potential to expand, upgrade, and design to suit your vision. Close to restaurants, beaches, and North Fork vineyards

Space to Dream. Winter Water Views. Your North Fork Chapter. Welcome to 185 Holden Avenue in Cutchogue, where a generous property and a desirable coastal location create an opportunity to make North Fork living your own. Situated on one of the largest available parcels in the Fleets Neck area, this four-bedroom, two-bath multi level home offers an elevated setting, winter water views, and an expansive yard within the Mattituck-Cutchogue School District. The outdoor space sets the stage. A spacious new paver patio welcomes summer barbecues, celebrations, and quiet evenings under the stars, while the sprawling lawn offers room for sports, gardening, and outdoor relaxation. With space to explore adding a pool, subject to required approvals, the property invites you to imagine a backyard retreat shaped around the way you live. A short walk brings you to the marina and some of the East End’s most beautiful beaches. The property also includes rights to keep either a kayak or Sunfish at the c

Now is your chance to own a piece of Mattituck, just minutes from Love Lane. This unique farmhouse offers character, potential, and flexibility, with zoning for both residential and professional use (RO). Step inside to a welcoming central hallway leading to two private rooms, one with a fireplace, plus a powder room and bright enclosed porch/mudroom. Hardwood flooring adds warmth and character. Upstairs, a spacious loft-style layout features vaulted ceilings, ambient lighting, an open living area, kitchen, bedroom, and full bathroom. A rear deck adds outdoor living space, while the full basement provides additional storage. Improvements include updated electric, two zone heating, central air conditioning, security system, and septic improvements. Ideally located near Love Lane, shops, restaurants, farm stands, wineries, and everything the North Fork has to offer. Low taxes complete this unique opportunity. Whether you’re looking for a full time residence, a home with office space, or

Welcome to 1320 Breakwater Road, where modern elegance meets the relaxed coastal charm of Long Island’s North Fork. Situated on 1.08 acres of beautifully maintained, level property in the heart of Mattituck, this completely renovated 5-bedroom, 2.5-bathroom residence offers approximately 3,000 square feet of thoughtfully designed living space, combining contemporary finishes with warmth, comfort, and exceptional versatility. Step inside to discover a bright, open-concept layout where natural light pours through brand-new windows, seamlessly connecting the spacious living room, dining area, and beautifully appointed kitchen. A charming wood-burning fireplace adds warmth and character, while generously sized bedrooms provide comfort and privacy throughout. A spacious two-car garage with impressive ceiling height adds convenience and flexibility. An expansive 2,200 square-foot unfinished basement with confirmed 8-foot ceilings offers tremendous potential for future recreational space, a h

Just add a farm stand to this prime high-visibility Peconic location! Set on 1.22 acres, this classic three-bedroom, one-and-a-half-bath home has the space and character that makes country living so appealing. Gorgeous vineyard views, great flexibility with a 3 bay garage perfect for a workshop, greenhouse, or storing vehicles. Owned solar panels also add to the ease of this property. A true North Fork original farmhouse with plenty of room to create memories and enjoy the North Fork country life. Could be you!

Discover the charm of North Fork living at 715 Bray Avenue, ideally situated in the heart of Laurel. Set on over half an acre adjacent to Hortons Creek, this inviting 3-bedroom, 1-bath ranch offers a wonderful blend of comfort, versatility, and coastal charm. Beyond its welcoming living spaces, the home features multiple bonus areas, providing endless possibilities for a home office, creative studio, recreation space, or whatever best suits your lifestyle. Adding to the property's appeal is a detached two-car garage, a greenhouse (hothouse) ideal for growing your own vegetables and plants, and multiple storage sheds, offering exceptional flexibility for hobbies, projects, and outdoor pursuits. The expansive grounds provide plenty of room to relax, entertain, garden, or potentially add a swimming pool, subject to necessary approvals, while enjoying the peaceful natural surroundings. With coveted beach rights, tranquil creek views, and convenient access to the North Fork's renowned viney