433 properties for sale in Southold

Welcome to 650 Grove Dr, a delightful 4-bedroom, 2-bathroom home nestled in the heart of the popular Reydon Shores community. This cherished, well-established residence offers a slight water view from the comfort of your living room and two upstairs bedrooms. The main level features a cozy bedroom, a full bathroom equipped with a washer and dryer, and an inviting eat-in kitchen and a dining room perfect for hosting memorable meals. Ascend to the upper level to find three more spacious bedrooms and another full bathroom. Step outside to experience the charm of the private beach community, complete with a marina and a beach just around the corner. This home, filled with endless memories of great summers, is an opportunity to create your own cherished moments. Experience the best of what the North Fork has to offer in this welcoming community where the sea meets the sky. Let the tranquility of 650 Grove Dr become your everyday reality

Welcome to this corner residence at Founders Village, where easy, low-maintenance living meets the North Fork lifestyle. This 1,200-square-foot home offers 2 bedrooms, 2 full baths and a full basement, giving you valuable storage and extra space that can be hard to find when downsizing to condominium living. The corner location provides added green space on multiple sides, along with a rear patio that creates a comfortable spot to relax outdoors. Inside, you’ll find wood floors, an eat-in kitchen with newer appliances, comfortable living and dining areas, and high ceilings that create a real open home feel. Residents enjoy a community pool, clubhouse and beautifully maintained grounds. A stroll down the sidewalk leads toward Southold Village, with local shops, restaurants, the LIRR and Hampton Jitney all nearby. Beach access is another added benefit. The property qualifies for both Southold Town and a Southold Park District beach parking permits, offering even more opportunity to enjoy

Miami modernism meets the north fork. Set on a spacious and private. 60-acre hilltop parcel in coveted Nassau Point, this fully updated four-bedroom modernist ranch offers an unexpected departure from the ordinary. Its traditional exterior gives little indication of the sleek, light-filled interiors within—an independently conceived home with the confident glamour of Miami and the relaxed ease of Cutchogue. Individual design matters. Rather than repeating a familiar, cookie-cutter floor plan, this residence has an architectural identity all its own, expressed through gleaming white marble floors, clean lines, generously proportioned rooms and a seamless connection between indoor and outdoor living. The result feels distinctive, sophisticated and refreshingly personal. At the heart of the home is a spectacular chef’s kitchen designed for serious cooking and effortless entertaining. It opens to a private garden courtyard, creating an intimate setting for morning coffee, outdoor dining or

Charming, private, and uniquely connected to the water, this cedar-shingled three-bedroom cottage offers a compelling combination of immediate enjoyment and future potential. Set on nearly an acre, the property includes a 50' wide section that extends to the bay, where a beachside double deck and stairs provide direct access to your private stretch of sandy beach. Inside, the living room is anchored by a beautiful fireplace and opens to a brick patio, creating an easy flow between indoor and outdoor living. Wrapped in glass, the sunroom addition serves as a cozy retreat, immersing you in the property's natural surroundings. Multiple en-suite bedrooms round out the offering. Whether enjoyed as a quintessential North Fork getaway or expanded to create a larger coastal residence, the setting is exceptional. True private bayfront at a price point that rarely exists

Set within the coveted enclave of Nassau Point, this exceptional 4,000-square-foot retreat offers privacy, timeless architecture, and an elevated North Fork lifestyle. Positioned on a shy acre with plenty of room for a pool, this beautifully designed home is crafted for effortless year-round living and entertaining. A dramatic Great Room with cathedral ceilings and wood floors anchors the residence, complemented by a chef’s kitchen, den, reading room, game room with wet bar, billiard room, wine cellar, and private second-floor primary suite with office. The home’s generous and versatile layout offers exceptional flexibility for separate guest quarters, extended living arrangements, or the potential for an owner-occupied accessory rental, subject to all applicable municipal approvals and permitting. Wraparound decks, lush gardens, a four-car garage, and full-house generator complete the property. Just moments from the Peconic Bay, residents enjoy access to private bay beaches and rights

Steeped in history dating back to the early 1800s, this five-bedroom, two-bathroom home once served as the main farmhouse of an expansive agricultural tract. Set on two sprawling acres, the property features a large gambrel barn, sweeping lawns, and a white picket fence that complements its classic farmhouse charm. Surrounded by preserved farmland, this pastoral setting is conveniently located in the heart of Southold Hamlet

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 is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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

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 thoughtfully designed 4 bedroom, 4.5-bath townhouse offers the perfect balance of sophistication and comfort, with interiors crafted from the highest-quality materials and finishes.Spanning approximately 2, 450 sq. ft. across two levels, the residence features light-filled open living spaces, including a great room with fireplace, dining area, and a chef's kitchen outfitted with premium stainless steel appliances, quartz countertops, and a spacious island. The seamless layout is ideal for both everyday living and entertaining. Upstairs, generously sized bedrooms, spa-inspired baths, and elegant details create a serene retreat. An attached one-car garage provides convenience. Beyond your front door, the Watermill Crossing community delivers resort-style amenities. A beautifully designed clubhouse includes a fitness center, lounge with catering kitchen and bar, while outside a stone patio surrounds an oversized gunite pool and spa. Set on 6.4 manicured acres, the neighborhood is jus

Millfarm Lane on Reserve Perfectly positioned on Millfarm Lane, one of Water Mill's most desired and consistently appreciating locations, this classic Hamptons traditional home captures the absolute best of Hamptons living. Positioned on a pristine 0.73-acre lot, abutting a 20+ acre forever-protected agricultural reserve. The home's layout is perfectly aligned with a highly coveted southeastern backyard exposure, bathing the primary living spaces in brilliant natural light and guaranteeing maximum, unobstructed sun across the pool during peak summer months. Ready for immediate luxury living today and for generations to come, the home offers 6,530 +/. SF of total living space (including the unfinished lower level with egress that awaits your imagination), 4 bedrooms, 5.5 baths, a fireplace, an attached 2-car garage, and a heated saltwater gunite pool. Thoughtfully expanded and renovated since 2019, the turnkey home is highlighted by 9' ceilings, high-end moldings, and easy indoor-outdoo

Looking for the ultimate North Fork retreat near the beach? Look no further. This exceptional Colonial-style residence offers a spacious, sun-drenched floor plan designed for comfortable everyday living and effortless entertaining. Step inside to a bright, inviting interior with generous room sizes, abundant natural light, and an easy, flowing layout. The main level features an updated eat-in kitchen with granite countertops and French doors opening to a private patio—perfect for morning coffee or evening sunsets. Entertain in the formal dining room, relax in the cozy den, or gather in the light-filled formal living room, anchored by a warm fireplace. Upstairs, a welcoming landing and lounge area leads to three generously sized guest bedrooms and a private primary Master Bedroom suite retreat. The primary suite offers a private walk-out balcony, spacious walk-in closet, and ensuite bath with a dedicated makeup vanity. A skylight-filled full bathroom adds even more natural light and cha

Two lots are being sold together! 601 watermill towd road & 591 watermill towd road are being sold together! This beautiful, bright six-bedroom, two-full-bath home sits on 1.055a and features a circular driveway, expansive back yard, outdoor shower and charming garden. The entry foyer leads to the sunlit living room featuring a wood burning fireplace, built-ins and dramatic floor-to-ceiling windows. The expansive eat-in kitchen and spacious family room share an open floor plan. Together, they are perfectly designed for dining & entertaining. They boast a wood burning fireplace and 3 sets of french doors which lead out to the oversized deck. A guest bedroom and full bath complete the first floor. The second floor includes the primary bedroom plus 4 additional bedrooms and full bath. 591 watermill towd road, a single & separate buildable lot is included in this sale. The additional, single & separate. 355a buildable lot is perfect for a pool, pool house and/or tennis/pickleball court. Th

TURNKEY SAG HARBOR RETREAT WITH POOL AND HOT TUB Ready for immediate luxury living in 2026, just moments from Sag Harbor Village. This cedar-shake traditional offers a polished Hamptons setting with a pool, hot tub, and bright, beachy interiors. The 2-story home features 2,000 +/. SF of living space with 3 bedrooms, 2.5 baths, and radiant heated floors. The main level is designed for easy everyday living, with a spacious living room, comfortable den, and an eat-in kitchen with stainless steel appliances. A nearby dining area opens through glass doors to the rear patio, creating a natural connection to the outdoor entertaining spaces. Upstairs, the generous ensuite primary bedroom includes a renovated bath and walk-in closet, while two additional bedrooms share a full bath. Outside, the property is designed for classic Hamptons living, with sunny poolside lounging, al fresco dining, and evenings in the hot tub. Set just outside Sag Harbor Village, the home offers convenient access to vi

Legal Three-Family in the Heart of Sag Harbor Village Opportunities like this rarely come to market in Sag Harbor Village. Set within the Historic District, moments from Main Street and the harbor, this circa-1850 Greek Revival is a legal three-family residence, a use that cannot be newly created under today’s zoning. Approximately 2,959 sq ft across three self-contained apartments, each with two bedrooms, one bath and a separate entrance. The two upper units each have a private deck, with water views from the top level. The exterior was restored in 2023 with cedar shake siding, a historic full-width front porch and a Federal-style entry. A detached 1.5; -story accessory building of approx. 518 sq ft with a full bath and loft serves as a private home office, and a private driveway provides off-street parking. A piece of Sag Harbor’s history, with income potential that almost never comes to the village

Introducing a stunning new construction nestled in the heart of Southampton, this exquisite property offers the perfect blend of modern luxury and serene natural beauty. Situated on a generous 0.5-acre lot, this home boasts 4 spacious bedrooms and 5 elegantly designed bathrooms, providing ample space for comfort and relaxation. The property is uniquely positioned with protected reserve land as its backyard, ensuring privacy and breathtaking views of nature's untouched beauty. The open-concept living spaces are flooded with natural light, highlighting the high-end finishes and meticulous attention to detail throughout the home. The gourmet kitchen is a chef's dream, featuring top-of-the-line appliances and a large island perfect for entertaining. Each bedroom is a private retreat, with the master suite offering a spa-like bathroom. Step outside to enjoy the tranquility of the surrounding landscape, with plenty of space for outdoor entertaining or simply soaking in the peaceful ambiance.

An exceptional opportunity to create your dream Hamptons retreat at 195 Jermain Avenue. Located in desirable Sag Harbor Village, this property offers a rare blank canvas for buyers looking to bring their own vision to life. The main residence has already been gutted, providing a head start on a complete transformation with the freedom to design and finish the interiors to your own taste. Adding to the property's appeal is a legal secondary cottage with a half bathroom, ideal for a home office, or additional flexible space. The grounds offer potential for a swimming pool and beautifully landscaped outdoor entertaining areas, creating a private village oasis. Conveniently located near Sag Harbor's renowned restaurants, boutiques, marinas, and waterfront, 195 Jermain Avenue combines village charm with exciting possibilities. Bring your architect, your imagination, and your vision. The next chapter is yours to create

This immaculately maintained and beautifully decorated townhouse at The Courtyards is located just a short drive from Southampton Village, its restaurants, shops, and renowned ocean beaches. The first floor features a bright and open living room, dining area, updated kitchen, full bath, and sliders leading to a private patio with space for outdoor dining, lounging, and a hot tub for relaxing and rewinding. Upstairs, the spacious primary suite includes a large bath with shower and Jacuzzi tub plus a walk-in closet, along with two additional spacious bedrooms and a full bath. The fully finished lower level offers an infrared sauna, exercise area, sectional sofa for relaxing and watching TV, and laundry room. The condo includes a one car garage. The Courtyards community features a heated pool, cabana with changing room, and playground

Welcome to this Year round, Summertime Paradise/Winter retreat. UNIQUE Oversized Gorgeous 6 bedroom, 4 full bathroom estate nestled on a private cul-de-sac Located in the exclusive SEA COVE ESTATES community of South Jamesport. Situated on nearly half an acre. This impressive 3,847 square foot home offers the perfect blend of luxury, comfort, and resort-style living. The dramatic living room showcases soaring vaulted cathedral ceilings, electric blinds, and one side of a stunning double-sided fireplace, while the adjoining first-floor bedroom features the other side, creating warmth and character in both spaces. 2 brand new Bathrooms. Second floor bedrooms have decks providing a relaxing waterview of Peconic Bay. Designed for both everyday living and unforgettable entertaining, the backyard is a true private oasis featuring a 16 x 32 in-ground pool with an electric solar cover, a fully equipped outdoor kitchen, Trex deck, gazebo, retractable awning, outdoor shower, and beautifully land