Southold Homes for Sale

Welcome to Southold, NY, a charming town nestled in the heart of Suffolk County, where picturesque landscapes meet a vibrant community spirit. Known for its stunning vineyards, pristine beaches, and rich maritime heritage, Southold offers a unique blend of rural tranquility and coastal charm. One of the standout features of this idyllic location is its highly regarded school district, Southold Union Free School District, which is dedicated to providing quality education and fostering a nurturing environment for students.

The Southold School District is known for its commitment to academic excellence, offering a comprehensive curriculum tailored to meet the diverse needs of its students. With small class sizes, dedicated teachers, and a strong emphasis on community involvement, families can rest assured that their children will receive a well-rounded education. The district is home to modern facilities, extracurricular activities, and a supportive atmosphere that encourages student growth and achievement.

For those considering a move to this enchanting area, there are numerous homes for sale that cater to a variety of lifestyles. Whether you’re looking for a cozy cottage by the beach, a spacious family home with room to grow, or a charming farmhouse surrounded by lush greenery, Southold has something for everyone. With its close-knit community, beautiful scenery, and access to top-notch educational resources, Southold is not just a place to live; it's a place to thrive. Explore the homes for sale today and discover the perfect property to call your own in this delightful corner of New York!

Newest Southold Homes for Sale

$799,000

3 Beds ⋅ 2 Baths ⋅ 1044282 MLS

Welcome to 650 Greenfields Lane, an inviting ranch-style home on just shy an acre of property, nestled in the heart of Southold, NY. This charming residence offers three bedrooms, and two full bathrooms, which includes a primary en suite that overlooks the back yard. The home's cozy living room features a traditional fireplace, perfect for creating a warm and welcoming atmosphere. The eat-in kitchen and separate dining room provide an ideal setting for entertaining or enjoying a quiet meal at home. While this home has been loved for many years, it is ready for your personal touch and updates to make it your own. The property sits on just shy of an acre, offering plenty of room to explore and enjoy the outdoors. Beyond the home itself, discover the convenience of being centrally located it is less than a mile from the village shops, restaurants, and public transportation and close to all the beaches, wineries and parks. Envision the potential of making this house your home.

650 Greenfields Lane, Southold

$3,250,000

5 Beds ⋅ 5 Baths ⋅ 1048014 MLS

Known as The Old King Farmhouse and Owl Hollow, this historic 1.05± acre compound is one of Peconic’s most distinctive properties, pairing a beautifully preserved c.1860 Italianate Victorian residence with a remarkably purpose-built artist’s studio in the heart of the North Fork. Rich in history and thoughtfully stewarded over time, the approximately 3,260-square-foot residence offers four bedrooms and two-and-a-half baths while preserving many of its original architectural details, including period fireplaces, wide-plank wood floors, oversized windows, and graciously proportioned rooms filled with natural light. The interiors strike a rare balance between historic character and understated elegance, allowing the home’s craftsmanship and surrounding landscape to take center stage. Across the grounds, Owl Hollow serves as an extraordinary extension of the property. The approximately 1,200-square-foot studio is defined by soaring timber trusses, dramatic north-facing windows, a wood-burning fireplace, and its own Certificate of Occupancy, offering exceptional flexibility as an artist’s studio, creative workspace, guest retreat, entertaining pavilion, or wellness space. Set among mature specimen trees, clipped hedges, perennial gardens, and a fenced vegetable garden, the grounds unfold as a series of outdoor rooms centered around a heated 18’ x 36’ saltwater pool. A rare pre-existing, non-conforming wattle-and-daub stable offers additional storage or future possibilities, while separate driveways, updated utilities, new septic systems, rental permits, and separate Certificates of Occupancy further enhance the property’s versatility. Both the residence and studio have an established history as luxury rentals. Located in the bucolic hamlet of Peconic, moments from renowned vineyards, farm stands, beaches, and marinas, The Old King Farmhouse and Owl Hollow represent an increasingly rare opportunity to own a historic North Fork compound where architecture, landscape, and creative living exist in perfect harmony.

1200 Indian Neck Lane, Peconic

$2,950,000

4 Beds ⋅ 4 Baths ⋅ 963793 MLS

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 gone.

9305 Soundview Avenue, Southold

$574,999

3 Beds ⋅ 1 Baths ⋅ 1043112 MLS

Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious .39-acre property in the heart of the North Fork will not disappoint. Offering comfortable single-level living with plenty of potential, this home is a wonderful opportunity to enjoy everything the Southold lifestyle has to offer. Inside, you'll find a functional and inviting layout featuring a comfortable living area, three nicely sized bedrooms, a full bathroom, dining room and an eat-in kitchen. The full basement provides an abundance of additional space for storage, utilities, a workshop, or the potential for future finishing. A detached garage adds even more storage and convenience. Outside, the generous .39-acre property offers plenty of room to relax, entertain, garden, or create your ideal outdoor retreat. Conveniently located near Southold's charming village, local shops and restaurants, beaches, wineries, farm stands, and all that the North Fork has to offer. Whether you're looking for a year-round residence or a weekend getaway, 2600 Boisseau Avenue offers a fantastic opportunity to make Southold home! With taxes less than $5k, what more can you ask for?

2600 Boisseau Avenue, Southold

$3,295,000

4 Beds ⋅ 5 Baths ⋅ 1039113 MLS

New Construction Luxury Southold Home underway set to be complete September 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, and both first and second level primary bedrooms with ensuite baths and walk-in-closets. All high-end finishes were used throughout including Natural Alaskan Cedar Siding, Anderson Windows, Kitchen-Aid 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 basement entrance, full bathroom, built in wine fridge, and custom glass doors leading to your Gym and Custom Cedar Sauna. Enjoy exclusive Southold Park District rights—offering access to private beaches, kayak launches, and Founders Landing—while being just minutes from stunning Long Island Sound beaches, scenic Sound View Dunes, world-class vineyards, farm stands, and charming village dining.

390 Wildberry Lane, Southold

$2,200,000

3 Beds ⋅ 3 Baths ⋅ 1038709 MLS

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

225 Lakeside Drive S, Southold

$1,277,000

4 Beds ⋅ 4 Baths ⋅ 1032396 MLS

Welcome to 1025 Seawood Drive, where space, comfort, and the North Fork lifestyle come together beautifully! Experience the relaxed sophistication of North Fork living in this beautifully, maintained, move-in-ready 4 bedroom, 3.5 bath Colonial in the heart of Southold. Filled with natural light and designed for modern living this home features 9' ceilings, hardwood floors and an easy-flowing layout designed for both everyday living and entertaining. The spacious open areas connect seamlessly to the gourmet eat in kitchen, featuring marble countertops, stainless steel appliances and abundant cabinetry, while a cozy fireplace adds warmth and character. A standout feature is the expansive lower/ground level with 10' ceilings and sliding glass doors opening directly to the backyard--offering outstanding potential for additional living space, perfect for great room, media room, gym, office and entertainment area. Outside enjoy the expansive deck and private, serene backyard ideal setting for morning coffee, summer gatherings, or quiet evenings at home. Perfectly positioned near Southold's beaches, wineries, farm stands, marinas, waterfront parks, boutique shops and top North Fork dining. This move-in-ready home delivers the space, privacy and effortless coastal living that makes the North Fork so special.

1025 Seawood Drive, Southold

$2,695,000

3 Beds ⋅ 2 Baths ⋅ 1036373 MLS

Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fencing lines the property, offering a sense of privacy and openness rarely found so close to everything the North Fork has to offer. The three-bedroom, two-bathroom farmhouse is complemented by a large barn, currently outfitted for horses. While perfect as-is, its use could easily extend beyond equestrian purposes and be reimagined to suit your needs. A heated pool overlooking the vineyards rounds out the grounds, offering the perfect spot for entertaining or unwinding. Located less than a mile from bay beaches and the restaurants and shops of Southold Hamlet, putting amenities and everyday convenience equally within reach. This is a rare opportunity to own a classic North Fork property that balances open land, everyday comfort, and easy access to it all.

2850 Main Bayview Road, Southold

$939,000

3 Beds ⋅ 4 Baths ⋅ 997034 MLS

Location!Location!Location! Some homes are beautiful, others are truly one of a kind. 595 Greenfields Lane is both! Set on nearly 1 acre of meticulously landscaped property on a quiet dead end street, this exceptional custom built home is located just moments away from the historic village of Southold and the very best of the North Fork! Just a mile from the beach and steps away from Long Island's renowned wineries & Farmstands. Built by the homeowner with an uncompromising commitment to quality and craftsmanship, this 3 bedroom, 3.5 bathroom residence offers approximately 2,950 square feet of thoughtfully designed living space. Soaring cathedral ceilings, skylights, custom crown molding, solid wood doors and gleaming hardwood floors are just some of the details that distinguish this home. A stunning chef's kitchen was designed with custom cabinetry, granite counters and new stainless steel appliances, flowing naturally into spacious living and entertaining areas. The luxurious primary suite features a vaulted ceiling and spa inspired new bathroom creating a serene atmosphere to unwind at the end of the day. Adding versatility is a fully finished basement with a separate entrance and spacious living quarters ideal for extended family or those seeking additional flexibility. Outside, the property truly comes alive. Lush landscaping surrounds sitting areas, a vibrant vegetable garden, in-ground sprinklers and a charming permitted cottage. A wood-burning pizza oven creates a natural gathering place for entertaining, while multiple matching sheds, a 2-car garage and an expansive driveway accommodating up to 10 vehicles provide remarkable functionality. Every aspect of this property reflects thoughtful design and pride of ownership, from it's superior construction to it's beautifully maintained grounds. With acclaimed farm stands, wineries, beaches, restaurants and timeless character of Southold Village and the North Fork all close by, this is more than a home, it's an opportunity to embrace the lifestyle that makes this area so desirable. A rare combination of craftmanship, privacy, flexibility and location.....595 Greenfields Lane is a property that truly deserves to be experienced. Come see for yourself what makes this Southold home so special!

595 Greenfields Lane, Southold

$2,795,000

4 Beds ⋅ 5 Baths ⋅ 1036799 MLS

The Laurel Collection by MarrCon is an exclusive enclave of eight newly constructed luxury homes ideally located in the heart of Southold. With only 3 residences remaining, this limited offering presents a rare opportunity to enjoy exceptional new construction in one of the North Fork’s most desirable locations. 1475 Laurel Avenue showcases The Laurel Model, the largest model within the collection, offering approximately 4,375 square feet of beautifully designed living space set on .80 acres. The property is complete with a 20' x 40' heated saltwater gunite pool with an automatic cover, surrounded by an expansive Napa Stone marble patio. There is also ample room to create a pool house or outdoor kitchen. Backing to preserved land that can never be developed, the property offers lasting privacy and a peaceful, serene setting. Inside, nine-foot ceilings span both the first and second floors, complemented by vaulted and coffered ceiling details and 8½-inch white oak flooring throughout. The first floor features two bedrooms, including a luxurious primary suite with a generous walk-in closet and private access to the masonry patio, backyard, pool and gardens. The dramatic great room is anchored by a 46-inch linear gas fireplace and flows seamlessly into the beautifully appointed chef’s kitchen, featuring custom inset cabinetry, marble countertops, high-end GE Monogram appliances and a wet bar. The first floor also includes an office or flexible-use space complete with a wall of windows, built-in shelving and a wine refrigerator. Upstairs, two additional ensuite bedrooms feature beautifully finished baths with large-format tile and custom vanities. A spacious family room and oversized laundry room with custom cabinetry and a sink complete the second level, along with an additional stackable washer and dryer for added convenience. The lower level offers tremendous potential for additional living and entertaining space and can be finished to suit, with nine-foot ceilings, an egress window and walkout access already in place. Perfectly positioned to enjoy everything the North Fork has to offer, The Laurel Collection is just moments from beautiful beaches, wineries, farm stands and the charming villages of Southold and Greenport.

1475 Laurel Avenue, Southold

$2,895,000

5 Beds ⋅ 6 Baths ⋅ 1037213 MLS

North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, vineyard views and crafted for effortless indoor-outdoor living. From the moment you enter, the home reveals a quiet sophistication, with natural light pouring through thoughtfully placed openings, creating a sense of calm and connection to its spectacular surroundings. Luxury finishes have been selected and wired for full smart home capability. Intuitively designed for both everyday living and elevated entertaining. Offering 5 bedrooms and 5 full bathrooms and one half bathroom, the layout balances both as a private retreat while still accommodating guests with ease. Featuring two primary en-suite bedrooms on both the first and second floors, three guest bedrooms and a full cabana-style bathroom in the walk-out basement for pool party guests. Salt water pool is 16x36, heated and surrounded by patio with outdoor kitchen the backyard is fully fenced in. This is a home that lives as beautifully as it presents - timeless, intentional, and distinctly North Fork.

1135 Wildberry Lane, Southold

$949,000

3 Beds ⋅ 2 Baths ⋅ 1036471 MLS

North Fork Coastal Living by the Sound. Welcome to 155 Second Avenue, located in the charming hamlet of Peconic. The beach retreat you've been looking for, just 500 feet from both private and town beach access at Goldsmiths Inlet Beach. Custom built in 2005 by the current owner, this thoughtfully constructed beach home reflects true pride of ownership. Featuring open-concept living, dining, and kitchen areas which flow into a HUGE outdoor second story balcony, where peekaboo water views and beautiful sunsets create the perfect backdrop for relaxing or entertaining. Ready for your personal touch, the home offers a wonderful opportunity to add your own style but gives the peace of mind of an elevated and well built home. Bring your kayak paddleboard or fishing pole, spend your days on the water and your evenings exploring nearby vineyards, farm stands, restaurants, and local landmarks including nearby Horton Point Lighthouse. Well built, wonderfully located, and surrounded by everything that makes the North Fork special, 155 Second Avenue offers an easy coastal lifestyle in the heart of Peconic.

155 2nd Avenue, Peconic

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.