Southold Real Estate

Welcome to Southold, New York – a charming town nestled on the picturesque North Fork of Long Island, in Suffolk County. Known for its stunning natural beauty and rich history, Southold offers a unique blend of coastal living, agricultural heritage, and vibrant community spirit.

With its scenic waterfront views, Southold is a haven for outdoor enthusiasts. From the tranquil beaches along the Long Island Sound to the lush vineyards and farms that dot the landscape, there’s no shortage of activities to enjoy. Whether you’re sailing, fishing, or simply taking a leisurely stroll along the shore, the serene environment here is truly captivating.

History buffs will appreciate Southold’s fascinating past, as it is one of the oldest English settlements in New York, established in 1640. The town is home to several historical landmarks, including the Southold Historical Society and the iconic First Presbyterian Church, which add to its charm and character.

Southold’s vibrant community is reflected in its local events, farmers' markets, and art shows, fostering a sense of belonging among residents. The town also boasts a variety of dining options, from quaint cafes to upscale restaurants, serving fresh, locally-sourced cuisine that showcases the region’s agricultural bounty.

For those seeking a peaceful yet engaging lifestyle, Southold offers a perfect balance. With its inviting neighborhoods, excellent schools, and a strong sense of community, it’s an ideal place to call home. Explore the beauty and charm of Southold – where every day feels like a vacation!

Newest Listings in Southold

$824,000

1050238 MLS

A rare opportunity to create a custom North Fork residence in desirable Wildberry Fields. This .61-acre level, wooded parcel is situated on a private 9-lot country road and backed by picturesque vineyards, offering beautiful vineyard views and a peaceful, private setting. Protective covenants help preserve the character and value of the community, requiring residences of more than 3,000 sq. ft. with natural exterior materials. Underground utilities are already in place. Located within the desirable Southold Park District, offering residents access to Founders Landing, Emerson Park and other Park District amenities, with opportunities for beach access, swimming, kayaking and seasonal boat and kayak slip lotteries. Just minutes from farm stands, acclaimed restaurants, wineries and Greenport Village. An exceptional opportunity for a luxury builder or buyer looking to create a custom North Fork home. Building options are available through North Fork Building Company, if desired. Bring your vision to life in one of Southold’s most beautiful settings.

705 Wildberry Lane, Southold

$789,000

3 Beds ⋅ 2 Baths ⋅ 1043515 MLS

Opportunity knocks in Southold, one of the North Fork's most desirable locations. Bring your vision and unlock the potential of this well positioned home. Set on .60 acres, with room for a pool and just a short stroll from Southold Town Beach, this 3 bedroom, 2 bath home has good bones and offers the perfect foundation for a stunning North Fork transformation. Highlights include a dramatic sunken living room with vaulted ceilings and a wall of windows, a wood burning fireplace, dining area with access to a wrap-around rear deck, a main floor primary with ensuite, bonus room with closet, wet bar, sunroom, and walk-out basement offering a ton of potential and access to the garage. Hardwood flooring throughout the main level. While the kitchen and baths are original, the roof and electrical box are new and the home's appealing layout creates an exceptional opportunity for investors, renovators, or buyers seeking to create their dream North Fork retreat. Enjoy easy access to beaches, wineries, farm stands, marinas, and Greenport Village. Offered as-is.

455 Stony Shore Drive, Southold

$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

$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

$629,000

1041384 MLS

Ideally Located Vacant Land. A Rare Opportunity to Create Your Own North Fork Retreat or Year-Round Home on Desirable Hyatt Road, a Quiet Setting Just Off Soundview Avenue in Southold. This Ideally Located Vacant Parcel is Just a Short Distance from Memorable McCabe’s Town Beach. The Lot is Reported to Include Coveted Deeded Rights to a Private Long Island Sound Beach. Enjoy the Tranquility of a Peaceful North Fork Setting While Remaining Just a Short Drive from the Vibrant Centers of Southold and Greenport, with Their Celebrated Restaurants, Shops, Wineries, Marinas, and Coastal Attractions. An Exceptional Opportunity to Build Your Dream Getaway or Year-Round Home and Embrace the Best of the North Fork Lifestyle—Beautiful Beaches, Picturesque Surroundings, and Relaxed Coastal Living. No Survey Available. See Photo for Approximate Lot Dimensions. Sellers Will Not Consider Offers with Contingencies. Road is a Private Road. Do Not Visit or Walk the Property Unattended. Buyer is Advised to Independently Verify the Accuracy of All Information

2560 Hyatt Road, 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

$550,000

2 Beds ⋅ 2 Baths ⋅ 1027409 MLS

Unit 3C offers a rare opportunity to create something truly your own. This 2-bedroom, 2-bath condo is ready for a new vision and offers the perfect blank canvas for buyers who would rather customize than compromise. There is tremendous potential to thoughtfully update the home to your style, selecting the finishes, fixtures, colors, and details you actually want along the way. The unfinished basement provides additional possibilities for storage or workspace. Bring your ideas and transform this property into a home designed around you—from the first renovation decision to the final finishing touch.

2555 Youngs Avenue Unit #3C, 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

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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.