Southold Real Estate

Welcome to Southold, a picturesque gem nestled in the heart of Suffolk County, New York. This charming town, located on the North Fork of Long Island, is renowned for its stunning landscapes, rich history, and vibrant community. With its serene beaches, lush vineyards, and quaint downtown area, Southold offers a unique blend of coastal charm and rural tranquility.

As one of the oldest towns in New York, Southold is steeped in history, dating back to its founding in 1640. The town boasts a wealth of historical landmarks, including the iconic Southold Historical Society and the beautifully preserved Horton Point Lighthouse, which offers breathtaking views of the Long Island Sound. Nature lovers will revel in the town's many parks and nature preserves, such as the Southold Town Beach and the nearby Orient Beach State Park, perfect for picnicking, hiking, and enjoying the stunning waterfront.

Southold is also a haven for food and wine enthusiasts, with numerous local vineyards and wineries producing some of the region's finest wines. The town's vibrant agricultural scene is complemented by charming farm stands and fresh seafood markets, making it easy to savor the flavors of the North Fork.

With a welcoming community spirit, excellent schools, and a variety of recreational activities, Southold is an ideal place to call home. Whether you're seeking a peaceful retreat or an active lifestyle, this enchanting town has something for everyone. Discover the magic of Southold and experience the perfect blend of small-town charm and natural beauty.

Newest Listings in Southold

$2,695,000

5 Beds ⋅ 4 Baths ⋅ 1031524 MLS

This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living space. With five bedrooms and four bathrooms, the home expands comfortably for guests yet feels equally intimate for smaller gatherings, striking a perfect balance for those looking to host but also enjoy a refined and exceptional East End retreat Stunning carpentry, high-end appliances, and designer fixtures carry throughout. The custom-built kitchen features bespoke cabinetry and hardware, flowing seamlessly into a dining area and a light-filled living room anchored by a wood-burning fireplace. Oversized windows and a vaulted ceiling define the dining room, which connects to an oversized back deck overlooking the sprawling backyard. Outside, a gunite, heated, saltwater pool complements the cedar-shingled accessory structure, which combines a pool house with its own bathroom, a garage, a covered outdoor patio with a gas fireplace, and an outdoor shower. Back inside, two additional guest bedrooms share a full bath on the second floor, while downstairs, two large recreation rooms offer further customization and flexibility. The location is just as compelling as the house itself, minutes from Goose Creek Beach, Cedar Beach, Croteaux Vineyards, and the many shops and restaurants of Southold Hamlet. This is a special property with a real point of view that you'll look forward to walking into each time you return home.

605 Cedar Drive, Southold

$799,000

1031247 MLS

Build your North Fork dream in the heart of Southold. This exceptional 0.96-acre parcel is nestled among mature trees and surrounded by the scenic beauty of farmland and nature. This peaceful setting with easy access to Long Island Sound beaches, with breathtaking sunsets, acclaimed wineries, farm stands, marinas, and charming village amenities. Buyer is responsible for verifying all zoning, permits, and permitted uses with the Town of Southold. Artist Rendering- For Illustrative Purposes Only. Images are artistic interpretations and should not be relied upon as representations of existing conditions, future improvements, or development potential. All land use, zoning, and building approvals are subject to review by the Town of Southold and applicable agencies.

13260 Soundview Avenue, Southold

$650,000

1017614 MLS

The Dune Road of the North Fork. Do you love the beach? You know that feeling, tranquility and the sound of the waves off in the distance. Well, this is your chance to capture it and create your safe haven, your wellness retreat. This is what the doctor ordered! Steps from Little Fish and Kenney's and McCabe Beaches. Hurry up, this one is going to go fast!

420 Lake Drive, Southold

$2,650,000

4 Beds ⋅ 4 Baths ⋅ 1023134 MLS

This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany decks invite you to soak in those bay views, entertain friends, or just unwind with the coastal breeze. Effortless, elevated, and ready for summer. This is the one you've been waiting for. Near Cedar and Goose Creek beach, Sophie's Rest, tasting rooms, farm stands, vineyards, and all that the North Fork is known for!

195 Williamsburg Drive, Southold

$2,150,000

3 Beds ⋅ 3 Baths ⋅ 1022803 MLS

Perfectly sited on a protected inlet on West Lake, with direct access to the pristine waters of the Little Peconic Bay, this exceptional waterfront retreat embodies the effortless elegance of North Fork living. Thoughtfully designed to embrace its spectacular setting, the home is filled with natural light and showcases captivating water views from its principal living spaces. The main level offers an inviting open-concept design, where a gracious living room with a gas fireplace, elegant dining area, and beautifully appointed chef's kitchen with premium finishes flow seamlessly onto an expansive waterfront deck, creating an ideal setting for both intimate gatherings and grand-scale entertaining. A private staircase leads to the large dock, with room for multiple boats and a permitted kayak launch, offering immediate access to some of the East End's finest boating, sailing, and fishing. Above, the rooftop observation deck captures sweeping panoramic vistas across Little Peconic Bay, Robins Island, and the ever-changing coastal landscape beyond. The finished lower level encompasses an additional 1,675 square feet of living space and features a spacious family room, two bedrooms, a bathroom, another fireplace, a wine cellar, and walls of sliding glass doors that blur the line between indoors and out, inviting the waterfront into every moment. Complete with private beach access, this is more than a home-it is a rare opportunity to embrace an extraordinary waterfront lifestyle where sunrise boat-rides, paddles, afternoons on the bay, and unforgettable sunsets become part of everyday life.

2245 Little Peconic Bay Lane, Southold

$1,475,000

4 Beds ⋅ 4 Baths ⋅ 1024798 MLS

Coveted Maple Lane setting in the heart of Southold Village with easy access to all Southold Village amenities and LIRR ~ This recently transformed shingled Craftsman Style residence offers 4 bedrooms, 3.5 baths, timeless architectural character, exceptional private outdoor living, and a truly special North Fork lifestyle. Beautifully landscaped with specimen plantings, the property is designed for relaxed year-round or seasonal enjoyment. Outdoor amenities include a new heated 16 x 32 inground saltwater pool, hot tub, outdoor shower, and gracious covered porches at both the front and rear of the home. Classic Craftsman details enhance the curb appeal, including Arts & Crafts-style columns on river rock bases, double-dipped cedar shingles, a custom garage door, and a signature Craftsman front door. Inside, the main level offers an inviting open layout with wood floors throughout. The spacious living room features a wood-burning fireplace, while the eat-in kitchen, dining room, and window-filled den provide warm, functional spaces for everyday living and entertaining. Both the kitchen and den open directly to the rear covered porches, creating an easy flow for indoor-outdoor living. The first floor also includes two bedrooms, one full bath, one half bath, and a mudroom/laundry room. Distinctive interior details include oak trim around the windows and doors, as well as a beautiful staircase with a one-of-a-kind custom newel post. Upstairs, the primary suite serves as a private retreat with a generous sitting and office area, two-sided gas fireplace, sauna, and a fabulous tiled bath with spacious walk-in shower. A newly added junior primary suite, completed in 2026, adds comfort, privacy, and flexibility for guests or extended stays. Just a few doors from the edge of charming Southold Village, the Southold Historical Society and close to Founders Landing Bay Beach and Park, this exceptional home offers easy access to the marina, restaurants, shops, wineries and NYC transportation. This is a rare Southold Village offering with remarkable character, amenities, and the superior North Fork location you have been looking for.

425 Maple Lane, Southold

$1,375,000

3 Beds ⋅ 2 Baths ⋅ 1024020 MLS

Perfectly positioned between Greenport and Southold, this classic cedar-shingled Cape offers an easygoing North Fork lifestyle with beaches, restaurants, and village amenities just minutes away. Inside, the first-floor open plan is anchored by a fireplace and a large kitchen flooded with natural light. Multiple sliding doors lead to a generous wraparound deck, outfitted for dining, lounging, and entertaining. An expanded second floor is devoted to a spacious primary suite with seperate office and a large ensuite bathroom. The backyard invites summer afternoons around the bocce court, and peekaboo water views across the street subtly remind of the home's coastal setting. A full basement provides great utility and flexibility. Comfortable, stylish, unpretentious, and exceptionally well-located, this home is as well-suited to weekends as it is to everyday living.

1050 Bayview Avenue, Southold

$1,385,000

4 Beds ⋅ 3 Baths ⋅ 1023884 MLS

Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeless charm with modern comforts. The main level features hardwood floors throughout, a spacious living room with a wood-burning fireplace, formal dining room, eat-in kitchen with granite countertops and pantry, a convenient half bath, and a first-floor bedroom currently used as a home office. Andersen windows and ceiling fans throughout provide comfort and abundant natural light. Upstairs, you’ll find a spacious primary suite with a private deck, walk-in shower, and Jacuzzi tub and additional two guest bedrooms which share an updated bath. The full unfinished basement has high ceilings and is perfect for future potential finishing and offers plenty of room for storage. Enjoy the peaceful outdoor setting from the inviting mahogany wraparound front porch or screened-in side porch. Plenty of room pool, garage, guest cottage and more! Close to Southold’s Kenneys, McCabe’s and Town Beach. A rare opportunity to own a private retreat with amazing grounds, perfect for year-round or part time living!

4408 Old North Road, Southold

$1,250,000

6 Beds ⋅ 3 Baths ⋅ 1013610 MLS

Every once in a while, a home comes along that just makes you smile-and this is one of them. Set on just under an acre in Southold, this classic farmhouse is full of charm, character, and even its own secret garden. With 6 bedrooms and 3 bathrooms, there's plenty of room for everyone, plus multiple living spaces, cozy sitting rooms, a dining area made for gathering, an open kitchen, laundry room, and a covered porch you'll never want to leave. The backyard has room for the pool you've been dreaming about, while the gardens and outdoor space feel like your own private escape. Just minutes from Cedar Beach and Goose Creek Beach, this is the kind of home that feels like summer all year long. Whether you're looking for a forever home, a North Fork getaway, or a place to make memories for generations, this farmhouse is ready for its next chapter.

13675 Main Bayview Road, Southold

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 1016785 MLS

Classic Americana meets the North Fork lifestyle on Southold's Bayview Peninsula. Set on a level half acre backing to protected town owned land, this four bedroom, three bath Center Hall Colonial combines timeless design, thoughtful updates, and an exceptional location near Southold's most sought-after waterfront destinations. A welcoming portico leads into a home with wood floors throughout. The living room features a wood burning fireplace, while the formal dining room overlooks the rear yard through a bay window. A butler's passthrough connects to the kitchen, complete with stone countertops, a massive center island, stainless steel appliances, and a stainless-steel range hood. The first floor includes a full bath and adjacent family room that could easily become a first-floor primary suite or private guest space. Upstairs, the primary suite offers a private bath and second floor laundry. Three additional bedrooms share a hall bath. Additional features include an attached two car garage with mudroom access, a full basement with outside entrance, and recently updated roof, heating system, and central air. Life on Bayview Peninsula is all about the water. Pine Neck Boat Ramp, Goose Creek Beach, and Cedar Beach are all nearby. Enjoy award winning wineries, farm stands, and restaurants throughout the North Fork, with the Orient Point Ferry just a short drive away for easy access to New England. Whether you are looking for a year-round residence or a North Fork getaway, 1075 Ships Drive offers an outstanding opportunity to enjoy coastal living in one of Southold's most desirable neighborhoods.

1075 Ships Drive, Southold

$999,000

2 Beds ⋅ 1 Baths ⋅ 1017744 MLS

The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by. This private community on Hashamomuck Pond offers 2 bedrooms, warm oak floors, spacious living room, and waterfront views galore. Enjoy kayaking, paddleboarding, fishing, and swimming right out your back door. This is the lifestyle you have thought about, why not make it happen now!

136 Bayview Avenue, Southold

$985,000

5 Beds ⋅ 2 Baths ⋅ 1017107 MLS

Welcome to 230 Booth Road, a prime Southold location offering effortless access to both Kenneys Beach and McCabe’s Beach-two of the North Fork’s most beloved Sound front destinations known for swimming, long shoreline walks, and unforgettable sunsets. This expanded cape provides exceptional flexibility for living and entertaining. The entry opens to a spacious living room with a cozy wood-burning fireplace, flowing into a dining room, both featuring oak floors currently protected by carpeting. The large eat-in kitchen offers abundant space for gatherings, with an adjacent laundry room and storage area that includes plumbing for an easy conversion to a powder room. Two bedrooms and a full bath complete the first floor. Upstairs, you’ll find three additional generous guest rooms and a full bath. An oversized walk-in attic presents potential for future expansion. The full basement offers ample storage, and Bilco doors make it simple to store outdoor furniture and seasonal items. Other features include a generator and new central air conditioning. The tranquil backyard provides plenty of room for summer entertaining. Whether you’re seeking a year-round residence or a seasonal escape, this home places you at the heart of the North Fork lifestyle—beautiful beaches, vineyards, farm stands, boutique shopping, and farm-to-table restaurants. This is the North Fork retreat you have been looking for.

230 Booth Road, 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.