Southold Real Estate

Welcome to Southold, NY – a charming community nestled in the heart of Suffolk County, where education meets opportunity! Southold is not just a picturesque town with stunning waterfront views and serene landscapes; it is also home to a highly regarded school district that prioritizes the growth and development of its students.

The Southold School District is known for its commitment to academic excellence and personalized education. With small class sizes and dedicated teachers, students receive the attention they need to thrive. The district serves grades K-12 and boasts a curriculum that is both rigorous and well-rounded, incorporating arts, sciences, and technology to prepare students for the challenges of the future.

Parents will appreciate the district's focus on fostering a supportive and inclusive environment, where every child is encouraged to explore their interests and develop their unique talents. Extracurricular activities abound, from sports teams to music programs, ensuring that students can find their passion outside of the classroom.

Additionally, Southold's idyllic setting offers a safe and nurturing community for families. The town's rich history and vibrant culture provide a perfect backdrop for educational experiences, with local museums, parks, and community events that enhance learning beyond school walls.

Choosing Southold means choosing a place where your child's education is valued, and their future is bright. With its exceptional school district and welcoming atmosphere, Southold is not just a place to live; it's a place to grow and thrive. Come discover the perfect blend of community and education in this beautiful corner of New York!

Newest Listings in Southold

$699,000

3 Beds ⋅ 1 Baths ⋅ 1060683 MLS

Welcome to 430 Grove Road, Southold — Where the North Fork Lifestyle Becomes Your Everyday Life! Imagine starting your mornings with coffee on your beautiful, window-filled enclosed porch, spending your afternoons exploring local vineyards, breweries, and beaches, and ending your evenings enjoying the peaceful charm of the North Fork. This inviting 3-bedroom ranch offers the perfect opportunity to embrace a lifestyle that feels like a vacation every day. Tucked away in a wonderful Southold setting, this home features a bright, enclosed porch surrounded by windows, a detached garage, and an outdoor shower — perfect for rinsing off after a day on the water or at the beach. Just down the street, enjoy convenient water access where you can launch your paddleboard, kayak, or canoe and explore the beauty of the surrounding waterways. Whether you're looking for a year-round residence, a weekend escape, or your very own North Fork retreat, this property offers so much more than a place to call home. You're not just purchasing a house — you're purchasing the North Fork lifestyle! From award-winning vineyards and local farm stands to waterfront dining, beautiful beaches, and endless outdoor adventures, everything that makes the North Fork so special is waiting for you at 430 Grove Road.

430 Grove Road, Southold

$999,000

5 Beds ⋅ 2 Baths ⋅ 1054880 MLS

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.

2220 Akerly Pond Lane, Southold

$1,695,000

3 Beds ⋅ 2 Baths ⋅ 1061179 MLS

Waterfront Living with Bay Access & Your Own Dock Enjoy beautiful water views from this 3-bedroom, 2-bath waterfront home with bay access and a private dock. A sunny eat-in kitchen, formal dining room, and hardwood floors create an inviting setting for everyday living and entertaining. Relax in the upper-level living room or gather in the lower-level family room, with two fireplaces adding warmth and charm. The primary suite features an ensuite bath and sliding doors to a private deck—a peaceful spot to start or end your day. A large deck overlooking the water offers even more space to entertain or simply enjoy the view. Two garages, cedar closet, enclosed blueberry and vegtable gardens, oil heat, and new central air conditioning complete this waterfront retreat.

2025 Little Peconic Bay Lane, Southold

$675,000

1059204 MLS

A rare opportunity to own one of the last remaining vacant parcels in the highly desirable Indian Neck Park Association. This .32-acre lot offers the chance to create your own vision in a sought-after beach community, just a few houses down from the private association bay beach. Set within an established neighborhood surrounded by beautiful homes, this property provides a unique opportunity to build a new home tailored to your lifestyle and take advantage of the relaxed North Fork setting. Not in a flood zone, and a flat level lot. Enjoy private beach rights to the pristine white sandy Peconic Bay, all while being part of a well-established community. Opportunities to purchase vacant land in this neighborhood are exceptionally limited—this may be your chance to secure one of the last available lots and create something of your own!

965 Smith Road, Peconic

$2,150,000

3 Beds ⋅ 2 Baths ⋅ 1058940 MLS

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.

1455 Cedar Point Drive E, Southold

$999,000

4 Beds ⋅ 4 Baths ⋅ 1059170 MLS

Welcome to 5045 Main Bayview Road, an inviting three-bedroom retreat nestled within Southold’s prestigious Goose Neck community, where privacy, coastal charm, and the relaxed elegance of North Fork living come together. Designed for effortless indoor-outdoor living, the home’s standout feature is its resort-style backyard, a private oasis complete with a beautiful swimming pool, expansive deck, and built-in barbecue. Whether spending leisurely afternoons poolside, dining outdoors, or entertaining family and friends, this exceptional outdoor setting is perfectly suited for enjoying the best of summer on the North Fork. The primary bedroom opens to a private deck overlooking the backyard, offering a peaceful place to begin or end the day while taking in the serene surroundings. A sunroom featuring a hot tub provides an additional space to relax and unwind throughout the seasons. Located within the coveted Goose Neck community, residents enjoy the added luxury of private beach access, creating the quintessential North Fork lifestyle just moments from home. Southold’s celebrated vineyards, farm stands, beaches, restaurants, shops, and charming village destinations are all within easy reach. Perfect as a year-round residence, sophisticated weekend escape, or summer retreat, 5045 Main Bayview Road presents a special opportunity to enjoy privacy, recreation, and coastal living in one of Southold’s most desirable settings.

Main Bayview Main Bayview, Southold

$1,250,000

2 Beds ⋅ 2 Baths ⋅ 1056663 MLS

Just a few hundred feet from Shagwong Marina and less than half a mile from New Suffolk Beach and Legends and Minnow restaurants, this renovated and expanded ranch offers turnkey living in the heart of New Suffolk. A 2021 addition added a large garage and second-floor living room with a full bath, providing valuable additional space and flexibility. Comfortable and easy to maintain as it stands, the property also offers room for a pool and future expansion. An appealing opportunity to enjoy one of the North Fork’s most desirable hamlets, with the waterfront, beach, dining, and boating all close at hand.

1045 Fanning Road, New Suffolk

$795,000

3 Beds ⋅ 2 Baths ⋅ 1053365 MLS

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!

29400 County Road 48, Peconic

$2,999,000

4 Beds ⋅ 6 Baths ⋅ 1052436 MLS

Once operated as a bed and breakfast, this distinctive property sits on 11.31 private acres, including 9.31 acres of open space and 2-acres of buildable space in one of Southold's most prestigious enclaves. Offering exceptional versatility and income potential, the property features a serving kitchen, dining room, library, five fireplaces, tile flooring throughout, and a four-car garage with a basement featuring 10-foot ceilings. An irrigation system and two-stall barn add to the appeal. A rare combination of privacy, space, and opportunity, ideal for horses, gardens, a potential income-producing venture, or future development.

9680 N Bayview Road, Southold

$2,698,000

4 Beds ⋅ 4 Baths ⋅ 1054890 MLS

Bay Haven — 1430 Bay Haven Lane, Southold Classic coastal architecture meets contemporary North Fork living in this newly built custom residence set within the Bay Haven beach community, just three houses from the private community beach. Designed for effortless North Fork living, the home offers 3,035 square feet of living space, with four bedrooms and four full baths, complemented by approximately 3,340 additional square feet of garage, pool house, storage/art, and under-house utility and storage space. Inside, 10 foot first-floor ceilings, 9 foot second floor ceilings, natural hardwood floors, abundant natural light, custom millwork, built-ins, and site-built closets create a refined yet relaxed interior. Two primary suites, one on each floor, offer flexibility for year-round living and guests. Each features a walk-in closet, ensuite bath, and electric fireplace, while radiant-heated floors enhance the primary bath spaces. The first floor suite also includes a private office, while the second-floor suite enjoys seasonal bay views. At the heart of the home is a locally handcrafted kitchen with cabinetry extending to the 10 foot ceiling, a 48-inch professional style gas range beneath a custom arched hood, dual dishwashers, smart combination wall oven, farmhouse sink, pot filler, dual-zone wine refrigeration, and extensive custom storage. Indoor and outdoor living flow naturally through the three-season room, complete with custom cabinetry, TV hook up and fireplace, to the landscaped grounds and a heated pool. A poolside mudroom provides direct access to a full bath, shower, and changing area. The pool house adds another layer of entertaining space with a wine bar, dual zone wine refrigeration, and glass doors opening directly to the pool. The property extends well beyond the main residence with a detached garage and approximately 770 square foot second floor storage, ideally suited for an Art Space, plus approximately 1,800 square feet of under-house storage and utility space. Behind the design is a substantial infrastructure package: a high-efficiency five zone heat pump heating and cooling system, 3 zones of radiant heat, comprehensive spray foam insulation, a hybrid heat-pump water heater, three stage whole house filtration, controlled under-house dehumidification, energy efficient heat pump pool heating, smart pool control and lighting systems, Ring security, an I/A septic system, and 300-amp electrical service. Bay Haven combines privacy, craftsmanship and modern comforts with immediate access to the Bay. Cedar Beach is just 1.5 miles away, with the shops and restaurants of Southold nearby. Seasonal second floor bay views and year round glimpses of the water complete a home equally suited to summer escapes and year-round North Fork living.

1430 Bay Haven Lane, Southold

$4,299,000

4 Beds ⋅ 3 Baths ⋅ 1053616 MLS

WELCOME TO PARADISE. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork presence of a setting from Nelson DeMille’s Plum Island—dramatic, intriguing and entirely unforgettable. With approximately 97 feet of private beach, panoramic views toward Shelter Island and the estate-lined shoreline beyond, plus community boating rights with access to the residents’ boat basin, the property offers exceptional privacy without sacrificing comfort or convenience. Custom built in 1993, the approximately 3,500-square-foot residence offers four bedrooms, three full baths and three levels designed for gracious year-round living. Bold proportions, soaring 20-foot ceilings, walls of glass and a sweeping staircase capture the confident glamour of grand-scale coastal architecture, while abundant natural light and extraordinary water views give the interiors a timeless quality. This is not a conventional beach house; it is a substantial bayfront residence designed to make an impression. The dramatic double-height great room is anchored by a rare natural coral-stone fireplace and opens to more than 1,500 square feet of exterior decking—an exceptional setting for entertaining, dining outdoors or simply watching the light move across the bay. A formal waterside dining room complements the spacious eat-in kitchen, which provides generous counter space and an inviting place for everyday gatherings. The main level also includes pantry and laundry areas, together with a flexible 4th bedroom or den and adjacent full bath—ideal for guests, a private home office or convenient first-floor living. Ascend the sweeping staircase to the waterfront primary suite, a private retreat featuring magnificent bay views, its own waterside terrace, a luxurious full bath and walk-in closet. Two additional bedrooms and another full bath complete the upper level. The finished lower level expands the home’s recreational possibilities with a game or media area, direct access to a waterside terrace and an attached multicar garage. Outside, the expansive, level grounds provide ample room for entertaining, recreation and quiet enjoyment amid beautiful natural surroundings. A private boardwalk leads directly to the sandy beach, where days can be spent swimming, fishing, kayaking, paddleboarding or launching a morning adventure on the bay. Although wonderfully private, the estate is only minutes from Southold Village and the restaurants, vineyards, farm stands, shops, beaches and boating destinations that define North Fork living. Additional amenities include public water, a supplemental well, oil-fired forced-air heat and central air conditioning. Rare acreage, substantial private beach frontage, community boating access and a dramatic waterfront residence come together in one extraordinary Southold offering. Paradise Found.

3525 Paradise Point Road, Southold

$1,100,000

4 Beds ⋅ 3 Baths ⋅ 1050202 MLS

Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of privacy and convenience. Surrounded by preserved land, large properties and a horse property, the picturesque 2.18-acre setting provides a peaceful retreat while remaining just minutes from restaurants, marinas, shops, wineries, beaches, and all attractions on the North Fork. This meticulously maintained single-level home features 4 bedrooms and 3 bathrooms, offering a versatile floor plan designed for comfortable living and entertaining. The private primary en-suite includes a beautifully updated bath with elegant tile work and soaking tub. Two additional guest bedrooms and updated hall bath provide ample accommodations, while a separate wing with its own private entrance offers endless possibilities. Ideal as a home office, guest quarters, or a secondary primary suite, this space includes a sitting room, bedroom, and full bath with a handicap-accessible shower. The spacious, light-filled kitchen is designed for both everyday living and entertaining. Featuring an abundance of cabinetry, expansive counter space, and an efficient layout, the kitchen offers plenty of room for meal preparation and storage. The open design flows into the dining area and living room, creating an inviting atmosphere for casual gatherings or larger celebrations. The dining area offers sliding doors leading to a large deck overlooking the scenic grounds, the perfect setting for outdoor dining, relaxing, or entertaining. The full basement with outside entrance offers endless possibilities for expansion of the living space if desired. Every detail of this residence reflects exceptional care and pride of ownership. Beautifully maintained, the home presents with the feel and quality of new construction. A rare opportunity to own a pristine country retreat with room for a pool, where privacy, natural beauty, and convenience come together in perfect harmony.

61341 Route 25, 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.