Southold Real Estate

Southold Real Estate

Welcome to Southold, New York – a picturesque gem nestled in the heart of Suffolk County on Long Island’s North Fork. Known for its charming small-town ambiance, Southold offers a unique blend of natural beauty, rich history, and vibrant community life.

As one of the oldest towns in New York, established in 1640, Southold is steeped in history, with colonial architecture and historic landmarks that tell the story of its early settlers. The town is surrounded by stunning coastal landscapes, featuring pristine beaches, serene bays, and lush vineyards that make Southold a true paradise for nature lovers and wine enthusiasts alike.

Outdoor enthusiasts will find plenty to explore, from the scenic hiking trails at the nearby Orient Beach State Park to the tranquil waters of the Long Island Sound, perfect for kayaking and sailing. The area is also home to a variety of local farms and wineries, offering visitors the chance to indulge in farm-fresh produce and award-winning wines.

Southold boasts a tight-knit community with a welcoming atmosphere, where local shops, quaint cafes, and family-owned restaurants create a delightful dining and shopping experience. The town hosts numerous events throughout the year, from farmers' markets to seasonal festivals, fostering a sense of belonging and connection among residents and visitors alike.

Whether you’re seeking a peaceful retreat, a vibrant community, or a place to call home, Southold stands out as a charming destination that beautifully captures the essence of coastal living. Come and discover the allure of Southold – where history, nature, and community come together in perfect harmony.

Newest Listings in 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.