Southold Real Estate

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Newest Listings in Southold

$2,999,000

4 Beds ⋅ 6 Baths ⋅ 1052436 MLS

Set on an extraordinary 11.31 private acres in one of Southold’s most prestigious enclaves, this expansive estate was built in 1997 yet thoughtfully designed to capture the timeless character and gracious proportions of a grand early-1900s country home. A stately approach, welcoming covered porches and impressive entry set the tone for generously scaled interiors designed for both everyday living and large-scale entertaining. The home features 4 spacious en suite bedrooms, grand living and dining spaces, a library, serving kitchen, 5 fireplaces and an abundance of room for family and guests. A separate apartment with its own entrance provides additional flexibility for extended family, guests, work-from-home needs or private accommodations. Once operated as a bed and breakfast, the residence offers a distinctive layout and exceptional versatility. Additional features include a 4-car garage, expansive basement with 10-foot ceilings, irrigation system and 2-stall barn. Of the 11.31 acres, approximately 9.31 acres are open space with an additional 2 acres of buildable land, creating a rare opportunity for a private compound, equestrian use, extensive gardens or future possibilities. A truly unique North Fork offering combining substantial acreage, grand proportions, architectural character and exceptional privacy.

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

$605,000

2 Beds ⋅ 2 Baths ⋅ 1051473 MLS

Welcome to this corner residence at Founders Village, where easy, low-maintenance living meets the North Fork lifestyle. This 1,200-square-foot home offers 2 bedrooms, 2 full baths and a full basement, giving you valuable storage and extra space that can be hard to find when downsizing to condominium living. The corner location provides added green space on multiple sides, along with a rear patio that creates a comfortable spot to relax outdoors. Inside, you’ll find wood floors, an eat-in kitchen with newer appliances, comfortable living and dining areas, and high ceilings that create a real open home feel. Residents enjoy a community pool, clubhouse and beautifully maintained grounds. A stroll down the sidewalk leads toward Southold Village, with local shops, restaurants, the LIRR and Hampton Jitney all nearby. Beach access is another added benefit. The property qualifies for both Southold Town and a Southold Park District beach parking permits, offering even more opportunity to enjoy the best of The Long Island Sound and The Peconic Bay beaches. With its private corner setting, full basement, generous storage and community amenities, this home offers a comfortable way to downsize without giving up the space or North Fork lifestyle you want. This is 55+ living, reimagined: all the space and freedom you love, none of the upkeep you don't. Corner Home 11A — where downsizing feels like an upgrade.

2555 Youngs Avenue Unit #11A

$1,495,000

4 Beds ⋅ 4 Baths ⋅ 1051232 MLS

Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom North Fork retreat. A newly installed bulkhead and existing private dock provide the perfect setting for boating, fishing, kayaking and unforgettable days on the water. Renovate, redesign and make it your own—all just minutes from Southold Village, beaches, vineyards and celebrated local restaurants. Property is being sold as-is.

3995 Wells Avenue, 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

$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

$549,999

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

$3,095,000

4 Beds ⋅ 5 Baths ⋅ 1039113 MLS

Ready to Move In -- New Construction Luxury Southold Home completed October 2026. Interior photos coming 10/11/26. 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 400 Series Windows, Luxury 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 entrance to the lower level, full lower level bathroom, built in wine fridge, and luxury oversized double glass doors leading to your Gym and Custom Cedar Sauna. Equipped with the latest smart home technology including Hard Wired Ring Camera System, 5 Zone Sonos Sound System, Hard Wired EERO wifi access points, Lutron Smart Lighting, Wifi Pool Equipment, Wifi Sprinkler control, and more. 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

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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.