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$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
$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
$2,899,000
4 Beds ⋅ 3 Baths ⋅ 1005049 MLS
Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this breathtaking waterfront residence blends Scandinavian chic design with warm modern coastal luxury. Set on .35 acres with direct water access, the home features 4 bedrooms, 3 full baths, 2,351 square feet of beautifully designed living space, plus a finished 1,166-square-foot lower level. Sun-drenched interiors showcase wide-plank wire-brushed white oak flooring, custom millwork and cabinetry, Restoration Hardware lighting, recessed lighting, and Sonos sound throughout both the home and outdoor entertaining spaces. Every room in the home captures stunning water views, creating a seamless connection to the surrounding waterfront setting. The spectacular gourmet kitchen is designed for both everyday living and entertaining, featuring a Sub-Zero refrigerator, Wolf gas cooktop and double ovens, quartz and Caesarstone countertops, oversized center island, Bosch and Fisher & Paykel dishwashers, and a stunning butler’s pantry accented with Cle Tile backsplash. The living room is equally impressive with a custom wood-burning fireplace, built-in cabinetry, and an elegant wet bar complete with Sub-Zero beverage refrigerator, wine refrigerator, ice machine, and designer finishes throughout. The fully finished lower level offers exceptional additional living space with a kitchenette, double egress windows, and Fujitsu mini-split system—ideal for guests, recreation, or extended entertaining. Upstairs, four spacious water-view bedrooms include a luxurious primary suite featuring cathedral planked ceilings, a handmade vintage wood mantel, private deck access, walk-in closet, and spa-inspired bath. Elegant lime-washed walls add warmth and character to every bathroom. Outdoor living is nothing short of extraordinary with expansive first and second floor decking, a rooftop deck with panoramic water views, premium IPE Brazilian hardwood decking, covered outdoor entertaining area with built-in heaters and ceiling fans, outdoor shower, wired railings, cedar shake siding, Andersen 400 Series windows and doors, and beautifully landscaped grounds surrounded by mature privacy hedges. A true boater’s paradise, the property accommodates a large boat and offers direct access to Peconic Bay, Shinnecock Bay, and nearby sandbars for boating, kayaking, paddleboarding, clamming, and enjoying the ultimate North Fork waterfront lifestyle.

405 Williamsburgh Drive, Southold
$1,550,000
4 Beds ⋅ 4 Baths ⋅ 953464 MLS
The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to create a retreat just moments from the beaches, vineyards, and beloved local destinations that define the North Fork. Here, tranquility meets convenience—you’re never far from the shoreline or the vibrant heartbeat of the community. New Construction Package – $1,550,000 This option delivers a thoughtfully designed 2,215 sq ft home that blends timeless details with coastal luxury. Plans include 4 bedrooms, 3 full baths with 9 foot ceilings throughout, creating an airy and elegant space. The first floor of the home features an open-concept kitchen, living, and dining perfect for hosting and easy flow of day-to-day living. Walk up the front porch and enter the front door to a spacious living room accompanied by a warm fireplace for those cooler nights. As you continue you’ll pass through the dining area with floor-to-ceiling doors that look out over the backyard. Enter the brand-new chef’s kitchen featuring a large kitchen island, stainless steel appliances, and beautiful walk-in pantry! The main floor also features a full bath and bedroom, perfect for guests or single-floor living. Upstairs, you’ll find 3 additional bedrooms — 2 that share the full bath in the hall, and a primary bedroom with walk-in-closet and en suite bathroom. Laundry is a breeze with a washer-dryer on the second floor! Outdoors, appreciate the intentional details designed with North Fork living in mind. The detached garage features a beautifully integrated pool cabana, accessed by a man door. Designed to suit outdoor entertaining and living, the cabana comes equipped with an island bar top, sink, half bath, and space for a grill — the perfect spot to entertain or wind down after a day at the beach with family or guests. At 500 Summer Lane, you’re less than 1.5 miles from some of Southold’s best gems like Croteaux Vineyard, Goose Creek Beach, Sophie’s Restaurant, and local farm/flower stands. A little further you’ll find the charming Southold Town, Cedar Beach, endless vineyards, Greenport Harbor Brewery, and so much more. The North Fork is Calling Your Name!

500 Summer Lane, Southold
$799,000
817145 MLS
Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life; You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom Conventional Septic System, (I/A NOT REQD.) Making It Ready For Your Grand Vision. Whether You're Looking To Build A Sprawling Family Estate, A Charming Vineyard Retreat, Or Anything In Between, The Possibilities Are Endless. Truly "Shovel Ready" Embrace The Tranquility Of Country Living With All The Benefits Of Being Near The Heart Of The North Fork’s Sought-After Attractions. Don’t Miss This Rare Opportunity To Create Your Own Slice Of Paradise!

1350 Hortons Lane, Southold

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.