ML# :882187   Rarely available in size, scope, and setting, this generational Nassau Point estate is a standout along the Peconic Bay—its beauty long admired by passing boaters. Set on 4.23 acres with over 300 feet of private beachfront, it offers unmatched privacy in one of the North Fork’s most desirable waterfront enclaves. At its heart is a nearly 9, 000-square-foot residence that masterfully blends timeless design with modern functionality. Expansive, light-filled living spaces frame sweeping bay views, while 8 bedrooms and 8.5 bathrooms are thoughtfully distributed across multiple wings for effortless living and entertaining. Amenities include a movie room, home gym, and sauna.A separate two-bedroom, two-bathroom guest cottage adds further flexibility for hosting. Outdoors, a deepwater dock provides direct access to Peconic Bay, while the waterside gunite pool, tennis court, and pool house create a true resort-like experience. The impeccably landscaped grounds are dotted with mature specimen trees and ornamental plantings, offering natural beauty and seclusion throughout.Every detail has been carefully curated to deliver a rare combination of scale, comfort, and coastal luxury—an offering of enduring significance, whether envisioned as a legacy compound or seasonal retreat.

ML# :888190   The estate of the late legendary New York art dealer Barbara Gladstone, this meticulously restored Gilded Age shingle-style home offers a rare opportunity to own one of the few remaining large, turn-of-the-century North Fork summer estates. Set on 140 feet of pristine bayfront with a private sandy beach, the primary residence spans over 10, 000 sq. ft. and seamlessly blends period architecture with modern luxury. Every element, from the doorknobs to the custom hardware, has been carefully curated, resulting in a warm, classic home defined by craftsmanship and elegance.Well suited for both grand entertaining and intimate gatherings, expansive living spaces feature soaring ceilings, multiple fireplaces, and thoughtfully designed moments throughout. Highlights on the first floor include a large waterside living room and dining room with charming fireplace alcoves, a sprawling chef’s kitchen with breakfast room and handsome butler’s pantry, a dedicated flower-cutting room with custom marble sink, and an enormous screened-in outdoor sitting porch complete with an outdoor dining room and kitchen. The second floor houses the large primary suite with an ensuite bath, extensive walk-in closets, a dressing room, and a cozy sitting room with an oversized fireplace. The balance of the second and third floors includes five additional waterside bedrooms, a library, an office, multiple wet bars, a laundry room, and five baths with steam showers and soaking tubs.Outside, lush, professionally designed perennial gardens and hedged lawns surround the property. A beautiful, private gunite pool sits on the waterside, offering a serene oasis overlooking the bay. Just beyond, a sweeping lawn with panoramic water views leads to a sandy path framed by sea grasses and wildflowers, guiding you down to the private bayfront beach. A charming carriage house adds further versatility, featuring a great room, home theater, and gym. The estate also includes a historic icehouse, preserving its rich legacy. Whether sitting by the bay, hosting holidays, or enjoying movie nights in the theater, this extraordinary property promises a lifestyle of laid-back elegance and tranquility.

ML# :881901   Cutchogue Showstopper!Designed by world-renowned architects Barnes Coy, this modern waterfront masterpiece is a rare blend of cutting-edge design and natural beauty. Perched atop a 55-foot bluff overlooking the Long Island Sound, this 4, 200 sq ft home offers breathtaking sunsets and a seamless fusion of sleek modern lines with warm, inviting elements. Located in a private neighborhood with its own park and private stairs to the beach!Flooded with natural light and crafted from premium materials, every detail speaks to exceptional quality and thoughtful design. Enjoy resort-style living with a heated saltwater gunite pool and hot tub, all set against the dramatic backdrop of open water views. A 1, 000+ sq ft rooftop deck provides panoramic vistas and the perfect space for entertaining or relaxing under the stars. Inside and out, the home is equipped with state-of-the-art smart home technology and integrated speakers, enhancing both convenience and ambiance. Truly one of the most extraordinary homes ever offered on the North Fork - modern, majestic, and simply unforgettable.

ML# :894800   Discover the timeless charm of Nassau Point, a picturesque enclave surrounded by the shimmering waters of Peconic Bay. Nestled near the peninsula’s tip this newly constructed three level masterpiece spans 8, 500 square feet of fine craftsmanship and luxury living.The impressive entry foyer immediately sets the tone for this grandeur lifestyle with front to back Living Room Doors, tasteful herringbone oak floors, 10’ ceilings, custom mill work and views beyond of the patio through a wall of glistering glass. The lavish designer kitchen showcases a 9’ island, Sub-Zero & Wolf appliances, 2 Bosch dishwashers, 3 wine fridges, and a room designated to a pantry closet. Adjacent to this open floor plan is the Dining Room and the great room with gas burning fireplace and wall to ceiling windows and doors accessing over 1, 000 square feet of covered and uncovered stone patios. There are six ensuite bedrooms (radiant heat) - one conveniently located in a separate wing on the first floor and the second floor boasts a spa-like bathroom and a private 400 square ft covered terrace. The lower ground level offers doors to the rear property & pool with outdoor shower and serves as a recreational area with beverage center, gym area and sauna. A separate room is the ideal space for a home theater and space for a wine cellar , whole house generator and A 30X60 stand up attic plus s 3 car garage with attic complete this rare find.Enjoy the allure of Nassau Point lifestyle with easy access to expansive sandy beaches, enchanting creeks, and rolling hills, all set within a landscape of neatly arranged streets and large, spacious homes. This gem is perfectly situated in the prosperous agricultural heart of the Northfork, offering tranquility and refined elegance. All within a short distance to Northfork’s best vineyards, farms, restaurants, marinas and all the unending activities it has to offer.

ML# :893733   NEW WATERFRONT CONSTRUCTIONThoughtfully crafted and beautifully finished, this 4-bedroom, 5-bath custom waterfront home offers over 2, 900 sq ft of elevated living space — a seamless blend of modern luxury and timeless coastal charm.Set in a peaceful, private location, it showcases stunning panoramic water views from nearly every room and effortless indoor-outdoor flow designed to embrace the natural surroundings and relaxed beach lifestyle.HIGHLIGHTS...4 spacious en suite bedrooms....5 bathrooms...2 light-filled living areas perfect for lounging or entertaining....Custom white oak cabinetry, vanities, and detailed millwork....White oak flooring throughout..... Chef’s kitchen....Sub-Zero refrigerator and wine fridge....Wolf stove....Sleek Dekton countertops....Expansive glass doors that open the kitchen to the outdoor living space with direct water views — perfect for hosting or unwinding by the shore....Second-floor outdoor lounge terrace overlooking the water....Separate garage with finished loft....Mahogany fencing....Professionally landscaped grounds.Located just minutes from the area’s best beaches, this brand-new waterfront home offers the ultimate combination of high-end design, natural beauty, and relaxed luxury living.

ML# :872345   Introducing an excellent opportunity to own a well-cultivated vineyard planted with premium varieties of Sauvignon Blanc, Merlot, and Riesling situated on the North Fork of Long Island. This boutique vineyard supplies grapes to vineyards and breweries, offering an addition to world-class fine wines and craft beverages. A preliminary site plan is available to develop a unique tasting room, enhancing the property’s potential. The existing 1800s farmhouse, rich in character, can be integrated into your vineyard vision or removed to suit your design aspirations. A spacious farm-sized barn/stable equipped with electricity and water provides further functional versatility. Set on 17.5 acres of beautiful North Fork agricultural land, the property comes with Development Rights Intact, presenting the opportunity for possible subdivision (buyer to perform due diligence). Ideally located moments from town, school, beaches, shops, transportation, vineyards, and wineries, this property offers exceptional exposure and accessibility. With endless potential, do not miss out on this wonderful opportunity to participate in everything NorthFork has to offer.

ML# :818321   Welcome to your dream home, a custom built luxury retreat just steps away from the pristine Fleet’s Neck Beach. Prepare to be captivated by this newly constructed masterpiece, where sophistication meets comfort in every meticulously designed detail. Step into a world of culinary excellence with a state of the art gourmet kitchen. It showcases not one, but two Sub-Zero refrigerators and a commanding 60 BlueStar range complete with six burners, a flat top, and a custom hood. The kitchen also features a Breville air fryer for healthy cooking adventures and a built-in Miele coffee maker for your morning rituals. The walk-in pantry provides generous storage with its custom shelving. The expansive living room, adorned with automatic blinds for your convenience, offers a tranquil escape centered around a sleek gas fireplace. It flows seamlessly into an entertainer’s paradise, a sophisticated bar area equipped with a Scotsman ice maker, two refrigeration drawers, a Sub-Zero 100+ bottle wine fridge, and chic open shelving. In addition, the home boasts two EuroCave wine refrigerators, each capable of holding over 150 bottles, ideal for wine enthusiasts. This residence offers not one but two lavish primary suites, one on each level. Each boasts spa-like en suite bathrooms complete with steam showers for the ultimate relaxation experience. Custom walk-in closets provide ample space, and the upstairs suite features French doors that open to a generous deck with a stunning pool area view. Stay fit in your private, fully equipped gym featuring an infrared sauna, Tonal, Peloton, Fight Club boxing system, gym flooring with additional insulation, TV, and fan. A spacious home office caters to your professional needs, while a sunroom with convertible windows and screens ensures year-round enjoyment. Venture outside to a private backyard oasis, where a heated saltwater pool invites you to unwind. New irrigation and lush landscaping create an enchanting ambiance, complemented by a built-in BBQ with refrigeration, a large paella or wok burner, a fire pit, and a cabana half bathroom, perfect for unforgettable gatherings. A Sonos sound system enhances this luxurious experience, providing impeccable audio quality throughout the house, the second floor terrace, and the backyard. A full house Generac generator ensures uninterrupted comfort and peace of mind. This unparalleled luxury home is move in ready for Summer 2025. It’s a must see to truly appreciate its endless comfort and sophisticated features.

ML# :873820   Experience iconic North Fork waterfront living at this exquisite retreat located in the heart of Cutchogue. Perfectly situated on over an acre of land with 150 feet of direct water frontage on East Creek, this designer-curated, turn-key home offers unrivaled luxury, serenity, and access to all the region’s most celebrated amenities—award-winning wineries, farm stands, pristine beaches, and boating access to Peconic Bay.This newly renovated five-bedroom, 3-bathroom residence blends refined coastal style with a thoughtful open-concept layout. At the heart of the home, the chef’s kitchen—appointed with white oak cabinetry, quartz counters, Sub-Zero and Wolf appliances, and a spacious island—flows seamlessly into a waterfront dining space and living area, all bathed in natural light and framed by breathtaking water views.Step into the cozy sitting room and enjoy year-round relaxation with a free-standing fireplace and panoramic views of the creek. Every bedroom in the home offers water vistas, including the expansive primary suite featuring a spa-like bath with soaking tub, double shower, and a cedar walk-in closet.Permit application is submitted for a future in-ground pool, allowing you to complete your dream backyard escape. The deep-water dock is ideal for boaters and kayakers alike with direct access to the bay.Enjoy seamless indoor-outdoor living with a large waterfront deck, perfect for al fresco dining and entertaining. Located minutes from Nassau Point, Fleets Neck Beach, and the charming villages of Greenport and Southold, this is truly North Fork living at its finest—relaxed luxury with water, wine, and farmland all around.

ML# :3584002   Iconic 1800s Barn with Modern Flair! This mid-1800s barn offers a rare opportunity to own a piece of North Fork’s rich history. Set on nearly 2.5 acres the property is a private sanctuary, featuring a lush natural perimeter of Skip Laurel and towering 16’ Leyland hedges, offering serene views and complete privacy. The barn is ready for expansion, presenting endless possibilities for customization. Bordering protected land, the property guarantees open, unspoiled views that will remain for years to come. Located in the charming hamlet of Cutchogue, minutes from the region’s best wineries, beaches, restaurants, and farmstands, this one of a kind home offers an idyllic escape. Don’t miss your chance to own this timeless North Fork treasure., Additional information: Appearance:Excellent, Separate Hotwater Heater:Yes

ML# :852968   This extraordinary lot is located in Cutchogue, A.K.A. The Sunniest Spot in New York State! A total of 11.57 acres including a shy 3-acre building envelope. This conservation subdivision is the perfect blend of natural beauty and development potential. 3 of the acres are newly planted with Merlot, Cabernet Sauvignon and Malbec grapes. Ideal for those seeking a harmonious balance of countryside farm views and being near all modern conveniences. This property presents an exceptional opportunity to create your dream home in an idyllic setting. An opportunity not to be missed!