ML# :3590145   You Have to See It in Person, This Home Feels Even More Incredible Than the Photos Show!People always say, “Wow, I knew it was going to be beautiful, but I didn’t expect it to feel like this!” There’s something about stepping inside that just clicks, the way the light moves through the space, the seamless indoor-outdoor flow, and the effortless luxury in every detail. If you think the photos are stunning, wait until you walk through the door.Stunning Resort-Style Home with Modern Smart Features on the North ForkDiscover a new level of luxury and sophistication in this North Fork masterpiece, the latest in a series of meticulously designed homes with exceptional amenities. This residence captures the essence of resort living, surrounded by the tranquil Islands End public golf course, the ever-popular Hellenic restaurant, and deeded sandy beach access with sweeping views of Shelter Island and the iconic Orient Lighthouse.The neighborhood beach and park offer paddleboard and kayak stations along the marina, but if you’re a boater, you’re in for a treat—private community boat slips give you direct access to the water. From here, it’s just a few nautical miles to Orient Point for world-class fishing or a short ride around the jetty to Greenport Village Harbor, where you can dock for dinner, stroll the waterfront, or explore the vibrant local scene.A Smart Home That Works for YouThis isn’t just a home—it’s an experience. Designed for both comfort and convenience, the state-of-the-art smart home system gives you remote access to:X Lighting and ambiance controlX Heating and air conditioning settingsX Whole-home indoor and outdoor audioX TVs in the second-floor lounge, main living areas, and a private basement media roomWhether you’re arriving for the weekend or living here full-time, everything is dialed in and ready before you even step inside.Space, Style & Effortless ComfortThe expansive floor plan offers not one, but two luxurious owner’s suites—one on the main level for ease of access and another on the second floor, offering a private retreat with elevated views. Two additional guest suites with en-suite baths provide space for friends and family to stay in complete comfort.The sleek, modern design is all about indoor-outdoor living, with oversized sliders that open onto a stunning backyard oasis.Your Private Resort AwaitsStep outside, and the magic continues. The elegant pool with a waterfall feature and LED evening lighting sets the stage for unforgettable summer nights. An optional outdoor kitchen, spacious dining area, and cozy fireplace lounge create the perfect setting for entertaining—or simply unwinding after a day on the water.Every inch of this home has been thoughtfully designed across three levels, blending top-tier craftsmanship, effortless functionality, and modern elegance.This is more than just a house—it’s a lifestyle. A rare opportunity to own a slice of resort-like paradise on the North Fork. You have to see it to believe it.

ML# :862263   Soundfront! Welcome to 2100 Sound Drive - offering water views from nearly every room, this unique property is part of the Eastern Sterling Shores community and is truly the Last of the Mohicans! Greeted by a welcoming circular driveway and situated atop a picturesque bluff, you’ll enjoy captivating views and summer breezes. Stairs lead to an enchanting enclosed bungalow while your own private oasis awaits beyond and within just 40’ of this pristine property are bountiful fish and lobster, ideal for the fishing enthusiast. At the center of this entertainer’s delight is an oversized living room accented with dramatic beamed ceilings, a stone wood-burning fireplace and custom built-ins. Four bedrooms, three full baths as well as an eat-in kitchen, formal dining room, all-season room, huge rear patio and attached 2-car garage, complete this special home. Located just a stone’s throw to Greenport Village with fine-dining, shopping and ferry access, don’t miss this incredible opportunity!

ML# :872722   Brand-New Coastal Retreat with Pool, Pool House & Deeded Bay Beach Rights.Introducing a stunning new construction that redefines North Fork luxury- offering 4, 500 square feet of beautiful living space across three levels, including a full walkout basement.With 4 bedrooms, 5 bathrooms, and an effortless indoor-outdoor flow, this exceptional home is designed for both upscale entertaining and relaxed everyday living.Step outside into your own private resort, where a 20 x 40 inground pool takes center sage, surrounded by an expansive patio, a cozy fire pit, and lush landscaping. The 500 square-foot pool house adds an elevated touch, complete with a wet bar, half bath, covered patio, and an outdoor shower - perfect for rinsing off after a sun-soaked day at your Deeded Peconic Bay beach just moments away.Inside, high ceilings, wide-open living spaces, and elegant finishes create a warm and inviting atmosphere. A gourmet kitchen, spa-inspired bathrooms and generous bedrooms offer comfort and style at every turn. The walkout lower level provides even more flexibility - ideal for a home theater, gym, or guest suite.An attached two-car garage ensures convenience with plenty of storage for beach or golf gear.Located one minute from the beautiful Islands End golf course and 3 minutes to historic Greenport Village, this home blends coastal serenity with village convenience.Whether you’re seeking a full-time residence or a luxe weekend escape, this property is a rare North Fork find that truly has it all.

ML# :3579812   This beautiful Queen Ann Victorian home includes a priceless location in the heart of Greenport Village. Built in 1897, many of the fine architectural detail in this home is still present today. There are 5 bedrooms in which three of them are ensuites. The property is loaded with gorgeous specimen plantings. There is a large barn behind the pergola covered courtyard. This home makes a perfect Bed and Breakfast (formerly Rubys Cove) with front and back staircases, large parlor rooms and an updated kitchen. Bay Avenue is an amazing location just steps to Main and Front Street shops, fine restaurants, and all transportation., Additional information: Appearance:Excellent, Interior Features:Lr/Dr, Separate Hotwater Heater:y

ML# :853979   Ideally located just minutes from the heart of historic Greenport, this beautifully crafted home offers the perfect blend of coastal elegance and modern comfort. Enjoy access to the serene shores of Peconic Bay where tranquil waters and scenic views invite daily relaxation. Entertain and impress your guests from the bricked patio, and heated saltwater pool. Professional, lush landscaped grounds and local produce from the farm around the road completes the Farm to Table setting!Experience the perfect blend of comfort and classic charm in this stunning 2-year-old farmhouse with expansive water views from multiple rooms. This beauty is located in the coveted Peconic Bay Estates. Meticulously designed and ready for immediate enjoyment, custom details, 4-bedroom, 3.5-bathroom home offers spacious, light-filled living crafted for both relaxation and sophistication. A bright and airy home office offers sweeping views of Greenport’s waterways truly an inspiring place to work or create.Whether you’re strolling the quaint streets of Greenport or enjoying the natural beauty right outside your door, this property offers a lifestyle rich in charm and convenience.

ML# :862399   Experience the best of North Fork coastal living in this beautifully appointed 3-bedroom, 2.5-bath waterfront condo with breathtaking views of Peconic Bay and Shelter Island. Enjoy your morning coffee as the sun rises or set sail from your dock just steps from your door. With spacious, light-filled interiors, two fireplaces and seamless indoor-outdoor flow, this home is designed for effortless living and entertaining by the sea. A rare offering in a coveted location-just a few minutes from all that Greenport has to offer; boating, shopping, dining, tasting rooms, art and more!

ML# :885384   Live your best life in this spectacular 5 bedroom bayfront home. Breathtaking panoramic water views from Shelter Island throughout Greenport Harbor to Pipes Cove, you will be able to sit on your private beach and watch all the activity of the Peconic Bay. This beachfront home offers a first floor bedroom en-suite, enclosed sunporch, open floor plan across the living room with wood burning fireplace, dining area into the kitchen. The second floor offers 4 large bedrooms and a full bathroom. There are hardwood floors, central air conditioning, laundry on both floors, partial full height basement, and a beautiful waterside composite deck to enjoy the most amazing water view!

ML# :869623   This is more than a renovation—it’s a revival of Greenport’s heritage. Originally built in the early 1900s, this farmhouse has been thoughtfully reimagined in 2024 with a full-scale, design-forward renovation that honors its storied past while embracing modern luxury.Featuring 4 bedrooms and 2.5 baths, every inch of this home has been meticulously updated with custom finishes, high-end fixtures, and timeless charm. Original elements such as reclaimed wood flooring, solid wood doors, and vintage crystal doorknobs have been beautifully preserved, blending seamlessly with contemporary additions.The first floor welcomes you with a cozy living room centered around a wood-burning fireplace, a stylish study or home office, a sun-drenched bedroom currently styled as a tranquil zen room, bright and airy dining room, and a chic half bath. The heart of the home is the chef’s kitchen—designed to impress—with custom cabinetry, Thor appliances, an oversized island, wine fridge, bar, desk nook, and expansive entertaining space with gliding bifold door to the backyard.Upstairs, two guest bedrooms share a well-appointed full bath, while the primary suite boasts cathedral ceilings, a spacious walk-in closet and a stunning ensuite bathroom.Indoor-outdoor living is effortless here. Slide open the custom bi-panel doors from the kitchen to access a new mahogany deck and private backyard—perfect for relaxing or entertaining. Room for a pool! The property also includes a garage and full basement for additional storage or future potential. Sellers are open to discussing the sale of furnishings separately, offering a turnkey opportunity for buyers seeking a fully styled home. Enjoy picturesque views of the neighboring Kontokosta Vineyard from both your front porch and bedroom. Ideally located just half a mile from Greenport Village’s restaurants, shops, wineries, and all! Perfectly situated between both 67 Steps and Norman Klipp beaches, each about .5 mile away. This home is a rare blend of history, character, and modern elegance. For buyers seeking classic charm without compromising on luxury—this is where the past and present come beautifully together!

ML# :3579596   This one-of-a-kind, mid-century modern was designed by renowned architect Claude Samton. Named Winged Weekend Flight, a wood hewn escape from city ways. When you enter, you will leave your worries behind. Incredible light and gorgeous landscape envelop this 3 bedroom, 1.5 bath sanctuary. Gunite pool with an automatic cover, Ipe decking and beach rights to a gorgeous sound front beach complement your experience. For cooler days, unwind by the fireplace after your evening beach stroll. Make this your refuge from everyday life!, Additional information: Appearance:Mint+, Interior Features:Lr/Dr

ML# :877496   Discover this meticulously renovated 3-bedroom, 2-bath corner property in charming Greenport, offering captivating water views and an expansive, beautifully landscaped garden.The elevated rear garden is a true sanctuary, featuring mature trees and a spacious patio that perfectly frames the picturesque Sterling Harbor, alive with sailboats and fishing vessels. A generous side garden, formerly an additional lot, provides exceptional privacy and ample space for a future pool or extensive landscaping, complementing the existing one-car garage.This restored home has been thoughtfully rebuilt, showcasing its original pine flooring and classic front porch. The inviting lower level boasts an open-concept kitchen and living area, complemented by a sun-drenched room with water views, separated by pocket doors—ideal for a formal dining room or a versatile third bedroom. A full bath on this level adds convenience.Upstairs, you’ll find two comfortable bedrooms and a dedicated small office area, all overlooking the serene rear garden and waterfront. A second full bath completes the upper floor.Beyond the home, boating enthusiasts will appreciate the opportunity for a seasonal boat slip, conveniently located just two blocks away (available for an additional fee). The detached garage also presents an exciting opportunity for a workshop or a future pool house. This home has been thoroughly renovated including a Nevien gas hot water cast iron radiator system, all new plumbing, electric, new town sewer, new roof, new Andersen windows, new walls and insulation throughout. All of this is just a short stroll from the vibrant heart of Greenport village and the sandy shores of Manhasset Beach. Owner/Broker