Nestled within the picturesque landscape of the East End of Long Island, 162 acres encompass the North Fork's largest commercially operating equestrian training & boarding facility. Originally founded by the Entenmann Family, The property is comprised of 3 parcels including 51+ Developable Acres. Positioned at the core of the estate stands a modest yet inviting home, offering four bedrooms and two bathrooms, alongside a quaint cottage designated for the farm's watchman. The esteemed property boasts rolling paddocks throughout the tract, two ponds, several boarding barns, workshops and detached structures. It features a half mile race track, in addition to two outdoor riding arenas. The indoor riding arena provides the necessary infrastructure to ride, train and retire horses of the highest caliber within this unparalleled equestrian sanctuary. The farm boasts three separate boarding stables with 90+ boarding stalls.

Nestled within the picturesque landscapes of the East End of Long Island, 162 acres encompasses the North Fork's largest commercially operating equestrian training & boarding facility. Originally founded by the Entenmann Family, The property encompasses 3 parcels including 51+ Developable Acres. Positioned at the core of the estate stands a modest yet inviting home, offering four bedrooms and two bathrooms, alongside a quaint cottage designated for the farm's watchman. The esteemed property boasts rolling paddocks throughout the tract, two ponds, several boarding barns, workshops and detached structures. It features a half mile race track, in addition to two outdoor riding arenas. The indoor riding arena provides the necessary infrastructure to ride, train and retire horses of the highest caliber within this unparalleled equestrian sanctuary. The farm boasts three separate boarding stables with 90+ boarding stalls.

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 Fork Discover 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 You This 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 control X Heating and air conditioning settings X Whole-home indoor and outdoor audio X TVs in the second-floor lounge, main living areas, and a private basement media room Whether 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 Comfort The 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 Awaits Step 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.

Welcome to your bespoke farmhouse retreat nestled in the serene beauty of the North Fork of Long Island. This custom-crafted home offers an unparalleled blend of luxury, comfort, and tranquility, enveloped by a meticulously designed landscape that creates a secluded oasis. Approaching the property, you're greeted by a custom landscape package featuring Belgian block pathways, crushed pea gravel, and towering 20-ft established trees and shrubs, evoking a sense of timeless elegance and privacy. Exterior lighting gracefully illuminates the walkways and architectural details, while wall wash cove lighting on the masonry-covered porch casts a gentle glow over the pool area, inviting you to unwind in its serene ambiance. Step into the enclosed backyard to discover a sanctuary of relaxation and entertainment, complete with elegant blue stone paths, a spacious entertaining patio, and an in-pool lounge deck with dual umbrella stands. A mesmerizing masonry water feature adds a touch of sophistication, while the in-pool beverage bench ensures refreshments are always close at hand. The rear of the house has been thoughtfully designed with architectural elements that tell a captivating story from every angle, creating a visual masterpiece that complements the surrounding landscape. Approach the double entry wood doors to find an oversized masonry sitting porch, perfect for indulging in weekend morning coffee conversations or simply soaking in the tranquil surroundings. Inside, the home boasts luxurious amenities at every turn. Off the foyer, a large den with custom cabinetry provides a peaceful retreat, while the two-story living room serves as the heart of the home, anchored by a granite fireplace and bathed in natural light. The professional kitchen is a chef's dream, featuring a Kohler pre-rinse faucet, a 45 inch workstation sink with sound deadening technology, and custom lighting that highlights the island and cabinet details. The open floor plan seamlessly flows into the dining space, offering stunning views of the yard, pool, and covered porch. A mudroom with slate plank floors and shoe lockers in the custom designed cabinetry leads to the laundry room, complete with a deep stainless steel sink, slide out laundry baskets for each of the four bedrooms and a pet washing station. The main floor suite boasts an elegant walk-in closet and a luxury bath fitted with a Toto washlet toilet, a freestanding soaking tub, and a roll-in shower. Upstairs, each bedroom offers ceiling details and attached bathrooms, while the custom open staircase leads to a finished basement featuring a movie theater, a home office space, and a beverage center. The walk-out basement opens to a covered cocktail patio and bluestone path leading to the pool deck. Located in a waterfront community with direct access to Goose Creek sandy beach, this home offers the ultimate retreat for those seeking luxury and tranquility on the North Fork. Don't miss your chance to experience the epitome of North Fork living.

Introducing largest operating equestrian facility on the North Fork of Long Island. This unparalleled property was once the original Entenmann's Equestrian Facility, boasting 107 acres. The farm features a four-bedroom, two-bathroom Home. The property includes 90 horse stalls distributed across three boarding barns, a well-maintained half-mile race track , a dedicated maintenance barn, and a nightwatchman's quarters for round-the-clock care. Several well-appointed paddocks and ample land ensure your horses thrive in a serene and spacious environment.

Discover 32.4 acres of prime land, perfect for agricultural pursuits and equestrian enthusiasts. This property features a 10,000 square foot indoor riding arena and is fully fenced for horses. Zoned RLC and APZ, it offers versatile opportunities for development. Ideally situated in the heart of the North Fork of Long Island, it is conveniently close to beautiful beaches and renowned vineyards. Don't miss this exceptional opportunity to own a piece of prime agricultural land in one of Long Island's most desirable locations.

Introducing an exceptional plot of land on Long Island's prestigious North Fork, perfect for building a luxurious private residence or a lucrative agricultural venture. This versatile property offers endless possibilities: create a generational farmstead, a sophisticated vineyard with a tasting room, or an equestrian compound. With a stunning pond, strategic roadside presence, and well-placed barns and woodshop, the land is both beautiful and functional. Zoned for Hamlet Residential and Rural Corridor, it supports various uses, from luxury homes to nurseries or farms. Maximize your investment by selling development rights to the county. The North Fork's reputation for vineyards, farms, and equestrian facilities ensures a thriving market and strong community support.

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 direct access to the serene shores of Pipes Cove Beach, 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.

Here's a stunning new construction home, part of a thoughtfully designed series that blends quality craftsmanship with modern convenience. Wide oak floors set the stage for an open floor plan, where a professional kitchen with oversized island flows into a spacious dining area and beverage bar - perfect for beach house gatherings. The living room in anchored by a cozy fireplace with built in bookcases, creating an inviting space to gather after a day biking and experiencing the hiking trails. Designed for comfort, the main level features a primary suite, along with a mudroom, laundry room, and a covered back porch overlooking a beautifully contoured yard. Upstairs, an open sitting/office room adds another cozy retreat, accompanied by a secondary primary suite, two additional bedrooms and a full bath. Need even more space? The finished basement with an outside entrance offers a full bath, ideal for media room, gym or home office. Located in the private Orient By The Sea beach community, this home offers access to miles of beach, scenic picnic spot with grilling and tables and some of the best sunsets over the water on the North Fork. Adjacent to Orient Beach State Park , you'll have easy access to a playground, nature trails, a popular summer concession stand, even kayak rentals. Plus, the charter fishing boats, Orient Point Ferry with access to Foxwoods Casino and entertainment 20 minutes off the New London Ferry, entertainment options abound.

Welcome to your dream beach home nestled in a serene beach community on the North Fork! This newly constructed residence offers the perfect blend of modern comfort and coastal charm, presenting an ideal sanctuary for those seeking the quintessential beach lifestyle. Upon entering, you'll be greeted by an inviting open floor plan, seamlessly connecting the living, dining, and kitchen areas, creating a spacious and airy ambiance perfect for both relaxing and entertaining. The main floor boasts a convenient mudroom/laundry area, providing easy access for one-level living convenience. With four bedrooms, with three of the bedrooms featuring its own attached bathroom, including one on the main floor, this home offers unparalleled comfort and privacy for all occupants. Whether hosting guests or enjoying personal retreats, everyone will appreciate the luxury and convenience of ensuite facilities. Step outside onto the covered porch, where summer dining awaits amidst the gentle sea breezes and tranquil views of the preserved land beyond the backyard. The fenced backyard, featuring a sparkling pool for refreshing dips on hot days and outdoor seating surrounding a cozy fire pit, ideal for gathering under the stars on summerl evenings. The sandy beach community adds to the allure, offering a park area complete with picnic tables, panoramic views of the water, and access to a sandy beach where summer breezes beckon for leisurely strolls along the shoreline. This property presents a rare opportunity to experience the best of North Fork beach living. Whether you're seeking a seasonal retreat or year-round residence, this home promises a lifestyle of comfort, convenience, and coastal charm. Don't miss your chance to make memories and create your own slice of paradise in this idyllic seaside haven., Additional information: Appearance:Pristine,Interior Features:Lr/Dr

This prime Southold property offers a fantastic opportunity for subdivision and development! Spanning over 4 acres, surrounded by development rights sold land and only half a mile to McCabes Beach, this idyllic North Fork property is ready to change hands, and this rare offering has incredible potential. Some ideas include subdividing the property and building another home on the back piece or updating and expanding the current residence to create a spectacular estate! The property includes a solid, well-built home from 1967 with a modernized kitchen and updated bathrooms (2020), oak wood floors throughout the first floor (under the carpets), Central Air Conditioning (on the first floor, but can be easily added to the second floor), generator, and a cozy living room with wood burning fireplace. The dining area has sliders to a large wood deck overlooking forever farm views. Other amenities include a two-car garage and a full, dry basement. The home is currently on well water with a filtration system, but public water in the street is available for hookup if desired. The roof was replaced about 10 years ago with 30-year shingles & the driveway was repaved within the last year. This property is not only well-maintained but also ready for your vision. Opportunities like this are rare, so don't miss out!, Additional information: Appearance:Excellent,Interior Features:Lr/Dr,Separate Hotwater Heater:Yes

This bright and airy Greenport property is bathed in natural light and offers timeless appeal and village convenience. Set on a rare double lot with beautiful mature trees, the home features a welcoming front porch and an open, flowing layout highlighted by original pine floors and period details. The house includes 3 bedrooms, 1.5 baths, a full basement, and an oversized two-car garage with an attached studio/workshop - ideal for creative or functional use. Just moments from Greenport Village’s shops, restaurants, Jitney, and LIRR, this is a standout opportunity in the heart of the North Fork.

Welcome to easy living in this charming three-bedroom ranch, perfectly set up for comfortable one-level living. Nestled on a desirable corner lot, this home offers a sense of privacy while still being close to all that Southold has to offer. Step inside and you’ll find oak floors that create a warm, natural flow throughout—from the sunny living room and dining area, all the way down the hall to the bedrooms and cozy den. The den features a classic wood-burning fireplace, perfect for relaxing evenings or chilly fall days. The kitchen is bright and welcoming, with plenty of natural light streaming in from windows that overlook the peaceful front courtyard. It’s ready for your personal touches and updates to truly make it your own. A clean, dry basement adds valuable storage or hobby space, while the covered front porch and garden areas provide a quiet spot to unwind or entertain. You’ll love how the outdoor spaces are thoughtfully tucked away, offering a peaceful retreat from the everyday. Located just moments from sandy beaches and the heart of Southold Village, this home blends convenience, charm, and opportunity in one great package.

This new construction home is crafted with exceptional attention to detail and investment in craftsmanship and infrastructure.. Designed for modern living, it features a custom landscape with water retainment, stone retaining walls, a cobblestone driveway apron, and a water containment system engineered to manage the heavy rains. Energy efficiency is prioritized with spray foam insulation to dramatically reduce heating and cooling costs. Inside, enjoy an open floor plan with a custom kitchen, an elegant bathroom with an infinity drain, organized closet systems, and beautiful oak floors. The lower level offers a walk-out basement entrance and is supported by a septic system for four-bedroom capacity. The backyard provides a private oasis with room for a pool, while the front boasts stunning views over the nearby rail trail. Just blocks away, explore local shops and enjoy the perks of North Shore beach membership. A fresh approach to creating a home that just makes you smile!, Additional information: Interior Features:Lr/Dr

This meticulously maintained 3-bedroom, 2-bath ranch is truly move-in ready, offering a seamless blend of comfort and practicality. The spacious first-floor layout is perfect for easy living, while the expansive lower-level entertainment area provides endless possibilities for relaxation or gatherings. The large detached garage offers ample storage or workspace. The property boasts mature plantings that enhance its inviting curb appeal, making it feel like home from the moment you arrive. Set in a peaceful neighborhood, you’ll enjoy the tranquility of country living while being just minutes from all the best the North Fork has to offer—vineyards, shops, and beautiful coastline.

This 4.6 acre residential building lot provides for a spacious homestead construction opportunity. Conveniently located at the gateway of the East End of Long Island, the sizeable parcel is ideal for a micro-farm or equestrian/agricultural influenced estate.

Located in the highly desirable Fleets Neck Community in Cutchogue, the sunniest hamlet in New York, this waterview Residential Building Lot presents a rare opportunity to create your dream home. With stunning views straight down East Creek, the property offers the tranquility of water view living. The two small waterfront cottages across the street are pre-existing, non-conforming, meaning they cannot be expanded upon, guaranteeing that the breathtaking water views will remain unspoiled for years to come. The lot also includes exclusive membership to the Fleets Neck Association Beach, providing access to a private, pristine white sand beach in perpetuity. Whether you are looking to build a forever home or simply enjoy the peaceful beauty of East Creek, this is a truly rare opportunity in one of Long Island's most sought-after communities.

This 2.2 acre residential building lot is located in a sequestered agricultural setting off of Fresh Pond Ave. Public water is available on the street to provide for a seamless construction opportunity. Conveniently located at the gateway of the East end of Long Island, the parcel provides for the perfect opportunity for one to construct their dream home estate.

Stunning vineyard views! Nestled in the heart of the North Fork's first vineyard is this sprawling, historic beauty. Steeped in history but with all the modern comforts and conveniences is the generous estate. Don't miss the one-of-a-kind North Fork sunrises from the primary suite or the picturesque sunsets from the gunite pool. Experience life on a working farm, while enjoying the seclusion and serenity of nearly 66 acres of a classic North Fork vineyard. Completely renovated, never lived in, and to be professionally furnished with designer grade places! July $40,000 - August-LD $40,000

Escape to this enchanting Craftsman style beachfront retreat on the coveted sandy beach, where stunning waterfront views and classic design create the perfect summer getaway. The front room's panoramic windows frame breathtaking vistas of the beach and gentle rhythm of lapping waves, filling the space with natural light and serenity. Just beyond, the open dining area offers water views making every meal a picturesque experience. Step outside to the spacious deck , where a charming shade-giving tree adds character and sense of tranquility- ideal for morning coffee or sunset gatherings. Available from August 17 through September 15, 2025; rent $15,000.

Charming Laurel Country Estates, comfortable three bedroom ranch, private bay beach for neighborhood residents. Central air conditioning. Rear yard with deck off kitchen for outdoor entertaining. Convenient to Mattituck Shopping Center, and recreational activities. Act now to reserve your desired dates for the 2025 Summer Season. Available: July and August through Labor Day. Additional information: Appearance:Very good

Brand New Tastefully Renovated Furnished Apartment conveniently located in the heart of Southold. The apartment is Available to rent for Year Round or flexible time-frame(s). Public transportation is in near proximity, along with everything else the North Fork has to offer.