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$5,750,000
13 Beds 7 Baths 1029909 MLS
LISTING IS FOR 6 HOMES AND .77 VACANT LAND! An exceptional opportunity to own a one-of-a-kind waterfront estate featuring 6 income-producing residences plus an adjoining nearly one-acre buildable lot, offering tremendous potential to expand the rental portfolio or create a spectacular multigenerational compound. The property includes two Bayfront homes—one offering 4 bedrooms and 3 bathrooms, the other has 3 bedrooms and 1.5 bathrooms—along with four additional cottages, including two 2-bedroom cottages and two 1-bedroom cottages. The adjacent buildable parcel presents endless possibilities, whether for a custom waterfront residence, additional income-producing opportunities, or the ultimate private estate. A rare investment with multiple revenue streams, redevelopment potential, and breathtaking waterfront setting. Please do not go on the property without a scheduled appointment.

18 Smith Lane, Jamesport

$2,650,000
4 Beds 4 Baths 1023134 MLS
This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhead, your own boat ramp, and instant access to the bay. With 4 bedrooms and 3.5 baths, including both a first-floor primary ensuite and a second-floor primary suite, there's room for everyone to spread out in style. Two mahogany decks invite you to soak in those bay views, entertain friends, or just unwind with the coastal breeze. Effortless, elevated, and ready for summer. This is the one you've been waiting for. Near Cedar and Goose Creek beach, Sophie's Rest, tasting rooms, farm stands, vineyards, and all that the North Fork is known for!

195 Williamsburg Drive, Southold

$825,000
1 Beds 1 Baths 1030134 MLS
Experience the best of Westhampton Beach waterfront living in this rare and exceptional co-op offering. This beautifully appointed 1-bedroom, 1-bath residence features approximately 750 square feet of bright, open-concept living space designed to maximize comfort while showcasing its spectacular waterfront setting with a huge 15’x9’ front deck & 28'x10' rear deck for the ultimate private outside entertainment experience. Wake up to views overlooking the town marina from the front of the home, then unwind each evening with breathtaking sunsets from your private waterfront retreat. The rear of the property features a bulkhead with a deeded boat slip accommodating a vessel up to 28 feet, creating the perfect opportunity to enjoy boating right from your backyard. Residents enjoy a beautifully maintained waterfront community complete with a sparkling pool, lush grounds, and an unbeatable location just moments from the charming Village of Westhampton Beach. Boutique shopping, acclaimed restaurants, ocean beaches, and everything the Village has to offer are all just a short distance away. Waterfront properties combining marina views, deeded boating, resort-style amenities, and walkable village convenience are exceptionally rare. Whether you’re searching for a year-round residence or the perfect coastal getaway, this is a truly one-of-a-kind opportunity to own a piece of Westhampton Beach waterfront living.

35 Library Avenue Unit #8 R, Westhampton Beach

$4,499,000
4 Beds 4 Baths 1029440 MLS
First time to the market, this rare expression of modern coastal luxury is an extraordinary waterfront estate on prestigious Rampasture Point, masterfully reimagined to offer an unparalleled living experience overlooking the tranquil waters of Tiana Bay. Every finish, texture, and architectural detail have been intentionally selected to create a residence that is as timeless as it is breathtaking. From the moment you arrive, the home's striking architectural presence commands attention. A magnificent, oversized pivot entry door creates an unforgettable first impression, setting the stage for the sophisticated interiors beyond. It immediately reflects the home's exceptional craftsmanship and design. Inside, the impeccably designed living space unfolds beneath soaring ceilings and walls of glass that frame spectacular waterfront vistas from nearly every room. Thoughtfully curated by a luxury interior designer, it showcases wide-plank white oak flooring, custom architectural millwork, exquisite Phillip Jeffrey designer wallcoverings, statement lighting, and handcrafted details that elevate every space into a work of art. The chef's kitchen serves as the true centerpiece of the home. Custom inset cabinetry, dramatic honed quartz countertops, handcrafted range hood, Thermador appliances, and sophisticated coffee bar create a space equally suited for quiet mornings and elegant entertaining. The kitchen flows into the dining and living areas, where uninterrupted views of Tiana Bay become part of the home's everyday backdrop. Anchored by a natural gas fireplace, the living room exudes warmth and sophistication. Bespoke built-in shelving has been thoughtfully designed to showcase artwork, books, collections, and sculptural decor. Designed for effortless modern living, this four-bedroom, three-and-a-half-bath smart home seamlessly blends cutting-edge technology with timeless elegance. Motorized shades throughout provide privacy and convenience while allowing the breathtaking waterfront scenery to remain the focal point. The primary suite is a sanctuary unlike any other. Soaring ceilings, designer lighting, and expansive walls of glass create an atmosphere of serenity and sophistication. Begin each morning at your private coffee bar before stepping onto your balcony, where spectacular sunrises over Tiana Bay become part of your daily ritual. The spa-inspired primary bath offers a retreat worthy of a five-star resort. A freestanding soaking tub is perfectly positioned beside a picture window overlooking the open bay. Luxury entertaining extends throughout the home with multiple beverage stations, including two built-in temperature-controlled wine refrigerators serving both the indoor and outdoor living spaces. Outside, resort-style living reaches its finest expression. Expansive waterfront decking seamlessly extends the home's living space, offering a fully equipped outdoor kitchen, elegant dining area, generous lounge seating, multiple gathering spaces, and an exceptional gazebo that provides the perfect setting for afternoon relaxation or sunset cocktails. Every outdoor space has been thoughtfully designed to celebrate the beauty of waterfront living. Beyond the deck, your own private beach awaits, offering direct access to kayaking, paddleboarding, boating, swimming, and peaceful walks along the shoreline. A whole-house generator provides year-round comfort ensuring uninterrupted enjoyment of this remarkable waterfront estate. Perfectly positioned just minutes from the world-renowned white sand beaches of Dune Road, premier marinas, waterfront dining, boutique shopping, and the very best of the Hamptons lifestyle, this exceptional residence represents one of Hampton Bays' most compelling waterfront offerings. This is more than a home—it is a legacy property. A designer waterfront estate where architecture, craftsmanship, and nature exist in perfect harmony, creating a lifestyle that is both effortless and extraordinary.

29 Tiana Circle, Hampton Bays

$1,489,999
4 Beds 4 Baths 1027742 MLS
Welcome to 21 Wilderness Road, an exceptional Colonial set on two private acres in the Village of Nissequogue, where timeless design and thoughtful updates come together in a private, serene setting. Offering 4 bedrooms and 4 bathrooms, this residence delivers generous living spaces, refined finishes, and effortless everyday comfort. Hardwood floors, detailed crown molding, and an inviting floor plan create a warm yet elegant atmosphere throughout. The updated kitchen is appointed with granite countertops, abundant cabinetry, and flows seamlessly into the main living areas, making it ideal for both entertaining and everyday living. A fireside sitting area offers the perfect place to gather, while a dedicated home office provides the flexibility to function as a fifth bedroom, guest suite, or private study. One of the home’s most desirable features is its private deeded access to the pristine Long Island Sound, where scenic water views and shoreline access offer an exceptional coastal lifestyle. Along with Additional highlights include, LOW TAXES, Horse property, an oversized two-car garage with attic storage, a newer Peerless boiler with a Riello burner, and an indirect hot water system for added efficiency. This home is surrounded by natural beauty, yet exceptionally connected, this residence is moments from boating, Nissequogue Golf Club, Stony Brook University and charming villages of St. James.

21 Wilderness Road, Nissequogue

$1,699,000
4 Beds 4 Baths 1029188 MLS
Private dock. Three independent buildings. Resort Waterfront Business zoning. Waterfront opportunities like this are exceptionally rare. Set along Penny Pond with direct boating access to Shinnecock Bay, this unique Hampton Bays compound offers an exceptional blend of waterfront living, investment potential, and flexibility. Whether enjoyed as a private retreat, multigenerational compound, income-producing property, or opportunity afforded by its coveted Resort Waterfront Business (RWB) zoning, this is a property that adapts to your vision. Comprising three independent structures, each with separate utilities, the compound includes a 1,488± sq. ft. main residence with 2 bedrooms and 2 full bathrooms, including a waterfront en-suite primary suite, a charming 2-bedroom waterfront cottage, and a detached two-car garage with an upper-level studio complete with a full bath and kitchenette. Expansive waterfront decks, generous outdoor living areas, an outdoor shower, ample parking, and a private dock with approximately 30 inches of water at low tide complete this distinctive offering, providing convenient boating access to Shinnecock Bay and endless enjoyment on the water. Properties that combine private docking, multiple legal structures, and valuable RWB zoning are seldom available. This is a rare chance to own one of Hampton Bays' most versatile waterfront properties.

35 Gardners Lane, Hampton Bays

$749,000
2 Beds 3 Baths 1023453 MLS
This beautiful waterfront home offers stunning water views and an exceptional combination of comfort and functionality. The home features two spacious bedrooms, with the flexibility to easily convert the layout into a third bedroom if desired. It includes two full bathrooms and one- half bath, along with a well-appointed kitchen, a comfortable den, and high ceilings that create a bright, open feel throughout. Additional features include central air conditioning, gas heat, a one-car garage, 220-volt electrical service, and abundant attic storage. For boating enthusiasts, the property offers side access for boat storage as well as a bulkhead for convenient docking. The primary bedroom opens onto a private deck, providing the perfect place to relax and enjoy the beautiful waterfront views Along with two walk- in closets This home is an ideal opportunity for anyone seeking a peaceful waterfront lifestyle with room to grow.

212 Shore Road, Lindenhurst

$3,995,000
7 Beds 6 Baths 1022766 MLS
Welcome to 38 Landing Meadow Road, Smithtown. Nestled on almost 23 picturesque and serene waterfront acres overlooking the renowned Nissequogue River this is a truly extraordinary North Shore retreat. Driving down the long private driveway your senses are alive to the possibilities of what is to appear. Surrounded by breathtaking natural beauty, the property includes agricultural land adjoining approx. 60 acres of protected preserve, creating an unmatched sense of privacy and tranquility. Wide open vistas, emerald lawns, magnificent mature trees and the grand nature of this idyllic scene are unmatched. Barns, stables, paddock, workshops, and multiple outbuildings provide endless possibilities for equestrian pursuits, farming, recreation, or creating your own private compound or purpose. This timeless Manor House built in 1828 offers nearly 6,000 square feet of living space, featuring 7 stately and spacious bedrooms and 6 bathrooms. The magnificent Estate is highlighted on the first floor by a warm and opening center hall with access to the rear property and patio, a formal living room, grand den with fireplace and the first floor is side property, den or library with a fireplace, truly formal dining room with a fireplace, an inviting eat-in kitchen designed for everyday living and entertaining and butlers pantry, family room or bedroom with a wet bar and two bathrooms. The charm and character of all of the rooms with so many original details of fireplace mantles and surrounds, stair mouldings and hardwood floors take you to another time. Besides the grand Manor home the property outside has an antique barn of approx. 7,500 square feet which offers the possibility of future use, and a caretakers suite inside. Also on the property is a “bank” barn with four 12x14’ horse stalls, a tack room and hayloft. Besides this barn is another smaller barn also with four 12x12’ horse stalls. On the grand 20 acre land preserve is extensive paddock and other fenced areas. Conveniently located near parks, golf clubs, beaches, wineries, charming villages, museums, and fine dining, this exceptional estate offers a rare opportunity to experience waterfront living at its finest. Walking in to this one-of-a-kind Estate you feel that 38 Landing Meadow Road Smithtown is a rare opportunity where history, nature and endless potential come together. Since the property adjoins multiple land preserve woodlands it ensures a forever-preserved backdrop and an exceptional North Shore lifestyle in which this legacy Estate can be yours and protected.

38 Landing Meadow Road, Smithtown

$1,799,999
7 Beds 5 Baths 1026344 MLS
A truly irreplaceable waterfront estate where timeless craftsmanship meets exceptional luxury. Originally built in 1928 and completely reconstructed in 1993/1994, this remarkable 5,700 sq. ft. residence is set on a private half-acre of deep-water waterfront in coveted West Islip, just minutes from Babylon Village & LIRR Main Line station. With incredibly low taxes, flood insurance under $1,500 per year, and grandfathered features that could never be approved under today's zoning, DEC, and New York State regulations, this is a once-in-a-generation offering. Designed for the discerning waterfront lifestyle, the property features a legal detached guest cottage complete with a studio apartment, full bath, washer/dryer, separate electric meter, and private waterfront deck—ideal for guests, extended family, or income-producing opportunities. Boating enthusiasts will appreciate two protected 35-foot boat piers with full pier walls, five oversized boat slips, 40 feet of private beach, deep water directly behind the property, and an unbeatable location just 500 feet from the open Great South Bay—eliminating the long canal runs found at most waterfront homes. Spanning three full levels of beautifully appointed living space, the 16-room main residence offers seven spacious bedrooms and 3.5 baths. Rich architectural details include exquisite original moldings, stunning 5/4 oak flooring, recessed lighting throughout, and meticulously restored circa-1930s light fixtures rewired for modern living. The luxurious primary suite opens through French doors to a private balcony overlooking the heated saltwater Gunite pool and tranquil river. A dramatic second-floor office boasts soaring 15-foot ceilings and sweeping views of the Great South Bay, while the expansive third-floor entertaining level features a custom wet bar, creating the ultimate game room and gathering space. The outdoor living experience is equally spectacular. Reconstructed in 2021, the commercial-grade heated Gunite pool features a saltwater system and is surrounded by an expansive entertaining area with a built-in Jacuzzi, cascading waterfall, river rock wall, and an oversized covered porch designed for effortless indoor-outdoor living. Westerly exposure delivers breathtaking sunset views over the water, while the rare absence of rear neighbors provides exceptional privacy. Recent improvements include Polyglass siding, ductless air conditioning, rebuilt decks and terrace, LED exterior lighting, and a beautifully renovated primary bathroom completed in 2025. Additional highlights include an eight-camera security system, a cobblestone driveway accommodating six vehicles, a two-car-deep garage, and rental income from the guest cottage to help offset carrying costs. Properties of this caliber simply cannot be recreated. Combining historic character, modern luxury, irreplaceable waterfront amenities, extraordinary boating access, and an unrivaled location, this is one of West Islip's most exceptional waterfront estates.

230 W Islip Road, West Islip

$1,499,750
4 Beds 3 Baths 1027328 MLS
Waterfront/Canal Living At Its Finest!! This Beautifully Designed Recently Built Colonial Offers An Open Concept Layout Perfect For Everyday Living While At The Same Time Provides An Entertainers Paradise! The Custom Eat In Kitchen Features A Large Center Island, Abundant Cabinetry, Quartz Counters, Pantry Room, And A Seamless Flow Into The Spacious Family Room With Gas Fireplace, A Formal Dining Room, Living Room And Half Bath Powder Room. Relax On The Covered Front Porch And Enjoy A Stately Entry Into A Beautiful Foyer Giving Way To The Second Level Including A Primary Suite With Walk-In-Closet, Private Balcony With Bay Views, And A Luxurious Ensuite Bathroom. Three Additional Generously Sized Bedrooms Provide Plenty Of Space, Laundry Conveniently Located On Second Level. This Home Also Offers Hardwood Floors Throughout, Central Air, In Ground Sprinklers, Outdoor Shed, Natural Gas Heating And Cooking, Attractive Paver Driveway/Walkways, Professional Landscaping, Professional Custom Outdoor Lighting Throughout The Exterior And Custom House Linear Lighting, A Backyard Oasis Is A Boaters/Entertainers Dream! Cana/Waterfront Living At Its Finest With Your Own Dock And Bulkheading! Backyard Features A Custom Paver Patio, Bulkhead, Dock, Heated In-Ground Mountain Lake Pool With Waterfall And Custom Lighting, Loop Lock Cover And A Mineral Frog Filtration System, Outdoor Kitchen, Firepit Entertainment Area. Dock Your Boat And Jet Ski's And Enjoy! Waterfront Living Just Moments From The Great South Bay, Built To FEMA Code, A Rare Opportunity To Enjoy A One Of A Kind Modern Construction in Amityville Village!

30 Berger Avenue, Amityville

$1,999,999
3 Beds 3 Baths 1022803 MLS
Rarely does a Southold waterfront property offer such a compelling combination of privacy, direct bay access, and expansive water views. Set on a protected inlet with a permitted dock and kayak launch, this three-bedroom, three-bath home is designed around its extraordinary setting. Sun-filled rooms open to a supersized waterfront deck, with a chef's kitchen with soapstone counters, a welcoming living room with fireplace, and water views throughout. The first-floor primary suite is a quiet retreat, and a rooftop observation deck captures sweeping vistas across Little Peconic Bay. The permitted lower level adds two bedrooms, a bath, a den, a second fireplace, and a wine cellar, with sliding doors opening to the water. The next owner also inherits a head start. The sellers have applied for a pool permit, so approvals are already in motion, and they have applied for a Grant toward a new IA septic system that transfers with the property. Approximately 3,900 square feet of finished living space on a half-acre, plus a one-car garage and shed, in a truly special Southold waterfront setting.

2245 Little Peconic Bay Lane, Southold

$2,149,999
4 Beds 4 Baths 1026094 MLS
Live the Waterfront Dream in Babylon Village Welcome to 75 Yacht Club Road — a stunning 2018-built bayfront estate offering 130 feet of vinyl bulkhead and 80 feet of pristine bay frontage, with sweeping, unobstructed views across Great South Bay to the Robert Moses Causeway Bridge, and Fire Island visible on clear days. Wake up to breathtaking sunrises and unwind to stunning sunset views from nearly every room in the house. This home sits in Babylon Village, one of the hottest neighborhoods on Long Island, with residents enjoying access to the village pool, village golf course, and the charming shopping and dining scene of downtown Babylon Village — all just minutes from your front door. Set on a quiet dead-end street, this is, quite simply, the best piece of waterfront and bayfront property in Babylon Village — the best views, the best location, and a once-in-a-lifetime opportunity to make it yours. Built to modern FEMA flood elevation standards, this home offers genuine peace of mind alongside luxury: flood insurance runs under $760 per year for maximum coverage, surcharges included. This home is as efficient as it is beautiful. Every exterior wall — including the crawl space — is fully spray foam insulated, resulting in remarkably low utility costs year-round, with the home comfortably maintained at 71 degrees in summer and 72 degrees; in winter. Sellers are happy to provide utility statements to any interested buyer, showing bills that stay in the hundreds of dollars, not even reaching a thousand a month. This is a true smart home from top to bottom — security cameras, alarm system, and appliances are all seamlessly integrated into a fully functional smart home setup, included with the sale. Monitor, control, and secure your home right from your phone. Natural hardwood flooring flows throughout every room, adding warmth and timeless craftsmanship to every space. Car enthusiasts, take note: EV Charger and the oversized 2-car garage was thoughtfully built with the height clearance and structural support needed for two auto lifts, offering the potential to store up to 4 vehicles indoors (lifts not included). The garage also comes equipped with three Garage Gator ceiling-mounted storage lifts, keeping bikes, seasonal gear, and equipment neatly stored overhead and off the floor. Boating life doesn't get easier than this. A boat lift rated for 14,000 lbs, a dedicated jet ski elevator lift, and a marine davit — each rated to 1,500 lbs — mean your entire fleet, including jet skis/wave runners, kayaks, and sailboats, is ready to go the moment you step outside. And here's the showstopper: the sale includes a 1997 Formula 312 Fast Tech race boat, valued at nearly $50,000, completely free of charge. Freshly refitted with two brand-new motors with less than two hours of run time, this boat is ready to hit the water immediately, with ownership transferring directly to the buyer at closing. Step into your new home and your new boat on day one. Inside, the home blends comfort and coastal elegance — an open, light-filled layout with a gourmet chef's dream kitchen featuring quartz countertops and stainless steel appliances, a primary suite with a spa-like bath (glass vessel sinks, Toto smart toilet), and a striking open-tread staircase that anchors the great room. Outside, low-maintenance synthetic turf and Nicolock paver patios front and back are made for entertaining, anchored by a built-in natural gas Weber grill — no more hauling or refilling propane tanks, ever. One of Long Island's most desirable villages. Waterfront homes like this rarely come available, and this one comes with its own ride.

75 Yacht Club Road, Babylon

$5,700,000
4 Beds 3 Baths 1024359 MLS
An Exclusive North Fork Bayfront Retreat in an Unrivaled Private Setting Experience the beauty of one of the North Fork’s most coveted private waterfront locations. Perfectly positioned beside protected land, this exceptional property offers sweeping views of Peconic Bay and a picturesque view of the Little Creek inlet its a setting that can never be replicated. Owned by the same family for generations, this remarkable waterfront property presents a once in a lifetime opportunity to own a truly special piece of North Fork history. Wake to breathtaking sunrises, take in the ever changing views of Peconic Bay and the creek inlet, and enjoy the privacy and serenity that make this one of the North Fork’s premier waterfront settings. A legacy property where protected land, spectacular water views, and unmatched privacy come together. Room for pool overlooking tranquil pristine sanctuary and creek. Private. Protected. One of a Kind.

Peconic

$15,950,000
4 Beds 6 Baths 1025305 MLS
5 Bluff Point Road is a remarkable new waterfront residence overlooking Morris Cove, where award-caliber architecture and waterfront living converge in one of Sag Harbor's most coveted settings. The home represents a thoughtful study in proportion, light, and connection to the surrounding landscape. Clad in cedar board-and-batten siding and complemented by a detached double-height garage of matching architectural character, the property has been conceived as a complete design statement. Designed for effortless indoor-outdoor living, expansive wraparound terraces and a covered roof deck seamlessly extend the home's living spaces, creating an exceptional setting for both everyday enjoyment and entertaining. The residence offers four bedrooms and five-and-a-half bathrooms, where expansive walls of glass frame uninterrupted water views and draw natural light deep into the interiors. The home's relationship to the waterfront is its defining feature. A newly constructed bulkhead and private dock accommodate a boat of approximately 24 feet (+/-), providing immediate access to Sag Harbor's waterways. Beyond, Morris Cove serves as a tranquil backdrop, with changing tides and spectacular sunsets becoming part of the daily experience. Outdoor living is equally compelling. Complementing the heated 11' x 20' Gunite pool are expansive wraparound landscaped Porcelain Stone patios and terraces, thoughtfully designed as a natural extension of the home's architecture. The terraces connect directly to the primary suite and upper-level hallway, while the roof deck enjoys panoramic views across Morris Cove and is thoughtfully outfitted with a dumbwaiter, as well as pre-plumbed and pre-wired for a future kitchenette, creating an extraordinary venue for entertaining above the water. Privately situated within the coveted Bluff Point community, directly across the cove from the John Steinbeck compound, now a writers' retreat, and moments from Sag Harbor Village, 25 Bluff Point Road offers a rare opportunity to acquire a newly built waterfront home distinguished by exceptional design, direct water access, and an enduring sense of place.

25 Bluff Point Road, Sag Harbor

$1,749,000
4 Beds 5 Baths 1025045 MLS
Experience the pinnacle of waterfront living in this exceptional newly constructed residence, perfectly situated on 1.19 acres of pristine waterfront property. Designed to capture breathtaking water views from nearly every room, this sophisticated 4-bedroom, 4.5-bathroom home seamlessly blends timeless elegance with modern luxury. The sun-filled open-concept floor plan is anchored by a stunning chef's kitchen featuring premium stainless-steel appliances, custom cabinetry, and an expansive island, all overlooking the tranquil waterfront. The spacious living and dining areas flow effortlessly to the rear deck, creating the perfect setting for indoor-outdoor entertaining while enjoying spectacular sunsets and refreshing bay breezes. Each of the four generously sized bedrooms is a private ensuite retreat, offering beautifully appointed bathrooms and exceptional comfort for family and guests. A stylish powder room adds convenience for entertaining. Outside, the expansive backyard leads to an impressive private dock capable of accommodating up to five boats, making this an extraordinary opportunity for boating enthusiasts. Whether you're setting out for a day on the water or returning home to relax on the spacious rear deck, this property offers an unparalleled waterfront lifestyle. Additional features include a two-car garage, quality craftsmanship throughout, and the peace of mind that comes with new construction. Offering privacy, luxury, and direct water access, this remarkable home is a rare opportunity to own a premier waterfront retreat minutes from the Hamptons, wineries and beaches.

255 Peconic Bay Boulevard, Aquebogue

$1,599,000
3 Beds 2 Baths 1024478 MLS
Welcome to 77 Bay Walk, a beautifully maintained 3-bedroom, 2-bath home in the heart of Fire Island Pines. Designed for effortless indoor-outdoor living, this inviting retreat features an open floor plan, abundant natural light, and two wood-burning fireplaces that add warmth and character. Step outside to your own private oasis with a saltwater swimming pool, hot tub, expansive sun decks, and beautifully landscaped gardens—perfect for entertaining or relaxing in complete privacy. Ideally located just moments from the bay, ocean beaches, and the vibrant Pines community, this exceptional property offers the perfect blend of comfort, style, and resort-style living. Whether you’re seeking a seasonal getaway, investment property, or your own island escape, 77 Bay Walk is a rare opportunity to own a piece of Fire Island Pines.

77 Bay Walk, Fire Island Pines

$4,950,000
1024073 MLS
A Once-in-a-Generation Hamptons Bayfront Resort Legacy Estate Looking for the Ultimate Hamptons Bayfront Resort and Waterfront ? Here it is. Presenting an extraordinarily rare, once-in-a-generation Hamptons Bayfront Resort and legacy estate on a spectacular stretch of pristine sandy Bay Beachfront. This exceptionally rare Hamptons Resort property and business opportunity offers six charming cottages with a total of 12 bedrooms, and 6 baths creating the ultimate private retreat, waterfront compound, or income-producing Bayfront business opportunity. A defining feature of this extraordinary offering is the expansive and exceptionally rare private fully equipped with water and electric two dock marina with dockage for up to 10 Boats, plus an additional 4 Jet Skis docks - an unmatched waterfront amenity rarely found in the Hamptons. Enjoy direct access to the open waters of Shinnecock Bay with effortless boating to the Atlantic Ocean. Set on a breathtaking sandy Bayfront Beach with panoramic water views and unforgettable sunrises, this one-of-a-kind waterfront oasis offers endless opportunities for recreation, relaxation, entertaining and business. Whether envisioned as a luxury family estate, boutique waterfront retreat, or premier resort-style business investment, this is a truly irreplaceable offering in one of the Hamptons' most coveted waterfront locations. Rarely does a Hamptons Bayfront business property of this style and scale, flexibility, and boating capacity ever become available.

71 W Tiana Road, Hampton Bays

$1,570,000
3 Beds 2 Baths 1022419 MLS
Experience effortless waterfront living in this impeccably renovated residence overlooking the open waters of Moriches Bay. Perfectly positioned with protected access via Orchard Neck Creek, this exceptional home offers the ideal balance of breathtaking bay views, boating convenience, and refined coastal living. Completely reimagined with uncompromising attention to detail, every space reflects quality craftsmanship and sophisticated design. The home showcases beautiful flooring, custom finishes, designer lighting, and top-of-the-line appliances, creating an elegant yet welcoming atmosphere throughout. Expansive windows fill the home with natural light while framing the ever-changing beauty of the bay. The spacious bedroom accommodations include a beautifully appointed primary bedroom featuring a cozy fireplace, while the luxurious designer bathroom has been renovated with exceptional finishes and timeless style. Two additional guest bedrooms and a conveniently located laundry area complete the interior. Outdoor living is equally impressive. An expansive waterfront deck provides the perfect setting for entertaining, dining al fresco, or simply unwinding while taking in panoramic views of Moriches Bay. The property offers ample room for a pool, creating the opportunity to design your own private waterfront oasis. A one-car garage adds everyday convenience. Whether you're heading out for a day of boating, kayaking, paddle boarding, or fishing, or simply enjoying spectacular sunrises, unforgettable sunsets, and the peaceful sound of the water from your own backyard, this remarkable home embodies the very best of East End waterfront living. Turnkey, beautifully renovated, and ideally situated, this is a rare opportunity to own a truly exceptional waterfront retreat.

40 Laura Lee Drive, Center Moriches

$1,899,999
1017889 MLS
Very near the eastern tip of Long Island’s renowned North Fork, this exceptional 1.37-acre beachfront property presents one of the few remaining opportunities to create a legacy waterfront estate in one of Orient’s most breathtaking coastal settings. Surrounded by panoramic views of Gardiners Bay, Long Island Sound, Plum Island, and the Connecticut shoreline, this remarkable homesite enjoys direct access to a sandy beach and the added distinction of neighboring protected Suffolk County parkland, preserving the natural beauty and open coastal landscape that define this extraordinary location. With approximately 125 feet of private beachfront, the property offers an ideal setting for relaxed coastal living and entertaining. The grounds provide ample space for hosting weekend guests, extended family, or friends escaping the city for beach days, outdoor dining, and slow, restorative mornings by the water. There is also the potential for a waterside pool (permits required), creating the opportunity to design a true resort-style coastal retreat. Wake to spectacular sunrises over Long Island Sound and embrace the quintessential North Fork lifestyle. Spend your days boating, kayaking, paddleboarding, fishing, swimming, beachcombing, or exploring the scenic trails and shoreline of nearby Orient Point County Park. Walk along the beach to take in views of the iconic Orient Point Lighthouse, affectionately known as the “Coffee Pot,” or take the nearby Cross Sound Ferry to New London for a day trip before returning home to the peace and privacy of your waterfront escape. Just minutes away, enjoy the charm of Orient Village, award-winning North Fork vineyards, local farm stands, marinas, and the iconic Duryea’s, where waterfront lunches and unforgettable sunset dinners are part of everyday life. For buyers seeking a more grounded way of living without sacrificing style, comfort, or design, this property offers a rare balance of sophistication, privacy, and direct beachfront access. It is a place to host, recharge, work remotely, spend summers, or simply step into a quieter rhythm of life. For city-area buyers ready to trade noise for salt air, open sky, and space to truly exhale, 1890 Lands End Road offers a rare North Fork escape that feels both elevated and effortlessly livable, where cinematic water views, natural beauty, and true coastal privacy come together in one extraordinary offering.

1890 Lands End Road, Orient Point

$3,500,000
3 Beds 1 Baths 1022911 MLS
Enjoy breathtaking western-facing views across Three Mile Harbor, a private beach, and close proximity to East Hampton Village from this exceptional waterfront offering. Nestled on a half-acre parcel in a Flood Zone X and across the street to a 16-acre nature preserve, the property presents a rare opportunity for both immediate enjoyment and future potential. The recently updated three-bedroom beach cottage provides a charming retreat, while the lot offers the ability to expand or construct a new residence, subject to applicable rules and regulations. There may also be the potential for a pool, subject to permitting and town approval. Spend your days on the water from your private beach, moor a boat nearby, and enjoy the very best of waterfront living. Spectacular sunsets over Three Mile Harbor complete this unique East Hampton opportunity.

21 Breeze Hill Road, East Hampton

$359,900
1 Baths 1022205 MLS
Location Location Location . . . Resort Style Living in this Totally Renovated Studio boasting 10ft Ceilings in the prestigious Westhampton House on highly coveted Dune Road. Located on the Garden Level this Meticulously updated Unit is only seconds away from the beautiful Sandy Beaches of the Atlantic and has a seamless blend of style, convenience, and coastal charm. Nestled on the edge of the Atlantic, this unit offers access to a suite of sought after amenities such as: expansive communal deck with Gas Grills and plush seating, a Heated Pool, Pool Deck and Private Beach protected by Lifeguards, clubhouse, gym, game room, bike storage room, laundry room, elevator, huge Private Parking lot on Dune Road and Beach and Bay access—all complemented by breathtaking Beach to Bay views. The open floor plan creates a welcoming space to entertain, while the thoughtfully crafted kitchen features elegant quartz countertops, a gas stove, and new cabinetry. Maximizing every inch of interior space, go outside and the Ocean becomes your backyard. Best value for the Price, this Coop is a short distance to John Scott’s hip Surf Shack restaurant and conveniently located to the vibrant Town of Westhampton Beach. Explore boutique shops, indulge in fine dining, or just soak up the sun at this iconic Hamptons destination. This is your opportunity to embrace the easy, coastal lifestyle that makes the Hamptons so legendary. This Complex is a Seasonal residence and is open from Mid April to Mid November. Equipped with new flooring and plenty of interior storage this Unit has a Brand New Ductless AC Unit that keeps the Apartment cool. If the weather is too cool you can turn on the heat to take the chill out of the air. The Bathroom is totally updated and has a large Stall Shower within. The apartment is being sold fully furnished. The artwork is negotiable and the Complex has two Parties a year: One on Memorial Day and One on July 4th.

585 Dune Road Unit #L10, Westhampton

$7,850,000
5 Beds 6 Baths 1021659 MLS
Westhampton Beach Waterfront | Where Every View Tells A Story Commanding over 200+ feet of pristine water frontage across 2.2 acres in the heart of Westhampton Beach, this brand-new construction is a rare convergence of architectural brilliance and effortless luxury. Designed with intention from the ground up, every room frames sweeping, unobstructed Bay views stretching all the way to Dune Road, a living canvas of breathtaking sunsets and shimmering water light. From the moment you arrive, the craftsmanship is unmistakable. A striking all-cedar exterior with a red cedar roof sets the tone, while Marvin modern doors and Ultimate windows frame every view with architectural precision. Inside, 8-inch white oak engineered hardwood floors flow seamlessly throughout, grounding every space with warmth and understated elegance. The state-of-the-art chef's kitchen is a masterclass in form and function, appointed with Sub-Zero and Wolf appliances, custom cabinetry, and a seamless open design that draws your eye effortlessly to the water beyond. The living room, anchored by a wet bar and Sub-Zero wine refrigerator, sets the stage for effortless entertaining at any scale. Five luxurious bedrooms and five-and-a-half spa-inspired baths are appointed with radiant heated floors, Toto fixtures, and California-style closets in every suite. Thoughtful technology and conveniences complete the picture, including Litron lighting, a Sonos sound system, private elevator, central vacuum system, dual laundry room, and two-car garage, ensuring every detail of daily living is as refined as it is effortless. Outside, the experience only deepens. IPE decking leads to a heated gunite pool, while a dedicated outdoor wellness area, complete with a sauna and outdoor shower, offers a private sanctuary built for restoration. A built-in BBQ creates an effortless setting for entertaining against the backdrop of 200+ feet of waterfront. This is the ultimate Hamptons experience, just minutes from the vibrant shops, dining, and culture of Westhampton Beach Village. 200+ feet of waterfront. Zero compromises.

9 E Division Street, Westhampton Beach

$3,995,000
4 Beds 4 Baths 1021398 MLS
We are proud to introduce Crest House, one of Cherry Grove's most extraordinary oceanfront estates. Commanding 120 feet of direct Atlantic Ocean frontage on a rare double lot spanning 0.37 acres. Built in 2012 and maintained with meticulous attention to detail, this 7,130 square foot post-and-beam residence rises three stories above the dunes and delivers an unmatched Fire Island living experience. Four bedrooms, three full baths, a powder room, soaring vaulted ceilings, three fireplaces, and a fully furnished interior make this a true turn-key retreat. The open-plan main level flows seamlessly into over 4,700 square feet of outdoor living - expansive decks, a heated pool, covered porch, and private courtyard - all framed by endless ocean views. Central air, forced air heat, and four zones of climate control ensure comfort in every season. Car-free Cherry Grove offers the rarest combination of privacy and community on the East End. Exit the ferry and enter a world where you're surrounded by nothing but the sounds of the ocean and the breeze. Properties of this caliber - this size, this position, this craftsmanship - simply do not come to market often.

55 Lewis Walk, Cherry Grove

$6,450,000
6 Beds 8 Baths 1021701 MLS
Introducing 1775 Point Pleasant, a newly constructed waterfront estate set on 1.8 acres with over 280 feet of pristine creek-frontage along iconic Mattituck Inlet. Thoughtfully designed and expertly crafted, this exceptional shingle sided Post-Modern style residence seamlessly blends timeless architecture with modern luxury. Spanning more than 7,000 square feet, the home showcases wide-plank hardwood flooring throughout, dual primary suites on both the first and second levels, a fully finished lower-level with private fitness studio, sauna, climate controlled wine storage, an unmatched custom lighting package, pre-wired recessed speaker system and expansive living spaces on all three levels designed for both everyday comfort and effortless entertaining. At the heart of the home is a chef's kitchen appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, multiple beverage stations and refined finishes throughout. Outdoors, resort-inspired amenities await, including a heated 22'x44' gunite pool surrounded by an expansive travertine terrace, fully equipped outdoor kitchen, a covered lounge with ceiling mounted heaters for those cooler nights and anchored by a third wood-burning fireplace, creating an ideal setting for waterfront entertaining. Finally, enjoy a manicured path of travertine stepping pads that lead to an oversized floating dock, equipped with water and electric, that can easily house a large boat with deep draft, perfectly capping off this incredible custom build opportunity. Offering an extraordinary combination of scale, privacy, craftsmanship, and lifestyle, 1775 Point Pleasant represents a rare opportunity to own a truly exceptional waterfront retreat on the North Fork.

1775 Point Pleasant Road, Mattituck

$935,000
1021649 MLS
Calling All Investors, Developers & End-Users!!! Beautiful 16,000+ Sqft. Waterfront Development Site In Sayville For Sale!!! The Property Is Located In The Heart Of Sayville 2 Blocks From The Sayville Ferry Service!!! The Property Is Situated Only Minutes From Montauk Hwy. & The Sayville LIRR!!! The Property Features Great Exposure, 26 Parking Spaces, Exceptional Views, BUS1 Zoning, Private Driveway, Low Property Taxes, +++!!! Neighbors Include Starbucks, Chase Bank, Costco, Restaurant Depot, Uncle Giuseppe’s Marketplace, Stop & Shop, CVS, Walgreens, Orangetheory Fitness, 7-Eleven, Dunkin’, Floor & Decor, SoBol, Friendly’s, Dollar Tree, Subway, +++!!! This Property Has A C/O For A Legal 2 Family!!! The Property Offers HUGE Upside Potential!!! This Could Be Your Next Development Site Or The Next Home For Your Business!!! Expenses: Taxes: $5,151.54 Ann.

48-52 Browns River Road, Sayville

$22,500,000
4 Beds 6 Baths 1021256 MLS
OCEANFRONT PROPERTY WITH PLANS IN PLACE FOR A SAOTA MASTERPIECE This incredible oceanfront property is set atop Montauk's oceanfront bluffs with permits & plans for an extraordinary SAOTA-designed residence- a rare fusion of world-class architecture, structural engineering, and resort-level living. Sculpted directly into the natural topography overlooking the Atlantic Ocean, the permitted home can be conceived not merely as a residence, but as a private coastal sanctuary where architecture disappears into the landscape and every space is oriented toward the horizon. Arriving through a private estate-style motor court, a grand pathway guides you to an impressive entrance that opens to breathtaking Atlantic Ocean views and architectural brilliance. Encompassing approx. 7,109 square feet of finished interior living space, the residence can include a four-bedroom, four-bath, two-and-a-half bath estate. Owners are welcomed into a home with plans defined by monumental pocketing glass walls, board-formed concrete, natural stone, charred wood detailing, and uninterrupted ocean views. Flowing effortlessly onto expansive oceanfront patios and dissolving the boundary between indoor and outdoor living transforming the home into an open-air pavilion above the Atlantic. Reflecting SAOTA's signature approach to blending architecture with the surrounding landscape, every space is thoughtfully designed to maximize light, views, the connection to the ocean with Montauk's natural beauty. Enjoy a dramatic oceanfront lounge, dining room, bar, and butler's pantry, seamlessly blending onto expansive terraces anchored by a custom fire feature, outdoor dining spaces, and an architectural pergola. At the edge of the bluff, plans include a spectacular cantilevered infinity-edge pool appears to float toward the ocean, complete with a swim-up bar, integrated seating, and panoramic views stretching across the Atlantic. Supported by one of the most respected design teams in the world, the pemitted residence represents a level of design, engineering, and entitlement complexity that would be impossible to replicate today along the Montauk coastline.

250 Old Montauk Highway, Montauk

$6,899,000
5 Beds 6 Baths 1019832 MLS
Anchored on the Atlantic.... The essence of Hamptons coastal luxury awaits on coveted Dune Road, just moments west of the Jessup Lane bridge. Perfectly positioned between the serene waters of Moriches Bay and the Atlantic Ocean, this extraordinary custom-renovated contemporary offers a rare opportunity to experience one of the most coveted lifestyles in the Hamptons—where every day begins with ocean breezes and ends with unforgettable waterfront sunsets. Set on .52 private acres with exclusive ocean access via your own private pathway to the beach, this spectacular 3,797-square-foot residence seamlessly blends sophisticated design with effortless coastal elegance. Featuring five luxurious ensuite bedrooms, five full baths, and one half bath, every bedroom is thoughtfully designed to capture breathtaking water views and opens to private decking, creating a seamless connection between indoors and out. Designed for elevated entertaining and relaxed seaside living, the chef’s kitchen is beautifully appointed with a Viking six-burner range with grill, Miele dishwasher, built-in Miele espresso station, wine cooler, Library/Media room with 80 inch TV, and exceptional custom finishes throughout. Crowning the home is an extraordinary rooftop deck with panoramic 360-degree views of both bay and ocean—an unrivaled setting for sunrise coffee, sunset cocktails, and stargazing under endless Hamptons skies. Luxury details abound, including copper gutters, central air, Kohler whole-house generator, and integrated Sonos sound system, ensuring both comfort and peace of mind year-round. Outdoor living is nothing short of spectacular. Expansive mahogany decking, lush professional landscaping, elegant new teak furnishings, and a beautifully refurbished heated gunite pool create a private resort-like setting designed for unforgettable summer gatherings or quiet moments of retreat. Offered fully furnished and professionally designed, this turnkey masterpiece embodies the very best of Hamptons living— where private ocean beach access, watching boats on Moriches Bay, and world-class dining in nearby Westhampton Beach become part of your everyday life. This is more than a home—it is Dune Road living at its finest.

291 Dune Road, Westhampton Beach

$1,911,000
3 Beds 4 Baths 1019903 MLS
"Mariner" 57 Old Boathouse Lane South - Introducing Canoe Place Boathouses, where Hamptons Home Ownership meets Luxury Hotel Service. Located just across the Shinnecock Canal from historic Canoe Place Inn, the Canoe Place Boathouses offer a rare blend of contemporary living, sought-after convenience, and celebrated Hamptons charm. All just a short drive from Manhattan-and just moments from three world renowned golf courses, beloved beaches and charming Hamptons Villages. Full service and designer-furnished by Benjamin Noriega-Ortiz, these 2- and 3-bedroom waterfront residences provide spacious interiors, private terraces, and panoramic canal views. With just 37 residences, these shingle-sided exteriors are inspired by the region's classic architecture and appointed with modern features like luxurious gourmet kitchens and cozy fireplaces. Thoughtfully designed to rejuvenate both body and spirit, these residences include graciously sized soaking tubs and private waterfront balconies. Each waterfront residence enjoys access to a "residents only" waterside pool & hot tub, fitness center, club lounge and dock. The Canoe Place Boathouses set a new standard in luxury lock-and-leave convenience in the Hamptons with all the resort concierge services at your disposal. Imagine being picked up right outside your door by a chartered yacht and whisked off to one of the many beautiful waterfront restaurants. Canoe Place Inn concierge can also set up a beautiful picnic lunch for a day at the beach. As a residence owner, enjoy priority access to Canoe Place Inn dining, spa services, and event spaces. Good Ground Tavern at Canoe Place offers a nostalgic atmosphere, blending the old- school charm of New England with modern sophistication. Plush seating, soft lighting, and elegant design details create a welcoming setting where guests can savor seasonal American cuisine, delivered with the signature excellence of Union Square Events, a Danny Meyer concept. As the site of America's oldest inn, Canoe Place has proudly welcomed travelers since 1697. Today, the resort's beautifully appointed private residences offer a rare combination of both rich history and an easier way to come home to the Hamptons. Unparalleled Access. Uncomplicated Ownership. The complete offering terms for the sale of membership interests in the homeowners association are in an offering plan available from the Sponsor. File No. H18-0004.

57 Old Boathouse Lane S, Hampton Bays

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