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$2,595,000
5 Beds ⋅ 3 Baths ⋅ 1049697 MLS
The Ultimate Resort Home, Just Steps from the Beach 253 Cottage Walk | Ocean Beach, NY 11770 | Fire Island Just four houses from the beach, 253 Cottage Walk sits on an oversized 6,000-square-foot lot with a huge 438-square-foot L-shaped pool, spa, sauna, outdoor kitchen, and nearly 2,000 square feet of deck space. This spacious 4+ bedroom, 3-bath home is the perfect setting to enjoy all the beauty and entertaining Fire Island has to offer. The private, fully fenced and gated grounds create a secluded oasis, featuring the incredible L-shaped sports pool with a large sun shelf for lounging, a big 7' × 7' spa that seats up to 8, and a 4-person cedar sauna. A beautiful new modern outdoor shower and full cabana bathroom complete the retreat. Whether you're grilling at the outdoor kitchen or gathering around the 12-foot outdoor bar, this home has it all. A dedicated turf area gives the kids and the games a home of their own. Inside, the two-story home offers four bedrooms plus a den with large French doors and its own closet, ideal as a home office or additional sleeping space, and three fully renovated bathrooms. Two of the bedrooms feature private en-suite baths. The renovated kitchen features custom finishes, two pantries, and views to the pool through the sliding glass doors. Beautiful renovations throughout— new flooring, paint, fixtures, and finishes — capture its true Fire Island beauty. Comfort is ensured throughout an extended season with ductless mini-split systems providing zoned climate control in every room, and a dedicated laundry room adds everyday convenience. The home also features a classic cedar shake exterior and a low flood insurance premium. With tremendous decking wrapping the first floor, plus an upper deck with partial ocean views off the primary bedroom, there is no shortage of outdoor space for dining and lounging. With the beach just steps away, a resort-style pool, deck, and yard, partial ocean views, and completely renovated interiors, 253 Cottage Walk checks every box for a truly exceptional Fire Island home!

253 Cottage Walk, Ocean Beach
$799,999
5 Beds ⋅ 2 Baths ⋅ 1045316 MLS
Welcome to this beautifully maintained 5-bedroom, 2-bath home, lovingly cared for by the same owners for many, many years! This spacious and inviting property offers a wonderful combination of charm, comfort, and versatility, with part of the home currently utilized as an Airbnb, providing an excellent opportunity for additional income potential. Inside, you’ll find beautiful wood floors, crown molding, a cozy fireplace, central air, gas heat, and a bright, inviting sunroom perfect for enjoying your morning coffee or relaxing at the end of the day. The bedrooms are generously sized and the primary accommodates king-size furniture, while the large 'granny' attic offers abundant storage. Step outside to an amazing entertaining yard featuring a sparkling inground pool, spacious deck, and plenty of room for gatherings and summer fun. The large driveway provides ample parking, complemented by a garage for additional storage and convenience. Cedar-impression vinyl siding adds attractive curb appeal with easy maintenance. Ideally located less than a mile from Main Street and the railroad station, and close to the Fire Island ferries, hospitals, shopping, dining, and transportation. Whether you’re looking for a spacious home, an entertaining oasis, or a property with income-producing potential, this well-loved home offers it all!

73 Maple Avenue, Bay Shore
$3,500,000
3 Beds ⋅ 4 Baths ⋅ 1045873 MLS
Set directly on the Atlantic in the coveted low 400s of Fire Island Pines, this contemporary oceanfront residence combines exceptional beachfront living with modern construction and year-round functionality. Built from the ground up in 2016 to post-Hurricane Sandy elevation and building standards, the fully permitted home offers three ocean-facing en-suite bedrooms, 3.5 baths, a heated saltwater pool, rooftop hot tub and private beach access via its own boardwalk. The open main living level features 11-foot ceilings, hardwood floors, expansive ocean-facing glass and a wood-burning fireplace. The kitchen is equipped with high-end appliances including a 36-inch refrigerator, gas range, wall oven, dishwasher, wine cooler and dedicated ice maker. Glass doors open directly to the oceanfront deck and heated saltwater pool, creating a seamless connection between the interior, outdoor living spaces and beach beyond. Upstairs, all three en-suite bedrooms enjoy ocean views and private balconies. Two are generously proportioned primary suites, while the rooftop terrace and hot tub offer panoramic views across the Atlantic and the Pines. Fully winterized with substantial heated storage beneath the home, recently replaced HVAC condensers and refinished hardwood floors. Extensively updated during the current ownership and offered fully furnished, excluding artwork. A turnkey oceanfront home designed for long summers, shoulder seasons and life in the Pines throughout the year.

418 Ocean Walk, Fire Island Pines
$1,599,000
6 Beds ⋅ 4 Baths ⋅ 1045401 MLS
Lovingly restored and thoughtfully enhanced by its current owners, this remarkable 1880 residence reflects years of careful stewardship And substantial investment. Every update was made to elevate everyday living while honoring the home's character and architectural integrity. Updates: 2021 : New Siding & Windows, New PVC & Aluminum Fencing. Leaf Filter on All Gutters 2021/2022 : Basement waterproofed ( Lifetime guarantee ) 2021/2022 : Pool heater & Filter 2022 : New Split Units 2023: Generator, 15 zone Sprinklers, Alarm system with 11 Cameras hooked up to Central Station, Doors 2024: New Kitchen & Appliances, Motorized Shades in Living Room 2025: New driveway, New walkway and Stoops 2026: 2.5 New Bathrooms, with Soaker tub on 2nd floor and wonderful shower on third floor 2026: Newly sealed bricks around pool and back walkway.

75 S Penataquit Avenue, Bay Shore
$1,695,000
4 Beds ⋅ 3 Baths ⋅ 1043341 MLS
Impeccably maintained, secluded Bay Walk property located eight minutes from the Waterfront. Renovated in 2025 including kitchen appliances; cabinetry; refinished hardwood floors; heated XL saltwater pool; hot tub; gas water heater; roof and fully serviced Andersen windows & doors. New furnishings throughout. Extensive mahogany decking. Wood burning fireplace and propane fire pit. Fully air conditioned. Generously proportioned primary en-suite features with additional fireplace. Three guest bedrooms (one king & two queen beds) with ample closets. Low operating expenses and $185k in 2026 gross rent; several weeks pre-booked in 2027. Straightforward mortgage financing – no open permits, violations, and conforming to zoning requirements. Being sold fully furnished & turnkey.

279 Bay Walk, Fire Island Pines
$1,650,000
3 Beds ⋅ 2 Baths ⋅ 1041244 MLS
Set amongst lush landscaping, 208 Midway Walk is a commanding presence with a storied history and architectural pedigree attributed to Bates Masi+ Architects. Cedar detailing inside and out presents 3 bedrooms and 2 full baths, double height ceilings and large windows bringing the indoors out. Extra deep lot and large pool + morning and afternoon decks, sun and shade options, makes for the ideal Fire Island retreat.

208 Midway Walk, Fire Island Pines
$2,000,000
9 Beds ⋅ 9 Baths ⋅ 1040354 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Home Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore
$3,300,000
3 Beds ⋅ 3 Baths ⋅ 1038274 MLS
One of Fire Island Pines’ most recognizable residences, the Pyramid House is an extraordinary expression of the experimental modernism that came to define the Pines. Designed circa 1960 by Buenos Aires–born architect Julio Kaufman, the house was later thoughtfully reimagined while preserving Kaufman’s iconic silhouette. A monumental steel-and-glass wall opens the soaring upper-level great room to sweeping views across the protected dunes of Fire Island National Seashore toward the Atlantic and bay beyond. Set at the quiet eastern edge of the Pines and bordering protected landscape, the approximately 2,100-square-foot residence offers an unusual degree of privacy. Built to a standard uncommon to Fire Island, its robust construction includes galvanized structural steel designed to endure the island environment. The current configuration offers three bedrooms and two-and-a-half baths. The lower level is devoted principally to an expansive primary suite with dressing areas, bath and private study, opening toward the pool and dunes. Across the secluded courtyard, three smaller pyramidal forms echo the geometry of the original house, with two guest bedrooms flanking a central bath. Recent improvements include central air conditioning, significant electrical upgrades, a new saltwater pool liner and updated pool mechanicals, along with 3M Prestige 70 window film applied to the Pyramid’s monumental glazing. For its next steward, the expansive lower level presents the possibility of another chapter of reinvention, potentially accommodating two additional ensuite bedrooms and creating a five-bedroom, four-and-a-half-bath residence.* The property’s successful history as a sought-after seasonal rental adds another dimension to its versatility. More than six decades after its creation, the Pyramid House remains remarkably private and unmistakably iconic—a landmark of Fire Island modernism ready for its next chapter. *Any potential reconfiguration is subject to applicable approvals and independent verification by the purchaser.

443 Sail Walk, Fire Island Pines
$2,200,000
10 Beds ⋅ 7 Baths ⋅ 1037620 MLS
Step back in time and experience the grandeur of this extraordinary 1850 Victorian estate, a truly one-of-a-kind residence where timeless architecture, remarkable scale, and old-world craftsmanship create something rarely found today. Set on 1.64 breathtaking, park-like acres, this magnificent property offers exceptional privacy, an inground pool, and endless possibilities. From the moment you enter, soaring ceilings, intricate crown moldings, beautiful hardwood floors, and exquisite period details capture the elegance and charm of a bygone era. Three expansive floors of living space feature a magnificent living room, grand banquet-sized formal dining room, large eat-in kitchen, and an inviting den with fireplace. The main residence offers an impressive ten bedrooms, seven full baths, and a full basement, providing extraordinary space and versatility. The estate also features a separate back house offering four additional bedrooms, two full baths, and a two-car garage, adding another remarkable dimension to this unique property. Rich in history and overflowing with character, this exceptional Victorian estate presents a rare opportunity to restore, reimagine, and create something truly spectacular. From its grand interior spaces to its sprawling grounds and resort-style pool, this is more than a home. It is a piece of history waiting for its next chapter. Make this extraordinary one-of-a-kind estate yours.

45 S Penataquit Avenue, Bay Shore
$975,000
3 Beds ⋅ 2 Baths ⋅ 1036096 MLS
A quintessential Cherry Grove cottage, cozy and unfussy, perfect for a relaxing beach vacation. There are three bedrooms and two bathrooms (the primary bedroom is en suite), Entertaining is easy with the kitchen open to the living area as well as the dining area. And the house features a spacious deck for outside dining, sunbathing, and lounging by the pool. Refresh yourself with an invigorating outdoor shower. Located in a quiet neighborhood, but still convenient to the nightlife and restaurants, the beach is just 4 houses off the beach, as is the trail through the Sunken Forest. The heated pool completes this lovely property.

259 East Walk, Cherry Grove
$2,000,000
1035730 MLS
Rare Waterfront Investment Opportunity On Penataquit Canal! This Exceptional Triplex Offers Over 180 Feet Of Prime Waterfront With 13 Private Boat Slips, Expansive Docking, And Breathtaking Views Of Fire Island. Situated At The End Of A Quiet Cul-De-Sac, This Unique Property Features A Total Of 9 Bedrooms And 9 Bathrooms, Including 5 Bedrooms With Private En-Suite Baths. Step Outside To A True Waterfront Oasis Featuring An In-Ground Pool With An In-Ground Hot Tub, A Stunning Brick Outdoor Kitchen, Expansive Paver Patio, And Swaying Palm Trees, Creating The Ultimate Resort-Style Setting For Entertaining Or Relaxing Along The Water. Whether You're Looking To Expand Your Investment Portfolio, Generate Exceptional Rental Income, Or Own A One-Of-A-Kind Waterfront Property With Endless Possibilities, This Incredible Offering Checks Every Box. A Rare Opportunity To Own A High-Income Producing Property In An Unbeatable Waterfront Location.

64 Mowbray Avenue, Bay Shore
$2,200,000
3 Beds ⋅ 3 Baths ⋅ 1033182 MLS
THE BEST THE PINES HAS TO OFFER. Gorgeous contemporary 2 bedroom, 3 bath offering seamless indoor/outdoor living. Private and luxurious the many amenities include a large heated pool & spacious deck, hot tub, central AC and heat, fireplace, television room that can be converted into a third bedroom & designer furnishings all set in beautifully landscaped gardens.

307 Shady Walk, Fire Island Pines
$4,490,000
5 Beds ⋅ 6 Baths ⋅ 1026874 MLS
Incredible New Construction Ocean & Bay View Home with Pool! Welcome to your dream coastal retreat in Ocean Bay Park, Fire Island! This stunning brand new construction bay view home for sale boasts 5 spacious bedrooms, 4 full bathrooms, and 2 half bathrooms across two floors, offering over 3,600 square feet of luxurious living space. Properties of this size and scale are extremely hard to come by on Fire Island. Set back on a massive 11,803 SF lot, this home lives large! The interior is immaculate, featuring top-of-the-line finishes, high ceilings, and an abundance of natural light. With 2 luxurious bedroom suites on the first level, and 2 additional bedrooms as well as the grand owner’s suite on the second floor, this home can accommodate an extended family. The primary bedroom has a wall of glass overlooking the bay, a huge walk in closet, balcony access, and an oversized spa bathroom with freestanding tub, walk in shower, dual sinks, and a separate water closet. The expansive great room is perfect for relaxing and entertaining with soaring 13’7” high ceilings and stunning views of the Great South Bay. The modern gourmet kitchen is a chef's delight, complete with high end appliances, a large center island, and plenty of counter and storage space. Enjoy dining alfresco while looking out over the bay on the large deck with pergola and built in outdoor kitchen, just off of the great room. There are laundry rooms and powder baths on both levels for your convenience. Step outside to your own private oasis, where you'll find a massive 30’ X 18’ heated salt water swimming pool and over 4,000 square feet of decking, including a screened in porch, covered outdoor area, and roof deck with breathtaking 360-degree views from bay to ocean. Enjoy stunning sunsets from the comfort of your own home, with uninterrupted vistas of the water and surrounding natural beauty. Situated across Bay Walk from a public green space, your unobstructed bay views are protected forever. Walk to the beach in 3 minutes or the ferry in just 1 minute! Conveniently located close to restaurants and the market in Ocean Bay Park or a quick bike ride to downtown Ocean Beach. This is an incredible opportunity to own a one-of-a-kind home in one of the most desirable locations on Fire Island. Don't miss out on the chance to make this brand new construction home for sale in Ocean Bay Park your own private paradise! Sold fully furnished. Affordable flood only $2,939/ Year!

2 Ocean Bay Boulevard, Ocean Bay Park
$1,995,000
3 Beds ⋅ 3 Baths ⋅ 1026332 MLS
Mid-century modernism as seen through the eyes of Horace Gifford. This 3 bedroom, 2.5 bath features all the modern & sophisticated hallmarks of Giffords genius - clean lines, open living space and seamless indoor/outdoor flow. All set in a private garden with large pool and multi purpose decking.

487 Tarpon Walk, Fire Island Pines
$1,099,000
5 Beds ⋅ 4 Baths ⋅ 1024524 MLS
Welcome to a home where timeless elegance meets exceptional craftsmanship in the heart of the Village of Brightwaters. Perfectly positioned on one of the area’s most sought-after streets, this beautifully appointed residence offers luxury finishes, flexible living spaces, and an extraordinary backyard retreat designed for both everyday living and unforgettable entertaining. At the heart of the home is a custom chef’s kitchen featuring granite countertops, under-cabinet and in-cabinet lighting, a double convection oven with a warming drawer, and an induction cooktop—a space as functional as it is beautiful. The stunning cathedral-ceiling primary suite is a true retreat, complete with two custom walk-in closets, new skylights that fill the room with natural light, and a spa-inspired primary bath featuring a luxurious soaking tub. Every upstairs bedroom and bathroom is enhanced with custom-designed closets, providing exceptional organization and storage. The versatile lower level offers brand-new flooring, a new full bathroom, and an expansive office suite with two private offices and a waiting room, making it ideal for a home-based business, professional workspace, guest quarters, multigenerational living, or a nanny suite. Step outside into your own private resort. The professionally designed backyard showcases a heated lap pool with cascading waterfalls, an outdoor fireplace, and a built-in outdoor kitchen with granite countertops, creating the perfect setting for entertaining or relaxing. An upper Trex deck overlooks the spectacular grounds, while a 12-zone in-ground sprinkler system keeps the lush landscaping looking its best. A circular driveway adds both elegance and convenience to the home’s impressive curb appeal. Located in the charming Village of Brightwaters, residents enjoy tree-lined streets, a private village park, tennis courts, a community dock, summer concerts, holiday celebrations, and a true small-town atmosphere—all while being just minutes from vibrant downtown Bay Shore, waterfront restaurants, Fire Island ferries, beaches, parks, and the LIRR for an easy commute to Manhattan. This is more than a home—it’s a lifestyle defined by luxury, comfort, and one of Long Island’s most desirable communities

236 Windsor Avenue, Brightwaters
$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
$2,500,000
4 Beds ⋅ 5 Baths ⋅ 1017237 MLS
Brand New Oceanfront Home with Pool! This stunning newly constructed residence offers the perfect blend of luxury, comfort, and breathtaking natural beauty. Featuring four spacious bedrooms, including two private primary ensuite retreats, and three-and-a-half beautifully appointed bathrooms, the home is designed for effortless coastal living. The bright and airy open-concept living, dining, and kitchen area is ideal for entertaining, with seamless indoor-outdoor flow and spectacular water views. Step outside to enjoy the fabulous new swimming pool and stylish cabana, creating your own private resort by the sea. Crowning this exceptional property is an expansive roof deck showcasing panoramic vistas of both the Atlantic Ocean and the Great South Bay—an unforgettable setting for sunrise coffee, sunset cocktails, and stargazing. A rare opportunity to own a brand-new oceanfront sanctuary in an incomparable location.

52 Lewis Walk, Cherry Grove
$1,750,000
7 Beds ⋅ 8 Baths ⋅ 1017133 MLS
Wisteria is a one-of-a-kind luxury retreat in Cherry Grove, Fire Island, completely rebuilt in 2020. This exceptional property features seven private en-suite bedrooms, including two poolside suites, a stunning open-concept living area with chef’s kitchen, and resort-style amenities throughout. Enjoy a solar-heated pool, meditation garden, covered outdoor dining pavilion, and a separate studio with full bath. The spectacular rooftop deck offers panoramic views from the Atlantic Ocean to the Great South Bay. A rare opportunity to experience the ultimate in Fire Island luxury and privacy

37 Bayview Walk, Cherry Grove
$1,275,000
2 Beds ⋅ 2 Baths ⋅ 1013722 MLS
Perched high and dry on the secondary dune with sensational ocean views this 2 bedroom 2 bathroom mid-century cottage presents an ideal opportunity for first time home buyers. The many amenities include 30'x14' solar heated pool, hot tub, outdoor shower, out door grill & primary bedroom with ensuite bath.

445 Sail Walk, Fire Island Pines
$3,600,000
5 Beds ⋅ 4 Baths ⋅ 1007104 MLS
Experience the best of Fire Island living in this newly constructed Ocean Bay Park home offering ocean views, bay views, and resort-style outdoor space. Designed for effortless summer living, this 5-bedroom, 4-bath retreat features bright open interiors, modern finishes, and seamless indoor-outdoor flow. Enjoy sunrise over the ocean, sunset over the bay, and long afternoons around your oversized heated pool. The expansive roof deck delivers panoramic views and the perfect setting for entertaining. A rare opportunity to own a turnkey luxury home under $4M in one of Fire Island’s most sought-after communities. Highlights: - Ocean views - Bay views - Huge heated pool - New construction - Roof deck - Under $4M - 5 bedrooms - 4 bathrooms

18 Ocean Bay Boulevard, Ocean Bay Park
$1,499,990
5 Beds ⋅ 4 Baths ⋅ 1001324 MLS
Nestled on Long Island’s coveted South Shore in desirable Bay Shore, this stunning five-bedroom ranch offers luxury living with a true resort-style feel. Beautifully landscaped grounds create a private backyard oasis featuring an Olympic-size swimming pool, expansive patio for entertaining, and a lighted professional tennis court for day or evening play. Inside, the home blends comfort and sophistication with an oversized family room ideal for gatherings, a sunroom showcasing panoramic yard views, and a chef’s kitchen featuring premium appliances, including a full-size Sub-Zero refrigerator and separate full-size Sub-Zero freezer with abundant storage. Recent upgrades include a Brand New sprinkler system, owned solar panels, a renovated double shower in the primary suite, updated heating and A/C in the kitchen, and a newly installed 5-ton central A/C unit. An upper-level bedroom with a private roof deck overlooks the pool and tennis court, completing this exceptional Bay Shore retreat. A rare opportunity to enjoy luxury, recreation, and effortless South Shore living.

9 Dove Lane, Bay Shore
$2,500,000
6 Beds ⋅ 7 Baths ⋅ 1006861 MLS
Perched high on the secondary dune on a corner lot we are pleased to offer Pines Bluff Overlook Guest House for sale. Comprised of 6 private guest suites all with ensuite baths. The many amenities include ,Apple TV, Central Air Conditioning, Fireplace, Heat, Hot Tub, Ocean Views, Outdoor Shower, Pool, Roof Deck, Wet Bar & Wifi.

362 Ocean Walk, Fire Island Pines
$1,799,000
4 Beds ⋅ 4 Baths ⋅ 1006212 MLS
Unparalleled privacy in this triple mint 4 bedroom, 4 bath home with a meticulous attention to detail. the large living/dining area opens onto a sun drenched pool deck featuring a  hot tub and a separate cabana which can easily double as an additional guest bedroom. Exceptional appointments and furnishings throughout including energy efficient & cost saving solar panels with an additional backup battery  providing a seamless power transfer in the event of power outages.  Other first class amenities include a chef's grade kitchen with Viking stove & refrigerator, Subzero ice maker, beautiful cherry wood cabinetry, central heat & A/C. Fully Winterized for year round enjoyment.

605 Shore Walk, Fire Island Pines
$2,075,000
7 Beds ⋅ 5 Baths ⋅ 995314 MLS
Just 600 feet from the ocean, Casablanca 2.0 is a fully reimagined 7-bedroom, 4.5-bath coastal retreat designed for seamless indoor-outdoor living and exceptional rental performance. Set behind a private, bamboo-lined approach, the home offers a rare blend of privacy, scale, and modern design in one of Fire Island’s most sought-after enclaves. Gut-renovated in 2023 and outfitted with all-new furnishings in 2024, the residence features a sun-drenched open-concept living space with wide-plank flooring, an electric fireplace, and walls of glass that lead to expansive multi-level decking. The chef’s kitchen is thoughtfully appointed with quartz countertops, a large island, custom cabinetry, and premium appliances—perfect for entertaining at scale. Seven well-proportioned bedrooms—all with queen or king accommodations—are designed for both comfort and flexibility. Multiple en-suite layouts, a Jack-and-Jill configuration, and additional flex space allow for effortless hosting while maintaining privacy. Outdoor living is elevated with a heated saltwater pool, rooftop deck, outdoor shower, and newly constructed decking throughout—creating a true resort-style setting ideal for both quiet retreats and vibrant summer gatherings. Built for both lifestyle and longevity, the home features elevated coastal construction, a new roof and siding, two 200-amp electrical panels, two water heaters, and a 9-zone energy-efficient split-system for individualized heating and cooling throughout. Offered fully furnished and turnkey, Casablanca 2.0 is not only a refined beachside escape but a proven high-performing asset with strong seasonal demand and consistent occupancy. A rare opportunity to own a private, design-forward retreat where luxury meets investment in the heart of Fire Island Pines. With strong seasonal demand and a layout optimized for group accommodations, Casablanca 2.0 has demonstrated exceptional rental performance, including high occupancy during peak summer months, consistent 5-star guest experiences, and efficient pricing for larger groups. Offered fully furnished and turnkey, it presents an immediate opportunity for income generation with long-term upside in a supply-constrained, globally recognized destination.

317 Sky Walk, Fire Island Pines
$2,500,000
4 Beds ⋅ 3 Baths ⋅ 988717 MLS
Featured in Architectural Digest, this extraordinary oceanfront residence on Steels Walk in Water Island, designed by acclaimed architect and designer Carl D’Aquino, is one of the most distinctive and architecturally significant properties on all of Fire Island. As co-founder of the internationally celebrated design firm D’Aquino Monaco, D’Aquino is renowned for creating homes that blend modernist architecture with warmth, craftsmanship, and a profound connection to their natural surroundings — a philosophy beautifully realized throughout this remarkable coastal retreat. Comprised of two dramatic octagonal-shaped structures seamlessly joined at the center, the home was thoughtfully conceived to embrace its breathtaking setting, where unobstructed views of the Atlantic Ocean, rolling dunes, and endless sky become part of everyday living. Every angle, sightline, and material was intentionally selected to create a seamless dialogue between architecture and landscape, resulting in a home that feels both visionary and deeply serene. Offering 4 bedrooms and 2.5 baths, the residence blends refined coastal sophistication with a tranquil, resort-like atmosphere. Expansive living spaces are carefully positioned to maximize privacy, natural light, and connection to the outdoors, creating an effortless flow between the interiors and the surrounding decks. Throughout the home, extraordinary craftsmanship and attention to detail elevate every space. The striking clapboard ceilings were meticulously installed piece by piece, creating warmth, texture, and architectural rhythm overhead — a labor-intensive design element that speaks to the level of artistry woven into the home. In the kitchen, custom cabinetry was handcrafted in Brooklyn, then carefully transported to Water Island in sections and thoughtfully assembled in place — a remarkable undertaking that reflects the bespoke nature of the residence and the uncompromising dedication to quality and design. The outdoor spaces are equally exceptional. A sprawling oceanfront deck unfolds toward the dunes and shoreline, offering multiple areas for lounging, dining, and entertaining against the ever-changing backdrop of the Atlantic. The heated pool is framed by sun-washed decking and lush landscaping, while a tranquil waterfall pond and curated gardens create moments of calm and seclusion throughout the property. Tucked above it all, the private second-floor deck off the primary suite offers sweeping ocean views and an unmatched sense of peace — ideal for quiet mornings, sunset cocktails, or stargazing beneath the open sky. Surrounded by nature and designed for complete privacy, this is more than a home — it is a rare coastal sanctuary unlike anything else on Water Island. Celebrated for its architecture, craftsmanship, setting, and atmosphere, this once-in-a-generation offering presents the opportunity to own a truly iconic stretch of Fire Island oceanfront.

1 Steels Walk, Water Island
$5,200,000
5 Beds ⋅ 6 Baths ⋅ 910335 MLS
Water Island Awaits. Two Iconic Buildings. One Majestic View. Location- Tucked between Fire Island Pines and Davis Park lies Water Island. With only 48 homes adjacent to the protected Fire Island National Seashore; Water Island creates a unique sense of remoteness and natural beauty — a true retreat for those seeking to unwind in quiet luxury. This secluded estate offers 200 feet of unobstructed Atlantic Ocean frontage; rare privacy and direct access to pristine beaches, all within an easy commute from New York City. Inspiration- A masterpiece of coastal design, this home has earned a place in the pages of several premier luxury publications. Designed by the legendary Scott Bromley of Bromley Caldari Architects with influence drawn from the craftsmanship and philosophies of George Nakashima and Hans Wegner, this expansive retreat is a study in balance — where modernist clarity meets organic warmth. The design embraces a sense of quiet luxury drawn from these iconic places: the barefoot elegance of Parrot Cay, the raw natural beauty of Big Sur, and the sculpted minimalism of Amangiri. Main House- The One-Bedroom Main House, a private and reimagined sanctuary for the Owners, sits nestled in the dunes. Inside, a warm composition of cedar and teak woods, white walls, and diffused light creates a tranquil atmosphere. The first floor serves as a serene sleeping suite, where spa-like bathing spaces are seamlessly integrated into the flow of everyday living. Above, the second floor opens fully to the landscape with expansive floor-to-ceiling windows and sliding glass doors that dissolve the boundary between indoors and out. Here, the Atlantic Ocean becomes both backdrop and focal point — a constant, calming presence, framed by architecture that gives it space to breathe. The dramatic cathedral ceiling in the main living space is punctuated by an oversized Noguchi hanging globe lighting fixture. Discover an airy chef’s kitchen where clean lines meet organic textures. Showcasing handcrafted wood cabinetry paired with caesarstone countertops – blending modern comforts like Sub-Zero, Wolf and Miele appliances. Oriented toward the coastline, the main living and dining spaces maintain a constant connection to the ocean, making it an integral part of the home’s daily life. Guest House- A meandering path through the sand joins the main house with the four-bedroom four bath guesthouse on the adjacent lot, a relaxed social hub featuring a bar, sun decks, an outdoor kitchen, and a pool — all designed to encourage barefoot living and effortless hospitality. From the moment you step inside the guest quarters you are enveloped by the integration of architectural elements – cool stainless steel, warm-toned woods, and white walls and ceilings – creating a layered, modern aesthetic. This interplay of textures brings depth and sophistication, blending functionality with high design for a space that feels both curated and comfortably livable. Details: 0 Charach & 1 West Walk Water Island, Fire Island, NY Two Structures on two adjacent lots (Total lot area - 10,000 sqft.) Connected by a Stone Path between the two Main House - 1 Bed 1.5 Bath Residence (Approx. 2,100 sqft.) 7.5’ x 5’ Custom Concrete Collaborative Panel Jacuzzi Guest House - 4 Bed 4 Full Bath Residence (Approx. 1,500 sqft.) 25’ x 9’ Custom Gunite Pool Outdoor Kitchen w/ Weber Gas Grill; Under Counter Refrigerator & Ice Maker Exterior: Clear Cedar 1X6 Clapboard Exterior Siding Mahogany and Cedar Clad Decks with Ipe hardwood trim accents Reilly double insulated, wind-borne debris rated Windows & Doors ‘Invarimate’ Contrarian Stainless Steel Roof System Interiors: Gothic European Oak Wood Floors White Washed 1X6 Clear Cedar Tongue & Groove Walls w/ Ipe hardwood trim accents Custom Designed Wood Veneer Cabinetry Caesarstone Kitchen Countertops Custom Ammonite Stone Bathroom Countertops Custom Teak Wood Sink Vessels

Charach & 1 West Walk, Water Island
$2,999,000
4 Beds ⋅ 4 Baths ⋅ 994515 MLS
Be among the first to experience this stunning new construction in Ocean Bay Park. Designed with an upside-down layout that maximizes natural light, views, and effortless coastal living, this 4-bedroom, 3.5-bath home offers a thoughtful blend of style, comfort, and functionality. The home features two private primary-style suites—one on each level—providing flexibility and privacy for owners and guests. The upper level is designed around an open-concept kitchen, dining, and living area, creating a bright and inviting space for gathering and entertaining. On the lower level, a screened-in porch offers the perfect place to relax and leads directly to the private pool, creating an ideal setting for summer days on Fire Island. A rooftop deck provides beautiful water views and refreshing coastal breezes, adding another level of outdoor living to this exceptional home. With its modern design, private pool, water views, and prime Ocean Bay Park setting, this is a rare opportunity to own a brand-new Fire Island retreat.

17 Superior Street, Ocean Bay Park
$1,899,000
5 Beds ⋅ 5 Baths ⋅ 982302 MLS
Welcome to Pines Living with Proven Income Potential. Private and thoughtfully designed, this exceptional 5-bedroom, 4-bath Fire Island Pines retreat offers the perfect blend of luxury, space, and income potential. Ideally located just moments from the harbor, beach, and Pines’ vibrant dining and nightlife, the home is set back from the boardwalk, creating a rare sense of privacy and seclusion. Spanning multiple levels, the home features a bright and open upper-level living space with sweeping Great South Bay views, a spacious living room, and a dining area accommodating up to 12 guests. The modern kitchen is fully equipped with updated appliances and designed for effortless entertaining. Multiple decks provide seamless indoor-outdoor living, including a front deck with bay views and a private rear deck overlooking the pool. The property offers five well-appointed bedrooms, including three en-suite bedrooms with king and queen layouts, plus additional guest accommodations providing flexibility and comfort for larger groups. A separate-entry pool-level suite adds an extra layer of privacy ideal for guests. Outdoor living is centered around a heated saltwater pool surrounded by an oversized deck, lounge areas, and an outdoor shower—perfect for relaxing or entertaining after a day at the beach. Additional features include central air conditioning, Sonos sound system throughout, high-speed internet, and a strong history of seasonal rental demand. A rare opportunity to own a turnkey property in one of Fire Island Pines’ most desirable and private settings.

287 Bay Walk, Fire Island Pines
$2,475,000
3 Beds ⋅ 2 Baths ⋅ 986803 MLS
Direct ocean views provide a beautiful backdrop to the open and airy living spaces throughout this exceptional oceanfront property. A 17-foot wall of glass in offering expansive water views opens out to a generously proportioned beachfront deck featuring saltwater pool and hot tub, creating a luxurious backdrop for outdoor living and entertaining. Designed for year-round living, the home is fully winterized with central heating, air conditioning, and a wood burning fireplace. Inside, you'll find three thoughtfully designed bedrooms and two updated bathrooms, each curated for comfort and style. The modern kitchen is equipped with top-of-the-line appliances, including a Sub-Zero refrigerator.

146 Ocean Walk, Fire Island Pines
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 978732 MLS
Unparalleled privacy in this triple mint 4 bedroom, 4 bath home with a meticulous attention to detail. the large living/dining area opens onto a sun drenched pool deck featuring a  hot tub and a separate cabana which can easily double as an additional guest bedroom. Exceptional appointments and furnishings throughout including energy efficient & cost saving solar panels with an additional backup battery  providing a seamless power transfer in the event of power outages.  Other first class amenities include a chef's grade kitchen with Viking stove & refrigerator, Subzero ice maker, beautiful cherry wood cabinetry, central heat & A/C. Fully Winterized for year round enjoyment.

605 Shore Walk, Fire Island Pines

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