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$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
$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
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
$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
$1,599,000
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
$1,650,000
4 Beds ⋅ 4 Baths ⋅ 1013751 MLS
Originally designed for renowned visionary Irving Cooperberg and masterfully built by William Katen in 1991, this timeless Fire Island Pines Contemporary has only grown more distinguished with age. Meticulously maintained and thoughtfully enhanced throughout the years, the home offers sweeping ocean views, exceptional privacy, and the effortless indoor-outdoor lifestyle that defines the very best of Fire Island living. Entertain and unwind across two levels of outdoor living and dining space, relax in the secluded garden hot tub, or take advantage of direct beach access just moments from your door. Perfectly positioned on prestigious Beach Hill Walk, the property enjoys a coveted location between the ocean and the vibrant communities of Fire Island Pines and our beloved sister community, Cherry Grove. Private. Exclusive. Handsome. Timeless. With a strong and proven rental history, 136 Beach Hill Walk offers not only an extraordinary lifestyle opportunity but also compelling investment potential. As interest and investment in Fire Island Pines continues to grow, perhaps it is your turn to become part of this remarkable community. NEW PHOTOS COMING SOON.

136 Beach Hill Walk, Fire Island Pines
$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
$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
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 1003027 MLS
Classic mid-century beach house with large saltwater pool is the last word in casual beach living.. Open floorplan and beautifully landscaped outdoor space. 3 bedrooms, 2.5 baths close to the harbor & a short walk to the beach.

293 Bay, Fire Island Pines
$2,150,000
7 Beds ⋅ 6 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
$1,749,999
5 Beds ⋅ 4 Baths ⋅ 999866 MLS
This one-of-a-kind, exceptionally spacious 5-bedroom, 4-bath residence has been fully renovated to the highest standards, offering the perfect blend of luxury, comfort, and privacy. Beautifully designed with contemporary finishes throughout, the home features an expansive open-concept gourmet kitchen and dining area that seamlessly flows onto a large outdoor entertaining deck complete with a pool, hot tub, and fire pit. Designed for both relaxation and entertaining, the property also includes central air conditioning, a dedicated recreation space, laundry room, and a panoramic rooftop deck with sweeping views. Rarely does a home of this size, quality, and privacy become available — an exceptional opportunity for luxurious coastal living.

337 Shell Walk, Fire Island Pines
$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
$1,000,000
4 Beds ⋅ 3 Baths ⋅ 964435 MLS
Excellent investment opportunity. 4 bedroom 3 bath bungalow with long rent history. Large private deck with hot tub. Open living / dining area and equal sized bedrooms. Roof deck ideal for sunset cocktailing.

313 Fire Island Boulevard, Fire Island Pines
$1,900,000
3 Beds ⋅ 3 Baths ⋅ 961696 MLS
One-of-a-kind Horace Gifford “tree house”. This 3 bedroom, 3 bathroom, dramatically set at the eastern edge of the Pines, is truly a one-of-a-kind residence. A spiral staircase leads you above the trees into the breathtaking, glass enclosed Great Room. Over 200o sq ft of multi level decking allows for both large scale entertaining or more intimate gatherings. While respecting Gifford’s original plan, the current owners have put their own stamp on the property including AC, working fireplace, heated pool, hot tub, poolside kitchenette, remodeled kitchen and appliances, complete bathroom renovations, heated stone floors in kitchen, all bathroom & entry & fully irrigated cutting garden. The heart stopping roof terrace soars above the tree line revealing the preserved dunes and Atlantic Ocean stretching eastward .

529 Sail Walk, Fire Island Pines
$1,095,000
2 Beds ⋅ 1 Baths ⋅ 958142 MLS
Floated over from the mainland in the mid 1950s 284 Bay Walk defines mid-century chic & simplicity. Smartly appointed with many original details still intact. 2 bedrooms, 1 bathroom plus dressing room there is plenty of room for expansion.

284 Bay Walk, Fire Island Pines
$1,195,000
2 Beds ⋅ 2 Baths ⋅ 955414 MLS
Classic shingled beach cottage available for the first time in 25 years. This “tiny but mighty” summer retreat offers superb amenity from the light filled solarium overlooking the large & inviting pool deck to the classic screened in porch ideal for kicking back with friends on long summer evenings. 2 bedrooms 1.5 baths, outdoor shower. Further amenities include central air / heat, hot tub, poolside cabana, handyman’s shed & beautiful native garden.

92 Teal Walk, Fire Island Pines
$1,825,000
4 Beds ⋅ 4 Baths ⋅ 952052 MLS
Designed in 1964 by Horace Gifford, this sophisticated, private & totally renovated mid-century represents the very best that the Pines has to offer. Set amid lush gardens and smartly furnished. 4 bedrooms, 3 full baths, 2 half baths. Large solar heated pool & wrap around decking.

617 Shore Walk, Fire Island Pines
$1,825,000
3 Beds ⋅ 4 Baths ⋅ 947421 MLS
Summer as imagined by Bromley Caldari Architects. This thoughtful & sophisticated contemporary represents the very best of Pines modernism. New 2016 construction with clean minimalist lines, this meticulously maintained triple mint property is both secluded within natural landscaping, yet steps from the harbor. A central unifying feature is the dramatic clerestory custom skylight providing soft natural light to the open living room, dining room, kitchen and hallway. Three large bedrooms with ensuite baths, beautifully finished with custom hand-made tiles and generous closets. Heating and air conditioning throughout. Large private sunny deck and pool area provide the perfect backdrop for casual beach living & entertaining. Delivered fully furnished with stylish high-end modern furnishings and fixtures. New pictures & video coming soon.

39 Lone Hill Walk, Fire Island Pines
$2,500,000
6 Beds ⋅ 7 Baths ⋅ 936477 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
$1,050,000
2 Beds ⋅ 1 Baths ⋅ 905132 MLS
Steps from the sand this airy adorable cozy 2 Bedroom 1 Bath beach cottage in Fire Island Pines pairs classic charm with easy low maintenance living. An open Living/Dining area flows to a sun splashed deck with pretty ocean views, perfect for morning coffee or a sunset cocktail. Two comfortable spacious bedrooms accommodates guests with ease while stepping outside enjoy the quiet settings on the deck with breathtaking views along with a private shower. A turnkey escape -beach life made simple.

451 Ocean Walk, Fire Island Pines
$1,275,000
2 Beds ⋅ 2 Baths ⋅ 884228 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
$2,100,000
4 Beds ⋅ 4 Baths ⋅ 877733 MLS
Representing a seamless combination of mid-century and contemporary influences, 172 Pine Walk represents Pines living at its refined. The double height & sunblasted open living / dining / kitchen / area provides for casual beach living at its most comfortable. The primary suite with ensuite bath offers views to the ocean and leads to a breathtaking roof terrace with superb 360 degree views ideal for both sunrise and sunset entertaining. 3 additional guest bedrooms and 2.5 baths. The many amenities include large heated pool and deck, central A/C, chef's grade kitchen, outdoor shower & landscaped gardens.

172 Pine Walk, Fire Island Pines

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