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$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

$1,395,000
4 Beds 2 Baths 988424 MLS
Elevated 4-bedroom, 2-bath home ideally situated in the heart of the Village of Ocean Beach. Thoughtfully updated, the home features a bright eat-in kitchen with stainless steel appliances and sleek quartz countertops, opening to a spacious, sun-drenched south-facing deck—perfect for entertaining. A wood-burning fireplace adds warmth and charm to the spacious living room, while the outdoor shower captures the essence of beach living. Both full baths have been beautifully renovated with newly tiled showers and frameless glass enclosures. Set on a 50 x 84 lot, the property offers the ideal blend of privacy and proximity—just a 5-minute walk to the beach and 3 minutes to town. Whether you’re seeking a personal retreat or a high-performing investment, this home delivers strong rental appeal along with low flood insurance of just $1,397/year.

449 Dehnhoff Walk, Ocean Beach

$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

$1,499,999
5 Beds 3 Baths 958869 MLS
This beautifully maintained 5-bedroom, 2.5-bath home is a standout investment and vacation retreat in the heart of Fire Island. Thoughtfully decorated with a charming nautical theme, the home offers a bright, coastal feel throughout. Split-unit air conditioning in every room ensures comfort all season long. Designed for year-round living, this home allows you to enjoy Fire Island in every season. The open-concept living and dining area is ideal for entertaining, comfortably accommodating large gatherings or relaxing after a day at the beach. Step outside to a delightful sitting area complete with an outdoor shower, perfect for embracing island living at its best. Centrally located and close to town, the property offers excellent accessibility to local attractions and amenities. Fire Island is a sought-after vacation destination, and village amenities include a community house and playground, with seasonal access to tennis and pickleball courts, and a marina. Whether you’re seeking a strong income producing rental, a year round residence, or a memorable getaway, this home delivers the ideal blend of comfort, location, and investment appeal.

180 Cottage Walk, Ocean Beach

$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

$4,495,000
5 Beds 7 Baths 902281 MLS
Stunning Ocean View 5 BR New Construction With Pool & Gym Situated on an ocean view double lot, one house back from the beach, this ground up new construction home is truly spectacular. With nearly 3,600 interior square feet and 2,680 square feet of mahogany decking, a 30’ swimming pool, panoramic ocean views, and multiple entertaining areas, this home does not disappoint. Enter through the dramatic double height entry foyer and continue upstairs to the spectacular great room with 11’ ceilings, spacious dining area with wet bar, ample living space, and stunning ocean views. The gourmet kitchen features abundant storage, quartz countertops, and top of the line appliances, including a 66” refrigerator and 48” Wolf range. The enviable walk-in pantry and massive 12 foot long island would delight any chef. Flow right out to the dedicated eating deck to enjoy the ocean views while you grill and dine al fresco. The exterior staircase connecting the pool deck level and the great room allows for easy entertaining. All 5 bedrooms in the home feature private en-suite bathrooms and sliding glass doors leading directly to outdoor spaces. In addition to 5 bedrooms, 5 full bathrooms, 2 half bathrooms, and an outdoor shower, the home also features a large den, an office/craft area, and a gym or flex space. The second floor “grand primary” suite has a large walk-in closet, and a spa bathroom with wet room shower & freestanding tub, double vanity, and private water closet. Watch the waves from your king size bed or your private balcony. There is also a “junior primary” suite on the first floor that includes stunning views, a luxurious en-suite bathroom, ample closets, and a king bed. With multiple outdoor spaces to lounge and gather, when it comes to entertaining, there is no shortage of spaces in this home! Whether sunbathing by the pool or relaxing in the shade of the covered deck, the outdoor bar with fridge, sink, and ice maker is sure to come in handy. Just when you thought the views couldn't get any better, head up to the roof deck for a bird's eye view of the beach, bay, and the island. A spacious spot for entertaining, the roof deck comes complete with a massive wet bar, including refrigerator, ice maker, and seating for 8. Luxury appointments throughout include ceramic tile floors, Andersen windows, and zero maintenance New Tech siding.

36 Cayuga Street, Ocean Bay Park

$2,599,000
4 Beds 3 Baths 902150 MLS
Fully Renovated Ocean Beach Home – 4BR/3BA with Pool, Steps from the Beach This beautifully gut-renovated two floor 4-bedroom, 3-bathroom home is perfectly located just six houses from the ocean and a short 3-minute walk to the heart of town. The home features high-end finishes throughout, including a sleek modern open-concept kitchen, custom bathrooms, and a bright thoughtfully designed living spaces. The primary bedroom includes a private ensuite bathroom, creating a peaceful and functional retreat. Outside, enjoy a private swimming pool and a spacious deck—ideal for relaxing or entertaining after a day at the beach. This home offers the perfect blend of modern design and unbeatable location—just a minute’s walk to the beach and moments from shops, dining, and ferry access perfect for your summer getaway. Affordable flood insurance only $995/year.

108 Ocean Road, Ocean Beach

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.