Refine Search
Sort by
123 Hiawatha Drive, Brightwaters
$879,000
4 Beds ⋅ 2 Baths ⋅ 1051913 MLS
Welcome to 123 Hiawatha Drive, located in the desirable Village of Brightwaters. This charming 4-bedroom, 2 full-bath expanded cape offers a warm and inviting layout designed for comfortable everyday living and entertaining. The home features beautiful hardwood floors, a spacious living area with a fireplace, and a modern kitchen featuring granite countertops. Three bedrooms are conveniently located on the first floor. Upstairs you will find a spacious master bedroom that includes an en-suite bathroom and versatile bonus room. Additional highlights include a one year old roof and brand new stucco. Outside, enjoy a private driveway, attached garage, patio, in-ground sprinklers, and a generously sized yard with plenty of space for entertaining and relaxation. Ideally situated in the heart of Brightwaters, this wonderful home combines character, modern updates, and exceptional village location. Move right in and start enjoying everything this beautiful home has to offer.

123 Hiawatha Drive, Brightwaters

110 N Park Avenue, Bay Shore
$735,000
4 Beds ⋅ 2 Baths ⋅ 1050572 MLS
Meet Sue Allen — a beautiful, recently updated 4-bedroom, 2-bath home looking to call her home. ?? ? Inside, you’ll find: • Updated stainless steel appliances • Beautiful granite countertops • A warm and inviting enclosed porch • Spacious bedrooms with room for the whole family • A comfortable layout perfect for everyday living and entertaining ?? Commuters will love the location! Sue Allen is just minutes from the Bay Shore train station, making travel into NYC convenient and easy. ??? You’re also only minutes away from the heart of Downtown Bay Shore, where you can enjoy restaurants, shopping, entertainment, nightlife, and everything this vibrant community has to offer. ?? Sue Allen isn’t just a house — she’s looking to make new memories with.

110 N Park Avenue, Bay Shore

253 Cottage Walk, Ocean Beach
$2,488,000
5 Beds ⋅ 3 Baths ⋅ 1049697 MLS
The Ultimate Resort Home, Just Steps from the Beach. 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' x 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

170 S Penataquit Avenue, Bay Shore
$3,599,000
3 Beds ⋅ 3 Baths ⋅ 1032772 MLS
SPECTACULAR 2.75-ACRE WATERFRONT CONTEMPORARY ESTATE A truly rare opportunity to own an extraordinary privately gated 3,800 sq. ft. waterfront estate set on 2.75 breathtaking acres with over 1,000 feet of bulkhead and spectacular water views. Step through the grand double glass doors into a stunning open-concept interior featuring soaring windows, beautiful ceramic flooring, and a magnificent chandelier overlooking the water. The home offers 3 bedrooms, 3 bathrooms, a second-floor loft, dining room, living room with fireplace, and a 3-car garage.The fabulous chef’s kitchen features custom wood cabinetry, a large granite island, and professional Wolf and Verona stainless-steel appliances. The luxurious primary en-suite offers a spa bath, walk-in closet, glass doors with balcony and deck with bay views, elevator access, along with a convenient second-floor laundry room. The waterfront lifestyle is truly exceptional, offering over 1,000 feet of bulkhead, a large boat slip accommodating two 65-foot yachts, a boat ramp, and a dedicated cut-out for multiple jet skis. A spacious boathouse and waterfront gazebo provide the perfect setting for enjoying the water, while a beautiful patio and pergola create an ideal space for outdoor entertaining and relaxation. Take in breathtaking sunsets with picturesque views of the Robert Moses Bridge. Additional amenities include a full-house generator, 27-zone sprinkler system, and an on-demand tankless hot water heater. Perfectly positioned approximately 60 minutes by LIRR to NYC for world-class dining, entertainment and shows, and approximately 60 minutes to the Hamptons and its renowned wineries. From your own home or the nearby local ferries, enjoy a quick 20 minute ride to Fire Island's Ocean Beach and other sought after destinations, where you can spend the day exploring charming shops, enjoying waterfront dining and live music, or relaxing on the beautiful white sand beaches. It's the perfect blend of waterfront living, convenience, and the quintessential Fire Island lifestyle. Conveniently located near shopping, transportation and everyday amenities. A magnificent waterfront estate. An extraordinary lifestyle. A rare opportunity. Call today for your private showing.

170 S Penataquit Avenue, Bay Shore

1320 Pine Acres Boulevard, Bay Shore
$689,000
4 Beds ⋅ 2 Baths ⋅ 1046243 MLS
Welcome to 1320 Pine Acres Blvd, a spacious high-ranch set on a generous lot in Bay Shore. The inviting exterior features a large driveway, one-car garage, mature surroundings, and a substantial backyard offering plenty of room for outdoor enjoyment. With its expansive footprint and oversized additions, this property presents a unique opportunity for buyers seeking space, versatility, and potential. Inside, the well-kept home offers 4 bedrooms, spacious living areas, natural woodwork, and hardwood floors that add warmth and character throughout. The generous room sizes provide flexibility for comfortable everyday living, entertaining, a home office, or additional living arrangements. The home's large additions create an abundance of interior space and offer potential for an in-law suite or possible two-family configuration, subject to required permits and approvals. Outside, the property continues to impress with its large lot, big backyard, driveway, attached one-car garage, and an additional detached one-car garage. Recent exterior improvements include a new roof installed approximately six months ago, new gutters, soffits, and related exterior work. The roof also includes a transferable warranty, providing added peace of mind for the next owner. The expansive grounds provide plenty of space for recreation, gardening, entertaining, or simply enjoying the outdoors. With its spacious layout, large additions, generous lot, and prime Bay Shore location, 1320 Pine Acres Blvd offers an exciting opportunity to make this versatile property your own.

1320 Pine Acres Boulevard, Bay Shore

418 Ocean Walk, Fire Island Pines
$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

31 E End Walk, Atlantique
$1,390,000
4 Beds ⋅ 2 Baths ⋅ 1043745 MLS
Exceptional Year-Round Atlantique Retreat with Panoramic Bay & Ocean Views Experience the beauty and tranquility of Atlantique from this exceptional winterized year-round home, ideally situated to capture breathtaking bay and ocean views. From the moment you arrive, the property’s extraordinary setting takes center stage, with sweeping water vistas and protected seashore directly to the east, offering a rare sense of privacy, natural beauty, and an unobstructed coastal landscape. Just a 6-minute walk to Atlantique's marina, playground, pickleball courts, and the chic beach bar destination "The Shack", you'll fall in love with Atlantique living. Designed for comfort year-round, the elevated home has a full basement for storage, providing abundant space for all your seasonal and recreational needs. An artesian well approximately 460 feet deep provides a private water source, while central vacuum, split A/C system, and a fireplace add comfort and convenience through all seasons. The property also includes an 8' x 10' storage shed, and an extra refrigerator/freezer in the basement, as well as a golf cart, making island living both enjoyable and convenient. Whether you’re relaxing by the fireplace in the winter, enjoying the ocean breeze in the summer, or simply taking in the stunning panoramic views, this property offers a truly special opportunity to enjoy Atlantique living in every season. With its spectacular, protected bay and ocean views, this home is the beach house you've been waiting for! Shown by appointment only. Seller prefers to maintain possession until mid-Summer 2027.

31 E End Walk, Atlantique

279 Bay Walk, Fire Island Pines
$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

502 Brooklyn Boulevard, Brightwaters
$777,000
2 Beds ⋅ 2 Baths ⋅ 1039689 MLS
This fully renovated 1924 Brightwaters Gem is the opposite of dull and boring! Sitting on nearly a third of an acre on a stunning tree lined block in the heart of the village, a sprawling 2 bedroom 2 bathroom ranch has been transformed into a one of a kind artistic masterpiece. Not just a pretty face, it has been robustly updated and maintained by the owner who is a well known and accomplished builder. Boasting top of the line gas heat, gas hot water, central air conditioning, 200 amp electricity with a generator hookup, newer roof, windows and more. The new kitchen is centered around an imported Italian Bertazzoni range, and the bathrooms retain their vintage charm while hiding all new components. Beneath the main living space awaits a full finished basement that will rock your socks off, and behind the house sits a detached garage that’s been similarly tweaked and tinkered to its best version. Extensive gardens, mature trees and landscaping ensure privacy in the fully fenced back yard. For the buyer that’s sick of seeing the same old stuff, and wants a home with a whole lot of soul, this is the one!

502 Brooklyn Boulevard, Brightwaters

16 West Drive, Bay Shore
$730,000
5 Beds ⋅ 3 Baths ⋅ 1040683 MLS
Welcome to 16 West Drive, Bayshore. This move-in ready spacious single-family home with updated plumbing and electrical, new roof and lot more!!. Home offers comfort, flexibility, and ample living space. Ideal for a variety of lifestyles, this home features a bright and functional layout with plenty of natural light throughout. The updated kitchen is equipped with custom cabinetry, quartz countertops, stainless steel appliances and a practical workspace for meal preparation, while the adjoining living and dining areas create a warm and inviting atmosphere. Generously sized bedrooms on both floors provide generous space for relaxation, work, or guests, making it perfect for larger households or those needing extra rooms for offices or hobbies. The full bathrooms are conveniently located for everyday ease. Don't miss this opportunity to own a well-maintained home in a desirable neighborhood!

16 West Drive, Bay Shore

101 Greene Walk, Cherry Grove
$950,000
3 Beds ⋅ 2 Baths ⋅ 1040771 MLS
Contemporary beach house featuring an inviting open-concept layout designed for easy, relaxed living. The bright and airy interior flows seamlessly into a modern, well-appointed kitchen, creating a comfortable space for both everyday living and entertaining. The grand primary bedroom is a wonderful private retreat, featuring sliding glass doors that open directly onto its own private deck—an ideal spot for morning coffee, quiet afternoons, or enjoying the ocean air. Ideally located just three houses from the beach, this home offers the perfect combination of style, comfort, and proximity to the ocean. Outside, a lovely garden and serene backyard setting create a peaceful, private atmosphere, perfect for relaxing, outdoor dining, and enjoying long summer days and evenings. A wonderful opportunity to own a stylish and tranquil beach retreat just steps from the ocean.

101 Greene Walk, Cherry Grove

64 Mowbray Avenue, Bay Shore
$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

443 Sail 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

45 S Penataquit Avenue, Bay Shore
$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

65 Island Walk, Lonelyville
$1,650,000
2 Beds ⋅ 2 Baths ⋅ 1037133 MLS
Tucked away in the quiet, understated community of Lonelyville, this completely gut-renovated 2-bedroom, 2-bath Fire Island retreat is a sophisticated take on modern beach living, where elevated design, quality craftsmanship, and effortless coastal style come together just moments from both the bay and ocean. Set within one of Fire Island’s more peaceful enclaves and just steps from pristine white-sand beaches, the home offers a rare sense of tranquility while keeping the ocean at the heart of everyday island living. Ocean views can be enjoyed from both the main living area and kitchen, creating a constant connection to the natural beauty just beyond your door. Thoughtfully reimagined from top to bottom, the home pairs a clean, modern beach-chic aesthetic with materials selected for both beauty and longevity. Wood-look European porcelain plank tile flooring flows throughout, complemented by European frameless cabinetry, Carrara stone countertops, a suite of Bosch appliances, and upscale dual-sliding Teza glass doors with German Blum hardware, further enhancing the home’s seamless connection between indoor and outdoor living. Just off the kitchen, a rare dedicated laundry and pantry room provides exceptional storage and everyday functionality, complete with a dedicated wine refrigerator, an especially desirable luxury for island living. Both full bathrooms continue the home’s refined aesthetic with dramatic full-height, large-format porcelain panels, European-style frameless vanities, and stone countertops. A luxurious outdoor shower offers the quintessential Fire Island experience with an elevated finish. The home’s exterior is equally impressive, showcasing Ipe Brazilian hardwood decking, mahogany siding and railings, and multiple outdoor spaces designed to embrace island living. Crowning the property is a rare rooftop sun deck with electric and breathtaking 360-degree views stretching across the Great South Bay and Atlantic Ocean, a truly special vantage point to take in both spectacular sunrises over the ocean and unforgettable sunsets across the bay, with afternoon sun and panoramic island views in between. Beyond its design, the home has been comprehensively updated for modern comfort and efficiency, including all-new plumbing and electrical, 200-amp electric service, tankless instant hot water, and split systems providing both heating and air conditioning. These modern comforts extend the home’s usability well beyond the height of summer, allowing it to be enjoyed earlier in the spring and later into the fall season. Turnkey, thoughtfully designed, and finished with exceptional attention to detail, this Lonelyville retreat offers the best of modern luxury without losing the relaxed simplicity that makes Fire Island so special, a beautifully finished home ready to be enjoyed from the moment you arrive and throughout an extended island season.

65 Island Walk, Lonelyville

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.

How much is your home worth?

Get instant property value now!