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$845,000
5 Beds 4 Baths 1020121 MLS
Nestled in the heart of the highly sought-after Village of Brightwaters, this charming residence offers the perfect blend of timeless character, everyday comfort, and an unbeatable location. Set on a beautifully sized property of approximately 0.22 acres, this home enjoys all the benefits of one of Long Island’s most picturesque waterfront communities. Located just moments from the village park, scenic canals, and Great South Bay, Brightwaters is known for its tree-lined streets, historic charm, and exceptional sense of community. Residents enjoy exclusive village amenities including a private beach, tennis and pickleball courts, a community dock, summer concerts, holiday celebrations, and year-round neighborhood events. Just minutes away are vibrant downtown Bay Shore, waterfront dining, Fire Island ferries, and the LIRR, providing convenient access to New York City. Whether you’re searching for a peaceful place to call home or looking to become part of one of Suffolk County’s most desirable villages, 1 South Lakeview Avenue presents an outstanding opportunity to enjoy the Brightwaters lifestyle. From morning walks along the lakes and canals to evenings spent by the bay, this is a community where neighbors become friends and every season offers something special. This is more than a home—it’s an opportunity to experience the unique lifestyle that has made Brightwaters one of Long Island’s most treasured villages.

1 S Lakeview Avenue, Brightwaters

$599,000
5 Beds 2 Baths 1023123 MLS
Property Overview Address: 2 Seminole Drive Location: Bay Shore School District Lot Size: 0.29 Acres (oversized for the neighborhood) Living Space: 1,574 square feet Layout: 5 Bedrooms, 2 Full Bathrooms Basement: Semi-finished with Bilco door access, weather strip kit recently installed, recently painted, storage/rec space, and a plumbing utility ejector pump Key Interior Features Flexible Entry: Two separate entrances for enhanced privacy and daily convenience. Cosmetic Updates: Freshly painted living areas, newly painted basement floor, and modern brushed nickel door hardware. Kitchen Upgrades: Equipped with a newer stove, dishwasher, sink and fresh paint. Modern Lighting: Artika Sunnyvale "fandeliers" with remote controls in 2 of the main-floor bedrooms. Safety: Brand-new, dual-function smoke and carbon monoxide detectors installed throughout. Mechanicals & Energy Efficiency Primary Heat Source: Recently serviced boiler featuring a brand-new second-floor heating circulator pump. Secondary Heat Source: Extra-large Country wood-burning stove capable of heating the entire home. Hot Water: High-efficiency 50-gallon water heater installed in November 2025. Utilities: Upgraded 200-amp electrical service, enhanced gas lines, and a dedicated plumbing ejector pump. Exterior Shell: Durable roof (2013), energy-efficient Andersen second-floor windows. Exterior & Parking Amenities Detached Garage: 2-car structure perfect for vehicles, a workshop, or hobby storage. Driveway: Oversized layout accommodating multiple vehicles easily. Huge Backyard: Enclosed in black chain link. BBQ Amenity: Dedicated gas line for BBQ (no more propane tanks needed). Pool Potential: Plenty of space to accommodate any type of pool layout. Maintenance: Recent gutter repairs, thorough cleaning, and draft-reducing basement door sealing completed.

2 Seminole Drive, Bay Shore

$4,850,000
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

$594,999
4 Beds 2 Baths 1021372 MLS
Welcome to this beautifully renovated 4-bedroom, 1.5-bath ranch, where modern updates meet comfortable one-level living. This move-in-ready home features a bright, open layout with stylish finishes throughout, creating the perfect space for both everyday living and entertaining. The updated kitchen flows seamlessly into the main living areas, while four generously sized bedrooms provide flexibility for family, guests, or a home office. A beautifully updated full bath and convenient half bath add to the home’s appeal. The 1.5-car garage offers ample room for parking and additional storage. Whether you’re relaxing indoors or enjoying the outdoor space, this fully renovated home is ready for its next owner. Don’t miss the opportunity to make this stunning ranch your own! *Hot tub as not represented* being gifted

1440 Lombardy Boulevard, Bay Shore

$3,099,000
5 Beds 3 Baths 1016728 MLS
Set directly on the oceanfront in Seaview, this classic Fire Island home offers a rare opportunity to own a property with a protected seashore dune directly in front of the home that cannot be built upon. The main house features a kitchen, dining room, living room, three bedrooms, and two bathrooms, including a half bath within one of the bedrooms and a full bathroom with exterior access. Additional sleeping spaces are located outside the main living area, including a separate bedroom with its own exterior entrance on the main level and an upper-level bedroom, also accessed exclusively from the outside, with a private half bath and beautiful ocean views. A true oceanfront property in a setting where the natural landscape takes center stage, this home offers the opportunity to enjoy the beauty, privacy, and timeless appeal of Seaview. With five bedrooms, three bathrooms, and a protected seashore dune between the home and the ocean, this is a rare chance to own a piece of the Fire Island shoreline.

58 Gale Avenue, Seaview

$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

$5,100,000
5 Beds 4 Baths 1009823 MLS
OCEAN FRONT SEAVIEW. 5 bedroom 2 bathrooms and 2 powder rooms. Gym, veggie garden, guest house (this is included in the 5 bedroom 1 half bath) chefs kitchen, laundry room, storage, dog run. This house is truly a home. Views, and privacy is rare on the ocean, yet this beauty has both. A true gem in the heart of seaview, with extra artistic style at every glance. Shade, sun, views, quiet, entertaining space, this deck has it all. You need to come tour this one, in order to really “get it”. 7x7 dunk pool can be added. Taxes approx 15k insurance “self-insured” SV Assn dues: $6,001.38 General Interior • Leight kitchen cabinetry (2015) • Enclosed Pantry • SubZero fridge/freezer-drawers • Integrated lighting • integrated pull-outs • New windows and sliders (2024) • Ceiling fans in 4 BRs Master Bedroom Suite (full renovation 2021) • New Skylight • Custom bathroom cabinetry • Custom walk-in closet • Custom desk and pet crate • Dual flush Toto washlet • Walk-in jet tub within shower enclosure • Heated shower floor • Heated main floor • Dual sink with slant-drain Shoulder Season add-ons • Heated floors in kitchen and 4 baths • HVAC system installed 2020 • Deck radiant heat for dining Guest Cottage • Complete refurbish with half-bath and closet space • Heated bathroom floor • Toto dual flush washlet • New windows Landscaping • Raised beds for both decorative and vegetable growing • Four-zone watering system w mobile app control • Interior deer-proof gardening space • Primary/secondary composting bins Other • New main deck, clear cedar, including all new posts (2024) • Two-level deck providing choice of privacy or elevated ocean view • All north-facing windows replaced 2025 • All lower level ‘storage areas’ waterproofed and painted (2025) • Heavy-duty gym flooring installed throughout 3 ‘rooms’. (2025) • New roof on main house (2019) • Solar panels providing 90-100% power to run the home (2019) • Two Rheem brand Gladiator 55 gal water heaters w/ leak detection and auto shutoff (2025)

61 Evergreen Avenue, Seaview

$1,500,000
2 Beds 2 Baths 1011815 MLS
Welcome to Admiralty, a luxury gated community this beautifully appointed waterfront residence, where boating, private beach access, and resort-style living creates an exclusive coastal lifestyle.This beautifully appointed 2-bedroom residence showcases elegant imported flooring, soaring cathedral ceilings, and a breathtaking living room centered around a warm and inviting fireplace. The spacious gourmet kitchen is designed for both everyday living and entertaining, featuring premium stainless-steel appliances, a stylish bar area, and an open, sophisticated layout. The primary suite offers a private spa-like bathroom and with two walk-in closets, while additional features include a washer and dryer, ample storage, a spacious garage, and attic space. Step outside to your private patio, perfect for hosting family gatherings or enjoying peaceful outdoor living. Boating enthusiasts will appreciate the deep-water marina with private dockage and direct access to the Great South Bay. Situated within a meticulously maintained 158-acre waterfront community, residents enjoy an unparalleled lifestyle with 24/7 gated security, a newly renovated clubhouse, fitness center with Pilates and other wellness classes, three tennis courts, a pickleball court, private gardens, kayaking, a private beach, and a resort-style swimming pool with lifeguards. Perfectly positioned across from Fire Island’s Kismet and Ocean Beach and just a short drive to the Hamptons, this rare offering delivers the ultimate blend of luxury, recreation, and waterfront elegance. It includes snow removal, grass mowing and outside maintenance.Conveniently located near public transportation and supermarkets for easy everyday living.Just minutes from Bay Shore, offering access to shopping, dining, waterfront parks,less than two miles from ferry terminals to fire island and only one hour from NYC via LIRR. Don't miss out. https://theadmiraltyhoa.org

202 Captains Way, Bay Shore

$1,350,000
4 Beds 2 Baths 1015727 MLS
This is truly a one-of-a-kind opportunity! An extraordinary, expansive ocean front property in Cherry Grove, featuring a rare double lot with stunning ocean frontage. It has never been offered before, and the possibilities here are truly endless. What sets this property apart is the land itself and the boundless potential it holds. A great location on the East end of the Grove, perched atop a high dune with breathtaking ocean views. This oceanfront home offers a rare opportunity to own a piece of timeless charm. Lovingly built in the early 1950s and maintained by the same owners for generations, this unique property is simply a must-see. Four spacious bedrooms, including a primary bedroom on the main floor and three additional bedrooms on the lower level. 1.5 bathrooms plus the added convenience of an outdoor shower perfect for rinsing off after a day at the beach. The main Floor is designed with the open-concept: living, dining, and kitchen areas creating a seamless flow for entertaining or enjoying quiet moments.

54 Lewis Walk, Cherry Grove

$1,500,000
3 Beds 3 Baths 1014328 MLS
Experience coastal living at its finest in this exceptional 3-bedroom, 3-bathroom home featuring stunning bay views from multiple levels and some of the most breathtaking panoramas in Cherry Grove. Relax on the spacious rear deck as you watch ferries glide across the bay and enjoy the ever-changing waterfront scenery. The primary suite opens to a charming Juliette balcony, offering a private retreat with picturesque bay views. For truly unforgettable sunsets and sweeping water vistas, the rooftop deck provides one of the area's most spectacular vantage points. The first floor features a bright, open-concept layout designed for effortless entertaining, with a spacious living room, dining area, and well-appointed kitchen, all accented by beautiful hardwood floors. This level also includes a comfortable guest bedroom, a full bath, and a convenient laundry/utility room. On the second floor, the primary suite offers a private en suite bath and direct access to the Juliette balcony overlooking the bay as well as a 3rd bedroom. At the top of the spiral staircase is a third full bath, along with a versatile loft-style space featuring a desk area and room for a pull-out sofa, creating additional sleeping accommodations for guests or work space. With its thoughtfully designed layout, multiple outdoor living spaces, and spectacular bay views from nearly every level, this remarkable home offers the perfect blend of comfort, style, and waterfront charm.

118 Bayview Walk, Cherry Grove

$1,645,000
3 Beds 3 Baths 1011905 MLS
Timeless Waterfront Retreat on the Great South Bay - Steeped in history and dating back to circa 1909, this exceptional waterfront home offers a rare opportunity to own a truly special property with a rich and storied past. Nestled along the shores of the Great South Bay, the residence features 3 bedrooms and 2.5 bathrooms, showcasing breathtaking sunset views and the unique charm of watching the ferry arrive each day. Beautifully remodeled while preserving its historic character, the home boasts gleaming hardwood floors, a stunning fieldstone fireplace, central air conditioning, satellite TV, and high-speed Wi-Fi. The inviting interior blends classic elegance with modern comfort, creating an ideal setting for year-round living or a seasonal escape. Outside, enjoy a heated swimming pool surrounded by mature gardens and established plantings that provide beauty and privacy. Additional amenities include an enclosed outdoor shower and a separate washer/dryer shed, enhancing the relaxed waterfront lifestyle. Offering unmatched scenery, character, and comfort, this remarkable property is a rare gem on the Great South Bay.

209 Bayview Walk, Cherry Grove

$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

$1,250,000
2 Beds 2 Baths 999263 MLS
Welcome to your perfect Ocean Beach escape! This turnkey coastal gem is in an unbeatable location, just moments from town and only 9 houses from the beach. Renovated from top to bottom in 2022, this pristine home perfectly blends modern updates with beach-house charm. Recent upgrades include a brand-new kitchen with all new appliances, updated plumbing and wiring, designer lighting, renovated bathrooms, new curtains, landscaping, bike rack, decking, and roof. There are two bedrooms on the first floor, one with a private half bathroom. The spiral staircase leads to a cozy loft offering additional lounge or sleeping space as well as access to attic storage space. Step outside to the private back deck, a quiet outdoor retreat perfect for entertaining, dining al fresco, or unwinding after a day at the beach. Offered fully furnished. Low taxes, affordable flood insurance and easy maintenance, this move-in-ready home is the ultimate Ocean Beach getaway or rental investment property!

574 Bayberry Walk, Ocean Beach

$2,999,999
1000213 MLS Pioneer Market BLDG.
Located in the heart of Fair Harbor’s vibrant downtown, Fair Harbor Market represents a rare opportunity to acquire one of Fire Island’s most established and successful grocery businesses. Serving the neighboring communities of Fair Harbor, Dunewood, Lonelyville, Atlantique, Saltaire, and Kismet, the market has been a cornerstone of Fire Island’s west end since 1968, operating as the area’s primary destination for groceries, prepared foods, deli service, meats, seafood, beach essentials, and everyday conveniences for generations of residents and summer visitors. Operating annually from May through October, the business benefits from steady, high-volume seasonal traffic in one of Fire Island’s most active and socially vibrant communities, known for its beach culture, lively summer atmosphere, and iconic sunset views. Offered together with the commercial real estate, this is a true turnkey investment opportunity featuring both a thriving business and an exceptionally well-positioned commercial property in a highly sought-after location. The market is thoughtfully laid out for efficient, high-volume operation and features four main grocery aisles, dedicated deli cases, and a large beverage section, creating a comprehensive shopping experience for both residents and vacationers. Behind the deli counter, a walk-in refrigeration box supports seamless food preparation and storage operations. The property is further equipped with a computerized house account system, ATM, commercial ice machine, new cooking hood with integrated fire suppression system, electric grill, walk-in freezer, dual walk-in coolers, extensive refrigerated display cases for dairy, meat, beer, beverages, frozen foods, and ice cream, as well as multiple box freezers and a high-capacity commercial ice maker. An adjoining breakfast, lunch, and ice cream window generates consistent foot traffic throughout the day and evening, while the second-floor two-bedroom apartment offers valuable owner accommodations, staff housing, or rental income potential. A longstanding Fire Island institution with nearly six decades of operating history, Fair Harbor Market offers the opportunity to own an iconic and deeply rooted business at the center of one of Fire Island’s most desirable summer communities.

21 Broadway, Fair Harbor

$859,000
6 Beds 3 Baths 1001272 MLS
Spacious multi-generational high ranch offering excellent flexibility and potential. This home features a rear two-level addition Many updates have been completed within the last two years, including the roof, siding, driveway, walkways, and fencing. The primary kitchen, updated, offers a modern open layout enhanced by a large skylight that brings in abundant natural light. The first floor has a private entrance and includes a bedroom, living room, dining area, full bathroom, and additional room, making it ideal for extended living arrangements. The property can easily be converted back to a 6-bedroom single-family residence while keeping the existing two-car garage. Move-in ready with generator hookup and in-ground sprinklers. Interior features include hardwood floors and hot water heating. STAR eligible. Buyer may qualify for property tax savings, subject to eligibility. Seller concessions may be considered.”

58 Oakridge Drive, Bay Shore

$1,499,000
4 Beds 2 Baths 1001150 MLS
Nestled in the heart of Seaview on an oversized 80' x 100' parcel, 6 Atlantic Avenue offers the rare combination of generous outdoor space, bay views, and a coveted location in one of Fire Island’s most beloved communities. This spacious four-bedroom, two-bath home is filled with natural light, featuring an expansive living room with bay window, generously sized bedrooms, and a bright, airy layout designed for effortless beach living. The enormous sun-drenched deck creates the perfect setting for outdoor dining, entertaining, or simply relaxing after a day at the beach. Mini-split heat and A/C provide modern comfort throughout the seasons. Ideally positioned in the quiet, highly desirable Seaview community—home to lifeguarded ocean and bay beaches, clay tennis courts, playground, kiddie pool, and a close-knit community atmosphere—yet just moments from the restaurants, shops, and energy of Ocean Beach. Whether you envision a classic Fire Island retreat, an investment property with strong rental appeal, or the site of your future dream home, this oversized property presents exceptional opportunity in a location that rarely disappoints. Flood insurance policy is assumable and costs $5,044/year.

6 Atlantic Avenue, Seaview

$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

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.