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$757,000
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
$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
$349,000
1 Baths ⋅ 1004042 MLS
Top Floor studio co-op at the Cherry Grove Inn. Enjoy views of the Atlantic Ocean from this lovely, corner apartment. Outoor seating area, coin-op laundry, shared outdoor shower and the most amazing common roof deck with 360 views of Fire Island, ocean & bay!! Subletting permitted. Pets permitted. Occupancy is approximately six months. Maintenance is 12 months.

176 Ocean Unit #15, Cherry Grove
$1,800,000
4 Beds ⋅ 4 Baths ⋅ 1024856 MLS
Special home on an oversized corner lot offering the perfect blend of privacy, space, and opportunity. This beautifully maintained 4-bedroom, 3.5-bath residence has been freshly painted, newly furnished, and is ready to enjoy. Take in bay views and spectacular sunsets from the recently renovated rooftop deck, an ideal setting for entertaining or relaxing after a day at the beach. With generous outdoor space and room to grow, the property also offers the potential for a 7' × 7' plunge (dunk) pool, creating your own private island oasis. A rare opportunity to own a spacious Fire Island home with views, privacy, and exceptional value. Priced to sell.

31 Ivy Avenue, Seaview
$2,000,000
4 Beds ⋅ 3 Baths ⋅ 1024800 MLS
Seaview Home for Sale on Fire Island – Just steps from the ocean. Classic 4-bedroom, 2.5-bath home with fully renovated kitchen and bathrooms. Bright, spacious, and filled with natural light. Timeless charm meets modern style. Enjoy sunny decks and room to expand. A large shed offers even more potential. 46 Crescent has everything you’d expect from a true Seaview retreat — in an ideal location. Just one block from Seaview Market, two blocks to the ferry, and three blocks to Ocean Beach. Come see this inviting home for yourself. Don’t miss your chance to experience Fire Island living with this exceptional vacation property for sale. Contact Real Estate on Fire Island today. Flood Insurance $4,140

46 crescent Avenue, Seaview
$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
$1,645,000
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
$1,175,000
1003608 MLS
A rare opportunity to own land in one of Fire Island's most beloved communities. Fair Harbor offers a classic beach town feel with easy ocean and bay access, a tight-knit neighborhood vibe, and a strong summer rental market. This is two separate parcels being sold together as one. This property is on the east side of Fifth Avenue on the bay side.

A 5 Avenue, Fair Harbor
$225,000
1 Baths ⋅ 1003401 MLS
Beautiful, main floor studio co-op apartment at the Cherry Grove Inn. Nicely renovated with new floors, updated kitchen and bath. Wi-Fi, thru-the-wall A/C, shared outdoor shower & coin-op laundry. Enjoy the best views of Fire Island from the roof deck... ocean, bay and fabulous sunsets! Seasonal occupancy, approximately six months each year with options to sublet both short term and seasonally.

176 Ocean Unit #9, Cherry Grove
$1,350,000
7 Beds ⋅ 7 Baths ⋅ 971902 MLS
Welcome to an exceptional opportunity in the heart of Cherry Grove, where spacious accommodations, outstanding outdoor living, and breathtaking Great South Bay views come together in one remarkable three-story property. Featuring 7 bedrooms and 6½ baths, this generously proportioned home offers an ideal combination of privacy, comfort, and entertaining space. Whether envisioned as a private vacation retreat, an investment property, or a high-demand rental opportunity, the home's versatile layout provides ample room for family and guests to gather while still offering plenty of space to unwind. The top-floor living level is the true showpiece of the residence, offering spectacular views of the Great South Bay through its elevated vantage point. A wraparound balcony extends the living space outdoors, creating an exceptional setting for morning coffee, sunset cocktails, entertaining, or simply enjoying the distinctive beauty of the surrounding landscape. Inside, the upper level features soaring ceilings and tile floors, creating an open, airy atmosphere. A wood-burning stove adds warmth and character, while the dedicated media room provides an inviting space for movie nights, watching the game, or relaxing with family and friends. The combination of expansive living areas, high ceilings, abundant outdoor space, and panoramic water views makes this level particularly well suited to entertaining. The home includes a spacious primary suite, along with six additional bedrooms, providing substantial flexibility for hosting guests, accommodating extended family, or maximizing rental potential. With 6½ baths, the property is exceptionally well equipped for larger groups and extended stays. Outdoor living is equally impressive. Multiple decks provide numerous areas for dining, lounging, and entertaining, while the property's fully fenced grounds offer added privacy and security. An outdoor shower provides a welcome convenience after a day at the beach, allowing everyone to rinse off before returning indoors. Additional storage and utility sheds offer practical space for gardening equipment, beach gear, and seasonal belongings. Location is another defining feature. The property is situated just steps from Cherry Grove's vibrant town center, placing restaurants, shops, nightlife, and the community's lively atmosphere within easy reach. At the same time, the home is conveniently located near one of New York's most beautiful ocean beaches, making it easy to enjoy long beach days, swimming, sunbathing, and the natural beauty of the barrier island. An outstanding choice for investment, vacation living, or rental income potential, this distinctive property offers the space and location to make the most of the Cherry Grove lifestyle. OneKey MLS #971902 This property is also available thru D.Katen Fire Island Properties.

154 Doctors Walk, Cherry Grove
$2,850,000
8 Beds ⋅ 7 Baths ⋅ 956138 MLS
Welcome to 259 Lakeview Avenue W, a breathtaking Spanish Revival residence set on an expansive 0.80-acre lot in the coveted Village of Brightwaters. This impeccably updated and remodeled estate seamlessly blends timeless elegance with modern luxury, offering over 7,700 square feet of refined living space across three levels. ***NOTE*** NEW CENTRAL AIR INSTALLED 2026**** Step inside to discover 17 grand rooms, including 8 spacious bedrooms and 5.55 beautifully appointed bathrooms. The home boasts a chef’s kitchen, adorned with custom woodwork, stainless steel appliances, and an open layout perfect for entertaining. Rich hardwood and tile floors run throughout, complemented by exquisite crown molding, high ceilings, and original architectural details. The main level features a formal living room, formal dining room, den, great room, butler’s pantry, mudroom, laundry room, and an elegant foyer. The second floor hosts the luxurious primary suite with a private deck, spa-like en suite bath, and multiple additional bedrooms, including guest quarters and an office. A full basement offers generous storage and utilities. Outside, enjoy a private resort-style oasis with multiple patios, a gazebo, and a stunning tiled and gunite gas heated saltwater pool and spa and gazebo. The gated property also includes a circular driveway, oversized private garage, and beautifully landscaped grounds with mature plantings and sprinkler systems. Located in the highly regarded Bay Shore School District and just minutes from beaches, golf, and dining, this is truly a rare opportunity to own one of Brightwaters’ most iconic homes. Village amenities include, docking, tennis, beach, parks, trash removal and code enforcement.

259 Lakeview Avenue W, Brightwaters

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.