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$1,465,000
5 Beds ⋅ 4 Baths ⋅ 951181 MLS
A distinguished 1925 French Provincial residence on one of Brightwaters most prestigious blocks features 5 bedrooms, 3.5 bathrooms and over 3,700 square feet of architectural living. Fully restored and renovated in 2026 just steps away from the water and the entrance to Gilbert Park. Set into .41 acres, this standout property welcomes you with timeless curb appeal highlighted by steeply pitched roof lines and asymmetrical massing, a hallmark of French Provincial architecture that is complimented by a charming, crushed stone driveway and detached two-car garage. A spacious European sunroom entryway with 10-foot finished ceilings immerses you in the home’s impressive scale and historic character. Original Ebony Oak Hardwoods and decorative millwork remain thoughtfully preserved throughout the floor plan. The main living room anchored by a wood-burning fireplace is wrapped in European revival style windows and detailed stepped crown molding finish a great room with enduring architectural appeal. Arched openings create a welcoming transition into the formal dining room which offers an elegant setting for entertaining in the heart of the home. The chef’s kitchen features quartz countertops, a full stainless steel appliance suite, gas cooking, custom wet bar with wine refrigerator and built-in wine storage. Water views from the kitchen add a rare and serene backdrop. A first-floor laundry room and dedicated private office provide modern functionality without compromise. The residence offers a total of five bedrooms and three-and-a-half baths, including a primary suite with tranquil water views, a full wall of windows, a generously sized walk-in closet, and a spa-inspired bath with dual vanities. Three bedrooms and a full hallway bathroom with charm and original details finish the second level while the third floor hosts another private bedroom with wonderful water views and an ensuite bath. Additional highlights include natural gas heating, central air conditioning, public sewers, and a location that embodies the charm and walkability of Brightwaters Village. A rare offering combining historic provenance, modern refinement, and water-adjacent living, 33 S. Windsor Avenue represents a truly elevated Brightwaters lifestyle for the most discerning South Shore buyer.

33 S Windsor Avenue, Brightwaters
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 974354 MLS
On a quiet tree lined street in the heart of the Village of Brightwaters, a tremendous 10 year young center hall colonial awaits its next owners! A perfect modern Layout: 4 bedrooms, 3 full Bathrooms, the open kitchen and living space everyone wants, as well as the formal living and dining rooms that make a proper home. Enter into a dramatic 2 story foyer, then continue on to the sprawling first floor living space with 10 foot ceilings and hardwood floors throughout. A chefs center island kitchen with high end stainless appliances, quartz counters, and even 2 sinks, overlooking an incredible great room with a gas fireplace, and bathed in natural light. Sliding glass doors lead to the newly installed paver patio, and beyond to the fully fenced yard space and gardens. Upstairs, an enormous Primary Suite wows with soaring cathedral ceilings, his and hers walk in closets, and an expansive primary bathroom with both a glass shower AND a spa tub, and of course a double vanity. 3 additional generously sized bedrooms and another full bath complete the second floor. Beneath the home an expansive full basement with an exterior entrance and extra tall ceilings offers incredible opportunity for an additional almost 1,300 square feet of living space. It also houses the important mechanicals, including the gas heat, gas hot water heater, central air conditioning, and 200amp electric with generator hook-up. A true 2 car attached garage with 14 foot ceilings could even house a couple car lifts for the auto enthusiast. This house was a stellar build in 2016, with a brilliant and timeless set of plans selected. At over 2800 square feet of living space not including the garage or basement, this home has the space and layout you would design today, in a style that honors the traditional nature and character of such an iconic neighborhood. This is the home of your dreams!

456 Pine Acres Boulevard, Brightwaters
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 989369 MLS
Welcome home to 93 S. Bay Avenue where classic sophistication meets coastal-inspired living in the heart of one of Brightwaters’ most desirable waterfront-adjacent locations. With impeccable curb appeal, balanced proportions, and lush landscaping, step inside to discover a spacious and inviting interior featuring rich hardwood flooring, elegant crown and base moldings, and beautifully curated finishes throughout. The welcoming entry foyer greets you and opens to the formal dining room highlighted by a light-filled bay window. The beautifully scaled formal living room, ideal for both casual and formal gatherings, is anchored by a stunning gas fireplace and sun-drenched bay window. Just off the living room, a private office provides the ideal work-from-home setting surrounded by serene outdoor views. The oversized eat-in kitchen is the heart of the home with granite countertops, stainless steel appliances, abundant cabinetry, and a peninsula for casual dining which flows into an expansive breakfast room with stunning parquet floors. There’s plenty of room for a large table and windows with views of the backyard and French doors that lead to the expansive wrap-around deck make this a room you’ll want to spend time in. There’s even more living space to enjoy in a beautifully scaled great room perfect for casual gatherings, relaxing evenings, and unwinding. The interior space continues with a stunning screened-in sunroom with skylights. Designed for multi-season enjoyment, the sunroom includes plexiglass inserts, allowing for use in the cooler months. The main level is complete with a beautifully updated full bathroom featuring skylight and custom tilework, along with an additional conveniently placed powder room. Upstairs, the primary bedroom is a serene retreat with two closets, including a walk-in closet. There are two additional well-proportioned bedrooms and a second full bathroom featuring elegant tile finishes and modern updates. The basement provides abundant storage, there’s a one-car attached garage and additional attic storage. Step outside to your private South Shore oasis with an expansive wrap-around deck overlooking a gardener’s dream setting, and a jacuzzi hot tub all creating the perfect setting to enjoy the famous Great South Bay breezes. This storybook Cape offers a rare blend of classic architecture, modern updates, and an elevated coastal lifestyle just moments from the Brightwaters Canal, Walker Beach, and the Brightwaters Lakes. Brightwaters Village residents enjoy amenities including private beach, boat docking, lakes, parks, tennis courts, and more. Conveniently located near Brightwaters Village, downtown Bay Shore’s shopping and dining, Fire Island Ferries, and Robert Moses Beach, with easy access to major highways for trips to the Hamptons or the Long Island Rail Road for travel to New York City, 93 S. Bay Avenue embodies quintessential South Shore living in one of Long Island’s most desirable coastal communities.

93 S Bay Avenue, Brightwaters
$970,000
5 Beds ⋅ 3 Baths ⋅ 962494 MLS
Welcome to 535 Brooklyn Blvd in Brightwaters- where charm, space and comfort come together in one exceptional home. Nestled in the Incorporated Village of Brightwaters, this expanded 5 bedroom, 3 full bath home offers far more than meets the eye. Thoughtfully designed for both everyday living and effortless entertaining, the home features a welcoming living room with a cozy fireplace and a tremendous great room with sliding glass doors that open to a private patio- creating the perfect flow for indoor/outdoor gatherings. The spacious primary bedroom is located on the main floor and boasts a custom walk in closet- plus an additional wall of closets- providing abundant storage. All bathrooms have been beautifully renovated with modern finishes and style. The expansive basement offers incredible potential for additional recreational space, a home gym, office, media room, or playroom. Having been thoughtfully expanded, this home is significantly larger than it appears and provides the space and flexibility today's buyers are seeking. Brightwaters amenities include the opportunity to keep your boat in the Brightwaters canal, access to Walker Beach, a summer camp program, community events like the Ragamuffin Parade, Easter Egg Hunt, Ice cream social and more... This is a rare opportunity to enjoy generous living space in Brightwaters Village. This home truly has it all.

535 Brooklyn Boulevard, Brightwaters
$879,000
4 Beds ⋅ 4 Baths ⋅ 988494 MLS
108 ft sprawling 4 bedroom 4 bath open floor plan, large rooms, covered front porch, picturesque Brightwaters village, storage shed

120 Mohawk Drive, Brightwaters
$725,000
4 Beds ⋅ 3 Baths ⋅ 971268 MLS
Located in the charming village of Brightwaters, this spacious colonial offers an incredible opportunity to create the home of your dreams. Featuring four bedrooms and two and a half bathrooms, this property provides a generous layout with endless potential. The home also includes a full finished basement, adding valuable extra space for entertainment, recreation, or storage. While the house does need some work, it presents a fantastic opportunity for buyers looking to customize and build their perfect home in a highly desirable neighborhood. Step outside to a beautiful backyard, offering plenty of space for outdoor living, gardening, or future upgrades. Don’t miss your chance to invest in a property with great bones, amazing potential, and an unbeatable location. Bring your vision and make this colonial your dream home! Opportunities like this in Brightwaters don’t last—schedule your showing today!

60 Iroquois Drive, Brightwaters
$705,000
2 Beds ⋅ 1 Baths ⋅ 993199 MLS
Welcome to this Storybook Tudor nestled on an oversize lot with lush lawns, mature trees, and layered landscaping that creates depth and privacy. At night, warm light spills from the windows, making the house glow like a lantern in the landscape. A true fairytale home blending old warm charm with modern touches. An oversized garage completes this home. It is truly a little bit magical, Distinctly Timeless. Many features include a fully fenced yard, 200 amp service, new washer/dryer, new on demand tankless gas heating system, upgraded landscaping, screened porch, roof max resurfacing to extend the life of the roof and more. Taxes include Village taxes. Enjoy all the Brightwaters Village amenities to include access to Walker Beach, docking, code enforcement all day and private security from midnight to 5pm, garbage pick up from rear of home, ice cream socials, and so much more! This home presents an opportunity to experience living in Brightwaters! Don't miss it!

544 Lombardy Boulevard, Brightwaters
$675,000
3 Beds ⋅ 2 Baths ⋅ 1015579 MLS
This Diamond 1915 Colonial Features 3 Bedrooms 1.5 Bathrooms, Living Room, Dining Room, Eat-in Kitchen with Stainless Steel Appliances, and full unfinished basement and laundry area. Beautiful Hardwood Floors all throughout. Nicely landscaped yard. In ground sprinkler, 2 car driveways. Close to Village shopping, restaurants, and parks. Come check out this beautiful home! MOVE IN READY!

77 Hiawatha Drive, Brightwaters
$645,000
3 Beds ⋅ 2 Baths ⋅ 939053 MLS
Welcome to this classic, charming Colonial in the highly desirable Brightwaters Village, a home that carries the kind of timeless character you simply can’t recreate today. A sun-filled enclosed porch sets the tone as you step into a spacious living room with a wood-burning fireplace, followed by a dining room and an eat-in kitchen with granite countertops. The main level also includes a half bath and a flexible bonus room ideal for a home office or additional living space. Upstairs you’ll find a full bathroom, pull-down attic access, and three bedrooms including a large primary with a walk-in closet. Wood floors run throughout the home, adding to its authentic charm. The unfinished basement offers great storage potential and includes a french drain. This corner lot features a compact rear yard complemented by a generous side yard that maximizes outdoor use and creative possibilities. Additional highlights include vinyl windows, 200-amp electric service, a deck area, shed, and a two-car garage with a walk-up attic. This home is perfect for someone ready to bring their vision to life and unlock the property’s full potential. Conveniently situated in the Bay Shore School District, the home offers close proximity to Bay Shore’s vibrant downtown, major highways, shopping, dining, hospitals, neighborhood parks, the LIRR, Fire Island ferry service, and nearby lakes, canals, and beaches.

31 Hiawatha Drive, Brightwaters
$615,000
3 Beds ⋅ 2 Baths ⋅ 924004 MLS
The wait is over! Welcome to 57 Hiawatha Drive — a charming Brightwaters gem that perfectly blends comfort, character, and convenience. From the moment you arrive, you’ll sense that this isn’t just a house — it’s the kind of home that wraps its arms around you. Step inside to find a living room centered around a cozy fireplace, ideal for relaxing evenings or hosting gatherings with friends and family. The open formal dining room flows effortlessly into a spacious den — perfect for movie nights, a home office, or play space. The kitchen is both functional and inviting, complete with electric cooking, an island, dishwasher, and plenty of cabinet space, making it the true heart of the home. This 3-bedroom, 2-bath home offers an easy and practical layout with a primary bedroom featuring its own full bath, and generous closet space. The additional bedrooms provide flexibility for family, guests, or a home workspace — and every room feels warm and welcoming thanks to central air and efficient radiator/baseboard heating systems. Downstairs, an unfinished partial basement offers additional storage or creative potential, while a garage converted for storage gives you even more flexibility for tools, hobbies, or seasonal decor. Modern upgrades ensure peace of mind: a 5-year-old hot water tank and boiler with expansion tank, new roof, security system, and above-ground oil tank add comfort and confidence for years to come. Step outside to enjoy the best of suburban living. A Trex deck provides the perfect spot for morning coffee or summer barbecues, overlooking a private backyard complete with a storage shed, in-ground sprinklers (IGS), and space to garden, play, or simply unwind. Every inch of the property has been designed for easy living — low maintenance, high enjoyment. Located in the heart of Brightwaters, this home places you minutes from village shops, waterfront parks, restaurants, schools, and the LIRR for easy commuting. This home delivers a rare combination of lifestyle, comfort, and value in an unbeatable location. Come experience the warmth that makes 57 Hiawatha Drive such a special place to call home. Don’t wait — your next chapter begins here.

57 Hiawatha Drive, 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.