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$899,000
4 Beds ⋅ 2 Baths ⋅ 1041275 MLS
Welcome to 556 N Windsor Avenue, a gracious 1902 Colonial offering exceptional space, character and versatility in the heart of Brightwaters Village. From the moment you enter the charming entry parlor and continue into the welcoming foyer with its grand staircase, the home immediately draws you in with its warmth, character and inviting sense of space. Designed with entertaining and everyday living in mind, the main level offers beautifully proportioned spaces throughout. The oversized living room provides plenty of room for multiple seating areas and is anchored by a wood-burning fireplace with a beautiful mantel and custom built-ins. Crown and base molding, recessed lighting and architectural details add to the room's character, while multiple openings create an easy connection to the adjoining wraparound den. Filled with windows and natural light, the enclosed wraparound den offers an inviting space to relax and entertain and features built-ins, a bar area with wine refrigerator, an integrated sound system and direct access to the backyard. At the heart of the home is the spacious chef's kitchen with radiant heated floors, rich cherry cabinetry, quartz countertops, stainless steel appliances, a breakfast bar with pendant lighting and a six-burner Viking range with center grill and oversized hood vented to the exterior. The kitchen opens to the large dining room with hardwood floors, a bay window, tray ceiling and sliding glass doors to the deck and yard. Just off the kitchen, a convenient mudroom with radiant-heated tile flooring provides direct backyard access and incorporates a perfectly placed laundry nook with additional storage. Completing the main level is a beautifully updated full bath with a classic clawfoot tub, pedestal sink and timeless tilework, along with a generously sized office with extensive closet storage. Currently used as a home office, this versatile room also offers the flexibility of a possible fifth-bedroom or comfortable guest space. Upstairs are four bedrooms, including a spacious primary bedroom with separate sleeping and sitting areas, generous closet space and a decorative fireplace mantel. An oversized updated full bath with tiled shower completes the second level and pull-down stairs from the hallway provide convenient access to the attic for additional storage. The partial basement provides even more storage and includes a cedar closet and workshop area. Outdoors, the home's inviting living spaces continue with a wood deck, paver patio, large fenced yard and established organic vegetable and flower gardens, creating a wonderful setting for outdoor dining, entertaining, gardening or simply relaxing. A newly repaved Belgian block-lined driveway provides abundant parking and leads to the detached two-car garage. Additional features include central air conditioning, two-zone natural gas heat, public sewers and a multi-room sound system with indoor and outdoor speakers. Offering four bedrooms plus a flexible first-floor office/possible fifth bedroom and two full baths, this move-in-ready home brings together exceptional space, character and the sought-after Brightwaters Village lifestyle. Enjoy close proximity to Wohseepee Park, Village shopping and dining, schools and major roadways, along with resident amenities including the Village beach, canal docking, Brightwaters lakes, tennis, dog park, private garbage collection and snow removal. Just minutes from Downtown Bay Shore, the Fire Island Ferries and Robert Moses State Park, 556 N Windsor Avenue offers the opportunity to enjoy all that Brightwaters and the Great South Bay lifestyle have to offer.

556 N Windsor Avenue, Brightwaters
$777,000
2 Beds ⋅ 2 Baths ⋅ 1039689 MLS
Millennial Grey Fans need not apply! 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
$689,900
4 Beds ⋅ 2 Baths ⋅ 1030408 MLS
Welcome to beautiful Brightwaters, one of Long Island's most charming and sought-after villages, known for its tree-lined streets, picturesque surroundings, and close proximity to scenic parks, walking trails, and waterfront beauty. This well maintained home offers the perfect blend of coziness and style.. Inside, enjoy year-round comfort with Central air conditioning and a brand new Bosch heat pump system, providing efficient heating and cooling. The home is also equipped with a convenient four zone in-ground sprinkler system to help maintain the lush landscaping.. Step outside to a beautiful, well- maintained backyard featuring a Trex deck, ideal for entertaining, outdoor dining, or simply relaxing in a peaceful setting. This property also offers a wonderful outdoor space for gatherings while enjoying all that this desirable community has to offer. The home provides the perfect opportunity to experience the exceptional lifestyle that Brightwaters is known for .... Don't miss your chance to make this home your own ....

555 N Windsor Avenue, Brightwaters
$959,999
4 Beds ⋅ 4 Baths ⋅ 1029408 MLS
Welcome to 414 Potter Boulevard, a beautifully renovated Colonial nestled in the heart of the Village of Brightwaters. This move-in ready home perfectly blends timeless charm with modern updates, offering exceptional comfort and style from the moment you arrive. The thoughtfully renovated interior features a stunning kitchen with contemporary finishes, beautifully updated bathrooms, and a brand-new roof, providing true peace of mind for years to come. A highly sought-after first-floor primary suite offers convenience, privacy, and flexible living, making this home ideal for a variety of lifestyles. Outside, you'll find a detached two-car garage, a spacious yard perfect for entertaining or relaxing, and the added benefit of low taxes. Located in one of Long Island's most desirable waterfront communities, you'll enjoy easy access to parks, marinas, village amenities, shopping, dining, and major transportation. If you've been searching for a turnkey home in Brightwaters that combines classic character with today's modern conveniences, 414 Potter Boulevard is one you won't want to miss.

414 Potter Boulevard, Brightwaters
$1,099,000
5 Beds ⋅ 4 Baths ⋅ 1024524 MLS
Welcome to a home where timeless elegance meets exceptional craftsmanship in the heart of the Village of Brightwaters. Perfectly positioned on one of the area’s most sought-after streets, this beautifully appointed residence offers luxury finishes, flexible living spaces, and an extraordinary backyard retreat designed for both everyday living and unforgettable entertaining. At the heart of the home is a custom chef’s kitchen featuring granite countertops, under-cabinet and in-cabinet lighting, a double convection oven with a warming drawer, and an induction cooktop—a space as functional as it is beautiful. The stunning cathedral-ceiling primary suite is a true retreat, complete with two custom walk-in closets, new skylights that fill the room with natural light, and a spa-inspired primary bath featuring a luxurious soaking tub. Every upstairs bedroom and bathroom is enhanced with custom-designed closets, providing exceptional organization and storage. The versatile lower level offers brand-new flooring, a new full bathroom, and an expansive office suite with two private offices and a waiting room, making it ideal for a home-based business, professional workspace, guest quarters, multigenerational living, or a nanny suite. Step outside into your own private resort. The professionally designed backyard showcases a heated lap pool with cascading waterfalls, an outdoor fireplace, and a built-in outdoor kitchen with granite countertops, creating the perfect setting for entertaining or relaxing. An upper Trex deck overlooks the spectacular grounds, while a 12-zone in-ground sprinkler system keeps the lush landscaping looking its best. A circular driveway adds both elegance and convenience to the home’s impressive curb appeal. Located in the charming Village of Brightwaters, residents enjoy tree-lined streets, a private village park, tennis courts, a community dock, summer concerts, holiday celebrations, and a true small-town atmosphere—all while being just minutes from vibrant downtown Bay Shore, waterfront restaurants, Fire Island ferries, beaches, parks, and the LIRR for an easy commute to Manhattan. This is more than a home—it’s a lifestyle defined by luxury, comfort, and one of Long Island’s most desirable communities

236 Windsor Avenue, Brightwaters
$975,000
4 Beds ⋅ 4 Baths ⋅ 999271 MLS
Discover the Potential in the Heart of Brightwaters Village Space, location, and lifestyle come together in this charming 3,000-square-foot Center Hall Colonial, beautifully situated on an impressive property in the heart of Brightwaters Village. With generously sized rooms and tremendous potential, this is a home ready for its next owner to bring their vision and make it their own. Inside, you’ll find hardwood floors throughout, a spacious living room, formal dining room, eat-in kitchen with granite countertops and stainless steel appliances, and an inviting den with a gas fireplace and sliding doors leading to the deck and backyard. Four generously sized bedrooms, four full baths, and a dedicated home office provide plenty of room for everyone. A full finished basement with a full bath and outside entrance offers even more flexible living space, while the two-car garage completes the home. Outside, the beautiful property provides plenty of room to entertain, relax, garden, and enjoy the seasons. But what truly sets this home apart is the opportunity to experience Village Life in Brightwaters. Stroll to charming village shops and restaurants, enjoy the neighborhood parks and picturesque lakes, spend summer days at the private village beach, or head out for an afternoon of boating on the Great South Bay. From the Grand Concourse to the waterfront, Brightwaters offers a special sense of community and a South Shore lifestyle that is difficult to duplicate. 3,000 square feet. Generous bedrooms. Beautiful property. Endless potential. Incredible location. Come bring your vision and discover everything this home and life in Brightwaters Village have to offer.

220 Windsor Avenue, Brightwaters
$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.