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$2,499,999
5 Beds 5 Baths 1015209 MLS
Welcome to 2 Greenwood Lane! A Massive Contemporary Estate situated on a premier, park-like acre within the prestigious Rolling Hills area of Syosset School District. This expansive 5-bedroom, 4.5-bathroom home offers an unparalleled combination of grand scale, structural integrity, and architectural warmth. From the moment you step into the soaring two-story center hall foyer, you are greeted by an inviting, open-concept layout that allows you to see the true expanse of the home. Designed for both grand entertaining and comfortable daily living, the main level features a sun-drenched formal living room, a gracious formal dining room, and a massive den off the kitchen complete with a custom bar—perfect for hosting gatherings. Upstairs, the sleeping quarters are remarkably spacious, highlighted by a sprawling primary suite featuring dual walk-in closets and a dedicated en-suite bath. A massive, full finished basement with high ceilings offers the perfect footprint for a home theater, gym, or recreation area. Step outside onto a trex deck and overlook your own private paradise. The meticulously landscaped, park-like yard features a sweeping patio surrounding a pristine in-ground pool—your private summer country club. This home has been meticulously maintained, it is the perfect opportunity to bring your own personal style and vision to a beautifully maintained estate. This is your chance to create a forever home of your own in one of Woodbury's most desirable neighborhoods. 3D Tour: https://my.matterport.com/show/?m=WmMqijM6QPP

2 Greenwood Lane, Woodbury

$1,020,000
2 Beds 3 Baths 1011780 MLS
Set within the highly sought after Woodland Pond Community, this exquisite Cedarwood model (largest) is perfectly positioned as a desirable end unit overlooking a serene and picturesque pond. Enjoy tranquil pond views with fountain and botanical setting. This exceptional residence combines elegance, comfort and timeless design. Meticulously maintained, this home showcases sophisticated finishes and artfully curated living spaces throughout. The living room features a beautiful fireplace, textured walls for gallery style art display and cathedral vaulted ceiling with skylight. The dining room is graciously set with French style patio doors offering easy access to private patio with stunning views of the tree lined shore of pond and beyond. Chef's kitchen offers stainless steel appliances, large pantry, convenient laundry room and garage access. The thoughtfully designed floor plan offers a spacious primary suite upstairs with a wall of windows overlooking the pond with large "spa" style bath with bidet and large walk in closet. Additionally, there is a second bedroom with an ensuite full bath and walk-in closet. The full finished basement provides abundant storage and endless possibilities for recreation, fitness, home office or game room. A two-car garage adds to the home's exceptional functionality. Woodland Pond offers resort-style amenities including tennis courts, basketball court, heated outdoor pool, kiddie pool, playground and a newly renovated clubhouse with fitness center, card rooms and event space. Minutes to shopping, restaurants, highways and trains. Syosset School District

84 Woodlake Drive W, Woodbury

$4,450,000
8 Beds 9 Baths 000011 MLS
Introducing the most sought-after home in Woodbury, 5 Kodiak Drive. An epitome of contemporary luxury nestled in Syosset School District. This architectural masterpiece redefines opulence with its sleek design and an array of innovative amenities, ensuring a lifestyle of unparalleled comfort and sophistication. Situated on a sprawling one-acre lot, this estate seamlessly combines modernity with timeless elegance. As you step through the grand entrance, you're greeted by a fusion of sleek lines and luxurious materials, setting the stage for an exceptional living experience. Crafted for the most discerning homeowner, this residence boasts 8 bedrooms and 9 bathrooms, each meticulously designed with premium finishes and thoughtful details. Smart climate control systems, integrated sound, and lighting elevate the living experience to new heights. The main level is a haven for relaxation and entertainment. A stylish bar room invites you to unwind by the fireplace, while the formal dining room offers the perfect setting for intimate gatherings. The gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, pizza oven, custom cabinetry, and a breakfast area overlooking the lush backyard. Outside, the expansive grounds offer a sanctuary for outdoor living. A private tennis court with overhead lighting provides endless opportunities for recreation, while the heated in-ground Gunite pool and cabana area offer a serene retreat for lazy afternoons and al fresco dining. The pool features an infinity edge and a mesmerizing water feature with multiple fire elements, creating a captivating ambiance. Upstairs, the primary suite is a luxurious escape, complete with a sitting area, private balcony, and spa-like ensuite bath featuring a soaking tub and steam shower. Four additional bedrooms, each with its own ensuite bathroom, provide ample space for family and guests. Downstairs, the lower level is a hub of activity, with a fitness room, billiards area, and home theater offering endless entertainment options. A three-car garage provides ample space for vehicles and storage, while smart home features ensure convenience and security. With its blend of contemporary design and timeless elegance, this estate sets a new standard for luxury living in Woodbury, NY, offering a lifestyle characterized by indulgence, sophistication, and unparalleled amenities.

5 Kodiak Drive, Woodbury

$1,848,000
5 Beds 4 Baths 1006505 MLS
Enjoy suburban calmness with city accessibility in the top-rated Syosset School District. Commuting is effortless with the Syosset LIRR station just minutes away, providing under 55-minute express service to Penn Station and Grand Central Madison. This secure, quiet home features a full ADT security system and underwent comprehensive renovations in 2018, including new infrastructure (roof, siding, windows, electric, and plumbing). The property offers five bedrooms, four bathrooms, and a light-filled kitchen with cozy radiant heat flooring. Expansive front and back decks perfect for outdoor family entertaining. Offering the perfect blend of lower taxes and unparalleled convenience, this home has it all. With expansive land available, you can extend your property to your desired size and enjoy endless possibilities for outdoor activities. Must see!!

249 Cold Spring Road, Syosset

$2,999,000
5 Beds 6 Baths 1005913 MLS
Welcome to Crest Hill! An extraordinary newly constructed luxury estate set on 2.02 private acres in the heart of prestigious Woodbury, New York. Quality construction built in 2024 and offered fully furnished and completely turnkey, this remarkable residence combines timeless elegance with modern sophistication for an unparalleled North Shore lifestyle. A grand mansion-style approach welcomes you home with an expansive front driveway framed by stately brick piers, already wired and prepared for iron security gates controlled directly from within the residence. Every detail has been thoughtfully designed to create a private sanctuary of luxury, comfort, and distinction. This magnificent 10-room Colonial offers 5 spacious bedrooms and 6 designer bathrooms, all flooded with natural sunlight through oversized windows and soaring architectural spaces. The dramatic sunlit entry foyer introduces the home with exquisite porcelain flooring and an impressive custom curved bridal staircase adorned with wrought iron and brass detailing. Designed for both elegant entertaining and everyday living, the open-concept layout seamlessly connects the gourmet kitchen to the grand great room featuring an elegant gas fireplace. The flow continues beautifully into the formal living room with a second gas fireplace toward the stunning double mahogany and glass entry doors that create a striking architectural statement. A first-floor guest or in-law suite provides ideal accommodations for extended family or visitors. Upstairs, the luxurious primary suite and second bedroom suite each feature private Juliet balconies overlooking the serene courtyard and surrounding natural landscape. Spa inspired designer baths throughout the home include premium finishes, with the principal bath featuring heated flooring for ultimate comfort. The fully finished lower level expands the home’s exceptional living space and includes a gym, two legal egresses, a media room wired and ready for a custom home theater, and endless possibilities for recreation, wellness, or private retreat spaces. Exterior features an outdoor kitchen with gas BBQ, sink, beverage cooler, storage and more. The double width driveway from top to bottom allows for passing another car and additional parking for parties. An extensive entertainment patio off the kitchen lends itself to another world of outdoor living. Permits are in place for an inground pool and lighting, approved by the town. The architecture of the home is complemented by concrete walls, special pathways, and a garden walk on the hillside. Crest Hill is truly an entertainer’s dream; a residence where luxury, privacy, and functionality exist in perfect harmony. Simply bring your designer bags and step into your own private world of sophistication. Ideally situated near the Long Island Rail Road, the Villages of Huntington and Cold Spring Harbor, and the renowned Woodbury shopping district, the location offers convenient access to elegant dining, boutique shopping, hiking trails, boating, fishing, and the very best of Long Island’s celebrated North Shore lifestyle. Beautiful Long Island beaches are just 15 minutes away by car. Crest Hill is more than a home, it is a statement of luxury living. Make this dream home your next stop! View 3d tour, click virtual tour link for video and more.

23 Woodbury Road, Woodbury

$2,099,999
6 Beds 5 Baths 1005538 MLS
Welcome to 119 Plainview Road — a place where elegance meets ease. This expansive 4,500-square-foot Colonial rests on over an acre of pondfront property in Woodbury, where every inch has been thoughtfully maintained to create a home that feels as effortless as it is impressive. Inside, six generous bedrooms and four and a half bathrooms offer space for family and guests alike, all finished with high-end appointments throughout. Every detail has been meticulously cared for, presenting in turn-key, move-in condition for the most discerning buyer. The true showpiece lies beyond the walls. Step outside to a country-club-caliber backyard where an inground pool anchors a private oasis overlooking serene pond views. Whether entertaining on a grand scale or enjoying a quiet morning by the water, the oversized lot delivers privacy and resort-style living rarely found this close to everything. Located within the prestigious Syosset School District and minutes from premier shopping, dining, and parkway access, this is a rare opportunity to own a true estate property on Long Island!

119 Plainview Road, Woodbury

$1,898,000
4 Beds 5 Baths 1005109 MLS
Welcome to this exceptional Hampton-style Colonial with your own gate, privately set on a flat 1 beautifully landscaped acre with heated pool and outdoor shower and powder room. An inviting oversized front porch overlooks lush emerald lawns, mature specimen trees, and beautifully landscaped grounds. A tranquil pond with a cascading waterfall, graceful Japanese maple, and vibrant seasonal blooms create a picturesque setting year-round. Stepping inside to discover oversized, sun-filled rooms and a seamless floor plan with beatiful wood floor and heated tile floor in multi areas. At the heart of the home is an extended chef's kitchen featuring granite countertop, high end appliances, custom cabinetry witha wine cooler, a breakfast nook, and a build in work station, all thoughtfully designed for entertaining. The family room with a wooden fireplace creates a warm and inviting gathering space, while large windows throughout the home frame picturesque views of the property. The 2nd floor has 4 spacious bedrooms with 3 full baths and the convenience of a laundry room. The luxurious primary suite offers a spa-inspired bath and an adjoining sitting area. A second en-suite bedroom provides additional flexibility for guests or multi-generational living with office/dressing room. The fully finished basement is an entertainer's dream, complete with a custom-built wet bar, recreation area and abundant storage. Step outside to your private backyard oasis featuring a heated in-ground pool, covered bluestone patio, outdoor kitchenette with gas grill, and a charming gazebo with skylight. There's a change room and powder room and outdoor shower next to the pool for convenience. Professionally landscaped grounds with mature trees, lush lawns, and elegant uplighting create a resort-like atmosphere. Located within the highly regarded Village Elementary School and South Woods Middle School boundaries, this home offering combines privacy, luxury, and convenience in one extraordinary setting, offering a lifestyle of elegance, tranquility, and year-round enjoyment. Otherhights including whole house water filtriation and central vacuum, gas cooking & heating, radiated floor for both primary bathrooms and the eat-in kitchen area. The ffenced property ensures privacy and security with gated access. Face to the famious the Town of Oyster Bay Golf Course and walking distance to the famious woodbury villiage for fine restarants and shopping and more! A rare and timeless Golden East Coast Gem!

316 S Woods Road, Woodbury

$3,995,000
5 Beds 6 Baths 1004527 MLS
Steeped in architectural pedigree and timeless elegance, this extraordinary Muttontown estate, on 3.84 bucolic acres, was designed by renowned architect Marion Sims Wyeth, celebrated for his iconic work on Mar-a-Lago in Palm Beach. Privately tucked behind an impeccably landscaped half mile-long drive off Route 106, the property unfolds as a secluded North Shore sanctuary of exceptional beauty and distinction. Set amidst sweeping lawns, manicured gardens, and picturesque equestrian grounds, the stately brick residence, crowned with a slate roof and introduced by a charming courtyard entry, exudes enduring sophistication. Inside, grand formal entertaining rooms showcase exquisite millwork, original hardwood floors, dramatic wrought-iron railings, and an abundance of French doors that flood the interiors with natural light while seamlessly connecting the home to its breathtaking surroundings. Offering five bedrooms and five-and-a-half baths, the home masterfully balances grandeur with comfort. The formal living room, complete with a fireplace and built-in wet bar, creates an inviting setting for entertaining, while the sunlit breakfast turret and updated chef’s kitchen, appointed with premium professional-grade appliances, provide effortless everyday functionality. A spacious family room and elegant powder room complete the main living spaces. The first-floor primary suite serves as a luxurious private retreat, featuring dual full baths, a fireplace, expansive walk-in closets, and an intimate sitting room. The upper level offers two generously proportioned bedrooms and a beautifully appointed full bath with a thoughtfully separated vanity and shower area. Completing the space is an expansive unfinished attic, presenting exceptional potential for storage or future customization. Additional highlights include a walk-out finished lower level with laundry, bedroom with full bathroom and direct access to the attached two-car garage. Designed for both gracious living and sophisticated entertaining, the residence boasts expansive slate terraces spanning the length of the home, overlooking the stone courtyard driveway, private gardens, charming pergola, and in-ground gunite pool - evoking the romance and refinement of a storybook North Shore estate. A true horse property, the fully fenced equestrian amenities are equally exceptional, featuring a pristine multi-stall barn built-by Morton, thoughtfully designed grazing paddocks, and scenic walking trails woven throughout the grounds. A truly rare offering, this remarkable estate presents an unparalleled opportunity to own a significant piece of Long Island history, all within the esteemed Syosset Central School District.

1780 Route 106 Unit #C, Muttontown

$1,288,000
5 Beds 4 Baths 1000693 MLS
Welcome to This Oversized and Beautifully Renovated Home Located in the Prestigious Syosset Woods Section! Conveniently Situated Just 5 Minutes from the Syosset LIRR Station, This Stunning Property Offers the Perfect Combination of Space, Comfort, and Modern Upgrades. Featuring 5–6 Spacious Bedrooms and 4 Full Bathrooms, This Home Has Been Extensively Renovated Throughout. Updates Include a Brand-New Roof, New Heating and Cooling System, New Kitchen with Modern Appliances, Anderson Windows, and Hardwood Floors Throughout. The Exterior Has Also Been Thoughtfully Improved with a Brand-New Concrete Sidewalk, Huge Newly Paved Driveway with Ample Parking, and Professionally Updated In-Ground Swimming Pool. Additional Features Include a Ring Security Camera System Protecting the Entire Property and a Prime Location Close to Shopping, Dining, Parks, Schools, and Transportation. Move-In Ready and Truly a Rare Opportunity in One of Syosset’s Most Desirable Neighborhoods!

18 Park Drive E, Syosset

$2,548,000
5 Beds 7 Baths 993715 MLS
Welcome to this exceptional custom-built Colonial nestled in the highly sought-after Swan Lake development of Woodbury, located within the award-winning Syosset School District. Boasting approximately 6,000 square feet of thoughtfully designed living space, this magnificent residence offers 12 spacious rooms, including 5 generously sized bedrooms—each featuring its own walk-in closet—and 6 full bathrooms. Crafted with superior quality and attention to detail, this home features stunning marble and granite finishes throughout, creating a timeless and elegant atmosphere. The expansive layout offers seamless flow, ideal for both everyday living and entertaining on a grand scale. The fully finished basement with outside entrance provides versatile additional living space, perfect for recreation, guests, or extended family. Step outside to a beautifully level and private backyard, where luxury meets lifestyle. The outdoor kitchen area is a true showpiece, complete with a pizza oven imported directly from Italy—perfect for entertaining and creating unforgettable experiences. This one-of-a-kind residence is more than just a home—it’s a true oasis offering sophistication, comfort, and exceptional craftsmanship in one of Woodbury’s premier locations.

21 Chauncey Place, Woodbury

$2,799,000
6 Beds 7 Baths 989842 MLS
Welcome to this exceptional home offering the perfect blend of luxury, space, and modern living. Boasting 6 spacious bedrooms and 6.5 beautifully appointed bathrooms, this residence is thoughtfully designed for both everyday comfort and upscale entertaining. The first floor features a seamless open-concept layout anchored by a stunning kitchen that flows effortlessly into expansive living, dining, and family room spaces—ideal for gatherings of any size. A versatile first-floor bedroom provides flexibility for guests, a home office, or multigenerational living, complemented by a nearby full bathroom as well as an additional powder room for added convenience. Upstairs, you’ll find five generously sized bedrooms and four full bathrooms, including a luxurious primary suite. A striking open walkway overlooks the living room below, creating a dramatic sense of space and natural light throughout the home. The fully finished basement elevates the home’s entertainment potential, complete with a dedicated gym, wet bar, and ample room for recreation, media, or hosting. Car enthusiasts and eco-conscious buyers alike will appreciate the oversized 3-car garage equipped with multiple EV charging stations. Step outside to a backyard oasis that seamlessly connects to nature while offering endless possibilities for outdoor living. Featuring an outdoor kitchen and expansive grounds, there’s plenty of space to add a pool, tennis court, or custom retreat tailored to your lifestyle. This is a rare opportunity to own a home that truly has it all—space, style, and unmatched versatility.

12 Chauncey Place, Woodbury

$819,888
3 Beds 3 Baths 990859 MLS
This Updated 3 Bedroom, 2.5 Bath Townhouse with a Full Finished Basement is located in The Woodlands Community within the Syosset School District! IT IS MOVE IN READY WITH A LOVELY SERENE LOCATION FACING THE BACK! The home has many upgrades such as Oak Hardwood Flooring and Recessed Lighting Throughout. The Eat in Kitchen has Granite Countertops, a Granite Island and Stainless-Steel Appliances. Continuing on the main level is a Pantry Closet, Half Bath, Washer/Dryer, Dining Room and a Living Room with a wood burning Fireplace. Upstairs is the Primary Bedroom featuring an En-Suite Bathroom and a large Walk in Closet. The 2nd and 3rd Bedroom as well as a Full Hallway Bathroom complete the upper level. The Lower Level features a Full Finished Basement and room for extra storage! Amenities include a Community Pool, Tennis, Basketball and Play Area. Enjoy all that this Community has to offer!

109 Aspen Drive E, Woodbury

$2,895,000
6 Beds 6 Baths 989712 MLS
Welcome to this stunning, fully gut-renovated Contemporary nestled on one of the largest lots in the prestigious gated community of Windemere — a rare 1.26-acre private cul-de-sac setting with room for a pool and endless possibilities. From the moment you arrive via the elegant circular driveway, this 5-bedroom, 5.5-bath showpiece makes an unforgettable impression. Thoughtfully designed with soaring ceiling heights and an open-concept layout, walls of glass and sliders flood every room with natural light, creating a bright, airy atmosphere throughout. The designer kitchen is a true centerpiece, featuring high-end appliances and seamlessly flowing into a sun-drenched sunroom and a massive great room — perfect for everyday living and effortless entertaining. A wet bar and sleek linear fireplace add sophistication to the living spaces, while the upstairs loft offers flexible additional living space. The main-floor primary suite is a private sanctuary unto itself, complete with sliding glass doors opening to the expansive Trex deck, floating stairs, a custom walk-in closet, and a spa-inspired bath boasting radiant heat flooring, a built-in towel warmer, and a freestanding soaking tub. Step outside to your own resort-style backyard retreat — a massive Trex deck with a full outdoor kitchen and multiple lounge and dining areas, with stairs leading down to the sprawling backyard. The full finished walk-out basement adds tremendous additional living and entertaining space, completing this exceptional offering. A truly rare opportunity in one of the area's most sought-after communities.

7 Windemere Crest, Woodbury

$1,488,000
4 Beds 3 Baths 982967 MLS
Welcome to a rare opportunity in the heart of Woodbury. This 4 bedroom, 2.5 bath Splanch style home is perfectly situated mid-block on a picturesque, tree-lined street. Step inside to discover a beautiful home with natural light and hardwood floors. The first floor features a renovated eat-in kitchen with stainless steel appliances, granite countertops and a formal dining room for entertaining. For colder nights, enjoy the family room with a wood burning fireplace. Also includes radiant floor heating The large primary bedroom features a wall of closets and a renovated en suite bathroom. Two additional bedrooms and hall bath complete the upstairs living. Designed for modern living, the home boasts a dedicated home office for remote work and a spacious mudroom with convenient main-floor laundry. The two-car garage includes an electric charger for sustainable living. Retreat to your private backyard oasis, framed by mature privacy trees. The highlight is the in-ground heated pool, complemented by a large brick patio, creating the perfect setting for summer entertaining and relaxation. This exceptional property is ready to be your forever home

3 Clemson Lane, Woodbury

$1,488,878
3 Beds 3 Baths 953870 MLS
Back on market! Showstopping and better than new, this completely gutted and fully renovated 3-bedroom, 2.5-bath Aspen model with a full basement showcases ultra-luxurious finishes throughout, seamlessly blending sleek modern design with the comfort of living in the highly desirable Woodbury Greens community. The home features radiant heated floors throughout, rich hardwood flooring, all-new insulation, and abundant natural light enhanced by skylights for both style and energy efficiency. At the heart of the home is a chef’s kitchen, thoughtfully designed with high-end finishes and functionality ideal for both everyday living and entertaining. The finished lower level is a true standout, offering a private sauna, media room, and home gym—creating an exceptional resort-style living experience. The primary suite is a serene retreat, complete with a spa-like bathroom featuring a luxurious steam shower. Additional highlights include a whole-home water filtration system, electric access to the finished attic, and a two-car garage for added convenience. Community amenities include a pool, tennis, pickleball, and basketball courts, delivering an elevated lifestyle in a premier setting.

24 Chestnut Lane, Woodbury

$1,298,000
3 Beds 3 Baths 911695 MLS
Welcome to this Exquisite End-Unit Vale Model in the Prestigious Guard-Gated Community of Hidden Ridge! This beautifully renovated residence offers 3 spacious bedrooms, 2.5 updated baths, a finished basement, and a 2-car garage with a private driveway. The updated kitchen features quartz countertops and stainless-steel appliances—designed with quality and attention to detail. The expansive primary suite includes a large walk-in closet and a renovated spa-like bath with a double vanity, soaking tub, and walk-in shower. The finished basement provides exceptional additional living space, complete with an air ventilation system and a custom wine cellar—ideal for both entertaining and everyday comfort. Additional highlights include gleaming hardwood floors, surround sound in the living room and a cozy fireplace. Step outside to your gated deck overlooking a lush greenbelt oasis—perfect for entertaining or simply relaxing in total privacy. Hidden Ridge offers resort-style amenities including a pool, tennis courts, clubhouse, and playground—delivering the ultimate country club lifestyle. Conveniently located near major highways, shopping, dining, parks, schools, and the LIRR. Prestigious Syosset School District (AP Willits Elementary, HB Thompson Middle, Syosset High School). Move right in and enjoy your own private oasis with luxury living at its finest! Seller financing available.

154 Hidden Ridge Drive, Syosset

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.