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7 The Rise, Woodbury
$4,988,000
6 Beds ⋅ 7 Baths ⋅ 935692 MLS
Modern Luxury to be built in The Gates of Woodbury. Welcome to 7 The Rise, a breathtaking custom-designed residence located in one of Woodbury’s most prestigious and sought-after neighborhoods. Set on a full one-acre property, this custom built masterpiece offers exceptional craftsmanship, refined architectural detail, and a lifestyle of elevated comfort. Inside, you’ll find soaring ceilings, expansive sun-filled living spaces, and 6 spacious en-suite bedrooms, each designed with sophistication and privacy in mind. The heart of the home features meticulously curated custom luxury finishes, from the chef’s kitchen to the spa-inspired baths, creating an atmosphere of effortless elegance throughout. Whether you’re entertaining or enjoying quiet moments at home, the seamless indoor-outdoor flow is unparalleled. The lush, landscaped property showcases a stunning gunite pool, perfect for summer relaxation and gatherings. Additional highlights include a 3-car garage, premium materials, and thoughtfully designed spaces ideal for both everyday living and grand-scale hosting. A rare opportunity to customize a truly extraordinary new construction home by on of Long Island's most distinguished luxury home builders. Located in the award winning Syosset School District.

7 The Rise, Woodbury
5 Kodiak Drive, 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
23 Woodbury Road, Woodbury
$2,999,000
5 Beds ⋅ 6 Baths ⋅ 1005913 MLS
Welcome to Crest Hill! An extraordinary luxury estate set on 2.02 private acres in the heart of prestigious Woodbury, New York. 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
7 Windemere Crest, 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
21 Chauncey Place, Woodbury
$2,548,000
5 Beds ⋅ 6 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
3 Aron Drive, Woodbury
$2,499,999
4 Beds ⋅ 4 Baths ⋅ 1049514 MLS
Welcome to 3 Aron Drive, a completely reimagined and fully renovated expanded Colonial in the highly desirable “Castle” section of Woodbury, within the sought-after Syosset School District. No expense was spared in transforming this exceptional 4-bedroom, 4-bath home, which showcases top-of-the-line materials, sophisticated finishes, and thoughtful craftsmanship throughout. Step inside to a fresh, modern interior filled with natural light and designed for today’s lifestyle. The beautifully redesigned living spaces offer an effortless flow for both everyday living and entertaining, while the stunning new kitchen serves as the heart of the home with high-end finishes, premium appliances, and a refined contemporary feel. Spacious living and dining areas provide the perfect setting for gatherings, while the inviting family room offers a comfortable place to unwind. Upstairs, four generously sized bedrooms provide ample space and storage, while the beautifully renovated bathrooms feature stylish, quality finishes. From the major systems to the smallest details, the home has been comprehensively updated to deliver modern comfort, functionality, and peace of mind. A full basement provides additional space and endless possibilities for a home gym, playroom, media room, office, or recreation area. Outside, the home sits on an oversized property of more than half an acre, offering a private, park-like backyard with plenty of room for entertaining, play, and outdoor enjoyment. Combining a premier Woodbury location, Syosset schools, expansive property, and a truly top-to-bottom renovation, 3 Aron Drive is a rare move-in-ready opportunity you will not want to miss. Make this extraordinary home your next home.

3 Aron Drive, Woodbury
39 Orchard Court, Woodbury
$2,349,000
6 Beds ⋅ 4 Baths ⋅ 1054993 MLS
Perched high on a hill within The Gates of Woodbury, this impressive 3600 square foot Colonial boasts 6 bedrooms, 3.5 baths - a compelling combination of space, privacy and versatility. Set on over one acre of fully fenced property, 39 Orchard Court enjoys an elevated presence and a beautifully level backyard. It's ideal for entertaining and offers plenty of room for future outdoor amenities such as a tennis or sport court. Inside, generously proportioned rooms present a flexible layout for everyday living and gatherings... including a spacious living room with fireplace and an additional sitting room through French doors. The expansive family room also features a wood-burning fireplace. A large eat-in kitchen and separate dining room provide ample space for casual meals or special occasions. Just off the kitchen, a dedicated gym room with wall-to-wall windows overlooks the beautiful backyard. Two main-level bedrooms and a full bath affords options for guests, home offices and multi-generational living. Upstairs, the primary bedroom features a fireplace, two walk-in closets and an en-suite bath with a steam shower and jacuzzi tub. Three additional oversized bedrooms complete the second floor. The full basement with egress includes a theatre room, sound-proof music room and abundant storage - so much potential for endless entertainment! A 3 car garage allows for additional space for vehicles and equipment. With its gracious setting, substantial square footage, expansive rooms and grounds, 39 Orchard Court gives you the room to explore so many possibilities. Gunite pool offered as-is. Conveniently located near all major highways, the train station and shopping centers, and within the Syosset School District. Don't miss this opportunity to live in The Gates! More pictures coming soon.

39 Orchard Court, Woodbury
2 Greenwood Lane, Woodbury
$2,299,999
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
21 Kodiak Drive, Woodbury
$2,200,000
5 Beds ⋅ 5 Baths ⋅ 992528 MLS
Located within the prestigious gated community of The Gates in Woodbury, this exceptional 5 bedroom, 5 bath residence offers the perfect blend of elegance and everyday livability on a breathtaking one acre park-like setting. Designed with entertaining in mind, the home features spacious principal rooms that flow seamlessly from one to the next. The inviting den is a true showstopper, anchored by a cozy fireplace, warmed by radiant heated floors, and opening directly to the patio through walkout access, making indoor-outdoor living effortless. The primary suite is a private retreat, complete with a beautifully renovated en suite bath. Step outside and discover a lush, expansive acre with endless possibilities, ample room to add a pool or simply enjoy the serene, park-like grounds as they are. Syosset School District.

21 Kodiak Drive, Woodbury
96 Plainview Road, Woodbury
$2,088,888
6 Beds ⋅ 6 Baths ⋅ 1020613 MLS
Nestled on one private acre in the heart of Woodbury, this exceptional center hall Colonial offers the perfect blend of timeless elegance, modern updates, and outstanding versatility. Set on a beautifully landscaped one-acre property, the home provides a peaceful retreat while remaining just minutes from shopping, major parkways, the LIRR, and Syosset schools. The main residence features 5 bedrooms and 4.5 bathrooms, and an attached 2 car garage, including a first-floor bedroom or office with an adjacent full bath, ideal for guests, extended family, or working from home. The gracious entry foyer welcomes you into a thoughtfully designed floor plan highlighted by hardwood floors, detailed millwork, and generously sized living spaces. The renovated eat-in kitchen is the heart of the home, showcasing custom white cabinetry, granite countertops, premium stainless steel appliances, a kitchen island with seating, and a bright breakfast area overlooking the private backyard. The kitchen flows seamlessly into the inviting family room with a wood-burning fireplace, while the formal dining room and elegant living room provide ideal spaces for entertaining. Just beyond the kitchen, a spacious elevated deck serves as a natural extension of the home's living space, featuring a built-in jacuzzi, multiple seating and lounge areas, and generous space for outdoor dining. Overlooking the resort-style pool and separate cabana/guest house, it provides the perfect setting for relaxing or entertaining while enjoying the privacy of the beautifully landscaped grounds. Upstairs, the spacious primary suite offers a walk-in closet and a beautifully updated en-suite bath. Three additional bedrooms share a well-appointed full hall bathroom. Adding tremendous value and flexibility is a separate pool cabana/guest house featuring a custom wet bar, bedroom, full bathroom, laundry, and its own attached two-car garage—providing a total of four garage bays across the two buildings. Whether used for entertaining, multigenerational living, long-term guests, a private home office, or recreation, this detached space offers endless possibilities. The secluded backyard provides exceptional privacy with mature landscaping and ample room to relax, entertain, or enjoy the outdoors. A rare opportunity to own a meticulously maintained estate offering exceptional living space, unmatched versatility, and one of Woodbury's most desirable locations.

96 Plainview Road, Woodbury
46 Plainview Road, Woodbury
$2,049,888
6 Beds ⋅ 5 Baths ⋅ 1059193 MLS
Discover unparalleled luxury in this stunning 4,333 sq ft uber luxurious New Construction, perfectly positioned on a sprawling half-acre in the heart of Woodbury. Located within the prestigious Syosset School District, this custom-built home offers modern elegance, top-tier finishes, and exceptional attention to detail throughout. Step inside to a sun-drenched, open-concept layout featuring a luxurious eat-in kitchen equipped with a massive center island, premium Sub-Zero/Wolf appliance package, and elegant custom cabinetry. The seamless flow continues into the spacious living room with a sleek see-through fireplace, a spacious formal dining room, a stunning a cozy den with an additional fireplace, and a versatile office or guest bedroom on the main level. The grand primary suite is a true retreat—offering soaring ceilings, multiple walk-in closets, and a spa-inspired bathroom with designer fixtures. Three additional bedrooms include a Jack and Jill bathroom and a private en-suite, ideal for family or guests. The fully finished basement provides exceptional bonus space with multiple egress windows, a bedroom, full bathroom, and endless possibilities for recreation, gym, or media room. Energy efficiency meets cutting-edge tech with owned solar panels and a Tesla Powerwall energy storage system. Enjoy built-in speakers throughout, and too many upgrades and extras to list. This is a rare opportunity to own a move-in-ready, luxury home in one of Long Island’s most desirable communities. A must-see!

46 Plainview Road, Woodbury
119 Plainview Road, Woodbury
$1,999,999
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
44 Plainview Road, Woodbury
$1,999,888
6 Beds ⋅ 5 Baths ⋅ 1039543 MLS
Experience exceptional luxury in this beautifully crafted 4,333 sq ft New Construction, ideally situated on a private half-acre in the heart of Woodbury and located within the highly regarded Syosset School District. Designed with both sophistication and everyday living in mind, this custom home showcases high-end finishes, thoughtful craftsmanship, and impressive attention to detail throughout. The sun-filled, open-concept main level features a spectacular eat-in kitchen with an oversized center island, premium Sub-Zero and Wolf appliance package, custom cabinetry, and elegant designer finishes. The kitchen flows seamlessly into the spacious living areas, including a dramatic living room with a sleek see-through fireplace, a generous formal dining room, a warm and inviting den with an additional fireplace, and a flexible first-floor office or guest bedroom. Upstairs, the grand primary suite offers a private retreat with soaring ceilings, multiple walk-in closets, and a spa-like bathroom featuring luxurious fixtures and finishes. Three additional bedrooms provide plenty of space, including a Jack-and-Jill bath and a private en-suite. The fully finished basement adds tremendous additional living space with multiple egress windows, a bedroom, full bathroom, and endless possibilities for a home gym, media room, recreation area, or additional guest space. Modern technology and energy efficiency are seamlessly incorporated with owned solar panels, a Tesla Powerwall energy storage system, built-in speakers throughout, and numerous additional upgrades. A rare opportunity to own a sophisticated, move-in-ready new construction home in one of Long Island's most sought-after communities. Luxury, comfort, and modern convenience come together beautifully in this exceptional Woodbury residence.

44 Plainview Road, Woodbury
10 Three Ponds Lane, Woodbury
$1,975,000
3 Beds ⋅ 4 Baths ⋅ 1061196 MLS
The Sagamore at Mill Ponds is an Exclusive Gated Community in Woodbury Featuring 76 Homes w/Soaring Ceilings and Walls of Black Clad Windows. Residents Enjoy the Private Clubhouse Offering Sitting Rooms w/Fireplace, Card Playing, Bar, Pool Table, TV, Gym, Golf Simulator, & Screening Room. Additional Amenities Include an Outdoor Pool, Gas Grill & Outdoor Seating, Fire Pit, Tennis & Pickleball Courts, Putting Green, Playground & Dog Park. The Community is Beautifully Landscaped Utilizing a Consistent Color Scheme. This Sought After End Unit Features 10' Ceilings & 8' Interior Solid Wood Doors on the Main Living Floor; 9' Ceilings & 7' Doors Complete the Second Floor & Basement. The Outdoor Views are Wonderful! Custom Shades Throughout. Spacious Primary Suite w/2 Walk In Closets & Double Door Balcony w/Double Screens. Watch the Sunsets! $280,000 of Upgrades Including: Custom Upgraded Center Island Kitchen & Butler's Pantry-Cabinetry to Ceiling, "Dekcon" Kitchen Counters & Backsplash, Oversize Built-In Sub-Zero Refrigerator, Stainless Range Hood & Built-In Microwave/Convection/Air Fryer. 5" Hardwood Flooring. Upgraded Plumbing, Electrical, Bathrooms, Paint & Hardware! Closets are Customized. Larger Deck w/Railings. Epoxy-Like Flooring in Waterproofed Basement & 2 Car Garage. High Efficiency 2 Zone Central Air & Gas Heating System & Tankless Gas Hot Water Heater. A Luxurious Townhouse End Unit Which Shows Off the Lovely Landscaping & Flowers Offering Privacy & Beauty. All Located in Woodbury, Within the Renowned Syosset School District and Offering Access to Town Parks and Tobay Beach.

10 Three Ponds Lane, Woodbury
23 Greenwich Avenue, Woodbury
$1,825,000
5 Beds ⋅ 7 Baths ⋅ 994262 MLS
NEW PRICE — Exceptional Hudson Valley value at $1,825,000. Over 7,500 SF of finished living space with heated pool, true 5-car garage, protected rear views and extensive outdoor living—all within reach of New York City. The Hudson Valley remains one of the New York metropolitan area's most overlooked suburban opportunities—a true hidden gem for buyers seeking more space, privacy, natural beauty, and quality of life. While many buyers begin in Westchester, Northern New Jersey, Long Island, or Connecticut, the Hudson Valley offers a compelling alternative: lower-density communities, mountains, parks, orchards, wineries, and dramatically more property for the money. Woodbury is particularly well positioned, with I-87, Harriman train station, Woodbury Common Premium Outlets, Bear Mountain and West Point all easily accessible. The property is in the Monroe-Woodbury Central School District. Monroe-Woodbury High School is rated A- by Niche and ranks relatively high among New York public high schools on SchoolDigger. The district also has a strong athletic tradition, including recent state championship success in cross country and deep Class AA football playoff runs. Against that backdrop, 23 Greenwich Ave stands out as an exceptional Hudson Valley mini estate. Set on 0.76 acre in The Greens of Woodbury, the home offers more than 7,500 square feet of finished living space, a heated pool, true five-car garage, extensive outdoor entertaining areas, and remarkable privacy. The rear borders protected Town of Woodbury land and Falkirk Golf Course, creating a permanent open backdrop with no future residential construction directly behind the home. The residence includes 5,312 square feet above grade plus approximately 2,200 square feet of fully finished lower-level living space, making it the largest home in The Greens of Woodbury. Years of substantial owner investment have transformed the original 2003 structure with hand-forged iron-and-glass entry doors, statement chandeliers, solid hardwood flooring, motorized window treatments, extensive landscaping and hardscaping, and whole-house solar installed in 2024. Inside, generous living and entertaining spaces include a dramatic two-story foyer and a soaring two-story great room/family room with expansive glass walls and a signature five-tier jade-based crystal chandelier, along with a formal dining room, chef's kitchen, and main-floor in-law suite with private balcony access. Upstairs, the expansive primary suite features a dual-aspect balcony, steam shower, whirlpool tub, two walk-in closets, and dedicated office or yoga space, along with additional en-suite bedrooms. The finished lower level adds approximately 2,200 square feet of recreation and guest space, including a bar area, billiards and ping pong areas, sauna with adjoining full bath, au pair or guest suite with en-suite bath, and multi-person whirlpool. Outside, a 792-square-foot heated pool with waterfall is surrounded by expansive stone-paver terraces and multiple entertaining areas, including a large grilling station, covered pavilion, and separate fire-pit lounge. Multi-level planted terraces, automated landscape lighting, retaining walls, and ornamental iron fencing complete the private setting. The approximately 1,482-square-foot attached garage provides true five-car capacity plus substantial workspace. There is no HOA. Woodbury Common and I-87 are about five minutes away, Harriman train station about nine minutes, Bear Mountain about 15 minutes, Legoland about 20 minutes, and West Point about 25 minutes. Manhattan is reachable by car in roughly 50 minutes under favorable traffic conditions. With five bedrooms, six full and one half baths, three fireplaces, heated pool, five-car garage, protected rear views, and genuine privacy, 23 Greenwich Ave captures exactly what makes the Hudson Valley such a compelling hidden gem: substantially more home, land, amenities, and lifestyle for the money.

23 Greenwich Avenue, Woodbury
4 Hunting Hill Road, Woodbury
$1,799,999
6 Beds ⋅ 4 Baths ⋅ 1059145 MLS
Elegant & Spacious 6-Bedroom Residence in Hunting Hill, Woodbury with Resort-Style Backyard Welcome to this beautifully updated and generously proportioned 6-bedroom, 3.5-bath residence, ideally located in the desirable Hunting Hill section of Woodbury. Offering an exceptional blend of elegance, comfort, and effortless entertaining, this home features a spacious layout, thoughtfully updated interiors, and a spectacular private outdoor retreat. Inside, the home showcases updated bathrooms, a beautifully appointed kitchen with granite countertops, hardwood floors, hi-hat lighting, and updated windows. The expansive floor plan includes two luxurious primary suites, offering exceptional flexibility, privacy, and comfort for family and guests. Additional highlights include a gas boiler, 200-amp electric service, whole-house water filtration system, central air conditioning updated in 2021, and a mini-split system for enhanced year-round comfort. A two-car garage, two storage sheds, and a new whole-house generator provide convenience, functionality, and peace of mind. Step outside and experience your own private resort-style oasis. The beautifully landscaped grounds feature a heated in-ground pool, covered outdoor patio with TV, expansive paver patio and side yard, fire pit, and in-ground sprinkler system—creating an exceptional setting for summer entertaining, relaxing poolside, or enjoying memorable gatherings with family and friends. The property also offers newer siding and a roof approximately 10 years old, along with meticulously maintained outdoor spaces that enhance the home's impressive curb appeal. A truly special Woodbury home—beautifully updated, thoughtfully designed, and ready to be enjoyed.

4 Hunting Hill Road, Woodbury
271 Syosset Woodbury Road, Woodbury
$1,799,000
5 Beds ⋅ 5 Baths ⋅ 1063529 MLS
Welcome to this spacious and inviting one-family Colonial home, offering a wonderful combination of classic charm, comfortable living, and exceptional space for everyday enjoyment and entertaining. The first floor features a generous and thoughtfully designed layout, including a welcoming formal living room, formal dining room perfect for hosting gatherings, and a comfortable spacious family room ideal for relaxation. The spacious eat-in kitchen offers a dedicated everyday dining area, providing a warm and inviting setting for casual meals. A full bathroom on the main level adds convenience and functionality. The second floor features five generously sized bedrooms and three full bathrooms, offering ample space and flexibility for a variety of living arrangements. Beautiful wood flooring adds warmth and character throughout the home. Additional highlights include several updates and improvements, new gas heating burner and gas hot water heater installed in 2025, providing added comfort and efficiency. finished basement offering valuable additional recreational and entertainment space, and an attached two-car garage providing convenient parking and storage. Step outside to enjoy the expansive backyard, offering plenty of room for outdoor entertaining, gardening, relaxation, and recreational activities. With its generous proportions, versatile floor plan, multiple living and entertaining areas, and a blend of traditional Colonial character and modern-day comfort, this home presents a wonderful opportunity for buyers seeking space, functionality, and long-term value. A spacious Colonial home with five bedrooms, four full bathrooms, a finished basement, a two-car garage, and an expansive backyard.

271 Syosset Woodbury Road, Woodbury
32 Lark Drive, Woodbury
$1,688,888
3 Beds ⋅ 3 Baths ⋅ 1022916 MLS
Welcome To This Beautifully Renovated Split Level Home Located In The Highly Sought After Community Of Woodbury Within the Award Winning Syosset Central School District.Perfectly Positioned On A Quiet Mid Block Location With Easy Access To Major Parkways And Transportation. This Exceptional Property Combines Luxury Comfort And Convenience.This Move In Ready Residence Features 3 Spacious Bedrooms, 2.5 Updated Bathrooms And A Fully Finished Basement Offering Versatile Living Space For Todays Lifestyle. The Heart Of The Homes Is The Stunning Gourmet Kitchen Thoughtfully Designed With Exquisite Cabinetry Granite Countertops And Hi End Stainless Steel Appliances Creating The Perfect Setting Fort Both Everyday Living And Entertaining.The Home Has Been Completely Updated And Boasts Recessed Lighting Throughout Central Air conditioning a High Efficiency Boiler Automatic Back Up Generator Security Camera System Climate Controlled 2 Car Garage with Built In Cabinets And In Ground Sprinkler System For Added Comfort And Peace Of Mind. The Inviting Den Features a Beautiful Gas Fireplace And A theatre Surround Sound System Creating The Ultimate Space For Relaxing Entertaining Or Enjoying Move Nights At Home.Step Outside Yo Your Private Backyard Oasis Situated On A Large Fenced In Property. Enjoy Days In The Sparkling In Ground Salt Water Heated Swimming Poll.Entertain Guests In The Outdoor Kitchen Or Simply Relax In The Beautifully Maintained Outdoor Space Designed For Year Round Enjoyment. Offering A Rare Combination Of Premium Upgrades Modern Amenities Exceptional Outdoor Living And a Prime Location This Home Presents An Outstanding Opportunity To Enjoy Luxury Living In One Of Long Islands Most Desirable Neighborhoods.

32 Lark Drive, Woodbury
10 Clemson Lane, Woodbury
$1,525,000
5 Beds ⋅ 4 Baths ⋅ 1025222 MLS
Expanded Splanch with Endless Possibilities in the Syosset School District! Offering approximately 3,170 square feet of versatile living space on .21 acres, this beautifully expanded Splanch is designed to accommodate today's evolving lifestyles. Featuring 5 spacious bedrooms and 3.5 baths, this exceptional home offers the flexibility of two primary bedroom suites—ideal for multi-generational living, extended guests, or the potential for rental income with proper permits. The heart of the home is the brand-new kitchen, thoughtfully updated with new cabinetry, countertops, backsplash, oven, dishwasher, microwave drawer, and cooktop exhaust, creating a stylish and functional space for everyday living and entertaining. A first-floor bedroom or home office adds even more versatility to the floor plan, while the finished basement provides valuable additional living space perfect for a recreation room, media room, gym, or play area. Completing the home is a 2-car garage with electric charger offering ample storage and convenience. Located in the Syosset School District, this exceptional home combines space, flexibility, and modern updates. Whether you're looking for room to grow, space for extended family, or a home with income potential, this property offers endless possibilities to fit your lifestyle.

10 Clemson Lane, Woodbury
24 Chestnut 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
49 Canterbury Road, Woodbury
$1,379,000
3 Beds ⋅ 3 Baths ⋅ 966567 MLS
An Exceptional Woodbury Retreat with Incredible Outdoor Living... Welcome to 49 Canterbury Road, a beautifully maintained expanded split-level home in Woodbury, NY, located within the Syosset School District and offering convenient access to Syosset, major highways, the Long Island Rail Road, shopping, dining, and nearby community parks. At the heart of the home is a beautifully updated, spacious eat-in kitchen featuring stainless steel appliances, an island, abundant cabinetry, generous prep space, and views overlooking the spectacular backyard. Sun-filled living and dining spaces flow effortlessly throughout the home, while two natural gas fireplaces bring warmth and character to the living and family rooms. The flexible floor plan features three generously sized bedrooms, two and a half bathrooms, and additional living space ideal for a home office, den, media room, playroom, or guest space. The finished lower level provides even more versatility and room to make the home your own. Step outside and discover what truly sets 49 Canterbury apart. The beautifully landscaped backyard creates an exceptional setting for outdoor living and entertaining, featuring an in-ground heated pool and generous areas for dining, gathering, relaxing, and enjoying the outdoors. Additional highlights include central air conditioning, generous storage, and a home that has been thoughtfully maintained over the years. Enjoy the updated kitchen, spacious layout, spectacular outdoor setting, and the opportunity to bring your own vision to select interior spaces over time. For buyers searching for a home in Woodbury or the Syosset School District, 49 Canterbury offers an exceptional combination of location, space, outdoor amenities, accessibility, and the opportunity to personalize a home to your own style. Experience the lifestyle, setting, and possibilities of 49 Canterbury Road—a distinctive Woodbury home with convenient access to everything the Syosset-Woodbury area has to offer.

49 Canterbury Road, Woodbury
60 Chestnut Lane, Woodbury
$1,249,000
4 Beds ⋅ 4 Baths ⋅ 1051323 MLS
Perfectly Located on the Greenbelt, this Rare updated Briarwood has all the bells and whistles. Newer Kitchen and Baths! Timeless elegance includes Brazilian Cherry Flooring, Detailed Moldings, Updated Marvin Windows, Solid Wood Doors, Wrought Iron and Wood Railings, Woodburning FP in Great Room, Custom Top of the Line Chefs Kitchen with Soft Close German designed Cabinetry System, Granite counters and Back Splash, High end SS appliances (Kitchenaide French Door refrigerator, Bosch Double Oven with Vented Hood, Bosch Convection Cooktop, Bosch DW) including GE Profile wine frig, Newer 3 zone Heating and CAC, CVAC, Newer LG Washer/Dryer, Cedar Closet. Trex Deck off Dining Room, Paver Patio off lower level Family Room, Lower Level with Separate Office/ Bedroom, Full Bathroom, New W/D in Laundry room and Cedar Closet. Tons of LED high hats. Pool and tennis/pickle ball and basketball.

60 Chestnut Lane, Woodbury
93 Eagle Chase, Woodbury
$1,200,000
2 Beds ⋅ 3 Baths ⋅ 1056673 MLS
Welcome to 93 Eagle Chase, an exceptional 2-bedroom, 2.5-bath townhouse nestled within the prestigious gated community of Eagle Chase in Woodbury. Set against a beautiful tranquil pond, this sophisticated home immediately welcomes you with soaring ceilings and an airy, open atmosphere. From the moment you step inside, the sense of space, natural light, and effortless flow creates an inviting feeling throughout. At the heart of the home is a completely remodeled open-concept kitchen, beautifully designed for both everyday living and entertaining. Featuring elegant quartz countertops, high-end appliances, and induction cooking, the kitchen seamlessly connects to the surrounding living and dining spaces, creating a modern and sophisticated gathering area. The spacious living room features a fireplace, adding warmth and character to the soaring, light-filled space. Abundant natural light and peaceful pond views create a beautiful backdrop, while the open layout offers an ideal balance of elegance and comfort for both entertaining and everyday living. The primary suite is a true private retreat, featuring its own balcony overlooking the beautiful pond. The suite is complemented by a beautifully remodeled en-suite bathroom with a double vanity and oversized shower. The second bedroom offers comfortable accommodations for family, guests, or a home office, while the additional half bath provides convenience for everyday living and entertaining. The fully finished basement offers valuable additional living space along with abundant storage, providing plenty of room for a recreation area, home office, media room, gym, or whatever best suits your lifestyle. A two-car garage with an epoxy floor adds convenience, functionality, and additional storage, while providing a polished and well-maintained space for your vehicles. Step outside to the pond-facing patio with a Trex deck, an inviting outdoor space designed for relaxing and entertaining while enjoying the peaceful water views. Enjoy a country club lifestyle, with an exceptional array of amenities including a clubhouse, fitness center, swimming pool, tennis, basketball, and pickleball courts. The gated community also offers 24-hour security, professional landscaping, and exterior maintenance, allowing you to enjoy a carefree lifestyle with resort-style amenities right outside your door. Conveniently located in Woodbury near major parkways, shopping, and dining. Syosset School District.

93 Eagle Chase, Woodbury
26 Canterbury Road, Woodbury
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 942967 MLS
Welcome to this charming split-level home, offering three spacious bedrooms, three full bathrooms and a half bath. The open concept living area boasts gleaming wood floors and an abundance of natural light. The kitchen is a chef's dream, featuring a large island, quartz counters, SS appliances and a vaulted ceiling with skylights. A dedicated playroom and a full finished basement provide ample space for recreation and storage. Outside, enjoy the expansive backyard with a patio, perfect for entertaining and a large deck for relaxing. Nestled on a peaceful dead-end street this property ensures privacy and tranquility on a generous lot.

26 Canterbury Road, Woodbury
71 Eagle Chase, Woodbury
$1,180,000
3 Beds ⋅ 3 Baths ⋅ 991676 MLS
Welcome to 71 Eagle Chase, a beautiful home in the prestigious 24-hour gated Eagle Chase community, featuring 3 bedrooms and 2.5 bathrooms. Enter through grand double doors into a bright, open-concept layout with soaring vaulted ceilings and a skylight that fills the space with natural light. The main level includes a guest bedroom with a private balcony, a home office, and a powder room. The eat-in kitchen flows seamlessly into the formal dining area and spacious living room, highlighted by a cathedral ceiling and a cozy wood-burning fireplace. Sliding doors lead to a deck patio, perfect for outdoor entertaining. Upstairs, the primary suite offers a vaulted ceiling, private balcony, two walk-in closets, and an en-suite bath with a soaking tub and separate shower. A third bedroom features two large closets, a balcony, and access to a full bath. An open landing provides space for a sitting area or reading nook, along with a conveniently located washer and dryer. Enjoy resort-style living with a newly renovated clubhouse featuring a gym, lounge, kitchen, locker rooms, pool, tennis, and pickleball. Located in the highly desirable Syosset School District. Short Sale Subject to Lenders Approval.

71 Eagle Chase, Woodbury
20 Canterbury Road, Woodbury
$999,000
3 Beds ⋅ 3 Baths ⋅ 1044983 MLS
Welcome to this charming split-level home nestled in the heart of Woodbury, located in the Syosset School District. Situated on an oversized 85'x150' lot, property offers plenty of space for entertaining, relaxing, and enjoying outdoor living. The beautifully established grounds feature mature specimen plantings adding privacy, character and natural beauty to the property. The home features 3 spacious bedrooms, 2.5 baths, and hardwood flooring throughout all bedrooms. A large den provides additional space for gatherings and everyday living. The 2-car garage offers ample parking and storage. Additional highlights include a gas heating system and a newer roof. Ideally located on a dead-end street within a cul-de-sac, this home offers both privacy and convenience. Enjoy close proximity to shopping, school, houses of worship and other local amenities. A wonderful opportunity to own a spacious home on a beautiful oversized property in desirable Woodbury location within the Syosset School District.

20 Canterbury Road, Woodbury
115 Woody Lane, Woodbury
$999,000
3 Beds ⋅ 3 Baths ⋅ 1037907 MLS
Welcome to this beautifully renovated and meticulously maintained condo in the heart of the prestigious Woodlands community. This impressive residence offers an open, airy layout with quality finishes and a fresh, modern feel throughout. The spacious eat-in kitchen features custom cabinetry, stainless steel appliances, quartz countertops, porcelain flooring and a center island that opens to the formal dining area - perfect for both everyday living and entertaining. The beautifully appointed primary suite offers a private en-suite bath and spacious walk-in closet. With three bathrooms in total, including two full baths, the home provides a thoughtful and functional layout. Additional highlights include hardwood floors, vaulted ceilings, skylights and a finished basement, providing additional living and recreational space. Enjoy the exceptional country club lifestyle The Woodlands has to offer, including a pool, tennis, pickleball, fitness room, playground and clubhouse. A wonderful opportunity to enjoy a beautifully appointed home, outstanding community amenities and an exceptional Woodbury location, Syosset Schools

115 Woody Lane, Woodbury
216 Woodbury Road, Woodbury
$899,900
4 Beds ⋅ 3 Baths ⋅ 1020349 MLS
Come and See this Oversized Colonial with 4 beds and 2.5 bath located in Syosset school district. Plenty of room for extended family. Close to shopping, transportation and major roadways.

216 Woodbury Road, Woodbury
2 Woodtree Drive, Woodbury
$899,000
3 Beds ⋅ 3 Baths ⋅ 1054251 MLS
Welcome to 2 Woodtree Drive at The Woodlands. This turnkey, DIAMOND-condition, 3-bedroom, 2.5-bathroom home awaits. This corner unit, gut-renovated in 2018, features top-of-the-line finishes, custom millwork, and a bright, open layout while maintaining a cozy feel throughout. Upon entry, you'll find a beautiful kitchen with stainless steel Bosch appliances, wooden cabinetry, and a bright double slider to the patio. The laundry area is conveniently located between the kitchen and the generously sized den/living room, with an adjacent dining room. This level also features a tastefully appointed half bathroom. Upstairs, the primary bed and bath are generously sized, with two additional bedrooms and one additional bathroom. Additionally, it has reverse osmosis drinking water, a full-house filtration system, and a Nest thermostat. This is easy living at its finest, with amenities including a clubhouse, tennis courts, a pool, and beautiful grounds. Minutes from trails and nature paths. Extremely close to the LIRR at both Cold Spring Harbor and Syosset stations. Syosset School District. **Parking lot is the first right when you come into The Woodlands - Park in any of the spots**

2 Woodtree Drive, Woodbury
266 Route 32, Woodbury
$525,000
1056587 MLS
A Rare Piece of Central Valley History Awaits Your Vision For the first time in over 60 years, one of the most prominent landmark properties in Central Valley is officially hitting the market. Situated right in the heart of the Hamlet Business District at the bustling intersection of Route 32 and Smith Clove Road, this mixed-use property offers a blank canvas for an ambitious business owner or a savvy real estate investor looking to build long-term wealth. High-Traffic Commercial Space The main level boasts over 1,500 square feet of versatile commercial space divided into three large, open rooms. It is an ideal setup for a retail boutique, professional office, or food service business. The location guarantees unmatched, round-the-clock exposure with more than 12,000 vehicles passing by each day. The current first-floor occupant—a beloved, multi-generational local business—is ready to downsize, leaving this prime footprint ready for its next chapter. Residential Income Potential Upstairs, with its own completely private entrance, sits an oversized 2-to-3-bedroom apartment. While this upper unit needs some TLC, it represents a fantastic value-add opportunity. You can renovate it to command premium residential rent, or live right above your shop for the ultimate live-work lifestyle. Parking and Convenience Parking is never an issue here. The property features a private driveway leading to a detached 2-car garage—perfect for extra storage or inventory—plus dedicated parking for 4 vehicles. For clients and customers, there is also ample municipal parking directly across the street. Surrounded by established local businesses, restaurants, and daily services, this is more than just a piece of real estate; it is a rare opportunity to anchor your business or portfolio at the busiest intersection in town.

266 Route 32, Woodbury

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.