Above $1 Million Woodbury NY Real Estate, Homes, Condos for Sale

The largest model in the highly sought-after Woodlands community, this beautifully renovated end-unit residence offers approximately 2,355 square feet of well-designed living space with an open floor plan, soaring two-story ceilings, and the privacy and abundant natural light of a desirable end-unit location. The spacious living and dining rooms flow effortlessly together and open through sliding glass doors to a private Trex deck, extending the living space outdoors to the backyard. A versatile den features a large walk-in storage closet plus an additional windowed alcove, ideal for a workspace or extra storage. The renovated kitchen opens to the main living areas, while the expanded primary suite includes a beautifully enlarged bath with a soaking tub, separate shower, and exceptional storage, a rare enhancement unique to this model. The oversized finished lower level offers exceptional flexibility with expansive recreation space, abundant storage, and a separate room ideal for a home office, gym, media room, or overnight guests. Ideally located in the heart of Woodbury, The Woodlands offers a convenient lifestyle just minutes from shopping, restaurants, parks, golf courses, the Long Island Rail Road, and major parkways, all within the award-winning Syosset Central School District. Residents also enjoy exceptional community amenities including a clubhouse with a fitness center, party room, card room, swimming pool, tennis and pickleball courts, basketball court, and playground.

26 Jennings Lane, Woodbury

$5,000,000

5 Beds ⋅ 6 Baths ⋅ 1028542 MLS

A One-of-a-Kind Custom Estate A masterpiece of custom craftsmanship and timeless design, this extraordinary estate offers nearly 6,000 square feet of luxurious living space—exclusive of the basement and three-car garage. Conceived, designed, and meticulously built by its owners, every detail reflects an uncompromising commitment to quality, elegance, and enduring value. Exceptional Property Highlights Architectural Distinction – The home’s striking exterior is clad in exquisite natural Turkish stone, quarried in Turkey, precision-cut overseas, and imported by container exclusively for this residence, creating a timeless and distinguished façade rarely found in today’s luxury homes. Resort-Caliber Outdoor Living – A spectacular custom-designed swimming pool, completed in 2025, anchors an extraordinary outdoor oasis. Over $1.8 Million Invested Outdoors – The grounds have been transformed into a private resort with over $1.8 million invested in the backyard, featuring a luxury swimming pool and a professional multi-sport court designed for tennis, pickleball, and basketball. Complete Landscape & Engineering Transformation – Originally situated on a steep hillside, the entire backyard was professionally re-engineered, reconstructed, and regraded to create an expansive, level outdoor living space that seamlessly combines beauty, functionality, and exceptional usability. Comprehensive Drainage System – A professionally engineered French drain system extends throughout the property, ensuring superior drainage and long-term protection. Newly Constructed Grand Driveway – A beautifully designed driveway, completed in 2025, enhances the home’s impressive curb appeal and grand arrival. Three-Car Garage – A spacious three-car garage provides generous room for vehicles, storage, and everyday convenience. Grand Lower Level – The full basement boasts impressive 10-foot clear ceilings, offering exceptional scale and endless possibilities for additional living and entertainment space. It also includes a custom-built reinforced bomb/storm shelter, providing an added level of security and peace of mind. Sophisticated Interior Living Five generously proportioned bedrooms and five-and-a-half luxurious bathrooms, thoughtfully designed for both everyday living and elegant entertaining. Three private bedroom suites, each with its own full en-suite bathroom, offering exceptional comfort and privacy for family members or guests. Two additional en-suite bedrooms, creating a home where every bedroom enjoys the comfort and convenience of its own dedicated bath. Every inch of this remarkable residence was thoughtfully envisioned and custom crafted by its owners. From the imported natural stone exterior to the extensive structural enhancements and resort-inspired grounds, this is a home of exceptional quality, timeless elegance, and enduring craftsmanship—a truly rare offering in today’s luxury market.

8 Headley Way, Woodbury

$2,390,000

5 Beds ⋅ 5 Baths ⋅ 1025514 MLS

Tucked behind the gates with a guard on duty, in the Windemere community, this architecturally distinctive contemporary was designed around light, volume, and an effortless connection to nature. Soaring vaulted ceilings rise approximately 20 feet above the principal living areas, where walls of floor-to-ceiling windows overlook park-like grounds and fill the home with natural light from the moment you step through its one-of-a-kind handcrafted sculptural double entry doors. The dramatic living room, anchored by a grand architectural wood-burning fireplace, flows into a formal dining area, scaled for large gatherings. A sculptural spiral staircase ascends to a gallery library overlooking the living room, richly appointed with wood paneling and extensive custom built-in bookcases — a true showpiece. Multi-zone audio carries music seamlessly throughout the whole home. The open, vaulted kitchen — outfitted with a Sub-Zero refrigerator, two Thermador wall ovens, and a Miele cooktop — connects directly to the family room and casual dining area, with a walk-in pantry and a laundry room with an additional Sub-Zero freezer. The main-level primary suite is a private retreat with a vaulted ceiling, floor-to-ceiling windows, and three walk-in closets. Its spa-inspired bath features a dry sauna, a walk-in shower with Schluter radiant heat in the floor, bench, and accent wall, a smart toilet in its own enclosed room, layered designer lighting, and a skylight overhead. A guest suite offers a marble en-suite bath and private outside entrance, while two additional bedrooms share a stunning, fully redone onyx Jack-and-Jill bath with radiant heated floors. Upstairs, a spacious loft makes an ideal teen retreat, office, or bonus room. The finished lower level adds a mirrored gym, hobby and recreation space, a room-size cedar closet, and multiple storage rooms. Outside, resort-style living awaits: a gas-heated saltwater pool, Trex deck accessed directly from the kitchen and living spaces, and tranquil pond views beyond the established landscaping. Community tennis and basketball courts, a circular driveway, two-car garage, and the highly regarded Syosset SD complete this rare offering.

27 Windemere Way, Woodbury

$2,395,000

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, 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. 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

$1,550,000

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

$2,350,000

4 Beds ⋅ 6 Baths ⋅ 1021074 MLS

A coveted corner F-Model at The Sagamore at Mill Pond — thoughtfully designed, beautifully finished, and ready to be called home. This is the one that stands out. Positioned as a corner unit facing South, the home gets exceptional natural light and a sense of privacy. Soaring ceilings and high-end finishes throughout make it clear this home was done to perfection. The living room, dining room, flow naturally together — great for entertaining but equally comfortable for everyday life. Beautiful custom finishes include wall coverings, upgraded wood floors, gas fireplace, mouldings, window treatments, lighting systems, and build-ins. Step outside to a private extended Trex deck with space for both outdoor dining and lounging, a seamless way to extend your living space. The upgraded kitchen is a true showstopper. Custom wood cabinetry extended to as wide and high as possible, marble countertops, and a large center island anchor the space, while the appliance lineup speaks for itself: a 6-burner Wolf cooktop, full Wolf oven, additional Wolf wall oven, Wolf microwave oven, Wolf warming drawer, and a Sub-Zero refrigerator/freezer, dishwasher, finished with a stainless steel hood. A separate fitted pantry and dedicated laundry room are right off the kitchen, keeping everything organized and out of sight. The primary suite on the main floor is a calm, comfortable retreat. Motorized Shades ensure privacy. Two fitted walk-in closets provide generous, well-organized storage. The bathroom features; double sinks, marble countertops, a marble shower, and a Toto washlet. Upstairs, there are two more bedrooms with en-suite baths, each with fitted walk-in closets. A large den/library complete with custom built ins round out the second floor, adding flexibility for a home office, reading room, playroom, or whatever your needs may be. Leaving no stone unturned, the two car garage is well-appointed featuring built-in storage solutions that complement the home's exceptional amenities. The lower level has a lot to offer: a dedicated exercise room, powder room, a bedroom with a full en-suite bathroom, a custom dog washing and grooming station, a spacious media room, and an additional flexible room that could easily become a recreation room, home office, or extra storage. There's genuine room to grow here. Club amenities include 24 hour security gatehouse, a clubhouse with a pool, tennis/pickleball court, golf simulator, 2 outdoor kitchens, putting green, fire pit and a screening room. Corner F-units at The Sagamore at Mill Pond don't come up often — and one finished at this level comes up even less. This is a special home.

63 Three Ponds Lane W, Woodbury

$2,200,000

3 Beds ⋅ 4 Baths ⋅ 1019662 MLS

Welcome to The Sagamore at Mills Pond, an exclusive gated luxury townhome community in the heart of Woodbury, one of Long Island's most sought-after North Shore communities. Located within the award-winning Blue Ribbon Syosset School District, Woodbury offers an exceptional lifestyle with beautiful parks, golf courses, fine dining, upscale shopping, fitness clubs, and convenient access to Manhattan, the Hamptons, and major parkways. This exceptional end-unit residence is one of the community's most beautifully appointed offerings, thoughtfully upgraded with every premium finish and feature available. With three bedrooms, three full baths, and one half bath, the home combines elegant design, modern convenience, and low-maintenance luxury living. The main level is designed for both comfortable everyday living and effortless entertaining. A spacious living room with a fireplace flows seamlessly into the dining area and a beautifully crafted chef's kitchen featuring premium appliances, custom cabinetry, quartz countertops, an oversized sink, generous island seating, under-cabinet lighting, and designer finishes throughout. Rich hardwood floors, soaring ceilings, recessed LED lighting, upgraded moldings, solid-core doors, a Lutron lighting system, automatic shades, and refined architectural details elevate every space. The first-floor primary suite offers a private retreat with generous walk-in closet space (2) and a luxurious spa-inspired bath featuring radiant heated floors, a double vanity, oversized porcelain tile, a frameless glass shower, Kohler fixtures, and thoughtfully selected designer finishes. Upstairs, two spacious en-suite bedrooms and a versatile loft/den provide comfortable accommodations for family, guests, or a dedicated home office. The unfinished lower level adds exceptional flexibility for a personal gym, office, den, and abundant storage, creating the ideal space for today's lifestyle. Positioned on a desirable corner lot, this end-unit residence enjoys a level of privacy rarely found in townhome living. The professionally landscaped backyard features a spacious fenced deck for outdoor entertaining, while the expansive side yard provides an unusually large lawn and added separation from neighboring homes, creating an open, single-family feel. Additional highlights include high-efficiency two-zone heating and cooling, high basement ceilings, a two-car garage with private driveway parking, black-clad windows, carriage-style garage doors, architectural shingle-style exteriors, and low-maintenance siding and trim. Residents of The Sagamore enjoy a truly resort-inspired lifestyle with a 24-hour staffed gatehouse and an exceptional private clubhouse offering a fitness center, golf simulator, movie screening room, entertainment spaces, outdoor swimming pool, tennis court, putting green, outdoor kitchen, fire pit, and beautifully landscaped grounds. This is a rare opportunity to own one of the community's premier end-unit residences—an impeccably upgraded home that seamlessly combines timeless elegance, exceptional craftsmanship, and effortless luxury in one of Woodbury's most desirable gated communities.

115 Three Ponds Lane E, Woodbury

$1,499,000

2 Beds ⋅ 2 Baths ⋅ 1018917 MLS

A rare opportunity to own a beautifully appointed Churchill Model in the sought-after 55+ gated community of Kensington Estates in Woodbury. Just four years young, this desirable main-level residence offers the ease of single-level living paired with premium finishes and thoughtful design.The spacial open-concept floor plan features a stately center-island kitchen and dining area, seamlessly flowing into the great room accented with gas fireplace and double French doors open to an expanded patio—perfect for relaxing or entertaining. The home offers a generously sized primary ensuite with two closets, a full bath with a relaxing soaking tub and double-sink vanity, a guest bedroom, full guest bath, convenient laundry room, custom closets and pantry, and an attached apoxy-finished one-car garage pre-wired for an EV charger, a full, unfinished basement with legal egress, providing abundant storage and endless possibilities for future living space. Quality finishes and upgrades abound, including hardwood flooring and crown molding throughout, Wolf six-burner gas range, Sub-Zero refrigerator, surround sound in the great room, custom closets, smart light switches, Ecobee smart thermostat, remote-controlled cellular shades, plantation shutters, SkyBell video doorbell, whole-house surge protector, additonal 100 amp service in basement, kitchen faucet water filtration system, natural gas cooking, heating and hot water, and central alarm system. The recently developed 80-unit enclave allows residents to enjoy a relaxed lifestyle that includes a beautifully appointed clubhouse featuring a welcoming fireplace lounge, card room, billiards, library and catering kitchen, gym, outdoor pool with comfortable seating areas for sun and shade, and tennis/pickleball courts. Ideally situated within the Township of Huntington on the Suffolk/Nassau border, Kensington Estates offers the privacy of a gated community while remaining conveniently close to the Northern State Parkway, the Long Island Expressway, the Cold Spring Harbor train station, local shopping and dining in Huntington, Cold Spring Harbor, and Plainview. If you've been searching for the convenience of main-level living without sacrificing space, storage, or outdoor enjoyment, this exceptional home is not to be missed.

227 Coach Drive, Woodbury

$2,680,000

5 Beds ⋅ 5 Baths ⋅ 1018908 MLS

Welcome to 6 Clearmeadow Ct, located in Hunters Run a premier 24-hour gated community within the highly sought-after Woodbury enclave andthe Syosset School District. This residence, set on a beautifully landscaped .65-acre lot, seamlessly blends timeless charm with modern sophistication. Originally built in 1987 and updated in 2026, the home offers 5 bedrooms and 4.5 bathrooms. A grand foyer with soaring ceilings opens to expansive living and dining areas designed for natural light and effortless flow. The reimagined layout provides spacious entertaining areas, flexible room configurations, and seamless indoor-outdoor living with an updated pool, upgraded patio and lush landscaping. The main level has been thoughtfully designed to highlight 5” white oak hardwood floors throughout, complemented by a newly renovated chef’s kitchen featuring custom cabinetry, an oversized walk-in pantry, and a full Viking appliance suite. The second floor offers a serene primary suite with a spa-inspired bathroom, complete with a soaking tub, standalone shower, custom double vanity, and generous walk-in closets. Three additional bedrooms provide generous space and versatility, featuring one with a private en suite and two that share an oversized, elegantly designed hallway bathroom. Large ready to use basement. Exterior enhancements further elevate the home’s appeal, featuring Pella windows, Azek trim and soffits, new pool pavers liner and equipment, an expansive patio, and a two-car garage with a circular driveway. Ideally located near premier shopping, dining, parks, and major commuter routes, this residence offers the perfect balance of privacy, luxury, and convenience delivering refined living in one of Woodbury’s most desirable communities. SF includes basement.

6 Clearmeadow Court, Woodbury

$1,288,000

4 Beds ⋅ 2 Baths ⋅ 1017959 MLS

Completely renovated and move-in ready! This stunning 4-bedroom, 3-bathroom home showcases a bright open floor plan with high-end finishes throughout. Features include a gorgeous new chef’s kitchen with quartz countertops, spacious living and dining areas, beautifully updated bathrooms, recessed lighting, hardwood floors, and a fully finished basement offering flexible living space. Located on a quiet street in the highly sought-after Syosset School District, with easy access to shopping, parks, restaurants, major roadways, and the LIRR. A rare opportunity to own a turnkey home in one of Woodbury’s most desirable neighborhoods.

17 Wren Drive, Woodbury

$2,599,999

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

$1,548,000

4 Beds ⋅ 3 Baths ⋅ 1013196 MLS

Nestled on a quiet cul-de-sac in the heart of Woodbury, this exceptional opportunity offers a beautifully maintained 4-bedroom, 2.5-bath home set on an oversized property within the highly acclaimed Syosset School District. Designed for both everyday living and entertaining, the home features spacious rooms, abundant natural light, and a seamless flow throughout. The chef's kitchen is equipped with premium appliances, ample cabinetry, and generous workspace, making it the heart of the home. Step outside to the expansive backyard, where the oversized lot provides endless possibilities for outdoor enjoyment, entertaining, recreation, or creating your own private retreat. Ideally located near shopping, dining, parks, golf courses, major parkways, and the Long Island Rail Road, this property offers an exceptional combination of location, space, and convenience. A rare opportunity to make this wonderful Woodbury home your own.

15 Joyce Court, Woodbury

$2,199,000

5 Beds ⋅ 4 Baths ⋅ 1011509 MLS

Welcome to 6 Polo Court, a beautifully maintained residence tucked away on a quiet cul-de-sac in desirable Woodbury. Set on an oversized lot, this spacious home offers an elegant layout designed for both comfortable everyday living and effortless entertaining. The home features 5 bedrooms, generous living and dining spaces, a bright eat-in kitchen, and multiple areas ideal for gathering, working, or relaxing. Large windows bring in natural light throughout, while the private backyard provides a wonderful setting for outdoor enjoyment, entertaining, or future customization. Located within the highly regarded Syosset Central School District, this home offers convenient access to shopping, dining, parks, major roadways, and nearby Long Island amenities. A rare opportunity to own a spacious Woodbury home in a prime location with exceptional potential. Note: ALL Photos are Virtually Polished.

6 Polo Court, Woodbury

$2,100,000

3 Beds ⋅ 4 Baths ⋅ 1009418 MLS

This Ascot End Unit is the largest unit situated in an over 18 acres community in Woodbury, Kensington Estates a 24 Hour Gated boutique development offers a carefree luxury-lifestyle for residents 55 and over. Experience effortless luxury living in this stunning two-story townhome, thoughtfully designed with elegance, comfort, and convenience in mind. A dramatic double-height entry welcomes you with soaring floor-to-ceiling windows that flood the home with natural sunlight, creating a bright and airy atmosphere throughout. The open-concept floor plan is ideal for both everyday living and entertaining, featuring a spacious living room with a gas fireplace, an inviting dining area, and a beautifully appointed eat-in kitchen complete with a large center island and abundant workspace. Sliding doors lead to a private rear patio, seamlessly blending indoor and outdoor living. The expansive first-floor primary suite offers the ultimate retreat with multiple walk-in closets and a luxurious spa-inspired bath featuring dual vanities and generous storage. A convenient main-level laundry room and private elevator providing access to all floors add to the home’s exceptional functionality. Upstairs, you’ll find two generously sized bedrooms, each with its own en-suite bath, along with a versatile loft space that can easily serve as a fourth bedroom, home office, or media room. Additional highlights include a two-car garage and a full unfinished basement offering endless possibilities for future expansion, recreation space, storage, or customization. This exclusive community includes 80 planned residences near the villages of Cold Spring Harbor, Huntington, and Syosset. High end Luxury condominiums with, green space, pool, tennis, fitness center, pond and private clubhouse. Additional information: Min Age:55

238 Coach Drive Unit #56, 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

$2,050,000

5 Beds ⋅ 4 Baths ⋅ 1006370 MLS

Perfectly positioned on a coveted mid-block location within The Gates of Woodbury, this impressive Center Hall Colonial is set on a beautiful one-acre property and offers an exceptional blend of space, comfort, and timeless design. Thoughtfully crafted for both everyday living and entertaining, the home features generously proportioned rooms, a classic and highly functional floor plan, and seamless flow throughout. A full basement provides abundant storage and potential for additional living or recreational space, and the attached two-car garage adds everyday convenience. Located within the Syosset School District

19 Seward Drive, Woodbury

$2,295,000

3 Beds ⋅ 5 Baths ⋅ 1009160 MLS

This elegant residence is set within the distinguished Sagamore at Mill Pond community in Woodbury, where residents enjoy the privacy and ease of a 24/7 gatehouse, along with a separate clubhouse featuring indoor entertainment space, a gym, screening room, golf simulator, and outdoor amenities including a tennis court, pool, outdoor kitchen, putting green, and community fire pit. Originally offered as the "Model Showcase" it is beautifully appointed with every bell and whistle the builder had to offer. This B-style model presents refined living with a thoughtful layout, quality finishes, and exceptional comfort across three levels. Designed for both everyday ease and gracious entertaining, the home blends convenience, privacy, and sophisticated low-maintenance living. The main level welcomes you with an open and inviting flow, where carefully selected details are showcased throughout. A spacious living room with fireplace, dining area, powder room, and beautifully designed kitchen with premium appliances, custom cabinetry, quartz countertops, an oversized sink, island seating, and elegant cabinet lighting create a polished and highly functional setting. Recessed LED lighting, hardwood floors, high ceilings, upgraded moldings, solid-core doors, a Lutron lighting system, automatic shades, and refined hardware further contribute to the home’s sophisticated feel. The first-floor primary suite serves as a private retreat with generous walk-in closet space and a luxurious bath featuring radiant heated floors, a double vanity, oversized porcelain tile, a frameless glass shower, Kohler fixtures, and designer-selected finishes. The second level includes two en-suite bedrooms and a den, providing flexible space for guests, work, or relaxation. The finished lower level expands the home’s living potential with a gym, office, den, powder room, and storage, creating excellent versatility for modern living. Set on a desirable corner property, the residence features a generous private backyard with a deck and professionally landscaped plantings. A spacious side yard with a large grassed area adds a rare sense of openness and separation between neighboring homes. Additional highlights include high-efficiency two-zone heating and cooling, high basement ceilings, architectural shingle-style exterior design, black-clad windows, low-maintenance siding and trim, carriage-style garage doors, a two-car garage, and private driveway parking. A rare opportunity within Sagamore at Woodbury, this residence combines luxury finishes, functional design, and low-maintenance living, all conveniently located near shopping, dining, and major highways while enjoying a prime North Shore setting.

102 Three Ponds Lane E, Woodbury

$2,199,000

6 Beds ⋅ 4 Baths ⋅ 1007122 MLS

Welcome to 251 Baird Court, nestled in the heart of Woodbury. This spacious 6-bedroom, 3.5-bathroom home offers the perfect blend of comfort, functionality, and outdoor living. Inside, you'll find a thoughtfully designed layout featuring a welcoming eat-in kitchen, a formal dining room ideal for entertaining, and generously sized bedrooms that provide ample space for family and guests. Additional value comes from the home's solar panel system, adding to the property's modern features and efficiency. The true highlight of this home is the exceptional backyard oasis. Just in time for the summer season, enjoy your own tropical-inspired retreat complete with an expansive deck and patio, shaded seating areas, and overhead fans to keep you comfortable on even the hottest days. When it's time to cool off, take a refreshing dip in the sparkling pool and enjoy the resort-style atmosphere right in your own backyard. Whether you're hosting large gatherings, enjoying family barbecues, or simply unwinding after a long day, this property offers endless entertaining possibilities and year-round enjoyment. A rare opportunity to own a beautifully appointed home with spacious living, solar panels, and an incredible outdoor lifestyle in one of Woodbury's most sought-after neighborhoods.

251 Baird Court, Woodbury

$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

$2,299,999

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

$1,998,000

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

$4,200,000

5 Beds ⋅ 4 Baths ⋅ 997030 MLS

A showpiece of craftsmanship, luxury, and timeless design—this extraordinary custom-built residence, completed in 2015 by Old World Quality Corp, was created with absolutely no expense spared and presents in pristine, like-new condition. Every detail was thoughtfully curated, blending impeccable construction with today’s most desired amenities. A grand interior unfolds with soaring 10-foot ceilings on the main level, elegant tray ceilings and 9-foot ceilings on the second floor, and a rare 9-foot finished lower level—creating an unmatched sense of scale and openness throughout. Exquisite custom millwork, designer finishes, radiant heat, hand-scraped hardwood flooring, integrated smart home technology, surround sound, and a full-house generator elevate everyday living to extraordinary. At the heart of the home, a spectacular chef’s kitchen is designed for both intimate gatherings and grand entertaining, flowing seamlessly into beautifully appointed living spaces. The luxurious primary suite is a true private retreat featuring a room-sized custom dressing closet and an indulgent spa-inspired bath. Every bedroom offers its own ensuite bath, delivering comfort, privacy, and sophistication for family and guests alike. The fully finished walk-out lower level is an exceptional extension of the home’s luxury living space offering 9-foot ceilings, multiple egress windows, a state-of-the-art gym, media lounge, full bath, and exceptional recreation space. Step outside to your own private resort—an extraordinary outdoor sanctuary designed for year-round enjoyment. Covered patio living, an outdoor kitchen with BBQ and bar seating, built-in firepit, pergola, expansive lawn, storage shed, and breathtaking specimen landscaping are complemented by exceptional stonework and masonry. The centerpiece: a stunning heated saltwater gunite pool with spa and cascading waterfall. Located within the Syosset Central School District, this one-of-a-kind home offers an uncompromising lifestyle where luxury, comfort, and craftsmanship converge. Too many extraordinary features to list—this is a home that must be experienced.

32 Elm Street, Woodbury

$2,599,000

4 Beds ⋅ 5 Baths ⋅ 000081 MLS

Set on a magnificent landscaped 1 acre, perfect location in The Gates of Woodbury. This completely expanded and redesigned 4-bedroom, 4.5-bath Farm Ranch offers the perfect blend of classic elegance and modern luxury. Bathed in exceptional natural light, this stunning home is defined by dramatic walls of windows creating a bright, airy ambiance throughout. Impeccably renovated with exceptional attention to detail, the home showcases sophisticated design, soaring ceilings, and an effortless open flow ideal for both everyday living and grand-scale entertaining. Rich hardwood floors extend throughout the entire home, enhancing the warmth and refinement of every space. The stunning white custom chef’s kitchen is the centerpiece of the home, featuring premium Thermador appliances, gas cooking, radiant heated floors, and a dramatic Carrera marble center island that opens seamlessly to an expansive family room with vaulted ceilings & fireplace with sliders out to Trex deck overlooking the serene backyard. The luxurious primary suite is a true private retreat, featuring soaring ceilings, a fireplace, two fully outfitted walk-in closets, and an additional wall of custom closets. The oversized spa-inspired primary bath offers radiant heated floors, a relaxing spa tub, oversized shower, and double marble-topped vanities with a dedicated makeup area, creating the ultimate sanctuary. Three fireplaces throughout the home add warmth and architectural character, while additional highlights include a full finished basement, whole-house generator, generously proportioned rooms, and refined custom details throughout. Outdoor living is equally impressive with an expansive Trex deck with electric roll out awning and brick patio overlooking the professionally manicured grounds, providing the perfect backdrop for relaxing or entertaining in complete privacy. A truly extraordinary residence that combines impeccable craftsmanship, modern comfort, and an elevated lifestyle beyond compare. 2 Car garage with epoxy floors. Located in the Syosset School District.

30 Orchard Drive, Woodbury

$1,799,000

5 Beds ⋅ 4 Baths ⋅ 999883 MLS

Welcome to 83 Joyce Lane in the highly sought after Woodbury Knolls. This beautifully expanded and renovated Farm Ranch offers approximately 4,200 square feet of thoughtfully designed living space. Expanded and renovated in 2023, this 5 bedroom, 4 bathroom home seamlessly blends modern luxury with comfortable everyday living. The sun filled interior features spacious open concept living areas, generously sized bedrooms, and beautifully updated finishes throughout. Designed for both entertaining and daily functionality, the home offers an effortless flow between the main living spaces and the private bedroom quarters. The primary suite features an oversized custom closet with built-in island, and a spacious primary bath with a large shower, double sink and free standing tub. The basement is finished with a large play area, home gym, bedroom, and full bath. Step outside to your own resort-style backyard retreat featuring a sparkling in-ground pool, expansive patio, and a built-in outdoor kitchen, perfect for summer entertaining and relaxing in complete privacy. Located in the heart of Woodbury and the award winning Syosset School District.

83 Joyce Lane, Woodbury

$1,299,000

5 Beds ⋅ 2 Baths ⋅ 992224 MLS

Welcome home to 193 Woodbury Road. This five-bedroom, one-and-a-half-bath Colonial built in 1908 has been exceptionally maintained and fully updated throughout. A large covered front porch and beautifully landscaped grounds set the tone the moment you arrive. Spanning three levels, the main level offers an open concept layout with generous living and dining areas, a completely updated kitchen, and an updated half bath. The second level features two bedrooms and a fully updated bath. The third level offers two additional bedrooms. The home has natural gas, a dedicated gas line to the grill, and Nest thermostats. A detached garage and just over one-third of an acre complete this move-in ready home

193 Woodbury Road, Woodbury

$1,980,000

5 Beds ⋅ 7 Baths ⋅ 994262 MLS

A HUDSON VALLEY MINI ESTATE WITH 7,500+ SQFT | BACKING ONTO PROTECTED LAND AND FALKIRK GOLF COURSE | 50 MIN TO MANHATTAN === WHAT SETS THIS HOME APART — THE LARGEST HOME IN THE GREENS OF WOODBURY: 5,312 sqft above grade plus 2,200 sqft fully finished lower level. Only home in the community at this scale. — A PERMANENT VIEW: 0.76-acre lot backs onto Town of Woodbury preserve land and Falkirk golf course. No new construction possible behind the property. — 50 MIN TO MANHATTAN: 9 min to Harriman train (NJ Transit direct to Penn Station in ~1 hour). 50 min via I-87 to GWB. Commutable daily or hybrid. — YEARS OF RELENTLESS INVESTMENT: 2003 shell is original. Most of what defines the home today—iron-and-glass doors, chandeliers, hardwoods, the 2,200 sqft lower level, entire backyard—is the owner's work. — NO HOA: Unusual at this caliber. True ownership, no recurring fees. === WHAT THE OWNER HAS BUILT The 2003 shell was built by The Greens of Woodbury's original developer. Almost everything visible today reflects the current owner's continuous investment. Inside: hand-forged iron-and-glass entry doors with smart fingerprint access. Three new chandeliers, anchored by the signature five-tier jade-based crystal piece. New solid hardwood throughout second floor. Motorized window treatments. 2,200 sqft finished lower level with new AC—wood flooring, bar area, billiards and ping pong, sauna with en-suite bath, au pair suite with en-suite bath, multi-person whirlpool. Outside: 792 sqft heated pool with waterfall (2020). Extensive stone paver patio at entertaining scale. Three distinct outdoor entertaining zones: banquet-scale grilling station in the main yard, covered pavilion on its own balcony, propane fire pit lounge on a separate balcony. Multi-level planted terraces with retaining walls and integrated automated lighting. Ornamental iron fenced rear yard. Whole-house solar (2024). Every visible system reflects 2020s standards. The next owner inherits a finished asset, not a project. === THE HOME 5 bedrooms. Six full and one half baths. Three fireplaces. Solid hardwood throughout all three levels. Circular stone paver driveway lined with Bradford Pear trees. Hand-forged iron-and-glass double entry doors open to a two-story foyer—a prelude to a five-tier jade-based crystal chandelier in the glass-wrapped great room. Generously scaled dining room, family room, chef's kitchen flow seamlessly across the main level. Six-burner range with built-in indoor grill, granite counters, custom cabinetry, island, walk-in pantry. Main-floor in-law suite with private balcony access offers single-level living. Upstairs, expansive primary suite anchors the second floor with dual-aspect balcony, steam shower, whirlpool tub, two walk-in closets, and dedicated office/yoga room. Two additional en-suite bedrooms; one with a home office that converts back to a bedroom. Attached 1,482 sqft garage—one of the home's most useful features—offers true five-car capacity with substantial workspace. === SCHOOLS & LOCATION Monroe-Woodbury Central School District — strong athletic tradition with cross country state championships (2022-2024) and Class AA football finals appearances. School bus stop at the front. 5 min to Woodbury Common Premium Outlets (world's largest luxury designer outlet, 250+ stores) and I-87. 9 min to Harriman train (direct to Penn Station in ~1 hour). West Point 25 min, Bear Mountain 15, Legoland 20. Orange County orchards, wineries, and farm-to-table restaurants throughout the area. A commuter location with the lifestyle of a country estate.

23 Greenwich Avenue, Woodbury

$2,798,000

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

$2,899,999

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

$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

$1,875,000

4 Beds ⋅ 3 Baths ⋅ 954217 MLS

Welcome to this spectacular ranch in the coveted Woodbury Estates. Impeccably maintained, this home exudes sophistication and architectural excellence. This stunning 4-bedroom, 3 bath home boasts an inviting open floor plan, ideal for both everyday living and entertaining. Situated on one acre of manicured property, this home provides the perfect blend of serenity and convenience. Upon entering, you are greeted by a large foyer with cathedral ceilings and a skylight. Double doors lead to the spacious den which offers a calm and inviting space for relaxing. The large living and dining room feature floor to ceiling windows that fill the house with an abundance of natural light. Recently renovated eat in kitchen kitchen features top-of-the-line appliances, granite countertops, center island & gas cooking. Large primary bedroom suite, 3 additional bedrooms and 2 full baths. Retreat to the private backyard oasis with multi tiered decking, making it an entertainer's delight. Additional amenities include hi-hats throughout, gas fireplace, custom moldings, 2-car garage, full basement and professional landscaping. Conveniently located near schools, shops, dinning, parks, and highways. Award-winning Syosset school district, Walt Whitman Elem/Thompson Middle School. Dont miss this remarkable home.

2 Yukon Drive, 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

$1,069,000

4 Beds ⋅ 3 Baths ⋅ 965549 MLS

Magnificent, spacious and beautifully updated, this rare 4 Bedroom | 3 Full Bath Woodlands Condo offers comfortable, move-in ready living in one of Woodbury’s most sought-after communities. The home features a luxurious open floor plan highlighted by a renovated eat-in kitchen with quartzite countertops, designer tile backsplash, updated flooring, and LED lighting throughout. A first-floor full bath with shower adds convenience and flexibility for guests or extended living. The sun-filled dining area flows seamlessly to a private outdoor setting, creating the perfect space for relaxing or entertaining. The generously sized primary suite offers a thoughtful layout, privacy, and ample storage. Updates completed within the most recent 3–4 years include refreshed vanities, modern appliances, mechanical improvements including boiler and tank, and continued interior enhancements that reflect pride of ownership. Residents enjoy The Woodlands lifestyle with resort-style amenities including tennis, pickleball, pool, clubhouse with racquetball, gym, playground, and beautifully maintained grounds. Spacious, updated, and ideally located — this exceptional home offers low-maintenance living with the feel of a private residence. Appearance: Diamond

54 Estate Court Unit #54, 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

$2,499,999

6 Beds ⋅ 4 Baths ⋅ 987944 MLS

Sun-drenched and beautifully designed, this 6 bedroom, 4 full bath, 4670 square foot contemporary home offers an expansive open floor plan with soaring ceilings and an effortless flow for both everyday living and entertaining. Generous room sizes throughout are complemented by a striking living room featuring a stacked stone accent wall with a gas fireplace. The updated, state-of-the-art eat-in kitchen is equipped with stainless steel appliances and Silestone countertops, blending style and functionality. The spacious primary suite offers a true retreat, complete with a luxurious oversized bath. The second floor includes an additional flexible space ideal as a sixth bedroom or den. The fully finished basement provides exceptional bonus space with a playroom, theater, gym, and abundant storage. Set on a beautifully landscaped .73-acre property, the backyard features a newer in-ground gunite pool, perfect for outdoor enjoyment. Located within the private, gated community of Windemere, residents enjoy access to tennis and a scenic lake. All within the Syosset School District.

18 Windemere Way, Woodbury

$1,379,000

3 Beds ⋅ 3 Baths ⋅ 966567 MLS

49 Canterbury, A RESORT STYLE RETREAT ... where sophisticated living meets effortless entertaining in one of Woodbury's most desirable neighborhoods! Privately set on beautifully landscaped grounds, this expanded split-level residence offers the perfect balance of elegance, comfort, and exceptional outdoor living. Thoughtfully maintained and impeccably cared for, every space reflects pride of ownership and timeless appeal. Inside, sun-filled living spaces flow seamlessly throughout the home, creating an inviting atmosphere for both everyday living and memorable gatherings. Two natural gas fireplaces anchor the living and family rooms, adding warmth, character, and year-round ambiance. The new modern spacious eat-in kitchen serves as the heart of the home, featuring stainless steel appliances, a center island, abundant storage, and views overlooking the spectacular backyard—allowing indoor and outdoor entertaining to blend effortlessly. Offering three generously sized bedrooms and three full bathrooms, the home's flexible floor plan also includes an additional living area ideal for a private home office, media room, library, or playroom, while the finished lower level provides even more versatile space for recreation, fitness, guests, or today's evolving lifestyle. The true showpiece awaits outdoors. Designed as a private backyard retreat, the resort-inspired property features a heated in-ground pool with a cascading waterfall, a recently installed liner, expansive patio and deck areas, and professionally landscaped grounds that create an atmosphere of complete privacy. Whether hosting elegant summer soirées, relaxing poolside, or enjoying quiet evenings under the stars, this outdoor sanctuary is designed to be enjoyed in every season. Perfectly located near award-winning Syosset schools, parks, shopping, fine dining, and convenient commuter routes, this exceptional residence delivers the lifestyle today's discerning buyers seek. This home is for you if you appreciate quality, privacy, and a home designed for both refined living and unforgettable entertaining, 49 Canterbury presents a rare opportunity to own a move-in-ready property in one of Woodbury's most coveted communities.

49 Canterbury Road, Woodbury

$2,349,999

4 Beds ⋅ 6 Baths ⋅ 987761 MLS

Welcome to 14 Pine Drive, a stately 4-bedroom, 6-bathroom residence nestled in the prestigious Hunting Hill community of Woodbury. Set on over an acre of flat, beautifully manicured land, this home offers an incredible lifestyle with a private tennis court and expansive outdoor space perfect for entertaining or relaxing in total privacy. Inside, the home opens with a grand entry foyer leading to a spacious formal living room and elegant dining room, ideal for hosting. The large, open-concept kitchen flows into a cozy den with views of the stunning backyard. The first floor also boasts two convenient half bathrooms and a luxurious primary suite featuring sliding doors that open to a private deck, along with a spa-like ensuite bathroom and generous walk-in closets. Upstairs, you'll find three additional bedrooms with excellent closet space and two full bathrooms, offering plenty of room for guests. The finished basement provides impressive recreation space, ideal for a media room, gym, or game area and a private room perfect for guests Located in one of Woodbury’s most sought-after neighborhoods, 14 Pine Drive offers privacy, space, and amenities that rarely come to market. Don’t miss this incredible opportunity.

14 Pine Drive, Woodbury

$2,299,000

4 Beds ⋅ 3 Baths ⋅ 986777 MLS

Privately set on a beautifully landscaped acre, this exceptional four bedroom ranch is approached by a long driveway, offering both privacy and a striking first impression. This beautiful home blends timeless architecture with modern updates, highlighted by soaring ceilings, walls of glass, skylights, and wide-plank white oak flooring that create a light-filled, open atmosphere throughout. A welcoming skylit entry introduces expansive living spaces designed for both comfortable living and elegant entertaining. The formal dining room flows effortlessly into a well-appointed butler’s pantry with custom cabinetry. The chef’s kitchen is the heart of the home, featuring custom floor-to-ceiling cabinetry, quartz countertops, a large center island with seating, premium stainless steel appliances including a double oven and cooktop, under-cabinet lighting, and polished concrete flooring. The adjacent breakfast area opens through sliding doors to the rear property, creating a seamless indoor-outdoor connection. A spacious great room space, with an open-concept setting offers exceptional flexibility in layout and design, featuring a soaring cathedral ceiling, multiple skylights that fill the space with natural light, a cozy gas fireplace, and expansive windows. Seamlessly connected to the formal living room, it provides endless possibilities for arranging and customizing the space to suit both everyday living and entertaining. The primary suite is a true retreat, offering a spacious sitting area, automated window treatments, multiple exposures for natural light, and a custom walk-in closet. The spa-inspired bath features radiant heated floors, a frameless glass shower, soaking tub, double floating vanity, and ample storage. Three additional bedrooms are generously sized with large closets and oversized windows. The finished lower level provides additional versatility for play space, a home office, recreation area ideal for today’s flexible lifestyle. The outdoor setting is equally impressive, featuring a fully fenced, park-like property with mature specimen trees and lush perennial gardens. A newly reconstructed heated saltwater pool with a waterfall feature is surrounded by custom concrete and maintenance-free decking, complemented by smart LED lighting for effortless ambiance. Additional highlights include new Andersen windows and doors, updated roofing and stucco exterior, gas heating, alarm system with remote access, underground sprinklers, new carpeting, radiant heat, and premium finishes throughout.

161 Yukon Drive, Woodbury

$1,699,888

3 Beds ⋅ 3 Baths ⋅ 985829 MLS

Welcome to this beautifully renovated luxury home located in the highly sought-after Syosset School District,located in the prestigious Woodbury community. Situated on an expansive 2-acre lot, this exceptional property offers privacy, space, and refined modern living. The main level features approximately 1,798 sq ft of thoughtfully designed living space, showcasing premium solid hardwood flooring throughout and a bright, open layout filled with natural light. The home has been fully updated with high-end materials and modern finishes, blending elegance with everyday functionality. This residence offers 3 spacious bedrooms and 3 full bathrooms, all tastefully designed with quality craftsmanship and contemporary style. A two-car garage adds convenience and functionality to this already impressive home. The fully finished basement adds approximately 1,500 sq ft of additional living space, perfect for a recreation area, home office, gym, or guest suite. Enjoy a prime location just minutes from Cold Spring Harbor LIRR station, providing a convenient commute to Manhattan in three stops. Elementary, middle, and high schools are all within a short 5–8 minute drive. A rare opportunity to own a move-in ready luxury home with expansive land, modern upgrades, and unbeatable convenience.

17 Woodbury Road, 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

$2,650,000

7 Beds ⋅ 6 Baths ⋅ 979421 MLS

Syosset School District, Private Lake, there is a band new swimming pool in the backyard and a fish pond in the front yard, New A/C, Kitchen with underfloor heating, home theater in the basement

117 Plainview Road, Woodbury

$2,150,000

6 Beds ⋅ 4 Baths ⋅ 977793 MLS

Welcome to the former Model home in the gated community of Hunters Run. Unique in architecture and design. This wonderful traditional Contemporary has the potential for 6 bedrooms! Elegant entertaining space. Kitchen & main living areas featured in Home magazine and were designed by a well known interior designer. An Anderson sliding door in the kitchen leads out to spacious .57 acre with outdoor kitchen that uses propane for cooking, hot tub, spectacular entertaining space and specimen landscaping. Entry to home has 2 story entry, room for grand piano, powder room and spacious closet. Living room with gas fireplace, picture windows, hi hat lighting, and beverage center with wet bar. Den has surround sound and large picture windows. Oversized dining room includes surround sound and room for large furniture. Primary bedroom with spacious bath with oversized Jacuzzi tub, separate shower and smart toilet is located on the first floor Upstairs 3 bedrooms with the possibility of the bonus room ( gym/ playroom) as additional bedroom. The basement has a potential for a bedroom / bath, office with egress windows, large room for pool table, wonderful storage and sound proof room for musicians. 3 Car Garage including 220 - port EV charging station, full house generator, 9 zone heating & cooling system, IGS, alarmed, and CVAC. Syosset School District

9 The Grasslands, Woodbury

$1,899,000

4 Beds ⋅ 5 Baths ⋅ 968244 MLS

Discover the perfect blend of mid-century elegance and expansive potential at 1 The Brae. Nestled on a sprawling 1.00-acre lot in one of Woodbury’s most coveted neighborhoods, this 4-bedroom, 5-bathroom residence offers a rare sanctuary of privacy and grace. Built in 1958 and spanning 2,707 square feet across two levels, the home features a thoughtful layout with a cozy fireplace and a versatile floor plan ready for your personal touch. Whether you envision a modern renovation or moving right into its classic charm, this property provides a lush, park-like setting perfect for grand-scale entertaining

1 The Brae, Woodbury

$1,899,999

5 Beds ⋅ 5 Baths ⋅ 971942 MLS

Beautiful Colonial Home on 1 Acre with Modern Upgrades & Resort-Style Amenities Spacious 5-bedroom, 3 full bath, 2 half bath Colonial with inground pool set on a private 1-acre lot. Updated kitchen features granite countertops and stainless steel appliances. This well-maintained home includes numerous recent upgrades: newer gas boiler (2 zones), brand-new hot water heater, and central air with updated ductwork. Owned solar panels provide energy efficiency. Enjoy outdoor living with a stunning in-ground pool (approx. 44x25) with a new heater, Deck, Patio, Porch along with an in-ground sprinkler system and a French drain for proper drainage. Additional features include EV charging capability, generator hookup, and a roof that is approximately 8 years old. Interior highlights include updated electrical (200 amps) and recessed lighting throughout. Exterior amenities include a 3-car garage and a circular driveway for ample parking, Generator hook up, Tesla Eva Charger. Approximately 3,400 sq ft of living space.

10 Hunting Hill Road, Woodbury

$1,450,000

4 Beds ⋅ 3 Baths ⋅ 973139 MLS

Welcome to this meticulously maintained ~2,900sqft Colonial in the heart of Woodbury, located within the award-winning Syosset Central School District. Positioned at the end of the block and bordering a nature preserve, with mature green giants lining the property for added privacy. This move-in ready home features 4 bedrooms, 3 full bathrooms, an open layout, and hardwood floors throughout. The main level is thoughtfully designed with scale and flow, featuring soaring ceilings, a spacious living room, formal dining room, and a formal family room. The centerpiece of the home is the brand-new beautifully appointed kitchen with updated appliances, extensive cabinetry, and a newly installed center island. Upstairs, a bright loft provides a versatile space for a home office or additional living area. The primary suite features soaring vaulted ceilings, a fully renovated spa-style bathroom with radiant heated floors, soaking tub, double vanity, bidet, oversized rain shower, and integrated Bluetooth. Three additional bedrooms are generously sized and complemented by a full bathroom. A washer and dryer are conveniently located on the second level. The full finished basement with a separate side entrance offers expansive, highly usable living space—ideal for a media room, gym, playroom, or additional entertaining area. The backyard is designed for entertaining, featuring pavers, a semi-inground pool, and mature landscaping. Additional highlights include new appliances, in-ground sprinklers, an above-ground oil tank, a well-maintained boiler and roof, and a two-car garage. A well-maintained, move-in ready home offering space, privacy, and location in one of Woodbury’s most desirable neighborhoods.

4 2nd Street, Woodbury

$2,998,000

5 Beds ⋅ 5 Baths ⋅ 966093 MLS

Architecturally distinguished and extensively updated, this stately custom Colonial set on nearly one acre of private cul-de-sac property in the heart of Woodbury. Offering 5,181 square feet of refined living space, this residence reflects timeless design, superior craftsmanship, and meticulous attention to detail. The home presents with a fresh, like-new aesthetic, highlighted by a fully renovated gourmet kitchen and 5 bathrooms redesigned and completed in 2022. A dramatic two-story foyer introduces 9-foot ceilings and a gracious floor plan designed for both elegant entertaining and comfortable everyday living. The gourmet chef’s kitchen, appointed with high-end appliances and quartz countertops, opens seamlessly to the breakfast area and flows through a fully equipped butler’s pantry featuring a bar sink, wine refrigerator, and additional under-counter refrigeration. The main level also features a formal dining room, family room, living room with fireplace, beautifully appointed bonus room with fireplace, ideal as a private library, executive office, or refined den, first-floor bedroom for extended family or nanny quarters, laundry room, powder room, and an additional full bath. Three fireplaces throughout the home provide warmth and architectural presence. The primary suite is a private sanctuary, offering a sitting retreat with shared gas fireplace with bedroom, an expansive walk-in closet, built-in dressing vanity, and a beautifully renovated spa-inspired bath (2022). A princess suite includes its own newly redesigned en-suite bath, while two additional bedrooms share a renovated Jack & Jill bath. Trey ceilings in bedrooms and vaulted ceilings in bathrooms enhance the home’s architectural character. Outdoor living is equally impressive with an expansive covered deck off the kitchen, large brick patio, and a gunite pool with heater (2018), all surrounded by mature landscaping that provides exceptional privacy. Additional highlights include a three-car garage, two staircases, radiant heat in bathrooms, 5-zone heating, 5-zone central air (2019), roof (2017), hot water heater (2018), garage doors (2018), and full-house water filtration system. Ideally located near transportation, shopping, and dining, and within the highly regarded Syosset School District, including Berry Hill Elementary, this exceptional Woodbury residence offers scale, privacy, and turnkey luxury in one of the area’s most desirable locations

15 Pironi Court, Woodbury

$1,699,000

5 Beds ⋅ 4 Baths ⋅ 957701 MLS

Privately set on over one acre in Woodbury’s prestigious Hunting Hills, this elegant center hall Colonial blends timeless architecture with modern comfort in the Syosset School District. Offering over 3,000 square feet, the home includes five bedrooms and 3.5 baths, with a sought-after first-floor guest suite. A marble foyer welcomes you into sun-drenched living spaces perfect for everyday living and entertaining. The custom chef's kitchen features radiant heated floors, Sub-Zero refrigerator and freezer, dual Bosch wall ovens, and opens to a bright sunroom with breakfast area. The formal dining room showcases custom built-ins, while the den with a wood-burning fireplace offers serene views of the resort-style grounds. Outside, enjoy a private retreat complete with a heated gunite pool, patio, pergola, and a cabana with full bath, changing area, and kitchenette. The finished basement provides additional lifestyle space with a home gym, pantry, cedar closet, and laundry. Completing the home are hardwood and porcelain floors, custom closets, Andersen windows, energy-efficient systems, multi-zone irrigation, and a two-car attached garage with interior access, a truly special offering in one of Woodbury’s most desirable neighborhoods.

65 Avery Road, 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

$1,200,000

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

$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

$1,750,000

5 Beds ⋅ 4 Baths ⋅ 932057 MLS

Elegant Move-In-Ready Ranch with Pool, Office, and Full Finished Basement in the Syosset School District. Welcome to 28 Elm Street, a beautifully renovated five-bedroom, three-bath ranch offering the perfect combination of modern design, functionality, and timeless comfort. Located on a quiet, tree-lined street in one of Woodbury’s most desirable neighborhoods, this home is ideal for everyday living and entertaining alike. Step inside to a sun-filled open layout 5 bedroom ranch with finished basement: Featuring a spacious living room, den, dining area, and chef’s kitchen with custom cabinetry, quartz countertops, and premium stainless-steel appliances. A separate home office provides the perfect space for work or study and gym. The main level offers five generous bedrooms, including a serene primary suite with an elegant ensuite bath. The fully finished lower level extends the living space with a guest bedroom, full bath, full attic with HVAC, recreation area, and gym—ideal for extended family or guests. Step outside to your private backyard oasis featuring a sparkling in-ground pool, expansive patio, and beautifully landscaped grounds—perfect for relaxing or hosting gatherings. Highlights: Five bedrooms + home office | Three full baths. Full finished basement with bedroom and bath. In-ground pool and private landscaped yard. Designer kitchen with quartz counters and premium appliances. Hardwood floors and recessed lighting throughout. Attached two-car garage and spacious driveway. Award-winning Syosset School District. Perfectly located near parks, shopping, and fine dining, 28 Elm Street combines luxury living with everyday comfort in the heart of Woodbury.

28 Elm Street, Woodbury

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