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$1,298,000
3 Beds ⋅ 3 Baths ⋅ 1031980 MLS
Move right into this beautifully updated 3-bedroom, 3 bath split-level home offering luxury finishes, generous living space, and true move-in readiness. A bright, open floor plan with gleaming hardwood floors and abundant natural light sets the tone for this exceptional home. The main level features a formal living room, spacious dining area with crystal chandelier, and seamless flow into an expansive great room with a wall of windows, and a charming window seat overlooking the backyard. At the heart of the home is a brand new open kitchen complete with quartz countertops, a large center island, stainless steel appliances, floor-to-ceiling cabinetry, a skylight, and a glass-paned door providing easy access to the home's outdoor living spaces — perfect for both everyday living and entertaining. The spacious primary suite offers a private en-suite bathroom and his and her closets. Two additional generously sized bedrooms provide ample closet space. A renovated main bathroom impresses with a double vanity featuring quartz countertops, a vaulted ceiling, skylight and stylish finishes. The lower level provides a large, yet cozy, den with a wood-burning stove, a powder room, and sliding glass doors leading outside, enhancing the home's indoor-outdoor flow. The basement features a laundry area with new washer/dryer and extensive storage. Outdoor living is equally impressive with a brand-new Trex deck featuring illuminated steps and posts, plus a large patio and beautifully landscaped yard. Additional highlights include a two-car garage, brand-new digital HVAC and central air system, in-ground sprinklers, Slomin’s security system, Ring doorbell/camera, storage shed, and more. A truly turnkey home combining modern upgrades, comfort, and exceptional functionality throughout.

7 Wren Drive, Woodbury
$1,749,888
4 Beds ⋅ 3 Baths ⋅ 1031591 MLS
Move right into this beautifully updated 4-bedroom, 3.5-bath Colonial set on a flat, landscaped .34-acre property in the Syosset School District. Designed for today's lifestyle, this light-filled home features an ideal layout with spacious rooms, hardwood floors, and seamless flow for everyday living and entertaining. The renovated eat-in kitchen, completed in 2017, showcases white cabinetry, quartz countertops, stainless steel appliances, and generous workspace for cooking and gathering. Family room with gas fireplace and sliders that lead to oversized patio. Updated bathrooms, a spacious primary suite with a large walk-in closet, and generously sized secondary bedrooms provide comfort and style throughout. The full finished basement offers exceptional bonus living space, while the private backyard is an entertainer's dream with a large patio, outdoor kitchen, bar area, sports court, and storage shed. Completing this exceptional home is a two-car garage and an unbeatable location close to shopping, parks, transportation, and all that Syosset/Woodbury has to offer.

30 Irving Drive, Woodbury
$2,699,000
5 Beds ⋅ 4 Baths ⋅ 1029820 MLS
Welcome to 4 Shannon Drive, a sprawling 4,095-square-foot home located in the heart of Woodbury. A stunning post modern 5 bedroom Colonial showcasing exceptional craftsmanship and timeless design. This elegant residence offers a spacious and versatile layout, featuring oversized rooms, soaring ceilings and sun-drenched rooms, sweeping staircase, and seamless flow for entertaining. At the heart of the home is a large chef’s center island kitchen equipped with top-of-the-line appliances, radiant heated flooring and custom Wood Cabinetry, ideal for culinary enthusiasts and gatherings of any size. Tucked away from the main living areas, a main floor guest bedroom and fully renovated bathroom offers privacy and independence. The second floor primary suite is defined by vaulted ceilings and the cozy glow of a gas fireplace. This expansive retreat features a walk-in closet and flows seamlessly into a reimagined, spa-inspired ensuite. Designed for rejuvenation, the bathroom offers a sleek double vanity, a deep jacuzzi tub for indulgent soaks, and an oversized steam shower, creating a private haven of sophisticated comfort. Additional 3 generously sized bedrooms provide flexibility for extended living. Additional features a finished basement with ample storage, a first floor laundry room, gas heat, central vacuum, State of the Art security and camera system, whole house water filtration system, 3 car garage, CAC plus so much more! Set on an incredible .46-acre landscaped property with In Ground Heated Pool and built in professional BBQ, this special home offers fabulous outdoor entertaining possibilities. Set in one of Long Island's most prestigious school districts, and just minutes to shopping, dining, and the train station, this home perfectly balances a lifestyle defined by style, scale, and a premier North Shore location.

4 Shannon Drive, 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
$2,395,000
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
$2,680,000
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
$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
$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
$2,799,000
6 Beds ⋅ 7 Baths ⋅ 989842 MLS
Welcome to this exceptional home offering the perfect blend of luxury, space, and modern living. Boasting 6 spacious bedrooms and 6.5 beautifully appointed bathrooms, this residence is thoughtfully designed for both everyday comfort and upscale entertaining. The first floor features a seamless open-concept layout anchored by a stunning kitchen that flows effortlessly into expansive living, dining, and family room spaces—ideal for gatherings of any size. A versatile first-floor bedroom provides flexibility for guests, a home office, or multigenerational living, complemented by a nearby full bathroom as well as an additional powder room for added convenience. Upstairs, you’ll find five generously sized bedrooms and four full bathrooms, including a luxurious primary suite. A striking open walkway overlooks the living room below, creating a dramatic sense of space and natural light throughout the home. The fully finished basement elevates the home’s entertainment potential, complete with a dedicated gym, wet bar, and ample room for recreation, media, or hosting. Car enthusiasts and eco-conscious buyers alike will appreciate the oversized 3-car garage equipped with multiple EV charging stations. Step outside to a backyard oasis that seamlessly connects to nature while offering endless possibilities for outdoor living. Featuring an outdoor kitchen and expansive grounds, there’s plenty of space to add a pool, tennis court, or custom retreat tailored to your lifestyle. This is a rare opportunity to own a home that truly has it all—space, style, and unmatched versatility.

12 Chauncey Place, Woodbury
$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
$1,180,000
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
$1,488,000
4 Beds ⋅ 3 Baths ⋅ 982967 MLS
Welcome to a rare opportunity in the heart of Woodbury. This 4 bedroom, 2.5 bath Splanch style home is perfectly situated mid-block on a picturesque, tree-lined street. Step inside to discover a beautiful home with natural light and hardwood floors. The first floor features a renovated eat-in kitchen with stainless steel appliances, granite countertops and a formal dining room for entertaining. For colder nights, enjoy the family room with a wood burning fireplace. Also includes radiant floor heating The large primary bedroom features a wall of closets and a renovated en suite bathroom. Two additional bedrooms and hall bath complete the upstairs living. Designed for modern living, the home boasts a dedicated home office for remote work and a spacious mudroom with convenient main-floor laundry. The two-car garage includes an electric charger for sustainable living. Retreat to your private backyard oasis, framed by mature privacy trees. The highlight is the in-ground heated pool, complemented by a large brick patio, creating the perfect setting for summer entertaining and relaxation. This exceptional property is ready to be your forever home

3 Clemson Lane, Woodbury
$1,200,000
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
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