Woodbury Real Estate

Welcome to Woodbury, New York – a hidden gem nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant community spirit, this charming town offers a perfect blend of suburban tranquility and easy access to urban amenities. Just a short drive from New York City, Woodbury provides residents with the ideal escape from the hustle and bustle while still being conveniently close to the excitement of the city.

Woodbury is renowned for its stunning natural beauty, featuring rolling hills, lush parks, and scenic trails that invite outdoor enthusiasts to explore. The town is home to several recreational facilities, including the popular Woodbury Common Premium Outlets, where shopping aficionados can find incredible deals on top brands. For families, Woodbury boasts excellent schools and a variety of community events throughout the year, fostering a strong sense of belonging among residents.

In addition to its recreational offerings, Woodbury is rich in history and culture. The town features a blend of charming architecture and modern developments, creating a unique atmosphere that appeals to diverse tastes. Whether you’re looking for a cozy single-family home or a spacious townhome, Woodbury’s real estate market has something for everyone.

With its friendly neighborhoods, top-notch amenities, and a commitment to community engagement, Woodbury, NY, is not just a place to live – it’s a place to thrive. Discover the lifestyle you’ve always dreamed of in this enchanting town, where every day feels like a getaway!

Newest Listings in Woodbury

$1,999,888

6 Beds ⋅ 5 Baths ⋅ 1039543 MLS

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

44 Plainview Road, Woodbury

$1,599,999

4 Beds ⋅ 4 Baths ⋅ 1039520 MLS

Welcome to 9 The Preserve, a luxurious townhouse ideally located in the heart of Woodbury. This beautiful four-bedroom, four-bathroom home offers the perfect combination of elegance, comfort, and modern living. Situated within the prestigious Preserve community, the home features a dedicated home office and beautifully designed open-concept living spaces, ideal for both everyday living and entertaining. Large windows fill the home with an abundance of natural light, creating a bright and inviting atmosphere throughout. The backyard overlooks the scenic Preserve pond, providing a peaceful setting and beautiful views. Residents enjoy access to an impressive private clubhouse featuring a private theater, state-of-the-art fitness center, and spacious party room—perfect for gatherings and entertaining. Spacious, sophisticated, and thoughtfully designed, 9 The Preserve offers an exceptional opportunity to enjoy luxury living, beautiful surroundings, and outstanding amenities in one of Woodbury’s most desirable communities.

9 The Preserve Unit #9, Woodbury

$2,688,000

4 Beds ⋅ 5 Baths ⋅ 1038912 MLS

Experience the pinnacle of refined living at The Sagamore at Mills Pond, where exceptional craftsmanship, sophisticated design, and resort-style amenities come together in this extraordinary four-bedroom, 4.5-bath end-unit residence. Ideally positioned within the community, this fully customized home enjoys one of the most coveted settings, with unobstructed pond views and an exceptional sense of privacy. Designed for both luxurious everyday living and effortless entertaining, the residence spans three levels, all connected by a private elevator. The dramatic two-story great room creates an impressive focal point, while custom lighting, a Lutron smart-home system, and thoughtfully curated finishes elevate every space. The chef’s kitchen is exceptionally appointed with Thermador appliances, two wall ovens, gas cooktop, built-in microwave, wine refrigerator, and warming drawer. A dedicated pantry and main-level laundry room add both functionality and convenience. The adjacent dining room features a stunning custom built-in with refrigeration and freezer drawers—an ideal complement for entertaining. The main-level primary suite is a private retreat, offering dual walk-in closets and a luxurious bath with radiant heated flooring. Upstairs, two additional bedrooms each feature en-suite baths, while a custom built-in office overlooks the spectacular great room, creating an inspiring workspace with a view. The fully finished custom lower level is designed for entertaining, complete with bespoke built-ins, a serving area and wet bar. A two-car garage, EV charger, four-zone heating and central air provide modern comfort and convenience throughout. Step outside to an extraordinary private entertaining space overlooking the pond. The fully customized outdoor kitchen features a built-in barbecue and fire pit, creating the perfect setting for sophisticated summer entertaining or relaxed evenings at home. Residents of this exclusive gated community enjoy an exceptional collection of amenities, including a resort-style pool, tennis and pickleball courts, and an elegant clubhouse designed for entertaining and recreation. The clubhouse features a golf simulator, billiards room, library, movie room, and outdoor barbecue areas. Set in the highly regarded Syosset School District.

78 Three Ponds Lane E, Woodbury

$799,999

3 Beds ⋅ 3 Baths ⋅ 1038513 MLS

Welcome to Woodland Pond, this updated and well-maintained 3-bedroom, 2.5-bathroom townhouse featuring a spacious layout with a formal dining room, central air conditioning, and a generously sized primary bedroom complete with a private en-suite bathroom. Enjoy outdoor living on the private brick patio, perfect for relaxing or entertaining. Residents of Woodland Pond enjoy an array of amenities, including swimming pool, tennis courts, a clubhouse, gym, and party room. Conveniently located and thoughtfully maintained, this townhouse offers comfortable living with an excellent selection of community amenities.

11 Clubhouse Court, Woodbury

$999,000

3 Beds ⋅ 3 Baths ⋅ 1037907 MLS

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

115 Woody Lane, Woodbury

$500,000

3 Beds ⋅ 3 Baths ⋅ 1034231 MLS

Welcome home to this beautifully custom-renovated 3-bedroom, 2.5-bath townhouse nestled on a quiet cul-de-sac in the highly sought-after Timber Ridge III community of Highland Mills. Offering approximately 1,963 square feet of living space, including the finished basement with an impressive oversized his-and-hers walk-in closet, this move-in-ready home combines modern style, comfort, and convenience. Step inside to a bright, open-concept layout featuring tasteful custom renovations and designer finishes throughout. The living, dining, and kitchen areas flow seamlessly together, creating an inviting space perfect for everyday living and entertaining. Upstairs, the spacious primary suite offers a private en-suite bath and an impressive oversized his-and-hers walk-in closet with abundant storage. Additional bedrooms provide plenty of space for family, guests, or a home office. Enjoy outdoor living on the private rear deck, perfect for morning coffee, relaxing in the sun, summer barbecues, and entertaining. Residents of Timber Ridge III also enjoy access to the community pool. Located in the Town of Woodbury, the home is approximately five minutes from Earl Reservoir Park, offering swimming, fishing, picnic areas, playgrounds, sports courts, and scenic walking paths. You'll also enjoy convenient access to Woodbury Common Premium Outlets, I-87, Route 17, commuter transportation, Harriman State Park, shopping, restaurants, and everyday conveniences. Located within the Monroe-Woodbury Central School District, 19 Helene Circle offers an exceptional combination of space, style, location, and Hudson Valley living. You will appreciate being located within the highly regarded Monroe-Woodbury Central School District, known for its strong academic programs, championship athletics, performing arts, Advanced Placement courses, and wide variety of extracurricular opportunities. Being sold As-Is. Refrigerator and chandeliers are excluded from the sale.

19 Helene Circle, Woodbury

$1,688,888

3 Beds ⋅ 3 Baths ⋅ 1022916 MLS

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

32 Lark Drive, Woodbury

$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 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 bath and private outside entrance. 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, composite (Trex) deck accessed directly from the kitchen and living room, and tranquil pond views beyond the established landscaping. Community tennis and pickleball courts, a circular driveway, two-car garage, and the highly regarded Syosset SD complete this rare offering.

27 Windemere Way, Woodbury

$2,288,888

6 Beds ⋅ 6 Baths ⋅ 1020613 MLS

Nestled on one private acre in the heart of Woodbury, this exceptional center hall Colonial offers the perfect blend of timeless elegance, modern updates, and outstanding versatility. Set on a beautifully landscaped one-acre property, the home provides a peaceful retreat while remaining just minutes from shopping, major parkways, the LIRR, and Syosset schools. The main residence features 5 bedrooms and 4.5 bathrooms, 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

$919,900

4 Beds ⋅ 3 Baths ⋅ 1020349 MLS

Come and See this Oversized Colonial with 4 beds and 2.5 bath located in Syosset school district. Plenty of room for extended family. Close to shopping, transportation and major roadways.

216 Woodbury Road, Woodbury

$1,525,000

5 Beds ⋅ 4 Baths ⋅ 1025222 MLS

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

10 Clemson Lane, Woodbury

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.