Woodbury Homes for Sale

Welcome to Woodbury, New York – a hidden gem nestled in the heart of Orange County. Known for its picturesque landscapes and tight-knit community, Woodbury offers a perfect blend of suburban tranquility and urban convenience. With its charming neighborhoods, top-rated schools, and an array of recreational activities, this vibrant town is an ideal place to call home.

Woodbury boasts an impressive array of amenities, including beautiful parks, hiking trails, and shopping destinations, ensuring that residents have everything they need right at their fingertips. The town is also conveniently located near major highways, making commuting to New York City and surrounding areas a breeze. Whether you're seeking a peaceful retreat or an active lifestyle, Woodbury has something for everyone.

For those considering a move, the housing market in Woodbury is diverse and inviting. From charming single-family homes to modern townhouses, there’s a wide variety of options to suit any lifestyle. Many properties feature spacious yards, updated kitchens, and stunning views of the surrounding hills, making them perfect for families and individuals alike. With homes for sale that cater to different tastes and budgets, you’re sure to find the perfect place to settle down.

Explore the wonderful community of Woodbury, where every day feels like a getaway. With its friendly atmosphere and beautiful homes, it’s no wonder why so many are choosing to make this delightful town their new home. Start your journey today and discover the endless possibilities that await you in Woodbury!

Newest Woodbury Homes for Sale

$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

$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

$2,390,000

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

$2,395,000

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

$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

$1,550,000

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

$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

$649,000

4 Beds ⋅ 3 Baths ⋅ 1013986 MLS

**Welcome to 383 Route 32, Central Valley** — a beautifully maintained **legal mother-daughter split-level home** offering the perfect combination of **space, versatility, and comfort**. Nestled on a **.35-acre lot** within the highly sought-after **Monroe-Woodbury School District**, this impressive home features **4 spacious bedrooms, 3 full bathrooms, and over 2,000+ sq. ft. of living space** designed for flexible living. Boasting **two full kitchens, two refrigerators, two stoves, hardwood and vinyl flooring, and a finished basement**, this unique layout is ideal for **extended family living, private guest quarters, or multi-generational flexibility**. Enjoy modern-day conveniences including **central air, oil heat, electric utilities, municipal water, septic system, and a pull-down attic for added storage**. Perfectly located near **shopping, schools, major highways, and just minutes from the New York State Thruway exit**, this home delivers the ideal balance of **peaceful suburban living with unmatched everyday convenience**. A rare opportunity offering **comfort, function, and endless potential** in a prime Central Valley location.

383 Route 32, 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.