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$479,999
3 Beds ⋅ 3 Baths ⋅ 1049258 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
$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
$1,249,999
3 Beds ⋅ 4 Baths ⋅ 1035676 MLS
Perfectly situated in The Greens at Woodbury, this beautiful 3-bedroom, 3.5-bath Aspen model offers an exceptional location near the cul-de-sac and community pool, along with a private backyard setting. The sun-filled interior showcases a sleek, modern aesthetic with hardwood floors throughout. At the heart of the home is a brand-new designer eat-in kitchen featuring custom cabinetry, quartz countertops, all-new appliances, and contemporary finishes, seamlessly combining style and functionality for everyday living and entertaining. The spacious living room creates a warm and sophisticated atmosphere, while the private terrace opens to a new Trex deck—an ideal setting for relaxing, outdoor dining, and entertaining. The oversized primary suite offers exceptional comfort and privacy, complemented by two additional generously sized bedrooms. Each bedroom features a custom walk-in closet, providing an exceptional amount of storage throughout the home. A full finished basement provides versatile additional space for a recreation room, home office, gym, or guest area. Additional updates include a new washing machine and dryer. Further highlights include a two-car garage, low monthly HOA fees, and access to resort-style community amenities, including a pool and tennis courts. A rare opportunity to own a beautifully updated, move-in-ready home in one of The Greens at Woodbury’s most desirable locations.

48 Chestnut Lane, 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
$1,298,000
3 Beds ⋅ 3 Baths ⋅ 1031980 MLS
Move right into this beautifully updated 3-bedroom, 3 bath split-level home located within the Syosset School District, 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. Upstairs, 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, 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
$1,088,000
3 Beds ⋅ 3 Baths ⋅ 1028929 MLS
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
$728,000
3 Beds ⋅ 3 Baths ⋅ 1013801 MLS
Enjoy the Lifestyle of Woodbury Village, a sought after townhouse community in the Syosset School district offering exceptional amenities including a pool, tennis courts and playground. This 3 Bedroom(currently configured as 2 bedrooms plus a loft that can easily be converted back to 3rd bedroom), 2.5 Bath home features all New Flooring, New Primary Bathroom and Deck. The Main Level offers a Powder Room, an EIK with all SS Appliances, Granite Countertops and Abundant Cabinetry. The Sun filled Open Dining Room and Living Room is Ideal for Entertaining, Featuring a Striking Stone Fireplace and Sliding Glass Doors to the New Deck. Upstairs, the Spacious Primary Bedroom boasts 2 Closets and a Beautifully Renovated En-Suite Bath. A Second Bedroom, Versatile Loft/Bedroom, and a Full Bathroom complete the Second Level. Move Right in and enjoy comfortable, low maintenance living with resort style amenities in a prime location.

5 Pond Path Unit #13, Woodbury
$869,999
3 Beds ⋅ 3 Baths ⋅ 1020633 MLS
Enjoy Country Club Living with amenities galore.This Updated Condo in Desirable Woodland Pond Convenient to all Features A Newer Stainless Steel Granite Eat in Kitchen with Excessive White cabinetry,3 Updated Bathrooms,Hard Wood Floors,Beautiful Mill work,Large Formal Dining Room,Step Down Living Room/Den with Ose to Trex Deck,Vaulted Ceiling,Skylight.Minutes to Shopping ,Restaurants,Public Transportation .Too Much to Mention. Amenities include Swimming Pools,Tennis Courts,Clubhouse,gym,party room Etc. Major Price Improvement

104 W Woodlake 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
$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
$868,000
3 Beds ⋅ 3 Baths ⋅ 990054 MLS
Welcome to a rare opportunity in the highly sought-after Woodlands community! This 3-bedroom, 2.5-bath townhouse offers space, light, and potential in a prime Syosset location within the top-rated Syosset School District, serving Baylis Elementary and H.B. Thompson Middle School. Offered in original condition, this home presents a rare opportunity to bring your vision to life and create a space tailored to your personal style. With great bones, a spacious layout, and abundant natural light, the potential is undeniable. The main level features an airy, open floor plan with soaring ceilings in the living room and sliding glass doors in both the living room and dining room leading to a private deck—ideal for seamless indoor-outdoor living and entertaining. A formal dining room and generously sized eat-in kitchen provide flexibility for both everyday living and hosting. The kitchen also offers direct access from the garage and includes a convenient laundry area. A standout feature is the expanded den, a versatile finished space offering additional living area that was converted by the Sponsor when the community was built. A conveniently located half bath completes this level. Upstairs, the home offers a primary en-suite with a large walk-in closet, two well-proportioned bedrooms, and a full hall bath. A spacious landing and hallway overlook the living room below, enhancing the home’s open and airy feel. The basement adds even more versatility, perfect for a recreation room, home office, gym, or additional storage. Additional highlights include a new HVAC system, an attached garage, and a private driveway with side-by-side parking for two vehicles. Enjoy resort-style living in this highly sought-after, amenity-rich pet-friendly community featuring tennis, pickleball, and basketball courts, a fitness center, clubhouse with social spaces, in-ground pool, kiddie pool, and playground. Conveniently located just minutes from shopping, dining, major highways, and the Town of Oyster Bay Golf Course. Bring your imagination and unlock the full potential of this exceptional home!

29 Jennings Lane, Woodbury
$819,888
3 Beds ⋅ 3 Baths ⋅ 990859 MLS
This Updated 3 Bedroom, 2.5 Bath Townhouse with a Full Finished Basement is located in The Woodlands Community within the Syosset School District! IT IS MOVE IN READY WITH A LOVELY SERENE LOCATION FACING THE BACK! The home has many upgrades such as Oak Hardwood Flooring and Recessed Lighting Throughout. The Eat in Kitchen has Granite Countertops, a Granite Island and Stainless-Steel Appliances. Continuing on the main level is a Pantry Closet, Half Bath, Washer/Dryer, Dining Room and a Living Room with a wood burning Fireplace. Upstairs is the Primary Bedroom featuring an En-Suite Bathroom and a large Walk in Closet. The 2nd and 3rd Bedroom as well as a Full Hallway Bathroom complete the upper level. The Lower Level features a Full Finished Basement and room for extra storage! Amenities include a Community Pool, Tennis, Basketball and Play Area. Enjoy all that this Community has to offer!

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

49 Canterbury Road, Woodbury
$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
$1,488,878
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

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.