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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.

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

$4,875,000

An extraordinary opportunity to own a luxurious new construction residence in Woodbury's prestigious Hunting Hills neighborhood, situated on a magnificent one-acre property. Showcasing sophisticated architecture, exceptional craftsmanship, and exquisite attention to detail, this stunning home offers 5 spacious bedrooms, 5.5 bathrooms, and an impressive floor plan designed for elegant entertaining and everyday living. Dramatic double-height ceilings, extensive custom millwork, and refined architectural details enhance the expansive living spaces. The impressive chef's kitchen is a centerpiece of the home, while a first-floor ensuite bedroom provides flexibility for guests or extended family. The luxurious primary suite features a spa-inspired bathroom and generous closet space. Additional highlights include a three-car garage, a substantial basement with 10-foot ceilings, and beautifully proportioned grounds offering ample space for outdoor entertaining, recreation, and a future pool. A rare opportunity to enjoy exceptional new construction in one of Woodbury's most desirable locations.

5 Beds ⋅ 6 Baths ⋅ 894990 MLS

An extraordinary opportunity to own a luxurious new construction residence in Woodbury's prestigious Hunting Hills neighborhood, situated on a magnificent one-acre property. Showcasing sophisticated architecture, exceptional craftsmanship, and exquisite attention to detail, this stunning home offers 5 spacious bedrooms, 5.5 bathrooms, and an impressive floor plan designed for elegant entertaining and everyday living. Dramatic double-height ceilings, extensive custom millwork, and refined architectural details enhance the expansive living spaces. The impressive chef's kitchen is a centerpiece of the home, while a first-floor ensuite bedroom provides flexibility for guests or extended family. The luxurious primary suite features a spa-inspired bathroom and generous closet space. Additional highlights include a three-car garage, a substantial basement with 10-foot ceilings, and beautifully proportioned grounds offering ample space for outdoor entertaining, recreation, and a future pool. A rare opportunity to enjoy exceptional new construction in one of Woodbury's most desirable locations.

1 Sycamore Drive, Woodbury

$4,450,000

Introducing the most sought-after home in Woodbury, 5 Kodiak Drive. An epitome of contemporary luxury nestled in Syosset School District. This architectural masterpiece redefines opulence with its sleek design and an array of innovative amenities, ensuring a lifestyle of unparalleled comfort and sophistication. Situated on a sprawling one-acre lot, this estate seamlessly combines modernity with timeless elegance. As you step through the grand entrance, you're greeted by a fusion of sleek lines and luxurious materials, setting the stage for an exceptional living experience. Crafted for the most discerning homeowner, this residence boasts 8 bedrooms and 9 bathrooms, each meticulously designed with premium finishes and thoughtful details. Smart climate control systems, integrated sound, and lighting elevate the living experience to new heights. The main level is a haven for relaxation and entertainment. A stylish bar room invites you to unwind by the fireplace, while the formal dining room offers the perfect setting for intimate gatherings. The gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, pizza oven, custom cabinetry, and a breakfast area overlooking the lush backyard. Outside, the expansive grounds offer a sanctuary for outdoor living. A private tennis court with overhead lighting provides endless opportunities for recreation, while the heated in-ground Gunite pool and cabana area offer a serene retreat for lazy afternoons and al fresco dining. The pool features an infinity edge and a mesmerizing water feature with multiple fire elements, creating a captivating ambiance. Upstairs, the primary suite is a luxurious escape, complete with a sitting area, private balcony, and spa-like ensuite bath featuring a soaking tub and steam shower. Four additional bedrooms, each with its own ensuite bathroom, provide ample space for family and guests. Downstairs, the lower level is a hub of activity, with a fitness room, billiards area, and home theater offering endless entertainment options. A three-car garage provides ample space for vehicles and storage, while smart home features ensure convenience and security. With its blend of contemporary design and timeless elegance, this estate sets a new standard for luxury living in Woodbury, NY, offering a lifestyle characterized by indulgence, sophistication, and unparalleled amenities.

8 Beds ⋅ 9 Baths ⋅ 000011 MLS

Introducing the most sought-after home in Woodbury, 5 Kodiak Drive. An epitome of contemporary luxury nestled in Syosset School District. This architectural masterpiece redefines opulence with its sleek design and an array of innovative amenities, ensuring a lifestyle of unparalleled comfort and sophistication. Situated on a sprawling one-acre lot, this estate seamlessly combines modernity with timeless elegance. As you step through the grand entrance, you're greeted by a fusion of sleek lines and luxurious materials, setting the stage for an exceptional living experience. Crafted for the most discerning homeowner, this residence boasts 8 bedrooms and 9 bathrooms, each meticulously designed with premium finishes and thoughtful details. Smart climate control systems, integrated sound, and lighting elevate the living experience to new heights. The main level is a haven for relaxation and entertainment. A stylish bar room invites you to unwind by the fireplace, while the formal dining room offers the perfect setting for intimate gatherings. The gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, pizza oven, custom cabinetry, and a breakfast area overlooking the lush backyard. Outside, the expansive grounds offer a sanctuary for outdoor living. A private tennis court with overhead lighting provides endless opportunities for recreation, while the heated in-ground Gunite pool and cabana area offer a serene retreat for lazy afternoons and al fresco dining. The pool features an infinity edge and a mesmerizing water feature with multiple fire elements, creating a captivating ambiance. Upstairs, the primary suite is a luxurious escape, complete with a sitting area, private balcony, and spa-like ensuite bath featuring a soaking tub and steam shower. Four additional bedrooms, each with its own ensuite bathroom, provide ample space for family and guests. Downstairs, the lower level is a hub of activity, with a fitness room, billiards area, and home theater offering endless entertainment options. A three-car garage provides ample space for vehicles and storage, while smart home features ensure convenience and security. With its blend of contemporary design and timeless elegance, this estate sets a new standard for luxury living in Woodbury, NY, offering a lifestyle characterized by indulgence, sophistication, and unparalleled amenities.

5 Kodiak Drive, Woodbury

$2,999,000

Welcome to Crest Hill! An extraordinary luxury estate set on 2.02 private acres in the heart of prestigious Woodbury, New York. 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.

5 Beds ⋅ 6 Baths ⋅ 1005913 MLS

Welcome to Crest Hill! An extraordinary luxury estate set on 2.02 private acres in the heart of prestigious Woodbury, New York. 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

$2,995,000

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

4 Beds ⋅ 6 Baths ⋅ 24163576 MLS

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury

$2,895,000

Welcome to this stunning, fully gut-renovated Contemporary nestled on one of the largest lots in the prestigious gated community of Windemere — a rare 1.26-acre private cul-de-sac setting with room for a pool and endless possibilities. From the moment you arrive via the elegant circular driveway, this 5-bedroom, 5.5-bath showpiece makes an unforgettable impression. Thoughtfully designed with soaring ceiling heights and an open-concept layout, walls of glass and sliders flood every room with natural light, creating a bright, airy atmosphere throughout. The designer kitchen is a true centerpiece, featuring high-end appliances and seamlessly flowing into a sun-drenched sunroom and a massive great room — perfect for everyday living and effortless entertaining. A wet bar and sleek linear fireplace add sophistication to the living spaces, while the upstairs loft offers flexible additional living space. The main-floor primary suite is a private sanctuary unto itself, complete with sliding glass doors opening to the expansive Trex deck, floating stairs, a custom walk-in closet, and a spa-inspired bath boasting radiant heat flooring, a built-in towel warmer, and a freestanding soaking tub. Step outside to your own resort-style backyard retreat — a massive Trex deck with a full outdoor kitchen and multiple lounge and dining areas, with stairs leading down to the sprawling backyard. The full finished walk-out basement adds tremendous additional living and entertaining space, completing this exceptional offering. A truly rare opportunity in one of the area's most sought-after communities.

6 Beds ⋅ 6 Baths ⋅ 989712 MLS

Welcome to this stunning, fully gut-renovated Contemporary nestled on one of the largest lots in the prestigious gated community of Windemere — a rare 1.26-acre private cul-de-sac setting with room for a pool and endless possibilities. From the moment you arrive via the elegant circular driveway, this 5-bedroom, 5.5-bath showpiece makes an unforgettable impression. Thoughtfully designed with soaring ceiling heights and an open-concept layout, walls of glass and sliders flood every room with natural light, creating a bright, airy atmosphere throughout. The designer kitchen is a true centerpiece, featuring high-end appliances and seamlessly flowing into a sun-drenched sunroom and a massive great room — perfect for everyday living and effortless entertaining. A wet bar and sleek linear fireplace add sophistication to the living spaces, while the upstairs loft offers flexible additional living space. The main-floor primary suite is a private sanctuary unto itself, complete with sliding glass doors opening to the expansive Trex deck, floating stairs, a custom walk-in closet, and a spa-inspired bath boasting radiant heat flooring, a built-in towel warmer, and a freestanding soaking tub. Step outside to your own resort-style backyard retreat — a massive Trex deck with a full outdoor kitchen and multiple lounge and dining areas, with stairs leading down to the sprawling backyard. The full finished walk-out basement adds tremendous additional living and entertaining space, completing this exceptional offering. A truly rare opportunity in one of the area's most sought-after communities.

7 Windemere Crest, Woodbury

$2,599,000

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.

6 Beds ⋅ 7 Baths ⋅ 1063885 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

$2,548,000

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.

5 Beds ⋅ 6 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

$2,499,999

Welcome to 3 Aron Drive, a completely reimagined and fully renovated expanded Colonial in the highly desirable “Castle” section of Woodbury, within the sought-after Syosset School District. No expense was spared in transforming this exceptional 4-bedroom, 4-bath home, which showcases top-of-the-line materials, sophisticated finishes, and thoughtful craftsmanship throughout. Step inside to a fresh, modern interior filled with natural light and designed for today’s lifestyle. The beautifully redesigned living spaces offer an effortless flow for both everyday living and entertaining, while the stunning new kitchen serves as the heart of the home with high-end finishes, premium appliances, and a refined contemporary feel. Spacious living and dining areas provide the perfect setting for gatherings, while the inviting family room offers a comfortable place to unwind. Upstairs, four generously sized bedrooms provide ample space and storage, while the beautifully renovated bathrooms feature stylish, quality finishes. From the major systems to the smallest details, the home has been comprehensively updated to deliver modern comfort, functionality, and peace of mind. A full basement provides additional space and endless possibilities for a home gym, playroom, media room, office, or recreation area. Outside, the home sits on an oversized property of more than half an acre, offering a private, park-like backyard with plenty of room for entertaining, play, and outdoor enjoyment. Combining a premier Woodbury location, Syosset schools, expansive property, and a truly top-to-bottom renovation, 3 Aron Drive is a rare move-in-ready opportunity you will not want to miss. Make this extraordinary home your next home.

4 Beds ⋅ 4 Baths ⋅ 1049514 MLS

Welcome to 3 Aron Drive, a completely reimagined and fully renovated expanded Colonial in the highly desirable “Castle” section of Woodbury, within the sought-after Syosset School District. No expense was spared in transforming this exceptional 4-bedroom, 4-bath home, which showcases top-of-the-line materials, sophisticated finishes, and thoughtful craftsmanship throughout. Step inside to a fresh, modern interior filled with natural light and designed for today’s lifestyle. The beautifully redesigned living spaces offer an effortless flow for both everyday living and entertaining, while the stunning new kitchen serves as the heart of the home with high-end finishes, premium appliances, and a refined contemporary feel. Spacious living and dining areas provide the perfect setting for gatherings, while the inviting family room offers a comfortable place to unwind. Upstairs, four generously sized bedrooms provide ample space and storage, while the beautifully renovated bathrooms feature stylish, quality finishes. From the major systems to the smallest details, the home has been comprehensively updated to deliver modern comfort, functionality, and peace of mind. A full basement provides additional space and endless possibilities for a home gym, playroom, media room, office, or recreation area. Outside, the home sits on an oversized property of more than half an acre, offering a private, park-like backyard with plenty of room for entertaining, play, and outdoor enjoyment. Combining a premier Woodbury location, Syosset schools, expansive property, and a truly top-to-bottom renovation, 3 Aron Drive is a rare move-in-ready opportunity you will not want to miss. Make this extraordinary home your next home.

3 Aron Drive, Woodbury

$2,495,990

Experience refined living in this beautifully renovated Colonial in Woodbury’s sought-after Swan Lake development, within the Syosset School District. A grand entrance welcomes you to 10 thoughtfully designed rooms, ideal for both everyday comfort and elegant entertaining. The formal living room offers a gracious gathering space, while the modern open kitchen features a center island and ample room for gourmet cooking. Five bedrooms include a convenient first-floor bedroom with a full bath. The primary suite is a private retreat, complete with a beautifully remodeled bathroom and custom-designed walk-in closets. Outdoors, enjoy an in-ground pool, outdoor kitchen, and expansive areas for entertaining. A full basement with an outside entrance provides abundant storage and flexible-use space. The three-car garage offers convenient access through the kitchen. Ideally located near transportation, this exceptional Woodbury home offers comfort, style, and convenience.

5 Beds ⋅ 4 Baths ⋅ 1062978 MLS

Experience refined living in this beautifully renovated Colonial in Woodbury’s sought-after Swan Lake development, within the Syosset School District. A grand entrance welcomes you to 10 thoughtfully designed rooms, ideal for both everyday comfort and elegant entertaining. The formal living room offers a gracious gathering space, while the modern open kitchen features a center island and ample room for gourmet cooking. Five bedrooms include a convenient first-floor bedroom with a full bath. The primary suite is a private retreat, complete with a beautifully remodeled bathroom and custom-designed walk-in closets. Outdoors, enjoy an in-ground pool, outdoor kitchen, and expansive areas for entertaining. A full basement with an outside entrance provides abundant storage and flexible-use space. The three-car garage offers convenient access through the kitchen. Ideally located near transportation, this exceptional Woodbury home offers comfort, style, and convenience.

6 Chauncey Place, Woodbury

$2,349,000

Perched high on a hill within The Gates of Woodbury, this impressive 3600 square foot Colonial boasts 6 bedrooms, 3.5 baths - a compelling combination of space, privacy and versatility. Set on over one acre of fully fenced property, 39 Orchard Court enjoys an elevated presence and a beautifully level backyard. It's ideal for entertaining and offers plenty of room for future outdoor amenities such as a tennis or sport court. Inside, generously proportioned rooms present a flexible layout for everyday living and gatherings... including a spacious living room with fireplace and an additional sitting room through French doors. The expansive family room also features a wood-burning fireplace. A large eat-in kitchen and separate dining room provide ample space for casual meals or special occasions. Just off the kitchen, a dedicated gym room with wall-to-wall windows overlooks the beautiful backyard. Two main-level bedrooms and a full bath affords options for guests, home offices and multi-generational living. Upstairs, the primary bedroom features a fireplace, two walk-in closets and an en-suite bath with a steam shower and jacuzzi tub. Three additional oversized bedrooms complete the second floor. The full basement with egress includes a theatre room, sound-proof music room and abundant storage - so much potential for endless entertainment! A 3 car garage allows for additional space for vehicles and equipment. With its gracious setting, substantial square footage, expansive rooms and grounds, 39 Orchard Court gives you the room to explore so many possibilities. Gunite pool offered as-is. Conveniently located near all major highways, the train station and shopping centers, and within the Syosset School District. Don't miss this opportunity to live in The Gates! More pictures coming soon.

6 Beds ⋅ 4 Baths ⋅ 1054993 MLS

Perched high on a hill within The Gates of Woodbury, this impressive 3600 square foot Colonial boasts 6 bedrooms, 3.5 baths - a compelling combination of space, privacy and versatility. Set on over one acre of fully fenced property, 39 Orchard Court enjoys an elevated presence and a beautifully level backyard. It's ideal for entertaining and offers plenty of room for future outdoor amenities such as a tennis or sport court. Inside, generously proportioned rooms present a flexible layout for everyday living and gatherings... including a spacious living room with fireplace and an additional sitting room through French doors. The expansive family room also features a wood-burning fireplace. A large eat-in kitchen and separate dining room provide ample space for casual meals or special occasions. Just off the kitchen, a dedicated gym room with wall-to-wall windows overlooks the beautiful backyard. Two main-level bedrooms and a full bath affords options for guests, home offices and multi-generational living. Upstairs, the primary bedroom features a fireplace, two walk-in closets and an en-suite bath with a steam shower and jacuzzi tub. Three additional oversized bedrooms complete the second floor. The full basement with egress includes a theatre room, sound-proof music room and abundant storage - so much potential for endless entertainment! A 3 car garage allows for additional space for vehicles and equipment. With its gracious setting, substantial square footage, expansive rooms and grounds, 39 Orchard Court gives you the room to explore so many possibilities. Gunite pool offered as-is. Conveniently located near all major highways, the train station and shopping centers, and within the Syosset School District. Don't miss this opportunity to live in The Gates! More pictures coming soon.

39 Orchard Court, Woodbury

$2,299,999

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

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

$2,200,000

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.

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

$2,149,900

Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully designed living space. Multiple bedroom suites and an open floor plan provide room for everyone, with inviting spaces for both everyday living and entertaining. The beautiful kitchen opens to a covered porch overlooking an expansive patio and gunite pool, creating a seamless connection between indoor and outdoor gatherings. Car enthusiasts will appreciate the remarkable garage and barn space. An attached, heated three-car garage is complemented by a lower-level garage with room for several additional vehicles. An impressive detached barn, constructed with steel and concrete, accommodates another six to eight cars and features heat, a half bath, glass garage doors, and both upper- and lower-level access. Outside, meticulous landscaping and a paved driveway enhance the setting, while a spacious front patio provides the perfect spot to enjoy the sunsets. An open meadow offers room for outdoor celebrations or potential equestrian use. With its generous living spaces, exceptional vehicle storage, and beautifully maintained grounds, this distinctive property offers far more than the ordinary.

5 Beds ⋅ 5 Baths ⋅ 24209591 MLS

Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully designed living space. Multiple bedroom suites and an open floor plan provide room for everyone, with inviting spaces for both everyday living and entertaining. The beautiful kitchen opens to a covered porch overlooking an expansive patio and gunite pool, creating a seamless connection between indoor and outdoor gatherings. Car enthusiasts will appreciate the remarkable garage and barn space. An attached, heated three-car garage is complemented by a lower-level garage with room for several additional vehicles. An impressive detached barn, constructed with steel and concrete, accommodates another six to eight cars and features heat, a half bath, glass garage doors, and both upper- and lower-level access. Outside, meticulous landscaping and a paved driveway enhance the setting, while a spacious front patio provides the perfect spot to enjoy the sunsets. An open meadow offers room for outdoor celebrations or potential equestrian use. With its generous living spaces, exceptional vehicle storage, and beautifully maintained grounds, this distinctive property offers far more than the ordinary.

348 Weekeepeemee Rd, Woodbury

$2,049,888

Discover unparalleled luxury in this stunning 4,333 sq ft uber luxurious New Construction, perfectly positioned on a sprawling half-acre in the heart of Woodbury. Located within the prestigious Syosset School District, this custom-built home offers modern elegance, top-tier finishes, and exceptional attention to detail throughout. Step inside to a sun-drenched, open-concept layout featuring a luxurious eat-in kitchen equipped with a massive center island, premium Sub-Zero/Wolf appliance package, and elegant custom cabinetry. The seamless flow continues into the spacious living room with a sleek see-through fireplace, a spacious formal dining room, a stunning a cozy den with an additional fireplace, and a versatile office or guest bedroom on the main level. The grand primary suite is a true retreat—offering soaring ceilings, multiple walk-in closets, and a spa-inspired bathroom with designer fixtures. Three additional bedrooms include a Jack and Jill bathroom and a private en-suite, ideal for family or guests. The fully finished basement provides exceptional bonus space with multiple egress windows, a bedroom, full bathroom, and endless possibilities for recreation, gym, or media room. Energy efficiency meets cutting-edge tech with owned solar panels and a Tesla Powerwall energy storage system. Enjoy built-in speakers throughout, and too many upgrades and extras to list. This is a rare opportunity to own a move-in-ready, luxury home in one of Long Island’s most desirable communities. A must-see!

6 Beds ⋅ 5 Baths ⋅ 1059193 MLS

Discover unparalleled luxury in this stunning 4,333 sq ft uber luxurious New Construction, perfectly positioned on a sprawling half-acre in the heart of Woodbury. Located within the prestigious Syosset School District, this custom-built home offers modern elegance, top-tier finishes, and exceptional attention to detail throughout. Step inside to a sun-drenched, open-concept layout featuring a luxurious eat-in kitchen equipped with a massive center island, premium Sub-Zero/Wolf appliance package, and elegant custom cabinetry. The seamless flow continues into the spacious living room with a sleek see-through fireplace, a spacious formal dining room, a stunning a cozy den with an additional fireplace, and a versatile office or guest bedroom on the main level. The grand primary suite is a true retreat—offering soaring ceilings, multiple walk-in closets, and a spa-inspired bathroom with designer fixtures. Three additional bedrooms include a Jack and Jill bathroom and a private en-suite, ideal for family or guests. The fully finished basement provides exceptional bonus space with multiple egress windows, a bedroom, full bathroom, and endless possibilities for recreation, gym, or media room. Energy efficiency meets cutting-edge tech with owned solar panels and a Tesla Powerwall energy storage system. Enjoy built-in speakers throughout, and too many upgrades and extras to list. This is a rare opportunity to own a move-in-ready, luxury home in one of Long Island’s most desirable communities. A must-see!

46 Plainview Road, Woodbury

$1,999,999

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!

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

$1,999,888

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.

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

$1,975,000

The Sagamore at Mill Ponds is an Exclusive Gated Community in Woodbury Featuring 76 Homes w/Soaring Ceilings and Walls of Black Clad Windows. Residents Enjoy the Private Clubhouse Offering Sitting Rooms w/Fireplace, Card Playing, Bar, Pool Table, TV, Gym, Golf Simulator, & Screening Room. Additional Amenities Include an Outdoor Pool, Gas Grill & Outdoor Seating, Fire Pit, Tennis & Pickleball Courts, Putting Green, Playground & Dog Park. The Community is Beautifully Landscaped Utilizing a Consistent Color Scheme. This Sought After End Unit Features 10' Ceilings & 8' Interior Solid Wood Doors on the Main Living Floor; 9' Ceilings & 7' Doors Complete the Second Floor & Basement. The Outdoor Views are Wonderful! Custom Shades Throughout. Spacious Primary Suite w/2 Walk In Closets & Double Door Balcony w/Double Screens. Watch the Sunsets! $280,000 of Upgrades Including: Custom Upgraded Center Island Kitchen & Butler's Pantry-Cabinetry to Ceiling, "Dekcon" Kitchen Counters & Backsplash, Oversize Built-In Sub-Zero Refrigerator, Stainless Range Hood & Built-In Microwave/Convection/Air Fryer. 5" Hardwood Flooring. Upgraded Plumbing, Electrical, Bathrooms, Paint & Hardware! Closets are Customized. Larger Deck w/Railings. Epoxy-Like Flooring in Waterproofed Basement & 2 Car Garage. High Efficiency 2 Zone Central Air & Gas Heating System & Tankless Gas Hot Water Heater. A Luxurious Townhouse End Unit Which Shows Off the Lovely Landscaping & Flowers Offering Privacy & Beauty. All Located in Woodbury, Within the Renowned Syosset School District and Offering Access to Town Parks and Tobay Beach.

3 Beds ⋅ 4 Baths ⋅ 1061196 MLS

The Sagamore at Mill Ponds is an Exclusive Gated Community in Woodbury Featuring 76 Homes w/Soaring Ceilings and Walls of Black Clad Windows. Residents Enjoy the Private Clubhouse Offering Sitting Rooms w/Fireplace, Card Playing, Bar, Pool Table, TV, Gym, Golf Simulator, & Screening Room. Additional Amenities Include an Outdoor Pool, Gas Grill & Outdoor Seating, Fire Pit, Tennis & Pickleball Courts, Putting Green, Playground & Dog Park. The Community is Beautifully Landscaped Utilizing a Consistent Color Scheme. This Sought After End Unit Features 10' Ceilings & 8' Interior Solid Wood Doors on the Main Living Floor; 9' Ceilings & 7' Doors Complete the Second Floor & Basement. The Outdoor Views are Wonderful! Custom Shades Throughout. Spacious Primary Suite w/2 Walk In Closets & Double Door Balcony w/Double Screens. Watch the Sunsets! $280,000 of Upgrades Including: Custom Upgraded Center Island Kitchen & Butler's Pantry-Cabinetry to Ceiling, "Dekcon" Kitchen Counters & Backsplash, Oversize Built-In Sub-Zero Refrigerator, Stainless Range Hood & Built-In Microwave/Convection/Air Fryer. 5" Hardwood Flooring. Upgraded Plumbing, Electrical, Bathrooms, Paint & Hardware! Closets are Customized. Larger Deck w/Railings. Epoxy-Like Flooring in Waterproofed Basement & 2 Car Garage. High Efficiency 2 Zone Central Air & Gas Heating System & Tankless Gas Hot Water Heater. A Luxurious Townhouse End Unit Which Shows Off the Lovely Landscaping & Flowers Offering Privacy & Beauty. All Located in Woodbury, Within the Renowned Syosset School District and Offering Access to Town Parks and Tobay Beach.

10 Three Ponds Lane, Woodbury

$1,825,000

NEW PRICE — Exceptional Hudson Valley value at $1,825,000. Over 7,500 SF of finished living space with heated pool, true 5-car garage, protected rear views and extensive outdoor living—all within reach of New York City. The Hudson Valley remains one of the New York metropolitan area's most overlooked suburban opportunities—a true hidden gem for buyers seeking more space, privacy, natural beauty, and quality of life. While many buyers begin in Westchester, Northern New Jersey, Long Island, or Connecticut, the Hudson Valley offers a compelling alternative: lower-density communities, mountains, parks, orchards, wineries, and dramatically more property for the money. Woodbury is particularly well positioned, with I-87, Harriman train station, Woodbury Common Premium Outlets, Bear Mountain and West Point all easily accessible. The property is in the Monroe-Woodbury Central School District. Monroe-Woodbury High School is rated A- by Niche and ranks relatively high among New York public high schools on SchoolDigger. The district also has a strong athletic tradition, including recent state championship success in cross country and deep Class AA football playoff runs. Against that backdrop, 23 Greenwich Ave stands out as an exceptional Hudson Valley mini estate. Set on 0.76 acre in The Greens of Woodbury, the home offers more than 7,500 square feet of finished living space, a heated pool, true five-car garage, extensive outdoor entertaining areas, and remarkable privacy. The rear borders protected Town of Woodbury land and Falkirk Golf Course, creating a permanent open backdrop with no future residential construction directly behind the home. The residence includes 5,312 square feet above grade plus approximately 2,200 square feet of fully finished lower-level living space, making it the largest home in The Greens of Woodbury. Years of substantial owner investment have transformed the original 2003 structure with hand-forged iron-and-glass entry doors, statement chandeliers, solid hardwood flooring, motorized window treatments, extensive landscaping and hardscaping, and whole-house solar installed in 2024. Inside, generous living and entertaining spaces include a dramatic two-story foyer and a soaring two-story great room/family room with expansive glass walls and a signature five-tier jade-based crystal chandelier, along with a formal dining room, chef's kitchen, and main-floor in-law suite with private balcony access. Upstairs, the expansive primary suite features a dual-aspect balcony, steam shower, whirlpool tub, two walk-in closets, and dedicated office or yoga space, along with additional en-suite bedrooms. The finished lower level adds approximately 2,200 square feet of recreation and guest space, including a bar area, billiards and ping pong areas, sauna with adjoining full bath, au pair or guest suite with en-suite bath, and multi-person whirlpool. Outside, a 792-square-foot heated pool with waterfall is surrounded by expansive stone-paver terraces and multiple entertaining areas, including a large grilling station, covered pavilion, and separate fire-pit lounge. Multi-level planted terraces, automated landscape lighting, retaining walls, and ornamental iron fencing complete the private setting. The approximately 1,482-square-foot attached garage provides true five-car capacity plus substantial workspace. There is no HOA. Woodbury Common and I-87 are about five minutes away, Harriman train station about nine minutes, Bear Mountain about 15 minutes, Legoland about 20 minutes, and West Point about 25 minutes. Manhattan is reachable by car in roughly 50 minutes under favorable traffic conditions. With five bedrooms, six full and one half baths, three fireplaces, heated pool, five-car garage, protected rear views, and genuine privacy, 23 Greenwich Ave captures exactly what makes the Hudson Valley such a compelling hidden gem: substantially more home, land, amenities, and lifestyle for the money.

5 Beds ⋅ 7 Baths ⋅ 994262 MLS

NEW PRICE — Exceptional Hudson Valley value at $1,825,000. Over 7,500 SF of finished living space with heated pool, true 5-car garage, protected rear views and extensive outdoor living—all within reach of New York City. The Hudson Valley remains one of the New York metropolitan area's most overlooked suburban opportunities—a true hidden gem for buyers seeking more space, privacy, natural beauty, and quality of life. While many buyers begin in Westchester, Northern New Jersey, Long Island, or Connecticut, the Hudson Valley offers a compelling alternative: lower-density communities, mountains, parks, orchards, wineries, and dramatically more property for the money. Woodbury is particularly well positioned, with I-87, Harriman train station, Woodbury Common Premium Outlets, Bear Mountain and West Point all easily accessible. The property is in the Monroe-Woodbury Central School District. Monroe-Woodbury High School is rated A- by Niche and ranks relatively high among New York public high schools on SchoolDigger. The district also has a strong athletic tradition, including recent state championship success in cross country and deep Class AA football playoff runs. Against that backdrop, 23 Greenwich Ave stands out as an exceptional Hudson Valley mini estate. Set on 0.76 acre in The Greens of Woodbury, the home offers more than 7,500 square feet of finished living space, a heated pool, true five-car garage, extensive outdoor entertaining areas, and remarkable privacy. The rear borders protected Town of Woodbury land and Falkirk Golf Course, creating a permanent open backdrop with no future residential construction directly behind the home. The residence includes 5,312 square feet above grade plus approximately 2,200 square feet of fully finished lower-level living space, making it the largest home in The Greens of Woodbury. Years of substantial owner investment have transformed the original 2003 structure with hand-forged iron-and-glass entry doors, statement chandeliers, solid hardwood flooring, motorized window treatments, extensive landscaping and hardscaping, and whole-house solar installed in 2024. Inside, generous living and entertaining spaces include a dramatic two-story foyer and a soaring two-story great room/family room with expansive glass walls and a signature five-tier jade-based crystal chandelier, along with a formal dining room, chef's kitchen, and main-floor in-law suite with private balcony access. Upstairs, the expansive primary suite features a dual-aspect balcony, steam shower, whirlpool tub, two walk-in closets, and dedicated office or yoga space, along with additional en-suite bedrooms. The finished lower level adds approximately 2,200 square feet of recreation and guest space, including a bar area, billiards and ping pong areas, sauna with adjoining full bath, au pair or guest suite with en-suite bath, and multi-person whirlpool. Outside, a 792-square-foot heated pool with waterfall is surrounded by expansive stone-paver terraces and multiple entertaining areas, including a large grilling station, covered pavilion, and separate fire-pit lounge. Multi-level planted terraces, automated landscape lighting, retaining walls, and ornamental iron fencing complete the private setting. The approximately 1,482-square-foot attached garage provides true five-car capacity plus substantial workspace. There is no HOA. Woodbury Common and I-87 are about five minutes away, Harriman train station about nine minutes, Bear Mountain about 15 minutes, Legoland about 20 minutes, and West Point about 25 minutes. Manhattan is reachable by car in roughly 50 minutes under favorable traffic conditions. With five bedrooms, six full and one half baths, three fireplaces, heated pool, five-car garage, protected rear views, and genuine privacy, 23 Greenwich Ave captures exactly what makes the Hudson Valley such a compelling hidden gem: substantially more home, land, amenities, and lifestyle for the money.

23 Greenwich Avenue, Woodbury

$1,799,999

Elegant & Spacious 6-Bedroom Residence in Hunting Hill, Woodbury with Resort-Style Backyard Welcome to this beautifully updated and generously proportioned 6-bedroom, 3.5-bath residence, ideally located in the desirable Hunting Hill section of Woodbury. Offering an exceptional blend of elegance, comfort, and effortless entertaining, this home features a spacious layout, thoughtfully updated interiors, and a spectacular private outdoor retreat. Inside, the home showcases updated bathrooms, a beautifully appointed kitchen with granite countertops, hardwood floors, hi-hat lighting, and updated windows. The expansive floor plan includes two luxurious primary suites, offering exceptional flexibility, privacy, and comfort for family and guests. Additional highlights include a gas boiler, 200-amp electric service, whole-house water filtration system, central air conditioning updated in 2021, and a mini-split system for enhanced year-round comfort. A two-car garage, two storage sheds, and a new whole-house generator provide convenience, functionality, and peace of mind. Step outside and experience your own private resort-style oasis. The beautifully landscaped grounds feature a heated in-ground pool, covered outdoor patio with TV, expansive paver patio and side yard, fire pit, and in-ground sprinkler system—creating an exceptional setting for summer entertaining, relaxing poolside, or enjoying memorable gatherings with family and friends. The property also offers newer siding and a roof approximately 10 years old, along with meticulously maintained outdoor spaces that enhance the home's impressive curb appeal. A truly special Woodbury home—beautifully updated, thoughtfully designed, and ready to be enjoyed.

6 Beds ⋅ 4 Baths ⋅ 1059145 MLS

Elegant & Spacious 6-Bedroom Residence in Hunting Hill, Woodbury with Resort-Style Backyard Welcome to this beautifully updated and generously proportioned 6-bedroom, 3.5-bath residence, ideally located in the desirable Hunting Hill section of Woodbury. Offering an exceptional blend of elegance, comfort, and effortless entertaining, this home features a spacious layout, thoughtfully updated interiors, and a spectacular private outdoor retreat. Inside, the home showcases updated bathrooms, a beautifully appointed kitchen with granite countertops, hardwood floors, hi-hat lighting, and updated windows. The expansive floor plan includes two luxurious primary suites, offering exceptional flexibility, privacy, and comfort for family and guests. Additional highlights include a gas boiler, 200-amp electric service, whole-house water filtration system, central air conditioning updated in 2021, and a mini-split system for enhanced year-round comfort. A two-car garage, two storage sheds, and a new whole-house generator provide convenience, functionality, and peace of mind. Step outside and experience your own private resort-style oasis. The beautifully landscaped grounds feature a heated in-ground pool, covered outdoor patio with TV, expansive paver patio and side yard, fire pit, and in-ground sprinkler system—creating an exceptional setting for summer entertaining, relaxing poolside, or enjoying memorable gatherings with family and friends. The property also offers newer siding and a roof approximately 10 years old, along with meticulously maintained outdoor spaces that enhance the home's impressive curb appeal. A truly special Woodbury home—beautifully updated, thoughtfully designed, and ready to be enjoyed.

4 Hunting Hill Road, Woodbury

$1,799,000

Welcome to this spacious and inviting one-family Colonial home, offering a wonderful combination of classic charm, comfortable living, and exceptional space for everyday enjoyment and entertaining. The first floor features a generous and thoughtfully designed layout, including a welcoming formal living room, formal dining room perfect for hosting gatherings, and a comfortable spacious family room ideal for relaxation. The spacious eat-in kitchen offers a dedicated everyday dining area, providing a warm and inviting setting for casual meals. A full bathroom on the main level adds convenience and functionality. The second floor features five generously sized bedrooms and three full bathrooms, offering ample space and flexibility for a variety of living arrangements. Beautiful wood flooring adds warmth and character throughout the home. Additional highlights include several updates and improvements, new gas heating burner and gas hot water heater installed in 2025, providing added comfort and efficiency. finished basement offering valuable additional recreational and entertainment space, and an attached two-car garage providing convenient parking and storage. Step outside to enjoy the expansive backyard, offering plenty of room for outdoor entertaining, gardening, relaxation, and recreational activities. With its generous proportions, versatile floor plan, multiple living and entertaining areas, and a blend of traditional Colonial character and modern-day comfort, this home presents a wonderful opportunity for buyers seeking space, functionality, and long-term value. A spacious Colonial home with five bedrooms, four full bathrooms, a finished basement, a two-car garage, and an expansive backyard.

5 Beds ⋅ 5 Baths ⋅ 1063529 MLS

Welcome to this spacious and inviting one-family Colonial home, offering a wonderful combination of classic charm, comfortable living, and exceptional space for everyday enjoyment and entertaining. The first floor features a generous and thoughtfully designed layout, including a welcoming formal living room, formal dining room perfect for hosting gatherings, and a comfortable spacious family room ideal for relaxation. The spacious eat-in kitchen offers a dedicated everyday dining area, providing a warm and inviting setting for casual meals. A full bathroom on the main level adds convenience and functionality. The second floor features five generously sized bedrooms and three full bathrooms, offering ample space and flexibility for a variety of living arrangements. Beautiful wood flooring adds warmth and character throughout the home. Additional highlights include several updates and improvements, new gas heating burner and gas hot water heater installed in 2025, providing added comfort and efficiency. finished basement offering valuable additional recreational and entertainment space, and an attached two-car garage providing convenient parking and storage. Step outside to enjoy the expansive backyard, offering plenty of room for outdoor entertaining, gardening, relaxation, and recreational activities. With its generous proportions, versatile floor plan, multiple living and entertaining areas, and a blend of traditional Colonial character and modern-day comfort, this home presents a wonderful opportunity for buyers seeking space, functionality, and long-term value. A spacious Colonial home with five bedrooms, four full bathrooms, a finished basement, a two-car garage, and an expansive backyard.

271 Syosset Woodbury Road, Woodbury

$1,688,888

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.

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

$1,599,000

New to market in the sought-after 55+ Kensington Estates gated community in Woodbury. Presenting a thoughtfully designed Chesapeake Model (end unit) offering second floor living with abundant natural light, featuring 3 bedrooms, 2.5 baths, a private elevator, and a one-car garage. The welcoming kitchen with center island, natural gas cooking, high-end stainless appliances,opens to the great room with gas fireplace and offer access to the open Trex balcony. The laundry room is conveniently located off the kitchen, while an elegant powder room is situated just down the hall. A separate dining area provides a lovely setting for more formal entertaining. The spacious primary suite with walk-in closets, has an elegantly appointed ensuite bath featuring herringbone ceramic tile flooring, a soaking tub, separate stall shower, and double-sink vanity with marble top. There are two additional bedrooms that share a Jack-and-Jill full bath. The hardwood floors, and deep floor, and crown moldings flow seamlessly throughout the home. This residence offers an exceptional combination of style, space, and ease. The 80-unit community allows residents to enjoy a relaxed lifestyle with a beautifully-appointed clubhouse featuring a welcoming lounge with fireplace, card and billiard room, library, catering kitchen, gym, outdoor heated pool with comfortable seating areas for sun and shade, and tennis/pickleball courts. Ideally situated within the Township of Huntington on the Suffolk/Nassau border, Kensington Estates is a gated community conveniently located near all, including the Northern State Parkway, LIE, Cold Spring Harbor train station, local shopping and dining in Huntington, Cold Spring Harbor and Plainview. Annual taxes under $10.000

3 Beds ⋅ 3 Baths ⋅ 1049153 MLS

New to market in the sought-after 55+ Kensington Estates gated community in Woodbury. Presenting a thoughtfully designed Chesapeake Model (end unit) offering second floor living with abundant natural light, featuring 3 bedrooms, 2.5 baths, a private elevator, and a one-car garage. The welcoming kitchen with center island, natural gas cooking, high-end stainless appliances,opens to the great room with gas fireplace and offer access to the open Trex balcony. The laundry room is conveniently located off the kitchen, while an elegant powder room is situated just down the hall. A separate dining area provides a lovely setting for more formal entertaining. The spacious primary suite with walk-in closets, has an elegantly appointed ensuite bath featuring herringbone ceramic tile flooring, a soaking tub, separate stall shower, and double-sink vanity with marble top. There are two additional bedrooms that share a Jack-and-Jill full bath. The hardwood floors, and deep floor, and crown moldings flow seamlessly throughout the home. This residence offers an exceptional combination of style, space, and ease. The 80-unit community allows residents to enjoy a relaxed lifestyle with a beautifully-appointed clubhouse featuring a welcoming lounge with fireplace, card and billiard room, library, catering kitchen, gym, outdoor heated pool with comfortable seating areas for sun and shade, and tennis/pickleball courts. Ideally situated within the Township of Huntington on the Suffolk/Nassau border, Kensington Estates is a gated community conveniently located near all, including the Northern State Parkway, LIE, Cold Spring Harbor train station, local shopping and dining in Huntington, Cold Spring Harbor and Plainview. Annual taxes under $10.000

221 Coach Drive, Woodbury

$1,590,000

It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.

4 Beds ⋅ 3 Baths ⋅ 24184948 MLS

It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.

40 Ruffin Rd, Woodbury

$1,525,000

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.

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

$1,488,878

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.

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

$1,450,000

Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in. Come enjoy the charming little town of Woodbury, only 90 minutes to NYC

3 Beds ⋅ 3 Baths ⋅ 24139312 MLS

Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in. Come enjoy the charming little town of Woodbury, only 90 minutes to NYC

819 Main St N, Woodbury

$1,395,000

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

3 Beds ⋅ 3 Baths ⋅ 24192284 MLS

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

$1,395,000

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

5 Beds ⋅ 5 Baths ⋅ 24168618 MLS

Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury

$1,379,000

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.

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

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