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1 Sycamore Drive, Woodbury
$4,875,000
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
6 Chauncey Place, Woodbury
$2,495,990
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
30 Elmwood Drive, Woodbury
$449,999
3 Beds ⋅ 3 Baths ⋅ 1063346 MLS
This move-in-ready, three-bedroom, two-bath ranch is located in Highland Mills within the Cornwall Central School District. The home offers approximately 1,408 square feet of main-level living space with a functional layout and inviting outdoor surroundings. A beautiful yard and surrounding woods create a peaceful setting for relaxing on the deck, gardening, or enjoying the outdoors. The full basement provides additional storage, while the one-car garage adds everyday convenience. Enjoy convenient access to shopping, dining, Hudson Valley hiking, and commuter routes to New York City. Eligible residents may also use Woodbury’s community pool and reservoir facilities for swimming, fishing, and other outdoor activities.

30 Elmwood Drive, Woodbury
12 Chauncey Place, Woodbury
$2,599,000
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
3 Stafford Avenue, Woodbury
$1,048,000
4 Beds ⋅ 3 Baths ⋅ 1063366 MLS
SHORT SALE! Can not walk property! No interior access. Ranch-style home featuring 4 bedrooms and 3 full bathrooms. Property is being sold as-is, subject to lender approval of short sale.

3 Stafford Avenue, Woodbury
221 Coach Drive, Woodbury
$1,599,000
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
271 Syosset Woodbury Road, Woodbury
$1,799,000
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
10 Three Ponds Lane, Woodbury
$1,975,000
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
67 Flanders Rd, Woodbury
$649,900
4 Beds ⋅ 4 Baths ⋅ 24213335 MLS
Welcome to this stunning, fully remodeled Colonial in Woodbury, located in beautiful Litchfield County! Situated on over 2 acres with a private pond, this home features 4 bedrooms, 2 full baths, 2 half baths, a fully remodeled basement, central air, and a 2-car garage with low taxes! Some of the recent updates include a new roof, windows, doors, and mechanicals. Enjoy peaceful pond views from the screened-in porch. This exceptional property is waiting for its new owner!

67 Flanders Rd, Woodbury
20 Canterbury Road, Woodbury
$999,000
3 Beds ⋅ 3 Baths ⋅ 1044983 MLS
Welcome to this charming split-level home nestled in the heart of Woodbury, located in the Syosset School District. Situated on an oversized 85'x150' lot, property offers plenty of space for entertaining, relaxing, and enjoying outdoor living. The beautifully established grounds feature mature specimen plantings adding privacy, character and natural beauty to the property. The home features 3 spacious bedrooms, 2.5 baths, and hardwood flooring throughout all bedrooms. A large den provides additional space for gatherings and everyday living. The 2-car garage offers ample parking and storage. Additional highlights include a gas heating system and a newer roof. Ideally located on a dead-end street within a cul-de-sac, this home offers both privacy and convenience. Enjoy close proximity to shopping, school, houses of worship and other local amenities. A wonderful opportunity to own a spacious home on a beautiful oversized property in desirable Woodbury location within the Syosset School District.

20 Canterbury Road, Woodbury
11 Judson Ave, Woodbury
$529,000
3 Beds ⋅ 2 Baths ⋅ 24210084 MLS
Looking for a convenient in town location? Built in 1940, this delightful vintage colonial is loaded with the charm of the 1940's. The front to back living room offers a fireplace, built ins as well as oak flooring. It also features a French door to the rear porch overlooking the spacious rear yard. Located adjacent to the kitchen, the formal dining room features a built-in china closet and oak flooring. A powder room and laundry area complete the main level. Upstairs, a front to back primary bedroom with oak flooring. There are two bedrooms and a full bath on this level. Need more room? The walk-up attic is floored provides the opportunity for future expansion. There is a rec room on the lower level for additional space.

11 Judson Ave, Woodbury
1217 Main St N, Woodbury
$699,900
3 Beds ⋅ 2 Baths ⋅ 24211238 MLS
Completely renovated and move-in ready, this three-bedroom ranch in North Woodbury has been gutted to the studs and beautifully rebuilt throughout. The open-concept layout features a gorgeous new kitchen with center island opening to a spacious family and dining area with plenty of room for larger gatherings. No detail was overlooked in the renovation. All three bedrooms feature hardwood floors, while the home also offers a new full bath, new laundry room, and a private side deck just off the entry. The finished lower level provides valuable additional living space for a family room, home office, exercise area, or recreation room. A rare opportunity to own a like-new ranch-style home in Woodbury with nothing left to do but move in and enjoy.

1217 Main St N, Woodbury
46 Plainview Road, Woodbury
$2,049,888
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
4 Hunting Hill Road, Woodbury
$1,799,999
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
266 Route 32, Woodbury
$525,000
1056587 MLS
A Rare Piece of Central Valley History Awaits Your Vision For the first time in over 60 years, one of the most prominent landmark properties in Central Valley is officially hitting the market. Situated right in the heart of the Hamlet Business District at the bustling intersection of Route 32 and Smith Clove Road, this mixed-use property offers a blank canvas for an ambitious business owner or a savvy real estate investor looking to build long-term wealth. High-Traffic Commercial Space The main level boasts over 1,500 square feet of versatile commercial space divided into three large, open rooms. It is an ideal setup for a retail boutique, professional office, or food service business. The location guarantees unmatched, round-the-clock exposure with more than 12,000 vehicles passing by each day. The current first-floor occupant—a beloved, multi-generational local business—is ready to downsize, leaving this prime footprint ready for its next chapter. Residential Income Potential Upstairs, with its own completely private entrance, sits an oversized 2-to-3-bedroom apartment. While this upper unit needs some TLC, it represents a fantastic value-add opportunity. You can renovate it to command premium residential rent, or live right above your shop for the ultimate live-work lifestyle. Parking and Convenience Parking is never an issue here. The property features a private driveway leading to a detached 2-car garage—perfect for extra storage or inventory—plus dedicated parking for 4 vehicles. For clients and customers, there is also ample municipal parking directly across the street. Surrounded by established local businesses, restaurants, and daily services, this is more than just a piece of real estate; it is a rare opportunity to anchor your business or portfolio at the busiest intersection in town.

266 Route 32, Woodbury
93 Eagle Chase, Woodbury
$1,200,000
2 Beds ⋅ 3 Baths ⋅ 1056673 MLS
Welcome to 93 Eagle Chase, an exceptional 2-bedroom, 2.5-bath townhouse nestled within the prestigious gated community of Eagle Chase in Woodbury. Set against a beautiful tranquil pond, this sophisticated home immediately welcomes you with soaring ceilings and an airy, open atmosphere. From the moment you step inside, the sense of space, natural light, and effortless flow creates an inviting feeling throughout. At the heart of the home is a completely remodeled open-concept kitchen, beautifully designed for both everyday living and entertaining. Featuring elegant quartz countertops, high-end appliances, and induction cooking, the kitchen seamlessly connects to the surrounding living and dining spaces, creating a modern and sophisticated gathering area. The spacious living room features a fireplace, adding warmth and character to the soaring, light-filled space. Abundant natural light and peaceful pond views create a beautiful backdrop, while the open layout offers an ideal balance of elegance and comfort for both entertaining and everyday living. The primary suite is a true private retreat, featuring its own balcony overlooking the beautiful pond. The suite is complemented by a beautifully remodeled en-suite bathroom with a double vanity and oversized shower. The second bedroom offers comfortable accommodations for family, guests, or a home office, while the additional half bath provides convenience for everyday living and entertaining. The fully finished basement offers valuable additional living space along with abundant storage, providing plenty of room for a recreation area, home office, media room, gym, or whatever best suits your lifestyle. A two-car garage with an epoxy floor adds convenience, functionality, and additional storage, while providing a polished and well-maintained space for your vehicles. Step outside to the pond-facing patio with a Trex deck, an inviting outdoor space designed for relaxing and entertaining while enjoying the peaceful water views. Enjoy a country club lifestyle, with an exceptional array of amenities including a clubhouse, fitness center, swimming pool, tennis, basketball, and pickleball courts. The gated community also offers 24-hour security, professional landscaping, and exterior maintenance, allowing you to enjoy a carefree lifestyle with resort-style amenities right outside your door. Conveniently located in Woodbury near major parkways, shopping, and dining. Syosset School District.

93 Eagle Chase, Woodbury
24 Roxbury Rd, Woodbury
$1,149,000
3 Beds ⋅ 3 Baths ⋅ 24209744 MLS
Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive Colonial-Contemporary residence offers an exceptional combination of privacy, natural beauty, and modern comfort on nearly 10 acres. Surrounded by mature trees, lush landscaping, and vibrant plantings, the property enjoys a peaceful, secluded setting with the gentle sounds of Transylvania Brook flowing just beyond the backyard. A long, paved, beautifully illuminated driveway leads to the home, where an impressive double-door entrance welcomes you into a spacious foyer featuring a unique indoor water feature. The thoughtfully designed interior offers three generously sized bedrooms, two-and-a-half beautifully renovated bathrooms with luxurious Italian marble tile, and recessed lighting throughout. The inviting lower-level family room opens through French doors to an expansive stone patio and a heated, inground Gunite swimming pool, creating an ideal setting for relaxing or entertaining. A bright four-season sunroom captures sweeping views of the surrounding landscape, while a dedicated office provides a comfortable and private work-from-home space. The spacious primary suite is a true retreat, featuring a walk-in closet, Jacuzzi tub, private balcony overlooking the pool, and a versatile bonus room that can be customized as a reading room, home gym, nursery, or additional living space. Additional fe

24 Roxbury Rd, Woodbury
39 Orchard Court, Woodbury
$2,349,000
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
1108 Evergreen Court Unit #65, Woodbury
$330,000
2 Beds ⋅ 2 Baths ⋅ 1056467 MLS
Welcome to 1108 Evergreen Court in Woodbury! This desirable end-unit condo offers added privacy and a great location next to the community pool. Enter through the foyer before heading upstairs to the main living area, where you’ll find a bright and inviting layout. The living room opens to a private deck, providing a great spot to relax and enjoy the outdoors. The galley-style kitchen offers convenient seating and opens to a separate dining area, perfect for everyday meals or entertaining. A detached garage with electric provides additional parking and storage, plus there is plenty of unassigned parking for residents and guests. Enjoy low-maintenance living with community amenities and convenient access to shopping, dining, recreation, and major roadways. With its end-unit location, deck, garage, ample parking, and proximity to the pool, 1108 Evergreen Court has plenty to offer!

1108 Evergreen Court Unit #65, Woodbury
74 Washington Road Unit 40, Woodbury
$290,000
2 Beds ⋅ 2 Baths ⋅ 24210496 MLS ⋅ Woodbury Village BLDG.
Rare opportunity in desirable Woodbury Village! This charming three-level townhouse offers flexible living space, beautiful natural light, and a peaceful setting in the heart of Woodbury. The main level welcomes you with a spacious living room featuring a large bay window and abundant natural light. The adjoining eat-in kitchen offers generous pantry storage and sliders leading to a private deck overlooking a lovely wooded green space-the perfect spot for morning coffee or relaxing outdoors. A convenient half bath with laundry and additional storage completes this level. Upstairs, you'll find two generously sized bedrooms with ample closet space, including a walk-in closet, along with a full bath and additional linen storage. The finished walk-out lower level adds valuable bonus space and offers endless possibilities as a home office, recreation room, guest space, gym, or additional living area. Sliding doors open to a covered outdoor area and backyard space. The basement has also been waterproofed and features newer carpeting. Additional features include space for a private garden, three portable air-conditioning units (one with heat), a basement dehumidifier, and deck furniture included by the seller. Woodbury Village offers a tranquil setting with expansive green space, mature trees, walking areas, and a river running through the complex-all while being conveniently located just minutes from Woodbury's shops, restaurants, and everyday amenities.

74 Washington Road Unit 40, Woodbury
348 Weekeepeemee Rd, Woodbury
$2,149,900
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
92 Quail Run Rd, Woodbury
$950,000
6 Beds ⋅ 4 Baths ⋅ 24209295 MLS
A private retreat with Million dollar views! Nestled at the end of a peaceful cul-de-sac, this 3800+ Colonial offers a rare combination of privacy, space, and breathtaking views. Set against a backdrop of rolling hills, with gorgeous sunsets - where every season brings a beautiful new view. Step inside and you'll be greeted by expansive LR/Great RM featuring soaring cathedral ceilings, freshly painted walls, and an abundance of natural light. Kitchen is appointed with granite countertops, SS appliances, double pantries, double sinks and a wine chiller making it functional and inviting. Rich Brazilian Cherry HW floors add warmth and elegance throughout the first floor. The first floor primary suite offers a peaceful retreat of its own, highlighted by a claw-foot soaking tub to relax while taking in the views. Upstairs, three additional bedrooms, along with a renovated full bathroom featuring marble walk-in shower and marble countertops. A cozy area(den) for family time and dedicated office space. Lets not forget the bonus living space above the garage. This separate entrance living space includes two-bedroom, kitchen, LR, laundry and garage space. The possibilities for extended family, guests, au pair, rental income or Airbnb option are endless.

92 Quail Run Rd, Woodbury
2 Pomperaug Rd, Woodbury
$875,000
3 Beds ⋅ 3 Baths ⋅ 24209527 MLS
Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby, yet is within walking distance to an amazing collection of local favorites, including fine restaurants, diners, a brewery, pub with live entertainment, and French bakery. No wonder they call it "Food-bury!" A stone path leads to a beautiful stone landing and a home filled with warmth and character. The spacious L-shaped living room offers two inviting gathering areas-one centered around a wood-burning fireplace with room for a grand piano, and the other warmed by a woodstove beside a full-wall library and second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three sides, perfect for breakfast, reading, art, TV, or simply enjoying the view. The charming country kitchen is exceptionally appointed with premium Viking, Miele, Sub-Zero, Dacor and Fisher & Paykel appliances, including an induction cooktop, wall and speed ovens, warming drawer and 2-drawer dishwasher. Thoughtful details include Waterworks fixtures, a pot filler, custom pull-out cabinetry and under-cabinet lighting. Two staircases lead to three restful bedrooms and two beautifully renovated full baths. The primary bath features a Waterworks vanity with quartz top and Waterworks hardware, while the second bath creates a spa-like retreat with a soaking tub and steam shower.

2 Pomperaug Rd, Woodbury
229 Bacon Pond Rd Unit 312, Woodbury
$199,900
2 Beds ⋅ 1 Baths ⋅ 24209657 MLS ⋅ Town In Country BLDG.
Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern flooring flows from the kitchen to the fireplace, offering a perfect place for family gatherings. Around the corner you'll find two bedrooms and 1 full bath - the bathroom has been updated and modernized featuring a brand new vanity and tiled shower. The slider door leads to a private patio which is just a short walk down to the in ground pool. Enjoy everything Woodbury has to offer - Rt. 6 is minutes away offering plenty of restaurants and shopping, with I84 just a short drive away. Whether you enjoy laying by the pool or hiking through a number of trails this is the perfect location for the discerning consumer.

229 Bacon Pond Rd Unit 312, Woodbury
63 Main St N, Woodbury
$849,900
4 Beds ⋅ 2 Baths ⋅ 24208978 MLS
Reader's Digest named Woodbury the "Most Charming Small Town in Connecticut" in 2024 and received the same recognition in 2020 and 2018.That fits this home perfectly. 63 Main St N is an 1850 antique home with a 2002 addition, offering 4 bedrooms, 2 updated bathrooms and 2,662 square feet of delight on 0.36 acres. It has the historic character people expect from Main Street - mahogany-floored wrap-around porch, oak floors, built-ins and fireplaces - while also having an open kitchen/dining/family-room layout, gas log fireplace, first-floor bedroom, updated bath and attached garage. The backyard should be another major focus. It has beautiful stone walls, an outdoor fireplace, new 43" outdoor gas grill, hot tub, irrigation system and a completely flat yard with room for entertaining and potentially a future pool.

63 Main St N, Woodbury
2 Woodtree Drive, Woodbury
$899,000
3 Beds ⋅ 3 Baths ⋅ 1054251 MLS
Welcome to 2 Woodtree Drive at The Woodlands. This turnkey, DIAMOND-condition, 3-bedroom, 2.5-bathroom home awaits. This corner unit, gut-renovated in 2018, features top-of-the-line finishes, custom millwork, and a bright, open layout while maintaining a cozy feel throughout. Upon entry, you'll find a beautiful kitchen with stainless steel Bosch appliances, wooden cabinetry, and a bright double slider to the patio. The laundry area is conveniently located between the kitchen and the generously sized den/living room, with an adjacent dining room. This level also features a tastefully appointed half bathroom. Upstairs, the primary bed and bath are generously sized, with two additional bedrooms and one additional bathroom. Additionally, it has reverse osmosis drinking water, a full-house filtration system, and a Nest thermostat. This is easy living at its finest, with amenities including a clubhouse, tennis courts, a pool, and beautiful grounds. Minutes from trails and nature paths. Extremely close to the LIRR at both Cold Spring Harbor and Syosset stations. Syosset School District. **Parking lot is the first right when you come into The Woodlands - Park in any of the spots**

2 Woodtree Drive, Woodbury
47 Woods Way Unit 47, Woodbury
$294,900
2 Beds ⋅ 2 Baths ⋅ 24209304 MLS ⋅ Woodlake BLDG.
Welcome to 47 Woods Way! This beautifully renovated Woodlake townhouse is truly move-in ready, offering stylish updates and the convenience of a garage just steps from your front door. Step inside to discover a gorgeous new kitchen featuring crisp white Shaker cabinetry, gleaming quartz countertops, and stainless steel appliances. New RevWood by Mohawk flooring flows throughout the first floor, complemented by a charming shiplap-accented fireplace that creates a warm and inviting focal point in the living room. Upstairs, the spacious primary suite offers a beautifully renovated ensuite bathroom, creating a private retreat at the end of the day. Enjoy a brand-new tiled shower with niche, modern vanity and tasteful finishes. The guest bathroom has also been thoughtfully updated with new porcelain tile flooring, oak vanity, new lighting, and mirror. Plush new wall-to-wall carpeting throughout the second floor lends a cozy, fresh feel to the bedrooms. A brand new hot water heater, and a two year old HVAC system add comfort and peace of mind. The amenities continue with a garage featuring a new door opener, plus a full unfinished basement offering excellent storage and flexibility. A newer washer and dryer and a private sun deck off the living room round out the package. With its fresh renovations, thoughtful updates, and convenient location, 47 Woods Way offers the perfect blend of style, comfort, and easy living. Just unpack and enjoy!

47 Woods Way Unit 47, Woodbury
578 Old Sherman Hill Rd, Woodbury
$550,000
3 Beds ⋅ 2 Baths ⋅ 24206868 MLS
Charming Brick Ranch on 2+ Acres Nestled on more than two acres in a peaceful setting, this well-built brick ranch offers the perfect blend of privacy, comfort, and convenience, with easy access to shopping, dining, and everyday amenities. The home has been freshly painted, meticulously maintained, and reflects pride of ownership throughout. Inside, you'll find a spacious and inviting floor plan featuring hardwood flooring in the living room and all three bedrooms, adding warmth and character to the main living spaces. The kitchen and pantry are finished with durable vinyl flooring, providing easy care and everyday practicality. The generously sized kitchen features ample counter space, a pantry, a cozy eating area, and a gas fireplace, making it an ideal gathering place for family and friends. The living room is enhanced by built-in bookcases, while the bedrooms offer hardwood floors and built-in desks, combining charm with functionality. The primary bedroom includes a private full bath, creating a comfortable retreat. Additional highlights include a lower-level room, a workshop with walkout access, a tandem garage with room for vehicles and storage, and a fully insulated walk-up attic offering exciting possibilities for future expansion, hobbies, or additional storage. If you're looking for a solidly constructed home with acreage, character, and room to grow, this property presents a rare opportunity to enjoy country-style tranquility without sacrificing convenien

578 Old Sherman Hill Rd, Woodbury
69 Nonnewaug Rd, Woodbury
$850,000
4 Beds ⋅ 3 Baths ⋅ 24208716 MLS
A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-bedroom, 3-bath home offers an incredible combination of space, privacy, and outdoor living. Surrounded by beautiful natural scenery, the expansive property provides plenty of room to spread out, explore, garden, entertain, or simply enjoy the peaceful setting. Spend warm summer days relaxing by the pool, host gatherings with family and friends, or unwind and take in the privacy of your own country retreat. Inside, the home offers a comfortable and inviting layout with three bedrooms and three full baths, providing plenty of space for everyday living and guests. But the lifestyle extends well beyond the walls-with nearly 10 acres and your own pool, there's plenty of opportunity to enjoy the property throughout the seasons. Located in the charming town of Woodbury, known for its quintessential New England character, historic appeal, local shops, restaurants, and picturesque countryside, this home offers a wonderful balance of privacy and convenience. If you've been dreaming of more land, more privacy, and a place where home feels like a getaway, 69 Nonnewaug Road is one you won't want to miss!

69 Nonnewaug Rd, Woodbury
60 Chestnut Lane, Woodbury
$1,249,000
4 Beds ⋅ 4 Baths ⋅ 1051323 MLS
Perfectly Located on the Greenbelt, this Rare updated Briarwood has all the bells and whistles. Newer Kitchen and Baths! Timeless elegance includes Brazilian Cherry Flooring, Detailed Moldings, Updated Marvin Windows, Solid Wood Doors, Wrought Iron and Wood Railings, Woodburning FP in Great Room, Custom Top of the Line Chefs Kitchen with Soft Close German designed Cabinetry System, Granite counters and Back Splash, High end SS appliances (Kitchenaide French Door refrigerator, Bosch Double Oven with Vented Hood, Bosch Convection Cooktop, Bosch DW) including GE Profile wine frig, Newer 3 zone Heating and CAC, CVAC, Newer LG Washer/Dryer, Cedar Closet. Trex Deck off Dining Room, Paver Patio off lower level Family Room, Lower Level with Separate Office/ Bedroom, Full Bathroom, New W/D in Laundry room and Cedar Closet. Tons of LED high hats. Pool and tennis/pickle ball and basketball.

60 Chestnut Lane, Woodbury

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