Woodbury Real Estate

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Newest Listings in 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

$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

$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

$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

$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

$124,900

1 Beds ⋅ 1 Baths ⋅ 24212678 MLS ⋅ Quassuk Heights Gardens BLDG.

Welcome to this delightful and exceptionally well cared for condo in the charming town of Woodbury! Just minutes from Main Street, this desirable first floor end unit offers plenty of light, a spacious bedroom, an open concept living/dining area, with wood floors throughout. There are great views of Litchfield County's rolling hills outside the front window and a tranquil shared patio in the back, abutting greenery and woodland. Why rent when you can own? HOA includes heat, hot water, trash, grounds maintenance, snow removal. No pets or smoking allowed.

22 Pilgrim Trl Unit G1, 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

$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

$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

$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

$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

$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

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

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.