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Woodbury, NY Homes for Sale with Pool

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  • /49

    $1,998,000

    • 4 Beds
    • 5 Baths
    • 2,890 Sq Ft

    316 S Woods Rd, Woodbury, NY 11797

    Welcome to this exceptional Hampton-style Colonial with your own gate, privately set on a flat 1 beautifully landscaped acre with heated pool and outdoor shower and powder room. An inviting oversized front porch overlooks lush emerald lawns, mature specimen trees, and beautifully landscaped grounds. A tranquil pond with a cascading waterfall, graceful Japanese maple, and vibrant seasonal blooms

    Agent Photo

    Michelle Zhao

    ZI Realty LLC

    316 S Woods Rd, Woodbury, NY 11797
  • /43

    $5,000,000

    • 5 Beds
    • 5.5 Baths
    • 6,696 Sq Ft

    8 Headley Way, Woodbury, NY 11797

    A One-of-a-Kind Custom Estate A masterpiece of custom craftsmanship and timeless design, this extraordinary estate offers nearly 6,000 square feet of luxurious living space—exclusive of the basement and three-car garage. Conceived, designed, and meticulously built by its owners, every detail reflects an uncompromising commitment to quality, elegance, and enduring value. Exceptional Property

    Agent Photo

    Khalidah Arifee

    Property Professionals Realty

    8 Headley Way, Woodbury, NY 11797
  • /33

    $4,450,000

    $300K PRICE DROP
    • 8 Beds
    • 9 Baths
    • 7,635 Sq Ft

    5 Kodiak Dr, Woodbury, NY 11797

    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

    Zach Elliott Nest Seekers LLC

    5 Kodiak Dr, Woodbury, NY 11797
  • /38

    $2,390,000

    • 5 Beds
    • 4.5 Baths
    • 5,416 Sq Ft

    27 Windemere Way, Woodbury, NY 11797

    Tucked behind the gates with a guard on duty, in the Windemere community, this architecturally distinctive contemporary was designed around light, volume, and an effortless connection to nature. Soaring vaulted ceilings rise approximately 20 feet above the principal living areas, where walls of floor-to-ceiling windows overlook park-like grounds and fill the home with natural light from the

    Irena Tsarevsky BERKSHIRE HATHAWAY

    27 Windemere Way, Woodbury, NY 11797
  • /16

    $2,199,000

    $81K PRICE DROP
    • 5 Beds
    • 3.5 Baths
    • 4,075 Sq Ft

    6 Polo Ct, Woodbury, NY 11797

    Welcome to 6 Polo Court, a beautifully maintained residence tucked away on a quiet cul-de-sac in desirable Woodbury. Set on an oversized lot, this spacious home offers an elegant layout designed for both comfortable everyday living and effortless entertaining. The home features 5 bedrooms, generous living and dining spaces, a bright eat-in kitchen, and multiple areas ideal for gathering, working,

    Daimian Dai Tru International Realty Corp

    6 Polo Ct, Woodbury, NY 11797
  • /50

    $2,650,000

    $140K PRICE DROP
    • 7 Beds
    • 5.5 Baths
    • 5,195 Sq Ft

    117 Plainview Rd, Woodbury, NY 11797

    Syosset School District, Private Lake, there is a band new swimming pool in the backyard and a fish pond in the front yard, New A/C, Kitchen with underfloor heating, home theater in the basement

    Baimei Wan Winzone Realty Inc

    117 Plainview Rd, Woodbury, NY 11797
  • /50

    $2,680,000

    • 5 Beds
    • 4.5 Baths
    • 3,739 Sq Ft

    6 Clearmeadow Ct, Woodbury, NY 11797

    Welcome to 6 Clearmeadow Ct, located in Hunters Run a premier 24-hour gated community within the highly sought-after Woodbury enclave andthe Syosset School District. This residence, set on a beautifully landscaped .65-acre lot, seamlessly blends timeless charm with modern sophistication. Originally built in 1987 and updated in 2026, the home offers 5 bedrooms and 4.5 bathrooms. A grand foyer with

    Josh Weisfeld W Brothers Brokerage LLC

    6 Clearmeadow Ct, Woodbury, NY 11797
  • /48

    $2,299,999

    $200K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,415 Sq Ft

    119 Plainview Rd, Woodbury, NY 11797

    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

    Jared Sarney Corcoran SRG Residential

    119 Plainview Rd, Woodbury, NY 11797
  • /26

    $1,488,000

    $57K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,565 Sq Ft

    3 Clemson Ln, Woodbury, NY 11797

    Welcome to a rare opportunity in the heart of Woodbury. This 4 bedroom, 2.5 bath Splanch style home is perfectly situated mid-block on a picturesque, tree-lined street.Step inside to discover a beautiful home with natural light and hardwood floors. The first floor features a renovated eat-in kitchen with stainless steel appliances, granite countertops and a formal dining room for

    Rochelle Jamnik Coldwell Banker American Homes

    3 Clemson Ln, Woodbury, NY 11797
  • /8

    $4,988,000

    • 6 Beds
    • 6.5 Baths
    • 7,049 Sq Ft

    7 the Rise, Woodbury, NY 11797

    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,

    Stephen Gaon Serhant East End LLC

    7 the Rise, Woodbury, NY 11797
  • /29

    $2,350,000

    • 4 Beds
    • 6 Baths
    • 2,892 Sq Ft

    63 Three Ponds Ln W, Woodbury, NY 11797

    A coveted corner F-Model at The Sagamore at Mill Pond — thoughtfully designed, beautifully finished, and ready to be called home. This is the one that stands out. Positioned as a corner unit facing South, the home gets exceptional natural light and a sense of privacy. Soaring ceilings and high-end finishes throughout make it clear this home was done to perfection. The living room, dining room,

    Andrea Wiener Daniel Gale Sothebys Intl Rlty

    63 Three Ponds Ln W, Woodbury, NY 11797
  • /36

    $2,050,000

    • 5 Beds
    • 3.5 Baths
    • 2,884 Sq Ft

    19 Seward Dr, Woodbury, NY 11797

    Perfectly positioned on a coveted mid-block location within The Gates of Woodbury, this impressive Center Hall Colonial is set on a beautiful one-acre property and offers an exceptional blend of space, comfort, and timeless design. Thoughtfully crafted for both everyday living and entertaining, the home features generously proportioned rooms, a classic and highly functional floor plan, and

    Fran Mazer Compass Greater NY LLC

    19 Seward Dr, Woodbury, NY 11797
  • /31

    $728,000

    • 3 Beds
    • 2.5 Baths
    • 1,481 Sq Ft

    5 Pond Path Unit 13, Woodbury, NY 11797

    Enjoy the Lifestyle of Woodbury Village, a sought after townhouse community in the Syosset School district offering exceptional amenities including a pool, tennis courts and playground. This 3 Bedroom(currently configured as 2 bedrooms plus a loft that can easily be converted back to 3rd bedroom), 2.5 Bath home features all New Flooring, New Primary Bathroom and Deck.The Main Level offers a

    Anne Fishbein Douglas Elliman Real Estate

    5 Pond Path Unit 13, Woodbury, NY 11797
  • /50

    $2,998,000

    $300K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,181 Sq Ft

    15 Pironi Ct, Woodbury, NY 11797

    Architecturally distinguished and extensively updated, this stately custom Colonial set on nearly one acre of private cul-de-sac property in the heart of Woodbury. Offering 5,181 square feet of refined living space, this residence reflects timeless design, superior craftsmanship, and meticulous attention to detail. The home presents with a fresh, like-new aesthetic, highlighted by a fully

    Steven Shaughnessy Charles Rutenberg Realty Inc

    15 Pironi Ct, Woodbury, NY 11797
  • /24

    $1,488,878

    Open Sat 12PM - 3PM
    • 3 Beds
    • 2.5 Baths
    • 2,182 Sq Ft

    24 Chestnut Ln, Woodbury, NY 11797

    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

    Eunice Ho Keller Williams Rty Gold Coast

    24 Chestnut Ln, Woodbury, NY 11797
  • /41

    $899,999

    • 3 Beds
    • 2.5 Baths
    • 1,740 Sq Ft

    104 Woodlake Dr W, Woodbury, NY 11797

    Enjoy Country Club Living with amenities galore.This Updated Condo in Desirable Woodland Pond Convenient to all Features A Newer Stainless Steel Granite Eat in Kitchen with Excessive White cabinetry,3 Updated Bathrooms,Hard Wood Floors,Beautiful Mill work,Large Formal Dining Room,Step Down Living Room/Den with Ose to Trex Deck,Vaulted Ceiling,Skylight.Minutes to Shopping ,Restaurants,Public

    Lenny Rosenfeld Douglas Elliman Real Estate

    104 Woodlake Dr W, Woodbury, NY 11797
  • /22

    $1,180,000

    • 3 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    71 Eagle Chase, Woodbury, NY 11797

    Welcome to 71 Eagle Chase, a beautiful home in the prestigious 24-hour gated Eagle Chase community, featuring 3 bedrooms and 2.5 bathrooms. Enter through grand double doors into a bright, open-concept layout with soaring vaulted ceilings and a skylight that fills the space with natural light. The main level includes a guest bedroom with a private balcony, a home office, and a powder room. The

    Amber Lin Keller Williams Rlty Landmark

    71 Eagle Chase, Woodbury, NY 11797
  • /38

    $2,395,000

    • 6 Beds
    • 5.5 Baths
    • 4,085 Sq Ft

    96 Plainview Rd, Woodbury, NY 11797

    Nestled on one private acre in the heart of Woodbury, this exceptional center hall Colonial offers the perfect blend of timeless elegance, modern updates, and outstanding versatility. Set on a beautifully landscaped one-acre property, the home provides a peaceful retreat while remaining just minutes from shopping, major parkways, the LIRR, and Syosset schools.The main residence features 5

    Michael Pesce BERKSHIRE HATHAWAY

    96 Plainview Rd, Woodbury, NY 11797
  • /50

    $2,599,999

    $129K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,671 Sq Ft

    2 Greenwood Ln, Woodbury, NY 11797

    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

    Lyndsey Gallagher Coldwell Banker American Homes

    2 Greenwood Ln, Woodbury, NY 11797
  • /29

    $1,288,000

    • 5 Beds
    • 4 Baths
    • 2,150 Sq Ft

    18 Park Dr E, Syosset, NY 11791

    Welcome to This Oversized and Beautifully Renovated Home Located in the Prestigious Syosset Woods Section!Conveniently Situated Just 5 Minutes from the Syosset LIRR Station, This Stunning Property Offers the Perfect Combination of Space, Comfort, and Modern Upgrades.Featuring 5–6 Spacious Bedrooms and 4 Full Bathrooms, This Home Has Been Extensively Renovated Throughout. Updates Include a

    David Lin Sweet Key Realty Group Inc

    18 Park Dr E, Syosset, NY 11791
  • /43

    $2,499,000

    $301K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    225 Laurel Ln, Syosset, NY 11791

    Nestled on two private, professionally landscaped acres in the Incorporated Village of Laurel Hollow, this completely renovated ranch offers the perfect blend of luxury, comfort, and effortless living. Thoughtfully reimagined with no expense spared, this turnkey home showcases exceptional craftsmanship, premium finishes, and timeless design. Featuring 3 bedrooms, 2.5 baths, a full finished

    Jyll Kata Signature Premier Properties

    225 Laurel Ln, Syosset, NY 11791
  • /6

    $830,000

    $69K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    175 the Vale, Syosset, NY 11791

    Most sought after gated condo in the Syosset area with owners suite on main floor. This 3 bedroom 3 bath sundrencehd home enhanced with generous high ceilings and skylights is a truly remarkable residence. Stone fireplace, huge deck and walk out lower level with a second deck that leads to a lush green private park like setting. Enjoy country club living in your own back yard. Hidden Ridge is a

    Ken Deutsch Deutsch Realty Inc

    175 the Vale, Syosset, NY 11791

Home Price Trends

Median Sale Price
$1,437,500
Median Single Family Sale Price
$1,920,000
Median Townhouse Sale Price
$990,000
Median 2 Bedroom Sale Price
$802,000
Average Price Per Sq Ft
$558
Number of Homes for Sale
29
Last 12 months Home Sales
92
Months of Supply
3.80
Median List Price
$1,575,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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