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27 Windemere Way

Woodbury, NY 11797
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Bed 5

Bed

Bath 5

Bath

SqFt5,416

Sqft

Acres0.61

Acre(Lot)

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 moment you step through its one-of-a-kind handcrafted sculptural double entry doors. The dramatic living room, anchored by a grand architectural wood-burning fireplace, flows into a formal dining area, scaled for large gatherings. A sculptural spiral staircase ascends to a gallery library overlooking the living room, richly appointed with wood paneling and extensive custom built-in bookcases — a true sh owpiece. Multi-zone audio carries music seamlessly throughout the whole home. The open, vaulted kitchen — outfitted with a Sub-Zero refrigerator, two Thermador wall ovens, and a Miele cooktop — connects directly to the family room and casual dining area, with a walk-in pantry and a laundry room with an additional Sub-Zero freezer. The main-level primary suite is a private retreat with a vaulted ceiling, floor-to-ceiling windows, and three walk-in closets. Its spa-inspired bath features a dry sauna, a walk-in shower with Schluter radiant heat in the floor, bench, and accent wall, a smart toilet in its own enclosed room, layered designer lighting, and a skylight overhead. A guest suite offers a marble en-suite bath and private outside entrance, while two additional bedrooms share a stunning, fully redone onyx Jack-and-Jill bath with radiant heated floors. Upstairs, a spacious loft makes an ideal teen retreat, office, or bonus room. The finished lower level adds a mirrored gym, hobby and recreation space, a room-size cedar closet, and multiple storage rooms. Outside, resort-style living awaits: a gas-heated saltwater pool, Trex deck accessed directly from the kitchen and living spaces, and tranquil pond views beyond the established landscaping. Community tennis and basketball courts, a circular driveway, two-car garage, and the highly regarded Syosset SD complete this rare offering.

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Detail Ic Property Details

Property Type : Residential

Price : $2,390,000

AD Id : 88120688

MLS Id : 1025514

Beds : 5

Lot Size : 0.61 Acre

Living Area Size : 5,416

Year Built : 1984

Garage : 2

County : Nassau

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Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 5 Full Baths: 4 Half Baths: 1

    Room Information

    Rooms Total: 10 Basement: Finished, Full
  • Flooring Information

    Ceramic Tile, Wood
  • Interior Features

    Central Vacuum, Eat-in Kitchen, Entrance Foyer, Granite Counters, His and Hers Closets, Kitchen Island, Open Floorplan, Sauna, Smart Thermostat, Soaking Tub, Sound System, Walk-In Closet(s) Appliances: Convection Oven, Dishwasher, Electric Oven, Freezer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Gas Water Heater Laundry Features: Laundry Room Window Features: Skylight(s)
  • Heating & Cooling

    Has Heating: Yes Heating: Natural Gas, Radiant Floor Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 1984 Building Area Total: 5416 Construction Materials: Stone, Vinyl Siding Patio And Porch Features: Deck, Patio Pool Features: Fenced, In Ground, Outdoor Pool, Pool Cover, Salt Water, Private Private Pool: Yes View: Water Association Fee Frequency: Monthly

  • Lot Information

    Lot Size Acres: 0.6067 Lot Size Square Feet: 26428 Lot Description: Back Yard

  • Listing Price Information

    Listing Price: $2390000

  • Tax Information

    Parcel Number: 2489-14-037-00-0027-0 Tax Lot: 27 Tax Block: 37 Annual Tax: $42894

  • Parking Information

    Driveway

    Garage Information

    Has Garage: Yes Garage Space: 2
    Homeowners Association Information
    Included Fees: Snow Removal HOA: $950.00 Association Amenities: Gated, Other, Tennis Court(s) Community Features: Gated, Tennis Court(s)

  • School Information

    Elementary School: Walt Whitman Elementary School
    Junior High School: H B Thompson Middle School
    Senior High School: Syosset Senior High School
  • Utility Information

    None
  • Location Information

    WaterSource: Public Security Features: Fire Alarm, Gated Community, Security Gate, Security System, Smoke Detector(s)
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
96 Plainview Road, Woodbury, NY, 11797 $2,395,000 6 6 4,085 4,085 SqFt
119 Plainview Road, Woodbury, NY, 11797 $2,299,999 6 5 4,415 4,415 SqFt
117 Plainview Road, Woodbury, NY, 11797 $2,650,000 7 6 5,195 5,195 SqFt
7 The Rise, Woodbury, NY, 11797 $4,988,000 6 7 7,049 7,049 SqFt
21 Kodiak Drive, Woodbury, NY, 11797 $2,200,000 5 5 3,401 3,401 SqFt
8 Kodiak Drive, Woodbury, NY, 11797 $2,499,999 5 5 4,004 4,004 SqFt
5 Kodiak Drive, Woodbury, NY, 11797 $4,450,000 8 9 7,635 7,635 SqFt
14 Pine Drive, Woodbury, NY, 11797 $2,349,999 4 6 4,288 4,288 SqFt
19 Seward Drive, Woodbury, NY, 11797 $2,050,000 5 4 2,884 2,884 SqFt
23 Woodbury Road, Woodbury, NY, 11797 $2,999,000 5 6 4,019 4,019 SqFt

The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

ByOwner last updated this listing 07/18/2026 @ 05:13

MLS: 1025514 LISTED BY: Irena CBR, BERKSHIRE HATHAWAY 516-200-5700 SOURCE: OneKey MLS

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