27 Windemere Way • Woodbury, NY 11797

$2,390,000 Beds: 5 • Baths: 4 full 1 partial • Sq. Feet: 5416 • MLS ID: 1025514 • Subdivision:School Dist: Syosset
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 showpiece. 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. View this listing at: http://samlee.laffey.com/mls=1025514

Property Features

  • Garage: 2
  • Taxes: $42,894
  • Basement: Yes
  • Fenced: Yes
  • Formal Dining: Yes
  • Swimming Pool: Yes
  • Sauna: Yes
  • Exterior: Stone,Vinyl Siding
  • Special View Info: Water
  • Lot Size: 0.61 Acres
  • Heating: Natural Gas,Radiant Floor
  • Cooling: Central Air
  • Year Built: 1984
  • Fireplaces: 2
  • Security: yes
  • Water: Public
  • Sewer: Public Sewer
  • On Market Date: 2026-07-17
  • Appliances: Convection Oven,Dishwasher,Electric Oven,Freezer,Gas Cooktop,Microwave,Refrigerator,Stainless Steel Appliance(s),Gas Water Heater
  • Association Amenities: Gated,Other,Tennis Court(s)
  • Association Fee: $950/Monthly
  • Association Fee Includes: Common Area Maintenance,Grounds Care,Snow Removal
  • Basement: Finished,Full
  • Building Area Total: 5416
  • Community Features: Gated,Tennis Court(s)
  • Exclusions: Chandelier in the L.R
  • Fireplace Features: Family Room,Living Room
  • Flooring: Ceramic Tile,Wood
  • GarageY/N: Yes
  • Gated Property: Y
  • Interior Features: First Floor Bedroom,First Floor Full Bath,Central Vacuum,Eat-in Kitchen,Entrance Foyer,Formal Dining,Granite Counters,His and Hers Closets,Kitchen Island,Open Floorplan,Primary Bathroom,Sauna,Smart Thermostat,Soaking Tub,Sound System,Walk-In Closet(s),Washer/Dryer Hookup
  • Laundry: Laundry Room
  • Lot Features: Back Yard
  • Attic: Partial
  • Number Of Kitchens: 1
  • Heating Zones: 4
  • Parcel Number: 2489-14-037-00-0027-0
  • Parking Features: Driveway
  • Patio And Porch: Deck,Patio
  • Pool Features: Fenced,In Ground,Outdoor Pool,Pool Cover,Salt Water
  • Rental Term: Monthly
  • Road Responsibility: Private Maintained Road
  • Rooms Total: 10
  • Security Features: Fire Alarm,Gated Community,Security Gate,Security System,Smoke Detector(s)
  • Skylight: Y
  • Utilities: None
  • Window Features: Floor to Ceiling Windows,Oversized Windows,Skylight(s),Wall of Windows

School Information

  • High School: Syosset Senior High School
  • Middle School: H B Thompson Middle School
  • Elementary School: Walt Whitman Elementary School
  • School District: Syosset
Printed July 18, 2026


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