27 Windemere Way, Woodbury, NY 11797

• 5 beds |
• 5 baths |
• 5,416 sqft

Property Description

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 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 bath and private outside entrance. 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, composite (Trex) deck accessed directly from the kitchen and living room, and tranquil pond views beyond the established landscaping. Community tennis and pickleball courts, a circular driveway, two-car garage, and the highly regarded Syosset SD complete this rare offering.

Listing Status:

Active

Data Last Updated:

August 10, 2026 at 11:22PM

Listing Office:

BERKSHIRE HATHAWAY : 516-200-5700

MLS ID:

1025514

Interior

• General: First Floor BedroomFirst Floor Full BathBuilt-in FeaturesCathedral Ceiling(s)Central VacuumEat-in KitchenEntrance FoyerFormal DiningGranite CountersHis and Hers ClosetsKitchen IslandOpen KitchenPrimary BathroomSaunaSmart ThermostatSoaking TubSound SystemSpeakersWalk-In Closet(s)Washer/Dryer HookupWet Bar
• Rooms: Dining AreaHome OfficeLibrary/DenLoft
• Appliances: Convection OvenDishwasherElectric OvenFreezerGas CooktopMicrowaveRefrigeratorStainless Steel Appliance(s)Gas Water Heater
• Laundry: Laundry Room
• Basement: FinishedFull
• Flooring: Ceramic TileWood
• A/C: Central Air
• Heating: Natural GasRadiant Floor
• Fireplace: Family RoomLiving RoomFireplaceFireplaces: 2

Exterior

• Style: Contemporary
• Other Structures: DeckPatio
• Pool: Electric HeatFencedIn GroundOutdoor PoolPool CoverSalt Water
• Parking: Driveway

Construction

• Windows: Floor to Ceiling WindowsOversized WindowsSkylight(s)Wall of Windows
• General: One

Location

• Road/Access: None
• HOA Amenities: GatedOtherPowered Boats AllowedRecreation FacilitiesSecuritySnow RemovalTennis Court(s)Common Area MaintenanceGrounds CareSnow RemovalTrash950.0Monthly
• Originating MLS: onekey2
• School District: Syosset
• County: Nassau County

Lot

• Zoning: 2489-14-037-00-0027-0
• View: Water

Utilities

• Utilities: None
• Water: Public
• Sewer: Public Sewer

Financial

• Source: onekey2
• Exclusions: Chandelier in the L.R