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27 Windemere Way

Woodbury, NY 11797
  • $2,390,000
  • STATUS: Active
  • ON SITE: 57 Days
  • MLS #: 1025514
Open House
UPDATED: 17 min ago
$2,390,000
  • 5
    BEDS
  • 0.61
    ACRES
  • 4
    BATHS
  • 1
    1/2 BATHS
  • 5,416
    SQFT
  • $441
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1984
County:
Area:

School Information

Elementary School:
School District:

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.

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© 2026 OneKey MLS. All rights reserved. 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 is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-09-12T16:24:17.943.
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27 Windemere Way Woodbury, NY 11797

  • Price: $2,390,000
  • Status: Active
  • On Site: 57 Days
  • Updated: 17 min ago
  • MLS #: 1025514
5
Beds
4
Baths
1
½ Baths
0.61
Acres
5,416
SQFT
$441
$/SQFT
1984
Built
Neighborhood:
Windemere
County:
Nassau
Area:
Oyster Bay
Elementary School:
Walt Whitman Elementary School
Middle School:
H B Thompson Middle School
High School:
Syosset Senior High School
School District:
Syosset
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.
Exterior Features

Architectural Style Contemporary Carport YN No Construction Materials StoneVinyl Siding Cross Street Windemere Dr. Garage YN Yes Levels One Lot Features Back Yard Parking Features Driveway Patio And Porch Features DeckPatio Pool Features Electric HeatFencedIn GroundOutdoor PoolPool CoverSalt Water Pool Private YN Yes Property Attached YN No Road Responsibility Private Maintained Road View Water Waterfront YN No Window Features Floor to Ceiling WindowsOversized WindowsSkylight(s)Wall of Windows

Interior Features

Additional Rooms Dining AreaHome OfficeLibrary/DenLoft Appliances Convection OvenDishwasherElectric OvenFreezerGas CooktopMicrowaveRefrigeratorStainless Steel Appliance(s)Gas Water Heater Attic Partial Basement Details FinishedFull Basement YN Yes Cooling Central Air Fireplace Features Family RoomLiving Room Fireplace YN Yes Fireplaces Total 2 Flooring Ceramic TileWood Interior Features 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 Laundry Features Laundry Room Number Of Heating Zones 4 Number Of Kitchens 1 Rooms Total 10 Security Features Fire AlarmGated CommunitySecurity GateSecurity SystemSmoke Detector(s)

Property Features

Association Amenities GatedOtherPowered Boats AllowedRecreation FacilitiesSecuritySnow RemovalTennis Court(s) Association Fee 950 Association Fee Frequency Monthly Association Fee Includes Common Area MaintenanceGrounds CareSnow RemovalTrash Association YN Yes Building Area Total 5416 Community Features GatedOtherTennis Court(s) Down Payment Resource YN No Electric Company PSEG Exclusions Chandelier in the L.R Heating Natural GasRadiant Floor Horse YN No Lease Considered YN No Property Condition Actual Property Sub Type Single Family Residence Road Frontage Type None Senior Community YN No Sewer Public Sewer Special Listing Conditions None Tax Annual Amount 42894 Tax Source Other Utilities None Water Source Public

Listing courtesy of Irena Tsarevsky Cbr of BERKSHIRE HATHAWAY: 516-200-5700
© 2026 OneKey MLS. All rights reserved.


© 2026 OneKey MLS. All rights reserved. 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 is deemed reliable but is not guaranteed accurate by the MLS or Mark Seiden Real Estate Team. Data last updated: 2026-09-12T16:24:17.943.
 
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