Single Family
27 Windemere Way
Pending · Oyster Bay · Nassau County, NY 11797
- Bedrooms
- 5 Beds
- Bathrooms
- 5 Baths
- Year built
- 1984
- Est. monthly taxes
- $3,574.5
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About this home
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 snapshot
- Days on site
- 59 days
- Listed on MLS
- Jul 17, 2026
- Full baths
- 4
- Half baths
- 1
- Annual property tax (MLS)
- $42,894
- Tax year
- 2026
- Association / maintenance fees (MLS)
- $950 / Monthly
- Fees include (MLS)
- Common Area Maintenance, Grounds Care, Snow Removal, Trash
- Area source (MLS)
- Public Records
- Listing brokerage
- BERKSHIRE HATHAWAY
- MLS ID
- KEY1025514
- Last updated
- Sep 23, 2026
General features
- Property type
- Single Family
- Property subtype
- Single Family Residence
- Year built
- 1984
- Garage
- Yes
- Garage spaces
- 2
- Parking
- Driveway
- Water source
- Public
- Sewer
- Public Sewer
- Utilities
- None
Interior features
- Basement
- Finished, Full
- Heating
- Natural Gas, Radiant Floor
- Cooling
- Central Air
- Interior
- First Floor Bedroom, First Floor Full Bath, Built-in Features, Cathedral Ceiling(s), Central Vacuum, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, His and Hers Closets, Kitchen Island, Open Kitchen, Primary Bathroom, Sauna, Smart Thermostat, Soaking Tub, Sound System, Speakers, Walk-In Closet(s), Washer/Dryer Hookup, Wet Bar
- Appliances
- Convection Oven, Dishwasher, Electric Oven, Freezer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Gas Water Heater
- Flooring
- Ceramic Tile, Wood
- Fireplace
- Yes
- Fireplaces
- 2
Exterior features
- Architectural style
- Contemporary
- Construction materials
- Stone, Vinyl Siding
- Private pool
- Yes
Schools (MLS)
- Elementary school
- Walt Whitman Elementary School
- Elementary school district
- Syosset
- Middle school
- H B Thompson Middle School
- Middle school district
- Syosset
- High school
- Syosset Senior High School
- High school district
- Syosset
School information is provided by the MLS. Confirm attendance eligibility with the school district.
Recent activity
- Listing updated from MLS
- MLS status changed
- First seen on this site
Location
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Estimated monthly principal & interest—
Monthly property taxNot provided
Monthly association / maintenance feesNot provided
Estimated monthly total of entered costs—
Listing data is supplied by the MLS and may change without notice.
