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MLS ID KEY1025514Last updated Sep 23, 2026

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
Property gallery0 / 38
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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

  1. Listing updated from MLS
  2. MLS status changed
  3. First seen on this site

Location

Oyster Bay · Nassau County, NY 11797Show interactive map
27 Windemere Way

Oyster Bay · Nassau County, NY 11797

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Estimate monthly payment

Loan detailsFixed-rate, fully amortizing loan. Edit the assumptions below; no market rate is supplied.
Property expenses (USD)
MLS amounts are prefilled when available and can be edited. Confirm what fees include. Unknown fee frequencies cannot be converted automatically.Property expenses: MLS values where available; missing values stay blank.

Estimated monthly principal & interest—

Monthly property taxNot provided

Monthly association / maintenance feesNot provided

Estimated monthly total of entered costs—

Excludes insurance, mortgage insurance, special assessments and lender fees. MLS taxes may reflect abatements or exemptions and can change.

Listing data is supplied by the MLS and may change without notice.