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27 Windemere WayWoodbury, NY 11797

For Sale

$2,390,000

Smart Buyer Rebate $23,900

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.

Listed by Irena Tsarevsky CBR

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BERKSHIRE HATHAWAY

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516-200-5700

Last updated July 30, 2026

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Source: OneKey #1025514

Listing Facts

  • TypeSingle-family
  • NeighborhoodWoodbury
  • Bedrooms5
  • Bathrooms5
  • Days on Prevu14
  • HOA/Maint. Fees$950/month
  • Taxes$42,894/year
  • Size5,416 sqft
  • Price per sqft$441

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

07/17/2026
Status changed to Active
$2,390,000
07/17/2026
Listed by BERKSHIRE HATHAWAY
$2,390,000

Property Details for 27 Windemere Way

Association

Amenities

  • Association Amenities: Gated, Other, Powered Boats Allowed, Recreation Facilities, Security, Snow Removal, Tennis Court(s)
  • Community Features: Gated, Other, Tennis Court(s)

Fees

  • Association Fee: $950.00 Monthly
  • Association Fee Includes: Common Area Maintenance, Grounds Care, Snow Removal, Trash

Exterior

Construction

  • Property Condition: Actual
  • Window Features: Floor To Ceiling Windows, Oversized Windows, Skylight(s), Wall Of Windows
  • Year Built: 1984
  • Architectural Style: Contemporary
  • Construction Materials: Stone, Vinyl Siding

Features

  • Patio And Porch Features: Deck, Patio
  • Pool Features: Electric Heat, Fenced, In Ground, Outdoor Pool, Pool Cover, Salt Water
  • Pool Private: Yes
  • View: Water

Measurements

  • Building Area Total: 5,416
  • Building Area Units: Square Feet
  • Lot Features: Back Yard
  • Lot Size Acres: 0.60
  • Lot Size Square Feet: 26,428

Financial

Taxes

  • Parcel Number: 2489-14-037-00-0027-0
  • Tax Annual Amount: $42,894.00
  • Tax Assessed Value: $1,405.00
  • Tax Year: 2026

Interior

Features

  • Appliances: Convection Oven, Dishwasher, Electric Oven, Freezer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Gas Water Heater
  • Fireplace Features: Family Room, Living Room
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Flooring: Ceramic Tile, Wood
  • Interior Features: 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
  • Spa Features: Bath

Measurements

  • Living Area: 5,416
  • Living Area Source: Public Records

Rooms

  • Basement: Finished, Full
  • Has Basement: Yes
  • Bathrooms Full: 4
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 5
  • Bedrooms Total: 5
  • Rooms Total: 10

Other

General

  • Exclusions: Chandelier in the L.R

Location

  • Subdivision Name: Windemere
  • Tax Block: 37
  • Tax Lot: 27

Parking

Parking

  • Garage Spaces: 2
  • Garage: Yes
  • Parking Features: Driveway

Schools

Elementary School

  • Elementary School: Walt Whitman Elementary School
  • Elementary School District: Syosset

High School

  • High School: Syosset Senior High School
  • High School District: Syosset

Middle or Junior School

  • Middle Or Junior School: H B Thompson Middle School
  • Middle Or Junior School District: Syosset

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Natural Gas, Radiant Floor
  • Laundry Features: Laundry Room
  • Sewer: Public Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 5 bathrooms in this single-family home at 27 Windemere Way.

What schools are nearby to 27 Windemere Way?

Nearby schools include the Walt Whitman Elementary School, H B Thompson Middle School, and Syosset Senior High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 27 Windemere Way.

What are the annual taxes for 27 Windemere Way?

Annual taxes for this single-family home are estimated at $42,894.

How does 27 Windemere Way compare to other single-family homes in Woodbury?

This single-family home is listed 4% below the average price for single-family homes in Woodbury and has been on the market for 55 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 5,416 sqft.

27 Windemere Way is a 5-bedroom, 5-bath single-family home for sale in Woodbury NY 11797. Available on Prevu for 14 days at $2,390,000. This residence features 5,416 square feet of living space, located in Woodbury. The median listing price for single-family homes in this area is $2,250,000. Nearby schools include Walt Whitman Elementary School, H B Thompson Middle School, and Syosset Senior High School. Additional amenities include private outdoor space, dishwasher, air conditioning, parking, and swimming pool. Browse more single-family home listings in Nassau County.

The data relating to real estate for sale on this website comes in part from the IDX Program of OneKey™ MLS. The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. Information Copyright 2026, OneKey™ MLS. All Rights Reserved.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.