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$2,390,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 5,416 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 27 Windemere Way

General

  • Price: $2,390,000
  • HOA FEE: $950/month
  • Taxes: $42,894
  • Status: Active
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 1025514
  • Updated: 7/27/2026
  • Added to Site: 42 day(s) ago

Interior

  • Number of Rooms: 10
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Family Room, Living Room
  • Appliances: Convection Oven, Dishwasher, Electric Oven, Freezer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Gas Water Heater
  • Laundry Facilities: Yes
  • Flooring: Ceramic Tile, Wood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Amenities: Gated, Other, Tennis Court(s)
  • Shared Amenities: Gated, Other, Powered Boats Allowed, Recreation Facilities, Security, Snow Removal, Tennis Court(s)
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Electric Heat, Fenced, In-Ground, Outdoor Pool, Pool Cover, Salt Water
  • Security/Safety: Fire Alarm, Gated Community, Security Gate, Security System, Smoke Detector(s)

Exterior

  • Porch/Patio/Deck: Deck, Patio

Parking

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

Location

  • County: Nassau County
  • Subdivision: Windemere
  • Cross Streets: Windemere Dr.

School Information

  • High School District: Syosset
  • Elementary School: Walt Whitman Elementary School
  • Middle School: H B Thompson Middle School
  • High School: Syosset Senior High School

Community

  • Association: Yes
  • Assoc. Fees Include: Common Area Maintenance, Grounds Care, Snow Removal, Trash

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Natural Gas, Radiant Floor
  • Heating Zones: 4

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: None

Structural Information

  • Architectural Style: Contemporary
  • Detached/Attached: Detached
  • Construction: Stone, Vinyl Siding
  • Basement: Yes
  • Basement Desc.: Finished, Full Basement
  • Windows: Floor to Ceiling Windows, Oversized Windows, Skylight(s), Wall of Windows
  • Building Size: 5416
  • Square Feet: 5,416
  • Sq. Ft. Source: Public Records
  • Year Built: 1984

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.6067
  • Lot Size (Sq. Ft.): 26,428
  • Frontage: None
  • Road Maintenance: Private Maintained Road
  • Lot Features: Back Yard

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $950
  • Assoc Fee Freq.: Monthly
  • Tax Amount: $42,894

Disclosures and Reports

  • Special Conditions: None
  • Exclusions: Chandelier in the L.R
  • Property ID: 2489-14-037-00-0027-0
  • Block: 37
  • Lot Number: 27

Listed by Berkshire Hathaway

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Listing agent

— 27 Windemere Way —

  • Berkshire Hathaway

516-200-5700

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NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 27 Windemere Way

School District:Syosset Central School District
NameGradesDistance
Walt Whitman Elementary School
482 Woodbury Road, Woodbury, NY 11797
K-50.5 mi
H B Thompson Middle School
98 Ann Dr, Syosset, NY 11791
6-82 mi
Syosset Senior High School
70 South Woods Road, Syosset, NY 11791
9-121.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 27 Windemere Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/17/2026
Listed
$2,390,000
117.27%
MLS
6/05/2017
Sold
$1,100,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 27 Windemere Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$41,019
344%
$1,405
2%
2024
$9,245
-72%
$1,380
-2%
2023
$32,469
14%
$1,405
—
2022
$28,392
-11%
$1,405
-7%
2021
$31,903
-6%
$1,509
-19%
2020
$33,880
7%
$1,870
-31%
2018
$31,688
-6%
$2,700
21%
2019
$33,880
-18%
$2,240
-17%
2016
$41,413
—
$2,700
-11%
2016
$41,413
6%
$3,040
-1%
2016
$39,098
-2%
$3,083
—
2014
$40,098
—
$3,083
-11%
2014
$40,098
—
$3,468
—
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Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Berkshire Hathaway

27 Windemere Way, Woodbury, NY 11797 (MLS# 1025514) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 27 Windemere Way is currently listed for $2,390,000 and was received on July 17, 2026. Want to learn more about 27 Windemere Way? Do you have questions about finding other Single Family real estate for sale in Woodbury? You can browse all Woodbury real estate or contact a Coldwell Banker agent to request more information.

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