27 Windemere Way Woodbury, NY $ 2,390,000
27 Windemere Way
$ 2,390,000
Recently Listed
Open House 7/19 1pm - 3pm
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27 Windemere Way

Woodbury, NY, 11797
$ 2,390,000
Bedrooms5 Baths4.1 Sq 5,416

Monthly Estimate*

$ 15,091

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Single Family Home for sale in Woodbury, NY

for $2,390,000 with 5 bedrooms and 4 full baths, 1 half bath. This 5,416 square foot home was built in 1984 on a lot size of 0.6067.

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-in 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 en-suite bath and private outside entrance, while 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, Trex deck accessed directly from the kitchen and living spaces, and tranquil pond views beyond the established landscaping. Community tennis and basketball courts, a circular driveway, two-car garage, and the highly regarded Syosset SD complete this rare offering.

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Open House

7/19/2026 1:00 PM - 3:00 PM
27 Windemere Way Woodbury, NY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 2,390,000

Bedrooms

5

Full Bath

4

Half Bath

1

Property Type

Single Family

Taxes

$ 42,894

Style

Contemporary

Lot Size

0.6067

Year Built

1984

Town/City

Woodbury

County/Region

Nassau

MLS | Web ID

1025514

Features
Interior
Interior Amenities First Floor Bedroom First Floor Full Bath Central Vacuum Eat-in Kitchen Entrance Foyer Formal Dining Granite Counters His and Hers Closets Kitchen Island Open Floorplan Primary Bathroom Sauna Smart T
Basement Finished Full
Flooring Ceramic Tile Wood
Total Fireplaces 2
Fireplace Features Family Room Living Room
Basement Features Finished Full
Basement (Y/N) Y
Window Features Floor to Ceiling Windows Oversized Windows Skylight(s) Wall of Windows
Half Baths 1
Total Bedrooms 5
Total Baths 5
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General
Sewer Public Sewer
Heating Natural Gas Radiant Floor
Cooling Central Air
Utilities None
Appliances Convection Oven Dishwasher Electric Oven Freezer Gas Cooktop Microwave Refrigerator Stainless Steel Appliance(s) Gas Water Heater
HOA Fee 950
Garage Spaces 2
Association Fee Includes Common Area Maintenance Grounds Care Snow Removal
Patio/Porch Features Deck Patio
Architectural Style Contemporary
Pool Features Fenced In Ground Outdoor Pool Pool Cover Salt Water
Security Features Fire Alarm Gated Community Security Gate Security System Smoke Detector(s)
Construction Materials Stone Vinyl Siding
Exclusions Chandelier in the L.R
Year Built 1984
View Water
Property Subtype Single Family Residence
Tax Year 2026
Parcel Number 2489-14-037-00-0027-0
Community Features Gated Tennis Court(s)
Assoc Fee Paid Per Monthly
County Nassau County
Property Type Residential
Association Amenities Gated Other Tennis Court(s)
HOA Y
Garage Y/N Y
Total Rooms 10
Full Baths 4
High School Syosset Senior High School
City Oyster Bay
Senior Community Y/N N
High School District Syosset
Carport Y/N N
Spa Features Bath
Elementary School Walt Whitman Elementary School
Property Attached Y/N N
Tax Annual Amount 42894
Middle/Junior High School H B Thompson Middle School
Property Condition Actual
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Syosset
Elementary School District Syosset
Tax Assessed Value 1405
Tax Lot 27
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Exterior
Parking Features Driveway Driveway
Water Source Public
Building Area Total 5416
Waterfront Y/N N
Road Frontage Type None
Road Responsibility Private Maintained Road
Horse Y/N N
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Internal Only
Street Number 1 27
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* Excluded Features
List By
Irena Tsarevsky CBR

Listing Agent

Berkshire Hathaway

Broker

516-200-5700

Contact

Affordability Calculator

$18,665
Per Month
81%
19%
0%
Monthly Principal & Interest
$15,091
Monthly Property Taxes
$3,575
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4099881 Elementary School
4101106 Middle School
Syosset Senior High School High School
Pricing History
DatePricePrice ChangeDescription
7/16/2026$2,390,000 Listed Price

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27 Windemere Way, Woodbury, NY, 11797 is a Single Family Home for sale at $2,390,000 with 5,416 sqft and a lot size of 0.6067. 27 Windemere Way has 5 bedrooms, 4.1 baths, and was built in 1984. The property's zip code is 11797 which is in Woodbury, NY