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$2,390,000

27 Windemere Way

Woodbury, NY
Pending
5
Bedrooms
4.5
Bathrooms
5,416
Square Feet
0.61
Lot Size (acres)
1984
Year Built
94
Days On Market

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 Information

Listing Updated
25 days ago
Listed By
Irena Tsarevsky CBR · BERKSHIRE HATHAWAY, 5162005700
MLS#
1025514
Source
OneKey MLS
Status
Pending

Facts & Features

Location

Community Information

Address
27 Windemere Way, Woodbury, NY 11797
City
Woodbury
County
Nassau
Neighborhood
Windemere
Zip Code
11797

Architecture

Bedrooms
5
Bathrooms
4.5
Year Built
1984
Style
Contemporary
Construction Materials
Vinyl Siding, Stone
Building Area
5,416 sq. ft.
Levels
One
Garage
Yes
Garage Spaces
2
Parking Features
Driveway

Features & Amenities

Interior Features
Cathedral Ceiling(s), Eat-in Kitchen, Walk-In Closet(s), Wet Bar, Kitchen Island, Central Vacuum, Granite Counters, Entrance Foyer, Smart Thermostat, Built-in Features, His and Hers Closets, Soaking Tub, Sound System, Sauna
Appliances
Dishwasher, Microwave, Refrigerator, Convection Oven, Gas Cooktop, Freezer, Gas Water Heater, Electric Oven, Stainless Steel Appliance(s)
Flooring
Ceramic Tile, Wood
Patio and Porch
Patio, Deck
Community Features
Gated, Other, Tennis Court(s)
Cooling
Central Air
Heating
Natural Gas, Radiant Floor

Property Features

Lot Size
0.61 Acres
Lot Features
Back Yard
View
Water
Water
Public
Sewer
Public Sewer
Utilities
None

Square Footage

Total
5,416 sq. ft.

Tax & Financial Information

List Price
$2,390,000
Annual Taxes
$42,894
Association Fee
$950 (paid Monthly)
Fee Includes
Snow Removal, Trash
Association Amenities
Snow Removal, Gated, Tennis Court(s), Other, Security, Recreation Facilities, Powered Boats Allowed

Schools

77/100
Walt Whitman Elementary School
Elementary · Grades KG–05 · 0.5 mi
Assigned school for this home
City
Woodbury
Students
391
Parent reviews
5.0★ avg · 2 reviews
Student body
61% White · 29% Asian · 4% Hispanic / Latino
Free/reduced lunch
11%
Phone
(516) 364-5823
54/100
H B Thompson Middle School
Middle · Grades 06–08 · 2 mi
Assigned school for this home
City
Syosset
Students
900
Student body
47% White · 46% Asian · 5% Hispanic / Latino
Free/reduced lunch
9%
Phone
(516) 364-5760
100/100
Syosset Senior High School
High · Grades 09–12 · 1.3 mi
Assigned school for this home
City
Syosset
Students
2,100
Parent reviews
5.0★ avg · 2 reviews
Student body
66% White · 29% Asian · 3% Hispanic / Latino
Free/reduced lunch
6%
Phone
(516) 364-5675
100/100
Berry Hill Elementary School
Elementary · Grades KG–05 · 1.9 mi
City
Syosset
Students
388
Student body
72% White · 24% Asian · 2% Hispanic / Latino
Free/reduced lunch
3%
Phone
(516) 364-5790
76/100
Village Elementary School
Elementary · Grades KG–05 · 1.9 mi
City
Syosset
Students
399
Parent reviews
5.0★ avg · 4 reviews
Student body
45% White · 42% Asian · 6% Hispanic / Latino
Free/reduced lunch
7%
Phone
(516) 364-5817
76/100
Judy Jacobs Parkway Elementary School
Elementary · Grades KG–04 · 2.1 mi
City
Plainview
Students
467
Student–teacher
10.2
Student body
52% White · 38% Asian · 7% Hispanic / Latino
Free/reduced lunch
10%
Phone
(516) 434-3358
69/100
Oakwood Primary Center
Elementary · Grades PK–02 · 1.6 mi
City
Huntington
Students
610
Parent reviews
4.0★ avg · 2 reviews
Student body
52% Hispanic / Latino · 36% White · 5% Black
Free/reduced lunch
46%
Phone
(631) 812-3500
56/100
South Woods Middle School
Middle · Grades 06–08 · 1.5 mi
City
Syosset
Students
746
Student body
46% Asian · 45% White · 5% Hispanic / Latino
Free/reduced lunch
12%
Phone
(516) 364-5621

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
07/16/2026Listed for sale$2,390,000

Listed by Irena Tsarevsky CBR · BERKSHIRE HATHAWAY · 5162005700

Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: September 23, 2026 at 7:13 AM | Source: OneKey MLS | MLS#: 1025514

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