New Listing - 07/17/2026

$2,390,000 ($441.29 per sqft)

Est. Mortgage $11,463/mo *

Quick Pre-Approval

Open House Schedule

07/19/2026
1:00 PM to 3:00 PM
Google calendar
Other calendars


27 Windemere Way, Woodbury, NY, 11797

27 Windemere Way, Woodbury, NY, 11797

10 rooms

5 beds

4 Full / 1 Half baths

1984

Contemporary

5,416 sqft

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.


Status:

Active

Type:

Single-family residential

Laundry Remarks:

Laundry Room

Garage:

2-car

Heating:

Natural Gas, Radiant Floor

Cooling:

Central Air

Basement:

Finished, Full

Parking:

Driveway

Acreage:

0.61

Est. Taxes:

$42,894

Assessment

$1,405

HOA Fee

$950 Monthly

Construction

Stone, Vinyl Siding

Utilities

None

Lot Description:

Back Yard

View Description:

Water

Amenities:

Gated, Other, Tennis Court(s)

Elementary School:

Walt Whitman Elementary School

Middle School:

H B Thompson Middle School

High School:

Syosset Senior High School

School District:

Syosset

Appliances:

Convection Oven, Dishwasher, Electric Oven, Freezer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Gas Water Heater

Pool:

Fenced, In Ground, Outdoor Pool, Pool Cover, Salt Water

MLS #:

1025514


Community Info

School Info

Walk Score

Mass Transit

Yelp



Listing courtesy of BERKSHIRE HATHAWAY 516-200-5700