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Anthony Trupia
REALTOR®
(516) 587-9895

27 Windemere Way, Woodbury, NY 11797

$2,390,000
  • 27 Windemere Way, Woodbury, NY 11797 Main Photo

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New to the Market Active
BEDS5 BATHS4 full 1 partial SQUARE FEET5,416 MLS#1025514
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLSyosset

Property Description

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.

27 Windemere Way | MLS# 1025514

This single family home located at 27 Windemere Way, Woodbury, NY 11797 is currently listed for sale with an asking price of $2,390,000. This property was built in 1984 and has 5 bedrooms and 4 full and 1 partial baths with 5416 sq. ft. Windemere Way is located within the Syosset school district. Search Woodbury real estate on anthonytrupia.cbamhomes.com today.

Property Features

Property Type: Residential - Single Family
Basement: Finished, Full
Basement: Yes
Cooling: Central Air
Fenced: Yes
Fireplaces: 2
Garage: 2
Heating: Natural Gas, Radiant Floor
Home Style: Contemporary
Lot Size: 0.61 Acres
Taxes: $42,894
Year Built: 1984

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 Thermostat
Soaking Tub
Sound System
Walk-In Closet(s)
Washer/Dryer Hookup

Feature Descriptions

Appliances: Convection Oven, Dishwasher, Electric Oven, Freezer, Gas Cooktop, Microwave, Refrigerator, Stainless Steel Appliance(s), Gas Water Heater
Association Amenities: Gated, Other, Tennis Court(s)
Association Fee: $950/Monthly
Association Fee Includes: Common Area Maintenance, Grounds Care, Snow Removal
Attic: Partial
Building Area Total: 5416
Community Features: Gated, Tennis Court(s)
Days on Site: 1
Exclusions: Chandelier in the L.R
Exterior: Stone, Vinyl Siding
Fireplace Features: Family Room, Living Room
Flooring: Ceramic Tile, Wood
Formal Dining: Yes
GarageY/N: Yes
Gated Property: Y
Heating Zones: 4
Laundry: Laundry Room
Lot Features: Back Yard
Number Of Kitchens: 1
On Market Date: 2026-07-17
Parcel Number: 2489-14-037-00-0027-0
Parking Features: Driveway
Patio And Porch: Deck, Patio
Pool Features: Fenced, In Ground, Outdoor Pool, Pool Cover, Salt Water
Rental Term: Monthly
Road Responsibility: Private Maintained Road
Rooms Total: 10
Sauna: Yes
Security: yes
Security Features: Fire Alarm, Gated Community, Security Gate, Security System, Smoke Detector(s)
Sewer: Public Sewer
Skylight: Y
Special View Info: Water
Swimming Pool: Yes
Utilities: None
Water: Public
Window Features: Floor to Ceiling Windows, Oversized Windows, Skylight(s), Wall of Windows

Local Schools

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

Estimate Your Payment

Estimated Payment

$ 16,356.72 per month $12,085.14 Principal & Interest $3,574.50 Property Tax $697.08 Homeowner's Insurance

Change Payment Information

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years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Listed By / Shown By

Listing By

Agency Name: BERKSHIRE HATHAWAY
Agency Contact: 516-200-5700

agent picture

Shown By

Agent Name: Anthony Trupia
Agent Phone: (516) 587-9895
Agency Title: Coldwell Banker American Homes

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