# 27 Windemere Way, Woodbury, NY 11797 > **TL;DR:** 5bd/5ba single family, $2,390,000 ($441/sqft), built 1984, 5,416 sqft. > Pool, Fireplace, View, A/C. Est. $13,732/mo. Listed 109 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $2,390,000 | | Price/sqft | $441 | | Bedrooms | 5 | | Bathrooms | 4 full, 1 half | | Square Feet | 5,416 | | Year Built | 1984 | | Lot Size | 26,428 sqft (0.61 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Pending | | Days on Market | 109 | ## Why This Home Stands Out - **Pool** - Patio, Deck - **Views** - Water ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $12,085 | | Estimated Insurance | $697 | | HOA | $950 | | **Total** | **$13,732** | ## Nearby Schools - **Elementary:** Walt Whitman Elementary School - **Middle:** H B Thompson Middle School - **High:** Syosset Senior High School ## Key Amenities - Pool - Fireplace - View - A/C - 2-car garage ## Property Highlights - Built in 1984 - 0.61 acre lot - Private pool - Fireplace ## Description ### Agent 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 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. ## Location - **Address:** 27 Windemere Way, Woodbury, NY 11797 - **County:** Nassau County - **Neighborhood:** Windemere - **Coordinates:** 40.820111, -73.461083 - **Google Maps:** https://www.google.com/maps?q=40.820111,-73.461083 ## Listing Agent - **Name:** Irena Tsarevsky CBR - **Brokerage:** Laffey International Realt Estate - **Broker Phone:** (516) 308-0550 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/27-Windemere-Way_Woodbury_NY_11797_M35665-46151?f=listhub&s=MLSLINY&m=1025514&c=propsimple) ## Photos ![27 Windemere Way - Photo 1](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f3637069408r.jpg) ![27 Windemere Way - Photo 2](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1624381332r.jpg) ![27 Windemere Way - Photo 3](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2602999211r.jpg) ![27 Windemere Way - Photo 4](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f501209466r.jpg) ![27 Windemere Way - Photo 5](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1643950370r.jpg) ![27 Windemere Way - Photo 6](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1534454378r.jpg) ![27 Windemere Way - Photo 7](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2075679902r.jpg) ![27 Windemere Way - Photo 8](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f607023876r.jpg) ![27 Windemere Way - Photo 9](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f804867724r.jpg) ![27 Windemere Way - Photo 10](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1454670891r.jpg) ![27 Windemere Way - Photo 11](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f444965790r.jpg) ![27 Windemere Way - Photo 12](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1939861272r.jpg) ![27 Windemere Way - Photo 13](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2789482234r.jpg) ![27 Windemere Way - Photo 14](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2879242269r.jpg) ![27 Windemere Way - Photo 15](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f3062609049r.jpg) ![27 Windemere Way - Photo 16](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1008387759r.jpg) ![27 Windemere Way - Photo 17](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f3208107324r.jpg) ![27 Windemere Way - Photo 18](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1066784236r.jpg) ![27 Windemere Way - Photo 19](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2351578908r.jpg) ![27 Windemere Way - Photo 20](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f3831773558r.jpg) ![27 Windemere Way - Photo 21](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1185849068r.jpg) ![27 Windemere Way - Photo 22](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2007940382r.jpg) ![27 Windemere Way - Photo 23](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f4055427217r.jpg) ![27 Windemere Way - Photo 24](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f291537186r.jpg) ![27 Windemere Way - Photo 25](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2581595525r.jpg) ![27 Windemere Way - Photo 26](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f3056047633r.jpg) ![27 Windemere Way - Photo 27](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f4256740981r.jpg) ![27 Windemere Way - Photo 28](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2898889831r.jpg) ![27 Windemere Way - Photo 29](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f3182207439r.jpg) ![27 Windemere Way - Photo 30](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2424237197r.jpg) ![27 Windemere Way - Photo 31](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f960704316r.jpg) ![27 Windemere Way - Photo 32](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1856195r.jpg) ![27 Windemere Way - Photo 33](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f4182175350r.jpg) ![27 Windemere Way - Photo 34](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1049265107r.jpg) ![27 Windemere Way - Photo 35](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f1689135404r.jpg) ![27 Windemere Way - Photo 36](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f2517151718r.jpg) ![27 Windemere Way - Photo 37](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f3785679731r.jpg) ![27 Windemere Way - Photo 38](http://lh.rdcpix.com/ccde4ebb6f0f9be17d2b34d1b5727f7cl-f4053470025r.jpg) --- **MLS#:** 1025514 | **Updated:** 2026-10-26 **Source:** listhub *Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/27-windemere-way-woodbury-ny-11797-228f955f50694d83ad52fbaf4d747dee) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/27-windemere-way-woodbury-ny-11797-228f955f50694d83ad52fbaf4d747dee#listing", "url": "https://www.propertysimple.ai/listing/27-windemere-way-woodbury-ny-11797-228f955f50694d83ad52fbaf4d747dee", "name": "27 Windemere Way, Woodbury, NY 11797", "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 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. 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