Welcome to Windmont--Windham's most exclusive gated community--where luxury living meets the serenity of a private, thousand-acre natural preserve. Opportunities to own here are few and far between, making this a truly rare offering. Enter through secured gates and follow a scenic road to a paved, winding driveway that leads to this beautifully updated contemporary home, privately sited on 5 acres and bordering over 1,000 acres of protected state and city land, delivering unmatched privacy, natural beauty, and direct access to trails right from your backyard. Step inside to a tiled foyer with a stunning wide, curved staircase and soaring ceilings, setting the tone for the home's elegant design. The residence is drenched in natural light throughout its 4,000 sq ft of living space, highlighted by gleaming wood floors and an open, airy layout. The main living spaces are designed to impress, featuring a dramatic great room with vaulted ceilings, exposed beams, a wood-burning fireplace, and a built-in wet bar--perfect for après-ski gatherings. From here, step out onto one of two expansive decks, including a brand-new deck with a new hot tub, all overlooking a peaceful, private yard. A secondary living room provides additional space to relax or entertain. The kitchen is both stylish and functional, offering stainless steel appliances, granite countertops, and seamless flow into a formal dining room through elegant French doors. With four bedrooms plus a generous flex room currently used as a fifth bedroom, there's room for everyone. The first-floor primary en-suite is a retreat of its own, featuring dual walk-in closets and a jetted soaking tub surrounded by windows with tranquil views of the outdoor firepit. **Included in the bedroom count are two en-suites--one on the first floor and one on the second--**providing comfort and privacy for both owners and guests. Architectural details such as arched doorways and multiple access points to the expansive decks enhance the home's charm, while seasonal ski slope views peek through the trees--reminding you just how close you are to the action. A mud/ski room and attached three-car garage make mountain living effortless, while recent upgrades--including a new roof, new deck and hot tub, freshly painted exterior, a water filtration system, generator, a newer a Buderus furnace (installed in 2022), new water pump, and a newly installed sewer riser for easier access to the septic system--ensure peace of mind. The home is equipped with a newer Buderus G215/6 (256K BTU) furnace, regularly serviced with its most recent service completed in December 2025. A Eufy security system is included in the sale, and high-speed fiber optic internet through Mid-Hudson Cable provides seamless connectivity for both work and leisure. Located just minutes to Windham Mountain Club, local golf courses, and the town's restaurants and shops, this property offers the perfect balance of privacy, luxury, and convenience--all just 2.5 hours from NYC.