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Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Open House on September 26, 10am -12:00 Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

3 Beds ⋅ 2 Baths ⋅ 5108371 MLS

756 Birch Hill Rd, Windham

$2,700,000

UNFORGETTABLE LUXURY | Distinctive, sophisticated and designed to leave a lasting impression, this exceptional custom Colonial by renowned builder DiPietro Homes offers 6,000+ sq. ft. of beautifully appointed living space. Thoughtfully enhanced with on-trend updates and improvements, this remarkable home blends exceptional craftsmanship with a fresh, elevated style for today's luxury lifestyle. From the moment you enter, custom millwork and impressive architectural details set this home apart. At the heart of the home, the stunning family room features a coffered ceiling and wood-burning fireplace, opening seamlessly to a showstopping chef's kitchen designed for both everyday living and effortless entertaining. Full-size refrigerator and freezer, generous workspace and a Butler's Pantry complement this thoughtfully designed space. An elegant dining room, private office and functional mudroom complete the main level. Upstairs, the luxurious primary suite is an unforgettable retreat with its own fireplace and spa-inspired bath featuring a soaking tub and steam shower. With 4 bedrooms, 5 bathrooms, a bonus room and a finished lower level offering a recreation room, full kitchen, built-ins and bath, there is exceptional space and versatility throughout. Outside, your private backyard awaits, complete with an in-ground saltwater pool with waterfall and a covered seating area perfect for relaxing, entertaining and enjoying summer days outdoors. Conveniently located near I-93, schools, shopping and community amenities, with Boston approximately 45 minutes away. A truly unforgettable home where luxury, comfort and exceptional design come together.

4 Beds ⋅ 6 Baths ⋅ 5104676 MLS

17 Bennington Rd, Windham

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