Windham, VT | 1113 Old Cheney Road

Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system provides efficient heating and air conditioning year-round. In 2024, the basement underwent major upgrades, including mitigation with an improved support and drainage system, along with the installation of two new water tanks—providing long-term confidence and reassurance for the next owner. Ideally located near Stratton Mountain, Ball Mountain Dam, and Jamaica State Park, this home is a perfect base for four-season recreation—from skiing and snowboarding to hiking, swimming, and exploring nature. A true turnkey retreat in an unbeatable location!

Set on a scenic country property in Windham, this expansive home offers exceptional space, flexibility and a setting with real character. Currently used as a large single-family residence, the home was originally built as a three-family property, with a common entrance serving two living areas and a separate entrance to the garden-level apartment. A central stairwell can connect the spaces, creating options for a large household, multi-generational living, guests, home offices or future reconfiguration. The three living areas include full kitchens, generous living rooms and a total of six bedrooms, with expansive rooms and large windows throughout. There is also ample storage and flexible space for a workshop, studio or dedicated home office. The grounds are where this property becomes especially memorable. Shaped over the years by an artist’s eye and a love of the land, the organic gardens feel established, abundant and wonderfully personal, with fruit trees, flowering shrubs, mature plantings and productive raised beds built at waist height. Several decks and screened porches invite you to slow down and take in the setting, while the property unfolds into a pond, large meadow, playing field, trout stream and walking trails, with views toward Turkey Mountain Ridge. There is a quiet, almost timeless quality here that is increasingly hard to find. Located off the beaten path in picturesque Windham, yet convenient to Southern Vermont skiing, hiking and year-round recreation, the property offers room to live, create, gather and breathe. The home does need TLC and updating, but its scale, versatile layout, organic gardens, land and natural setting make it a true diamond in the rough with tremendous potential.

Welcome to Cloister Falls, a truly special offering in the Green Mountains! Tucked among extensive grounds with mature gardens, a pond, and thoughtfully landscaped outdoor spaces, this 3+ bed plus den and office, 3 bath log home offers a setting that feels connected to the surrounding Vermont landscape. The property's signature feature is its swimming hole and waterfall , a natural gathering place for relaxing, entertaining, or enjoying the sound of moving water right outside your door. Inside, the home has both comfortable and impressive gathering spaces and a flexible floor plan. The formal living room is centered around a stone wood-burning fireplace and framed by natural wood details and rich textures throughout. The country kitchen features cherry cabinetry, granite countertops, and a vintage-inspired Glenwood propane and wood cookstove with plenty of workspace, counter and storage. The main level also includes a library or office space, spacious den, and solarium, creating multiple options for work, hobbies, or quiet retreat spaces.The second floor offers two inviting guest bedrooms one with a view of the pond and gardens and the either with its own balcony. A generously sized guest bath is also on this level along with a primary suite featuring a private bath and dual walk-in closets. An attached two-car garage with 2nd floor adds convenience while the surrounding grounds provide room to garden, explore, and enjoy the outdoors through every season. The walk to the screen house past the pond gives a secret garden feel. From there, take the foot bridge into your 25 acres for exploration. This is a property where the landscape and home come together to create a special experience and offering that doesn’t come along often.

Bring your vision to life on 33.34 acres in the scenic hills of Windham, Vermont. This partially completed home offers a rare opportunity to finish a thoughtfully designed residence surrounded by open meadows, established trails, and an idyllic rural setting. Designed with a 4 bedroom septic system, the home is ready for the next owner to complete the interior and exterior finishes. The clapboard siding remains unfinished, and the lower level walk out basement is plumbed for a third full bathroom, offering additional flexibility for finished living space. A substantial 24' x 48' completed foundation is in place for the planned garage. It will accommodate a 24' x 24' two car garage plus an additional 24' x 24' area of approximately 552 square feet, ready to be finished and purposed according to your needs, ideal for a workshop, studio, storage, recreation space, or other use. The land is equally appealing, with expansive meadows featuring tillable soils formerly used to grow organic fruits and vegetables, established trails, mature woods, and high quality gravel on the property. Adding to the sense of privacy and protected open space, the property abuts a National Wildlife Refuge along its western and northern boundaries. Enjoy gardening, exploring the trails, working on projects, or simply taking in the peaceful Vermont landscape. Conveniently located within reach of Stratton, Magic, and Bromley Mountains and the villages of Londonderry, Chester, and Grafton. An exceptional opportunity to complete a substantial Vermont property and create something truly your own.

Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer. Designed for gathering and relaxing, the home features two spacious living areas, providing plenty of room for family and guests. A cozy wood stove creates the perfect après-ski atmosphere, while the inviting three-season porch offers a peaceful place to enjoy the natural surroundings from spring through fall. The level, secluded lot provides privacy and outdoor enjoyment, with ample space for entertaining, gardening, or simply unwinding. Conveniently located near Stratton, Bromley, Manchester, and local dining and shopping, this property is equally suited as a full-time residence, vacation retreat, or investment opportunity. Experience the best of Vermont living in a location that puts adventure and relaxation right at your doorstep.

Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and only 3/4 mile to Jamaica State Park, outdoor recreation, dining, and local shops are all close by. Stratton Mountain and Mount Snow are both just 20–25 minutes away, making this an excellent four-season retreat or full-time residence. Inside, the home offers hardwood floors throughout, generous living space, and a wonderful sunroom with a woodstove hookup perfect for cozy evenings year-round. Additional highlights include a paved driveway, easy access to Route 30, an attached garage and workshop space.. For added transparency and peace of mind, the seller has completed a pre-listing property inspection, which is attached in the MLS. Lovingly owned by the same family since it was built, this home is filled with warmth, history, and opportunity for its next chapter. This property has full time tenants and need a minimum of 24 hours notice, longer preferred, on showings. Closing can happen October 1 or after.