Windham Vermont Real Estate

Great location for primary or vacation home. Near Burbee Pond in Windhame. 2.6 acres and possibly small commercial. 4 Plus bedrooms with one full bath and a half bath on main floor. Home is ready for your improvements. Close to ski resorts!

This tidy log home is located 30 minutes or less from 5 ski areas! From Windham there are many directions to choose with activities like hiking and biking right out the door and restaurants, shops and recreation within a short drive. On a quiet dead end dirt road in the heart of Windham, this cute Vermont log home offers the kind of peace and privacy that is getting harder to find. Set in the clearing of four acres of wooded land, this property feels like a private retreat, surrounded by conservation land and abundant wildlife. The log home blends rustic charm with comfortable living. The warm wood finishes on the interior, vaulted ceiling, newly supported, and a cozy loft create an atmosphere that invites you to slow down and relax! Immerse in nature while enjoying coffee on the porch or evenings under the stars on the back deck. The West Windham Valley is the home of a beautiful natural waterfall, providing a scenic escape and reminder of the area's untouched beauty. This is an ideal setting for outdoor enthusiasts , nature lovers and anyone seeking a quiet country lifestyle. Price increase reflects work done to reinforce roof structure. If you have been looking for a true Vermont getaway, this property delivers!

In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here.

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.

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. 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.

Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam board, and the foundation is sealed with full drainage installed around the perimeter. Step inside to a light-filled interior with new flooring, walls, and fixtures throughout. The spacious kitchen features Big Chill appliances and opens to a lovely front porch overlooking the old stone walls that border the property. A fenced-in yard makes this ideal for pets, and the water filtration system with UV light ensures clean living. You’ll also find a new washer and dryer, a new septic system, and thoughtful design throughout. Close to skiing at Magic (10 min), Bromley and Stratton (20–25 min), and just 15 minutes to downtown Londonderry. Hike, bike, or snowmobile with access to VAST trails and Timber Ridge nearby. Come see what makes this rare offering a great opportunity!

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.

Brand-new construction in beautiful Windham, Vermont! This thoughtfully designed three-bedroom home with an additional bonus room offers the comfort, efficiency, and ease of new construction paired with a peaceful Vermont setting. Filled with natural light, the home features bright, welcoming living spaces and a versatile floor plan designed for both everyday living and weekend escapes. The bonus room provides valuable flexibility for a home office, guest space, playroom, or den. An attached two-car garage makes Vermont living especially convenient, providing sheltered parking along with plenty of room for skis, bikes, outdoor gear, and storage. Outside, the yard offers space to relax, play, garden, or entertain, while the firepit creates the perfect gathering spot for summer evenings, crisp fall nights, and après-ski get-togethers. Located in the quiet mountain community of Windham, this property puts four-season recreation within easy reach. Five major ski areas—Stratton, Bromley, Magic Mountain, Okemo, and Mount Snow—are all located within approximately 35 miles of town, providing an incredible variety of winter adventures. When the snow melts, explore nearby hiking and biking trails, enjoy fishing, paddling and swimming, or spend the day at destinations such as Lowell Lake and Jamaica State Parks. The greater Windham region is known for its extensive trail network and abundant opportunities for hiking, mountain biking, snowshoeing, cross-country skiing, and snowmobiling. Whether you're searching for a full-time Vermont residence or a low-maintenance mountain getaway, this newly built home offers a wonderful combination of modern comfort, outdoor space, and access to everything that makes Southern Vermont special.

Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A dedicated entry drop zone keeps gear organized after long days outdoors. The layout offers strong separation of space across three levels, including an en-suite primary, additional bedrooms, and a top-floor loft ideal for overflow sleeping or a recreation zone. The lower level adds a second living area with a wood-burning stove, plus guest accommodations. Outdoor living is equally dialed in, with an upper deck featuring a brand-new hot tub, a newly built firepit, and a natural landscape that includes meadow, stream, and wooded acreage. A three-car garage adds practical year-round convenience. Located within a 20-minute drive to Stratton, Magic, and Bromley, and directly adjacent to the VAST snowmobile trail system, this property offers immediate access to Vermont’s top winter and summer activities.

Set on 53 private acres with mountain views, this four-bedroom, three-bath home offers the space and setting to enjoy every season. Built in 2007 and located just a short drive from Stratton, Bromley, Magic, and Okemo, it's equally suited as a full-time residence or a mountain retreat. The heart of the home is a welcoming great room with a floor-to-ceiling stone fireplace and a wall of windows that frames the surrounding landscape. The open-concept kitchen, dining, and living areas make it easy to gather after a day outdoors. A spacious primary suite provides a comfortable retreat, while a loft, game room, walk-out lower level, and oversized mudroom offer room for everyone and all the gear that comes with Vermont living. An attached two-car garage adds everyday convenience. The home is offered furnished. Steps from the house, and into the meadow is a 22' x 30' barn that expands the possibilities. Three overhead doors make it ideal for storing snowmobiles, ATVs, tractors, or other equipment, and there's room for horses as well. The unfinished second floor is already equipped with lighting and six windows that fill the space with natural light, ready for a workshop, studio, or future expansion. The VAST trail is at the end of the road, ride your snowmoobile direct from the house to miles of connected trails. Stone steps built into a classic Vermont stone wall lead from the house to the meadow below, adding to the property's charm and connection to the landscape. Whether your weekends are spent skiing, snowmobiling, hiking, or simply enjoying the peace and quiet, this property offers the best of Vermont living. As the wall art inside the home suggests: "Snowmobile. Ski. Rest."