Windham, VT Classified Ad Listings

313 Dover Rd. Step back in time while enjoying the comforts of today in this classic 1800s post-and-beam Cape set on 2 peaceful acres in the Vermont countryside. Rich in character and timeless charm, this 4-bedroom, 3-bath home showcases the warmth and craftsmanship of a bygone era with exposed beams, inviting living spaces, and room for family and guests. Outside, you'll find established peren...

Welcome to 1722 Under the Mountain Road, a private 3.02-acre retreat in a tranquil setting surrounded by horse farms, with views of Stratton Mountain. This 2-bedroom rustic cabin is nestled in a former Morgan horse farm. Full of character, the main home features wood frame, wide plank floors throughout, with an open concept layout. The floorplan includes a full kitchen, a dining room, and a liv...

30 Back St. Tucked away on Back Street yet close to Newfane Village, this expanded 1790 Cape offers 3 beds, 3 baths, more than 2,300 square feet of living space, 2 acres adjoining Smith Brook! Main living areas are bright, open, airy, beautiful wood floors, ample windows, spacious great room incorporating living and dining areas opening to additional seating space, a bar area, breakfast room, a...

6795 VT Route 100. Motivated sellers! Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a varie...

3715 Route 11. Beautifully expanded and fully renovated 18th-century farmhouse, thoughtfully reimagined by Gray Interiors of Darien, CT. This home blends timeless charm with an elegant yet relaxed New England feel. All systems and mechanicals have been completely updated and modernized. Stylish barnboard accents complement marble countertops, custom cabinetry, high-end finishes like the Shaws s...

667 W Hill Rd. Charming 3 bedroom Okemo chalet in a private setting just minutes from the Okemo base lodge. Well positioned on a level lot accented by stone walls and offering a backyard perfectly suited for all your favorite lawn games. Spacious wrap around deck offers excellent outside entertainment space and includes a separate pad ready for your new hot tub. Entry mudroom includes built ins...

5892 Route 100. Charming Farmhouse Gem in the Heart of Londonderry Welcome home to this inviting 2-bedroom, bonus room and 2-bathroom residence centrally located in Londonderry, VT a dream location for outdoor enthusiasts with quick, convenient access to world-class skiing at Magic, Bromley, Stratton, and Okemo Mountains in the winter. Summer and fall you are close to hiking the multitude of tr...

206 Smith Rd. Looking for a project? Featuring a drilled well, existing septic, electric, and driveway, you have a good start for a new build, renovation or a combination of the two. The cabin has been added onto many times, making room for a growing family. The land is mostly level, with some nice plantings and the house sits back a little distance from the neighbors. The well is being shared,...

Meadow Rd Lot 4. Private 2.53+/- acre state approved building lot located at the end of a dead-end, private road. Positioned at the south end of Ludlow off East Hill Road, this lot offers easy access to town amenities and the Okemo Ski Area. Possible views of Okemo with clearing.

1787 Route 100 N. From location to layout, this home offers the best of Vermont living. Set along scenic Route 100 in the heart of the lakes region, you'll enjoy year-round recreation just minutes from Okemo Mountain Resort, Killington Resort, and Plymouth State Park. This thoughtfully remodeled farmhouse blends classic charm with modern updates. Offering 3 bedrooms and 4 bathrooms, the home fe...

190 Depot St. Tucked into a quiet, sunny setting just steps from Jamaica State Park and the heart of Jamaica Village, this charming two-bedroom plus loft Cape offers the perfect blend of Vermont character, comfort, and convenience. Filled with natural light and warm wood accents, the home has an inviting feel from the moment you step inside. A spacious mudroom provides a practical entry for eve...

55 Wallis View Ln. Winter Seasonal Rental Ski Home available November 1, 2026 through April 15, 2027. Price is $35,000. plus $7000 for utility deposit and $5000 security deposit. All funds due prior to rental start. Beautiful views from this large cape-style home. Open kitchen to living room with stone fireplace. Comfortable, warm and spacious. Fully-equipped kitchen for the chef. All linens pr...

51 Burbee Ln. OPEN HOUSE SAT. OCT 3 10:00 TO 1:00 Amazing contemporary post and beam overlooking the West River Valley offers views, views, views. This whimsical open concept home flows from kitchen to dining area and the living room wraps around a soaring central stone fireplace. The living room's cathedral ceiling has wonderful natural light from top to bottom and accesses a large deck for en...

640 cross Road. Lots and Land for sale in Londonderry, VT for $1,700,000. The lot size is 61.36.. An exceptional opportunity to establish a private Vermont estate on approximately 61.36 acres, offering stunning panoramic views of Stratton and Bromley Mountains and located a short drive from Magic Mountain. The site is fully prepared for construction, with utilities, services, and a gravel road ...

24 Mowrey Rd. Already operating as a successful short-term rental, 24 Mowrey Road offers the space, setting, and amenities buyers are looking for in a Southern Vermont getaway. Set on 2.3 acres along a town-maintained dead-end road, this spacious 4-bedroom, 4-bath home is positioned between Stratton and Mount Snow, with easy access to year-round recreation. Inside, the open great room creates a...

42 Blackberry Ln. Only 8 miles from Stratton Mountain, this extra-large expanded farmhouse provides ample space, quiet, and tons of classic Vermont charm. Set in a lush garden landscape surrounded by meadows, a stone wall, perennial gardens, an apple orchard, a barn, and multiple outbuildings, the home feels like old Vermont while being close to major amenities. The original home is from the 19...

Kick off your ski boots and cozy up by the oversized stone fireplace; 6 Town Farm Road is the kind of place that invites you to stay awhile. Currently enjoyed as a beloved vacation home and Airbnb, this quintessential Vermont property is ready for whatever comes next. This property feels private while the best of Vermont is still within easy reach. Crown Point Country Club is two minutes away, ...

"Creek Side Charm" Escape to your own secluded retreat! Step into an open, light filled layout where warm wood interiors and cozy living spaces invite you to relax! A classic barn with an oversized two car garage, with a bonus space above for extra storage, potential... A perfect "get-away" for those seeking comfort, serenity and nature at their doorstep! Minutes to skiing, hiking and in the he...

Set at the top of the desirable Greensprings community, this spacious three-bedroom condominium offers a private Vermont retreat with views toward the Mount Snow trails and the added benefit of backing up to the quiet privacy of the surrounding Vermont forest. The main living level features a dramatic vaulted living room with warm wood accents, a fireplace, and generous gathering spaces designe...

56 River Bend Drive. Single Family Home for sale in Springfield, VT for $389,900 with 3 bedrooms and 1 full bath. This 1,840 square foot home was built in 1970 on a lot size of 1.3.. Riverfront properties rarely come on the market, but this gem is in a sweet cul-de-sac, with stunning views from the house and deck and with access to the river. Put your canoe in and enjoy a lazy day on the water....