Windham, VT Classified Ad Listings

96 Paradise Ln. Private Mount Holly retreat just ten minutes from Okemo Mountain! Set on 5+ peaceful acres, this property offers the perfect balance of privacy, recreation, and year-round convenience. Enjoy quiet country surroundings with easy access to Okemo, downtown Ludlow, the lakes region, and VAST trail access for snowmobile adventures. The main house has a new roof. This warm and invitin...

628 Townshend Rd. One of only two stone houses in the charming town of Grafton, this stately home is a truly special opportunity. Perched on a hill across from the renowned Grafton Cheese Company, the property offers easy access to village amenities and year-round recreation at Grafton Ponds Outdoor Center. Inside, you'll find a spacious and inviting layout: Large front living room with exposed...

1871 Route 103. Historic Train Stationhouse! Unique design and character in a prime ski location on 4 acres with a private pond. This efficient historic gem was relocated to the current more convenient location with added acreage and a commercial outbuilding. The owned solar power offers low cost of living and years of energy benefits for new owners. This property features 2 bedrooms and 2 bath...

548 Crow Hill Rd. Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for. Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improveme...

165 Stone Hollow Rd. Welcome to an extraordinary property where Vermont living meets year-round recreation and relaxation. Located a mile from the center of Londonderry and within 20 minutes of three ski resorts. This spacious 4-bedroom, 3-bath home offers a truly uncommon amenity: your very own private indoor pool. Imagine having a private wellness retreat with recreation spaces, and gathering...

224 Cobble Ridge Rd. Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations. Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where...

35 Theron Fisher Rd. Nestled along the Saxtons River, moments from historic Grafton, this beautifully restored Colonial farmhouse offers a rare blend of Vermont history, modern luxury, and exceptional curb appeal. Originally built circa 1820, the home has been meticulously reimagined and rebuilt with extraordinary attention to quality and architectural integrity. The renovation includes new plu...

1260 Grafton Rd. A wonderful retreat on 35+/- acres in Chester is ready for new owners to enjoy. The gated, serpentine driveway threads its way through the woods and by the large pond, taking in the lovely, open meadow with stone works and gardens leading to the classic custom 2+ bedroom, 3 bath chalet in an absolutely charming setting. As if transported from the Alps, the architectural feature...

Condition: New, Make: Ferris Industries, Model: ISX 2200 60 in. Kawasaki FX781V EVO 30.5 hp, Year: 2026, Color: Red, Dealer: Benny's Power, Phone: 802-875-2020. THE LEADER IN SUSPENSION TECHNOLOGY FOR TURF Take productivity and comfort up a notch. The ISX 2200 boasts our most advanced suspension technology ForeFront Suspension, ensuring operator comfort. A redesigned 2-belt iCD + cutting system...

Condition: New, Make: Ferris Industries, Model: IS 700 60 in. Briggs & Stratton CXi 27 hp, Year: 2026, Color: Red, Dealer: Benny's Power, Phone: 802-875-2020. COMMERCIAL COMPONENTS AT AN AMAZING VALUE FOR LANDSCAPERS AND LARGE PROPERTY OWNERS Mow more lawn in less time. The IS 700 Series, with up to five feet of cutting width, features our patented suspension technology, iCD Cutting System, hea...

691 Black Bear Rd. A long winding driveway through a mountain of foliage leads you to this extraordinary mountain-modern retreat, perched high above nearly 200 acres of protected Vermont wilderness. Thoughtfully crafted by Big Pine Builders LLC, this striking off-grid solar home seamlessly blends contemporary design with Vermont's rugged natural beauty, allowing you to live on the sun's rhythm ...

64 County Rd. CONTINUE TO SHOW PLEASE!! Enjoy the ease of single-level living in this 2008 single-wide home set on 2.5 peaceful Vermont acres. The open concept kitchen and living area is filled with natural light, creating a warm and inviting atmosphere. Offering three bedrooms, one full bath, and a convenient laundry area. Recent improvements include new carpeting and fresh interior paint, mak...

68 Mount Gilboa Road. Property for Rent in Westmoreland, NH for $3,600 with 3 bedrooms and 2 full baths. This 1,740 square foot property was built in 1989 on a lot size of 12.44.. Welcome home to Mt Gilboa Rd! This beautifully maintained, custom built 3 bed, 2 bath home on 12+ acres is now available for rent! Enjoy a peaceful wooded setting in this recently updated home featuring a brand new ki...

Route 100. Discover the beauty and tranquility of this picturesque wooded parcel-approximately 35 acres-nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a larg...

54 Main St. This home IS quintessential Grafton Vermont! Built c. 1850 this stately 4 over 4 colonial served as the Parsonage for the Grafton Church as it is still referred to this day. Privately owned for nearly 30 years this handsome home is ready for new stewardship. Spacious and sturdy, this vintage gem offers plenty of space and has been updated for today's lifestyle. The first floor offer...

476 Missing Link Rd. 5 acres of magical Ct River frontage. This site boasts 2 wide open fields. The septic design for a 5 bdrm septic is in the first field. The seller has obtained permission from the state for a driveway curb cut (Missing Link Rd, is State Rte 5) The land sits 80 ft above the river, so flooding is not an issue but you'll have the most peaceful, private views of the water. Ther...

2072 N Main St. This is your chance to own in downtown Londonderry! You have the option of commercial, residential or BOTH. One unit is currently set up for residential use with living area and 3/4 bath on the first level and three bedrooms and full bath on the second floor. The second unit has been used for commercial use in the past with open space and 1/2 bath on the first floor with 3 rooms...

251 Pratt Bridge Rd. Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas and the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated BandB. Pr...

258 Chester Rd. Set on a beautifully landscaped parcel just minutes from the heart of historic Grafton, this meticulously maintained residence offers timeless New England charm, exceptional craftsmanship, and inviting spaces. Surrounded by mature trees, perennial gardens, and lush lawns, the property provides a peaceful setting with the perfect balance of privacy and convenience. Inside, warm h...

2063 Houghtonville Rd. Seasonal Rental!! Charming schoolhouse not far from the village. First floor hosts an open floor plan kitchen, dining, and livingroom. Plus a reading nook and full bath with washer/dryer. Two bedrooms with a full bath on the second floor. Available for the winter 2026-2027 season. Offered at 3,000.00 per month all inclusive. Credit check and references required. Come and ...