Windham, VT Classified Ad Listings

2936 Shunpike Rd. There is no place and home and no better place to call home than Mount Holly. Welcome to this quality log home with Okemo View! Step into a warm and inviting open main level with gorgeous hardwood floors, vaulted ceiling, stone wood burning fireplace and updated custom kitchen. Main level primary suite with jetted tub in the primary bath and large closet. Main level includes a...

123 Nichols Rd. HIGH-QUALITY NEW CONSTRUCTION | 123 Nichols Hill Road, Peru, Vermont Rarely does an opportunity like this come to market in Peru, Vermont, a brand new, high-quality, luxury residence offering the perfect combination of refined construction, privacy, expansive mountain views, a private pond, and a beautifully renovated guest house. The main residence was thoughtfully designed for...

81 Main St. Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by ...

231 VT Route 100. Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL and MOUND SEPTIC SYSTEM just installed in August 2026. Updated elec...

000F-320 Bourbon Run. This 1-acre wooded lot in Jamaica permitted for a 3 bedroom , Vermont offers a unique opportunity for peaceful living in a quiet town with no zoning restrictions. Jamaica maintains its own roads and is home to a State Park that provides excellent camping and summer recreational activities. The property is conveniently located near major ski resorts including Stratton, Brom...

1871 W Hill Rd. Welcome to your fully furnished chalet-style escape in Townshend, Vermont. Tucked away at the end of a private drive on 10 partially cleared, usable acres, this 2-bedroom, 2-bathroom home offers the perfect blend of comfort and Vermont charm. With four separate sleeping areas, there's plenty of space. The first-floor primary suite provides a private retreat with its own ensuite ...

From Tue Oct 13 until Wed Oct 14. Our October 13th Museum Deaccession Sale features vintage and historical clothing, textiles and accessories from Purdue University's Costume via the Middlebury College Antique Collection, The M. Estella Sprague Costume Collection and select private estates. This four hundred lot sale is packed with new-to-market lingerie, vintage and antique gowns, opera coats,...

From Tue Oct 20 until Wed Oct 21. Flying Pig Auctions is excited to present the Estate of Ron & Lori Lunn of Massachusetts combined with several other estates & collections to make this an exciting auction filled with treasures that span eras & genres and includes all types of items! SO MANY ITEMS that we are conducting a THREE-DAY AUCTION! Ron & Lori Lunn's house was their hobby. Together they...

8559 VT Route 30 Lots 2 And 3. Double the Lots, Half the Drama. Why buy one lot when you can have two for the price of... well, this one? Here are 4.68 acres of "ready-to-go" land. Permits are secured for a 3 bedroom house on each lot, and the septic is already there, so you don't have to spend your weekends at town hall meetings. Build on both, or build on one and sell the other to that friend...

2903 State Forest Rd. This is such a blank canvas for you to make your own. Taken down to the studs with a newer roof, windows, and siding, this home is ready for you to come in and make it your own. Seller has never lived here, so the Buyer will have to do their due diligence. Lot is currently 1.5 acres, but the boundary line will be adjusted prior to closing to make the lot around 5+/- acres ...

540 Scottsville Road. Single Family Home for sale in Danby, VT for $75,000 with 5 bedrooms and 1 full bath. This 1,894 square foot home was built in 1790 on a lot size of 2.3.. Bring your vision to 504 Scottsville Road in Danby! This property offers a unique opportunity for those looking for a renovation project, homestead, or potential redevelopment opportunity in a beautiful Vermont setting. ...

2721 Vermont Route 155. The Best of Vermont Living. At the heart of the home, a custom-crafted chef's kitchen serves as a welcoming gathering place, while warm wood floors and an open living area create an inviting atmosphere for everyday living and effortless entertaining. Throughout the residence, oversized windows frame expansive country views, grounding you in the natural beauty of your sur...

W Hill Rd. West Hill Road is situated prominently on a mountainside, offering breathtaking views that stretch across the valley to the north, with clearing there will be scenic beauty of the area. This property presents an exceptional opportunity for individuals looking to construct their dream home or a private compound, with an abundance of possibilities limited only by one's imagination. Loc...

2506 Healdville Rd. Belmont Retreat with Long-Range Views... Enjoy peaceful surroundings and beautiful long-range eastern views from this charming three-bedroom, two-bath modified ranch on 1.72 picturesque acres in Belmont. The cozy kitchen flows into a spacious dining area, while abundant natural light fills the inviting family room, which opens to an oversized deck, perfect for relaxing and e...

11 Ledge Road. Lots and Land for sale in Dover, VT for $69,500. The lot size is 1.04.. Lovely wooded building site in the Dover Hills not far from the Mount Snow ski resort, nearby lakes, villages, shopping, and dining. Backs up to a 250+ acre property for great privacy to the rear, with easy access to snowmobile trails, easterly view potential, and a 4 bedroom septic design in place.. Lot Feat...

239 Harwood Pl. Welcome to this one-of-a-kind hexagonal home nestled in the heart of the West River Valley, where thoughtful updates meet Vermont character and a truly special setting. This 2-bedroom, 2-bath residence offers a unique architectural design with vaulted ceilings, abundant natural light, and a layout that feels both open and inviting. The property is very private and also boasts se...

556 Sawmill Rd. Tucked into a tree-lined one-acre lot in Wardsboro, Vermont, this special property offers just the right amount of privacy while keeping you close to everything Southern Vermont has to offer. Ideally located just 12 minutes from Mount Snow and 20 minutes from Stratton Mountain Resort, the property offers easy access to year-round recreation. Start the morning on the large front ...

Forrester Rd. Lot 4 IS 4 acres! This private setting is less than 3 miles to Stratton Mountain Resort with easy access in the no zoning town of Jamaica. Five Bedroom Existing State Issued Wastewater Permit WW-2-2200 along with survey already in place for this lot. Being subdivided off a larger 200+ acre parcel. Power existing on current right of way and is also access to this wooded lot. Reside...

4027 Route 100 Hwy. Attention Buyers looking for a Turn Key property and or business location: Proven Short Term Rental Income, 142k gross over the past 8 years with 2 of those years virtually closed due to COVID. 135k net. Being on Route 100 gives you easy access to everything including Commercial and Mixed Use prime location. Welcome to Your Vermont Retreat on scenic Route 100 in Wardsboro. B...

33 Old Ridge Road. Single Family Home for sale in Winhall, VT for $1,235,000 with 4 bedrooms and 4 full baths, 1 half bath. This 3,060 square foot home was built in 2002 on a lot size of 1.1.. Stratton Mountain Club AVAILABLE to the purchaser of this exceptional Stratton Resort Residence in High Meadow! This home's design and fit and finish creates the mountain ambiance you look for:Commanding ...