Windham, VT Classified Ad Listings

177 Old Tavern Rd. Renovated in 2024, this timber frame sits on 5.75 pastoral acres. This property offers sunrise views, beautiful sun all day and a peaceful setting with pond on a quiet country road. The house has 4 bedrooms, 3 full baths, and an office. Wide plank original pine floors, open timber frame concept and all new baths with heated floors. Custom white oak cabinets in the kitchen and...

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...

564 Goodaleville Rd. Set along a quiet back road on the Winhall River, this beautifully reimagined former schoolhouse blends timeless Vermont character with thoughtful modern updates. Built around the historic Goodaleville Road schoolhouse with a timber-frame addition and renovated by Vermont Country Builders, the home reflects exceptional craftsmanship, energy efficiency, and enduring design. ...

4427 W Hill Rd S. A true Vermont lodge in every sense-warm, welcoming, beautifully appointed, and designed to bring people together. This exceptional mountain retreat combines the character and comfort buyers dream about in a Vermont home with the space, amenities, and proven rental history that make it equally appealing as an investment. The property has enjoyed a strong rental history with re...

226 Hoey Rd. Historic Rowen Farm is an extraordinary Vermont country property, where the character of a circa-1812 Federal farmhouse has been preserved with exceptional care and paired with refined modern comfort on 77.68 private acres of reclaimed meadow, woodland and mountain views. Original wide-plank floors, exposed beams, doors, period details and four wood-burning fireplaces speak to the ...

8 Winhall Station Rd. Welcome to 8 Winhall Station Road in South Londonderry, a well-located three-bedroom, two-full-bath Vermont home offering convenient access to some of Southern Vermont's best year-round recreation. Several major ski resorts are within easy driving distance, along with nearby hiking trails, campgrounds, swimming, biking, and countless opportunities to enjoy the Green Mounta...

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 ...

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...

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...

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. ...

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...

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...

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...

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...

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...