Cavendish, VT | 2055 & 2071 Main & 28 Pleasant Street

Where History Meets Possibility. An 1862 Schoolhouse Reimagined. Step back in time and into opportunity. Built in 1862, this remarkable historic schoolhouse has been lovingly preserved, its character and craftsmanship thoughtfully maintained while seamlessly supporting modern use. Since 1973, the building has served as the home of a thriving distribution business, proof of its adaptability, strength, and enduring design. Inside, original details remain intact: upper glass transom windows above the interior doors, warm pine floors worn smooth by generations, and a classic belfry still standing proudly above, ready to ring once again. The fireproof safe that is in the builiding needs to stay. Every inch of space has been meticulously finished with custom trim and thoughtfully designed shelving, maximizing both beauty and functionality. Updated windows enhance efficiency, while mini-split systems provide supplemental heat in cooler months and air conditioning through the summer. The property’s 3.70-acre open lot allows for impressive accessibility, semi-trucks can easily enter, turn, and load, making commercial use entirely viable. Yet the charm of the structure invites imagination far beyond its current role. Envision a distinctive live/work residence, a destination-worthy Airbnb, a creative studio, gallery, event space, boutique distribution hub, or transform it into a singular single-family home rich with character and story. Historic soul. Modern comfort. Boundless potential. Dream big, this one is ready. Also listed as Commercial, MLS# 5077754.

If you're looking for the ultime village ski house look no more! This four bedroom three and a half bath TURN KEY home is nestled in the village of Proctorsville. Home to Singletons Store, Outer Limits Brewery, Murdoch's On The Green and much more walking distance away. Step into this lovely well appointed home and you'll feel right at home. The kitchen boasts granite counters with a large breakfast bar. Oak cabinetry, mostly stainless steel appliances, tile backsplash and under counter lighting. You'll love the open concept of the kitchen and dining room, with a granite two sided fireplace. Mozie on into the large living room with space for the whole crew and cozy up to the other side of the fireplace. The first floor is completed with an en-suite bedroom with a beautiful view of Hawks Mountain, the bathroom is finished with a tiled shower and a natural wood vanity. Rounding off the main floor with a half bath laundry room combo and a convenient corner nook for gear storage. Upstairs you find another en-suite bedroom with double sink, natural wood vanity and tiled shower. The two other large bedrooms share a full bath. One bedroom with a balcony overlooking Hawks Mountain State Forest which is a healthy walk away for recreating. Now down the the lower level where the fun begins. Pool table, foosball or a game of cards, pick your favorite. This Ultimate Village Ski House is priced to sell! Come take a look today!

Private, yet accessible location on South Hill. These are hard to come by! Nicely set back from the road is this two-story contemporary with room for family and guests. Nice lawn area as well as wooded acreage. You will enjoy your peace and quiet as you sit out on your covered porch with a cup of coffee or a cocktail! Enter into a small mudroom and you have a half flight of stairs going either up or down. On the upper level, you have three accessory rooms...den, office, and bonus room that would be a great laundry room. Nice kitchen space with light and it's open to the dining room and living room. Slider out to the huge, covered porch and large open deck. There's a woodstove hookup in the living room. On the lower level, there are three good sized bedrooms and a large family room with a walk out entrance and windows on three walls. This will be a wonderful home for the next owner. The current owner has enjoyed 25 years here. You can be next!

Tucked into a wooded setting just minutes from Okemo Mountain and Ludlow Village, this easy-keeping Saltbox makes a comfortable and uncomplicated Vermont home base. The main level features an open kitchen, dining and living area with vaulted ceilings, hardwood floors and a centrally located wood stove, plus a bedroom and full bath. Upstairs, an open balcony overlooks the living area and leads to two additional bedrooms and a second bath. The walkout lower level offers a den, laundry and generous storage space. A detached two-car garage and woodshed provide plenty of room for vehicles, snowmobiles and outdoor gear. Recent improvements include a new boiler and hot water heater (2025), hardwood flooring (2020) and a standing seam roof (2019). Convenient, comfortable and easy to maintain; just the kind of Vermont getaway that is close to everything be it hiking, biking, snowmobiling, skiing and golf!

Located just 10 minutes from downtown Ludlow’s vibrant shopping and dining, and the world class slopes of Okemo Mountain, this property delivers the ultimate year round Vermont lifestyle.Escape to Your Cozy Southern Vermont Sanctuary Nestled in charming Cavendish. This 3 bedroom home seamlessly blends rustic character with modern comfort. Inside, gather around the wood burning stove or prepare delicious meals in the fully equipped kitchen featuring the farmhouse sink. The thoughtful layout offers flexible living with a main floor bedroom and bath alongside two bedrooms and a full bathroom upstairs. Outside you will find a carport with attached shed for plenty of storage, keep the wood dry for the stove or snow off your car. Outside enjoy the fenced in yard or unwind around the fire pit under the stars. Don't miss out schedule your private showing today!

Three properties are being sold together with some owner terms possible. Investors, Dreamers, Skiers, Business Owners...Many possibilities and much potential. Bring your ideas. Weddings in the barn? Indoor growing? A ski house? A cafe or store? Lots of flexibility with no zoning. Renovations can continue or property can be sold as it is. In the past, the Okemo Shuttle has stopped across the street at Mill Street. It is a quick drive to Proctorsville - bakery, brewery, restaurant, store. 2071 Main Street could be used as a single family or two units. The town currently lists 7 bedrooms. The upper level is almost renovated with still a few things to do and the prep work has begun in the lower level. Live in the upper unit and have your business in the lower unit or have another income-producing unit or make into one amazing single-family home. Even the attic was once used as living space perhaps as part of a third unit. The chimney flashing has been addressed, slate work done, a membrane roof over the bay window area installed, some support work and vapor barrier added in basement, many windows reglazed, soffit and fascia painted, etc. The cosmetic work in the upper unit is done with the bathroom in progress. The barn that is on 2071 Main Street has had work done to the roof (sheathing boards, slate, and ridge cap). The upper level is an impressive open space. The lower workshop area of the barn needs flooring work. 2055 Main Street was once a large building built around 1880 and was the Fletcher Library. It was most recently a 4-unit apartment building with office space on the lower level. After a fire, the newer concrete foundation at the back of the structure was capped and covered for a future use. This property also has a large barn which has had work done to the roof. 28 Pleasant Street is behind the Main Street properties and has a separate access off Pleasant Street. Schedule your tour today! One of the owners is a licensed real estate broker.

A Rare 17-Acre Vermont Retreat Just Minutes from Okemo! This beautifully maintained property offers the perfect blend of open land, gardens, privacy, and convenience, with 3 bedrooms and 2 baths and an abundance of outdoor amenities. Expansive lawns and fields create a picturesque setting complemented by mature apple and pear trees, blueberry bushes, incredible established gardens, stone walls, and even a striking tulip tree. Two ponds add to the property's natural beauty and provide peaceful places to relax and enjoy the outdoors. The property also features a beautifully crafted two-story Amish-built garage offering excellent storage and workspace, plus a dedicated campsite with its own well, ideal for guests, recreational use, or creating your own private getaway. Despite its generous acreage, the property is remarkably low maintenance and offers plenty of room to enjoy without feeling overwhelmed by the land. Located less than 5 minutes from town and just 10 minutes from Okemo Mountain Resort, this is an exceptional four-season property with easy access to skiing, hiking, biking, lakes, dining, and village amenities. Whether you're looking for a private Vermont homestead, a recreational retreat, or a property with room for gardening and outdoor pursuits, this one-of-a-kind offering is ready to enjoy. Visit the Okemo real estate community today. Taxes are based on town assessment.

Tucked into the Vermont hills on 15 private acres, this inviting property offers the space and setting to bring your homesteading vision to life. The cozy floor plan features an open kitchen and dining area warmed by a woodstove, along with a sunny living room offering direct access to the covered porch. A full bathroom completes the main level. Upstairs, you’ll find two spacious bedrooms, while the walkout basement offers excellent potential for additional usable space. Outside, a newly installed greenhouse and shed provide a wonderful start for gardening, equipment storage, or small-scale agricultural pursuits. A spring-fed pond adds beauty and character to the landscape, and trails wind throughout the acreage for hiking, snowshoeing, and exploring. Set well away from Route 131, the property feels peaceful and secluded, yet enjoys convenient access to the main road at the bottom of the driveway. Whether you envision cultivating gardens, keeping animals, or creating a private Vermont retreat, this property offers an appealing combination of acreage, natural features, existing improvements, and privacy. Visit the Okemo real estate community today. Taxes are based on town assessment.

If you are seeking a spot to call home where Mother Nature is your neighbor and best friend, look no further. The moment you arrive; you are immediately drawn to the land across the road. Your own grove of trees with brook frontage and your very own swimming hole. You will spend hours every single day sitting or lying in your hammock in the timber frame Creek House. It is the most therapeutic spot you can ever imagine. Head back across the road to the camp compound. The main cabin is decorated exactly like you would imagine your get away to be...natural wood, artifacts, artwork. Enter into the living room with full size futon recessed into the wall. There's a foldout LLBean chair that sleeps another guest. The Harmon pellet stove is a great thing to have all winter long. The dining room and kitchen are open to each other. The kitchen is small, but it has everything you need! The primary bedroom is good sized, and it opens to the full bath with laundry. The guest cottage is steps away. It is a 2018, 28 foot camper. This has a second kitchen, living area (with fold out bed) 3/4 bath and bedroom. The screen porch attached to the camper is gigantic. No doubt you will spend a lot of time here. There are so many more extras...the workshop building, the outside storage room, the private outside shower, the fire pit, the garden, and the big side lawn for games. This is on the town gravel road, but not a single neighbor in sight. Close to snowmobile trails, 10 minutes to Okemo, Fox Run Golf, or the lakes. You might think this is a summer only spot, but it's well insulated by Vermont Foam and ready for you to enjoy year-round. Sellers are sad to leave. They created a little bit of heaven here. Their renovation and additions are great. The septic system is for a 3 BR house. Plenty of room for you to add on. Between the two cabins, you can sleep 8-10 people. Everything you see in the photos will stay. Sellers retiring and moving on. You are the lucky one who can take over.