Properties Near 66 Duttonsville School Drive Cavendish, VT

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. 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.

Nestled in the desirable Okemo Pines community, this 4-bedroom, 3.5-bath home offers the perfect blend of comfort, charm, and convenience, only minutes from Okemo Mountain Resort. Thoughtfully designed for year-round enjoyment, the home features multiple seasonal living areas, including a large deck with Okemo views, a sunroom, and a covered porch with mountain views. The house offers privacy from the road with an emphasis on light and views to the south. Enter the oversized one-car garage with tremendous storage space for your skis, bikes, fishing poles, and more. Warm up by the inviting wood-burning fireplace after a day on the slopes or gather with friends and family in the open-concept living and dining area. With four generously sized bedrooms and ample bathrooms, there's room for everyone to spread out and unwind. Three of the bedrooms and two baths occupy the top floor, along with an office off the primary bedroom. The lower level features a large game room along with a bedroom and full bath. There is also extra sewer capacity for future expansion possibilities. The front lawn is level and features a stone retaining wall, perennials, and ample room for entertaining. Located near Ludlow village, you are close to excellent dining, shopping, and all the amenities this vibrant mountain town has to offer. Whether you are looking for a vacation getaway or a full-time residence, this home offers the quintessential Vermont lifestyle in an unbeatable location.

Nestled on 10 picturesque rolling acres, just minutes from Chester Village Green and Okemo Mountain Resort, this beautiful country home offers the perfect blend of charm, comfort, and convenience. The property features established gardens, apple trees, blueberry bushes, and a stone patio—ideal for relaxing or entertaining. Inside, you’ll find two levels of well-designed living space. The spacious kitchen is a true centerpiece, complete with granite countertops, a large island, stainless steel appliances, and abundant cabinetry. The sunlit dining room opens directly to a back deck, creating an easy indoor-outdoor flow for gatherings. The inviting living room features wood flooring and a cozy pellet stove, while a den with a gas fireplace provides an additional comfortable retreat. The main level also includes a convenient half bath and a versatile bonus room, perfect for a home office, playroom, or guest space. Upstairs, the en suite primary bedroom offers a private haven, complemented by three additional bedrooms and a full bath—plenty of room for family and guests. Additional highlights include a full walk-out basement, attached two-car garage, and a breezeway with laundry. A detached garage with upper-level storage adds even more flexibility. Outdoors, you’ll also find a chicken coop and an above-ground pool. Located close to the airport, skiing, snowmobiling trails, shopping, and endless outdoor recreation, this property is a true Vermont retreat. Additional photos coming soon.

Beautiful Cape-style home set in picturesque Cavendish, Vermont, offering a seamless blend of modern design and Craftsman-quality finishes. This thoughtfully designed home features a striking dual fireplace and a unique dual-access kitchen with counters on both sides—ideal for entertaining. The kitchen is equipped with stainless steel appliances, including a gas stove, perfect for the home chef. Set on a property that borders a budding state forest, this home offers privacy and direct access to nature. Enjoy your own private pond, ideal for fishing, swimming, or simply relaxing in a serene setting. Whether you're looking for a full-time residence or the perfect Vermont getaway, this property delivers. Conveniently located in the heart of ski country, with easy access to Okemo Mountain and a short drive to scenic river views, this location is a dream for outdoor enthusiasts year-round. A rare opportunity to own a property that combines comfort, craftsmanship, and the best of Vermont living

Winter, Spring, Summer or Fall, this is a bit of heaven for the nature lover! Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The back yard has lawn area with room for games, gardens or pets. When you are peering out any of the windows toward the back of the house you overlook a giant pond and wetland, home to a terrific assortment of wildlife. Head out to paddle & bring your binoculars! The home offers so much. You will enjoy the family room with high ceilings & great shelving for your collections. There is a more formal living room & dining room along with a very nice L-shaped kitchen. There are 2 bedrooms down & 2 bedrooms up. 2 full baths & 1 three quarter. Above the garage there is a large bonus room & a huge studio...currently a music studio, but it could be a great for exercise, artwork, craft space, play space, or even your office. Just about everything you see in the pictures is included in the sale...furnished & ready for you. Super location with Okemo in one direction passing by Singleton's store, Knapp Pond State Wildlife Area or Ascutney Outdoors for hiking, biking, skiing or tubing in another. Walk, run or bike to your heart's content on the backroads. This home and property is absolutely perfect for those seeking peace and tranquility!

Your opportunity to own a coveted ground floor 3br plus loft /3.5ba unit of which only 4 were built out of 54 units. The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has wooded private views. These sought after ground floor units give flexibility to owners as you can stay on one side while renting out the other with the lockout capabilities. The furnace and hot water tank have recently been updated saving you future headaches and expenses. From skiing in the winter, to the lakes in the summer, golf in the spring, or hiking in the fall, this area has so much to enjoy. You can explore the area with endless adventures or stay at the resort enjoying all the amenities on site. Conveniently located inside The Castle Resort is a fine dining, French influenced American cuisine restaurant. Relax at the Aveda spa with a massage, use the fitness center, or take a Pilates class all on site at the resort. A year-round heated, salt water pool and tennis courts are more amenities you'll enjoy! After a day on the slopes at Okemo Mountain, relaxing by the fireplace or indulging in all the Castle Resort has to offer, truly make it a perfect getaway! Visit the Okemo real estate community today. Taxes are based on current town assessment.

Welcome to The Castle Hill Resort and Spa where you'll find this beautiful three bedroom, three and a half bath, condominium with loft and bonus room. The kitchen with custom cherry cabinetry, granite counters and stainless steel appliances that will satisfy any chef's needs is open to the living, dining area. Which have soaring cathedral ceilings and a wall of windows flooding in the natural light. A french door leading to the spacious deck so you can take in the Vermont fresh air is private with wooded views. Enjoy the flames of the gas fireplace in the living room after a long day on the slopes. The condo has been tastefully decorated and the furnishings are included. The spacious primary suite is fit for any king or queen, with a two person jetted tub, custom tiled separate shower with seat the complete the primary bath. The second bedroom en-suite, has it's own sitting room that can be locked out and rented separately. Upstairs to the bunk room, 3/4 bath, loft area and bonus room are a great space for guests or the kids. The amenities at the Castle include the Aveda Spa, workout facility with Life Fitness machines, free weights and a cardio room, inground heated year round salt pool, hot tub, tennis and pickle ball courts. Massage, manicures and pedicures are offered for a fee. Enjoy the culinary delight of Chef Fonz who is on premise at the Castle Restaurant and Inn, providing meals fit for any King and Queen! Choose this condo as your Vermont retreat and be treated like royalty at the Castle Hill Resort and Spa!