Properties Near 66 Duttonsville School Drive Cavendish, VT

Charming Cape Cod Home in a Serene Country Setting – 10.10 Acres Welcome to this beautifully transformed Cape Cod-style home, nestled on just over 10 acres of picturesque countryside. Offering a perfect blend of classic charm and modern convenience, this inviting property is ideal for those seeking tranquility and space. Step onto the welcoming front porch, where you can relax and take in the peaceful views of the surrounding landscape. Inside, you'll find a warm and inviting atmosphere, featuring a well-appointed kitchen, spacious living areas, and ample natural light throughout. The expansive property offers endless possibilities—whether you're looking to garden, keep animals, or simply enjoy the beauty of nature. With rolling meadows, pond, mature trees, and plenty of open space, this land is a true retreat. And, if you'd prefer to tinker, this 3 bay garage will not disappoint, with ample space for all of the toys. Conveniently located near both Okemo and Killington, yet offering the privacy of country living, this home is a rare gem. Don’t miss your chance to own a piece of paradise—schedule your private tour today! Excellent Airbnb rental history, being sold mostly furnished.

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.

Welcome to the House of Fives—ideally located five miles from Okemo, five minutes to Ludlow, and offering five bedrooms for comfortable mountain living. This spacious log home features two great rooms plus a third living area, providing ample space to spread out for one or even two families. The open-concept main level seamlessly connects the kitchen, living, and dining areas, centered around a pellet-burning fireplace insert. With two sets of sliders and overhead windows, natural light pours into the space, creating a bright and inviting atmosphere. Step outside onto the large deck to further enhance your outdoor living experience. The expansive unfinished area of the lower level offers a blank canvas for a game room, workshop, or additional storage. A fun loft overlooks the main living area, while knotty pine paneling throughout delivers a warm, classic cabin feel. Outdoor enthusiasts will love the direct access to the VAST snowmobile trail—ride right from your home, with plenty of room for friends to park their sleds too. Set on 23 acres, the property even offers the opportunity to create your own private trails through the woods. Visit the Okemo real estate community today. Taxes are based on the town assessment.

Discover your private Vermont sanctuary on 36 acres of forest and pond. This contemporary 4-bedroom, 3-bath home blends comfort and style with an open floor plan, spacious kitchen, and living area anchored by a wood-burning fireplace. Slider doors open to a wraparound deck with a hot tub, perfect for enjoying the tranquility of nature. Two primary suites, including a first-floor option, plus two additional large bedrooms, offer flexible living for family and guests. Additional features include a mudroom and attached 2-car garage. Lovingly cared for by the same family for over 25 years, this retreat embodies the quintessential Vermont lifestyle—peaceful, private, and close to the outdoors. Just minutes from Okemo Mountain, Ludlow, and Chester, enjoy skiing, hiking, local shops, and dining. A true year-round escape where nature, recreation, and small-town charm come together.

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!

The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. 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 furnance and hot water tank have recently been updated. The Castle Resort & Spa is beautiful and enjoyed year-round. 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.

Stunning contemporary home on 6+ acres. Great proximity to the Upper Valley/RT 91 and only 12 miles to skiing at Okemo! Sit in the panoramic south facing dining room and take in the Black River and local mountain views. Your own Vermont paradise! Quiet dead end road. This 1973 residence has a 2008 addition and has been transformed over the years. Many upgrades and updates, some just completed! Recent work includes new faux stone facade, upgrades to the lower level gym space, some new lighting fixtures and exterior trim paint. Since the 2008 addition, upgrades include a renovated kitchen, two Italian marble baths, a Bosch boiler, wood ceilings with added insulation, some new Anderson windows and skylights and a new deck, to name just a few! Please see the full list of improvements totaling over $120k. Gracious single story living with laundry in the lower level. Wonderful built-ins throughout this home. The main level boasts a gorgeous great room with a soapstone lined rumford fireplace, a kitchen with hickory cabinets and granite and a sunny dining area. There is a newer full deck situated high up in the wooded canopy. Two bedrooms and a full bath. The upstairs enclosed loft includes a comfortable master suite. The lower walkout level offers a very comfortable flex space, a sleeping area, a beautiful potbelly stove and a full bath. There is a sauna and also a hot tub just outside the door. Do not miss this! Open house Saturday, December 13 from 10 am to 1 pm!

One of only four units like this in the complex of 54 condos. This unique 3 bedroom plus loft with three and a half baths is a town house layout. Walk directly into abundant mudroom, no stairs involved. The walk in owners closet with custom cubbies will be more than adequate for all of your gear. The entire condo has been tastefully decorated by a professional and the furnishings that are included are in great condition. The open floor plan of the living, dining and kitchen will keep everyone together to get cozy in front of fireplace or breakaway to the loft for some privacy and or gaming. You'll love the spacious primary suite, with a two person jetted tub and custom tiled separate shower with granite seat to 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 third en suite bedroom, full bath, loft area and bonus room are a great space for guests. 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. Enjoy the culinary delight of Chef Fonz who is on premise at the Castle Restaurant and Inn, providing meals fit for a King and Queen! Choose this condo as your Vermont retreat and be treated like royalty at the Castle Hill Resort and Spa!