Cavendish, VT | 66 Duttonsville School Drive

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!

Classic Vermont charm meets tasteful updates at this inviting Ludlow farmhouse, less than two miles from Okemo Mountain Resort. With five bedrooms, four baths, and generous gathering spaces, this furnished home is ready for your next chapter. A practical mudroom welcomes you inside, where beautiful hardwood floors run throughout. Gather around the stone wood-burning fireplace in the spacious living area, prepare meals in the expansive chef’s kitchen, or settle into the sunroom for a quiet afternoon. Outside, the hot tub offers a relaxing finish to a day on the mountain. The large, level, fully fenced yard provides privacy and plenty of room for lawn games, outdoor dining, and entertaining, while a detached two-car garage adds convenient parking and storage. Updated wiring and the septic system further complement the property. Ludlow’s parks, restaurants, shops, and farmers market are less than five minutes away, putting village amenities and year-round recreation within easy reach. Whether you’re seeking a Vermont retreat, primary residence, or investment opportunity, this beautifully updated farmhouse is being sold furnished and ready to enjoy. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Set on just under 12 private acres with generous views of Okemo Mountain, this charming chalet captures the warmth and character of a classic Vermont ski home, all just minutes from Okemo and Ludlow Village. Soaring ceilings, natural wood details, and expansive windows frame the mountain setting, while the open floor plan provides an inviting space for gathering and entertaining. Enter through the lower-level mudroom, with plenty of room to store skis, boots, and four-season gear. From there, step into a cozy family room featuring a wood stove, a perfect spot for unwinding after a day on the slopes or trails. Upstairs, the main living area features an open-concept kitchen, dining, and living space filled with natural light. Cathedral ceilings, floor-to-ceiling windows, and a second wood stove create a bright and welcoming atmosphere while showcasing the surrounding views. Two bedrooms and a full bathroom are also located on this level. Above, the loft offers a private primary suite with its own full bathroom. Enjoy a peaceful mountain setting with convenient access to skiing, lakes, golf, hiking, snowmobiling, and year-round recreation throughout the Okemo Valley. Easy access to the VAST snowmobile trail adds to the property’s appeal. Whether used as a Vermont getaway or a four-season home, this property offers privacy, views, and proximity to everything the area has to offer. Visit the Okemo real estate community today. Taxes are based on town assessment.

Welcome to this charming, easy-care country home nestled on a private road in the heart of Cavendish, Vermont. Offering 4 bedrooms and two bathrooms, this inviting property combines comfortable living with the peaceful beauty of its natural surroundings. A covered front porch welcomes you into the foyer, where you'll immediately appreciate the open-concept floor plan designed for everyday living and effortless entertaining. The spacious living room features a cozy gas fireplace and flows seamlessly into the dining area, where a sliding glass door opens to the side deck, creating the perfect indoor-outdoor gathering space. The well-appointed updated kitchen overlooks the living and dining areas and features a center island, making meal preparation and conversation easy. The main level also includes a primary bedroom and a three-quarter bathroom, offering flexibility for office space or one-level living. Upstairs, you'll find three bedrooms and a full bathroom complete with a relaxing soaking tub. Outside, enjoy the tranquility of Vermont living with a level front yard, beautifully maintained gardens, and a spacious deck surrounded by nature. A covered front porch provides the perfect place to unwind on warm summer evenings, while the 3-sided carport offers added convenience year-round. The basement is ready to finish with egress-rated windows and bathroom drains plumbed, creating a great upside to increasing value! This home has a five-star energy rating. Located near Okemo Mountain and minutes from local schools, Singleton's General Store, the Cavendish Town Green, and several local restaurants, this home offers the perfect balance of country privacy and small-town convenience. Whether you're searching for a full-time residence or a Vermont retreat, this property is ready to welcome you home. (This house has a septic rated for 12 people!) Visit the Okemo real estate community today. Taxes are based on town assessment.

Welcome to your private country oasis. Nestled in a serene and peaceful setting, this pretty, two-level country home perfectly blends rustic charm with modern convenience. As you step inside, you are immediately greeted by an inviting open-concept living, dining, and kitchen area designed for seamless everyday living and effortless entertaining. This home features a magnificent stone wood-burning fireplace, ideal for warming up on crisp Vermont evenings. On warmer days, you will enjoy air conditioning. Vaulted ceilings with exposed wood beams enhance the spacious, airy feel while preserving that quintessential country warmth. The thoughtful architectural layout offers maximum flexibility, with bedrooms and bathrooms conveniently located on both levels. The lower level is dedicated to a spacious and private primary bedroom suite, serving as a peaceful retreat complete with direct, walk-out access to the yard. Upstairs and downstairs, the home delivers a true country feeling, making it easy to relax and unwind. Step outside to enjoy the beautiful covered back deck, the perfect spot for morning coffee, evening dining, or simply listening to the sounds of nature. The home sits on a nice open yard that offers abundant space for outdoor recreation, gardening, or lawn games. Adding to the utility of the property is a detached two-car garage, providing excellent storage for vehicles, ski gear, and outdoor equipment. Location is everything, and this property puts the best of the region right at your fingertips. You are just minutes away from world-class skiing and riding at Okemo Mountain Resort, championship golfing, local boutique shopping, and diverse dining options. Plus, the nearby lakes region offers endless summer boating, swimming, and fishing. Whether you are looking for a year-round residence or a premier four-season vacation getaway, this country home offers the privacy you crave with the convenience you need.

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!

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.