Cavendish, VT | 990 Main Street

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.

Set back in the woods on a quiet road, this property is within 5 minutes of Okemo Mountain Resort, golfing, shopping and dining. The open concept floor plan on the main level is inviting and warm, offering enough space for friends and family to gather. A wall of windows allows you to watch the winter snowfall, admire the summer greenery and the fall foliage, while also overlooking the back deck. The main floor also has an airlock mudroom along with two bedrooms, a full bath and a half bath. The upper floor has a nice loft, a bedroom, a bonus room/office and a 1/2 bath. There is also a 1 car garage with storage space!

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.

Nestled in the peaceful hills of Cavendish, this inviting three-bedroom, two-and-a-half-bath home offers privacy, breathtaking views of Mount Ascutney, and easy access to year-round recreation. Just 10 minutes from Okemo Mountain Resort, it is ideally situated for enjoying skiing, hiking, biking, golf, nearby lakes, and local shops and restaurants. Designed for comfortable mountain living, the home features a bright, open gathering space centered around a cozy fireplace. The well-equipped kitchen flows easily into the dining and living areas, creating a welcoming setting for meals, conversation, and relaxing after a day outdoors. Three comfortable bedrooms provide ample accommodations, while the lower-level game room with a pool table offers additional space for recreation and entertaining. Step outside onto the spacious deck and take in beautiful views. Enjoy morning coffee surrounded by the quiet countryside, host a summer barbecue, or gather around the outdoor fire pit beneath Vermont’s star-filled skies. The natural setting provides a sense of seclusion without sacrificing convenience. With state parks, area lakes, charming Vermont villages, and Okemo all within easy reach, 312 Tierney Road is a welcoming retreat from which to experience the best of every Vermont season. Visit the Okemo real estate community today. Taxes are based on town assessment.

Discover the quintessential Vermont mountain getaway at this inviting 3 bedroom, 2-bath South Hill home, offered fully furnished and turnkey with a proven short-term rental history. Whether you’re looking for a private retreat, an income-producing property, or the best of both, this home is ready to enjoy from day one. Set in the heart of the Okemo Valley, the location offers exceptional four-season appeal. Spend winter days skiing and snowboarding at Okemo, then return home to the warmth of a wood-burning fireplace and a relaxing soak in the 6-person hot tub. In summer and fall, enjoy hiking, biking, golf, lakes and the wonderful level and private back yard. Inside the wood two living areas, and a spacious lower-level recreation area provide plenty of room to gather and unwind. The eat-in kitchen features a massive granite-topped island with generous seating perfect for morning coffee or après-adventure meals with family and friends. Outside, the expansive two-tier deck creates an ideal setting for dining, entertaining, or simply enjoying the fresh mountain air. A detached shed provides convenient storage for skis, bikes, and other outdoor gear. With its desirable South Hill location, strong rental history, comfortable furnishings, and immediate access to the Okemo Valley lifestyle, this is a truly turnkey Vermont property with the flexibility to enjoy now and rent when you’re away.

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!

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!

Tucked along a quiet side street in Ludlow Village, 16 Smith Street is filled with warmth, character, and timeless New England charm. Beautiful wood floors, rich natural woodwork, and classic pocket doors highlight the home’s craftsmanship, while a spacious wraparound porch invites you to slow down and enjoy village life. Inside, the large country kitchen features an eat-in island and opens to an additional flexible space ideal for a breakfast nook or cozy sitting area. The inviting living room is warmed by a pellet stove, perfect for taking away the chill after a day on the slopes. With three bedrooms and three bathrooms, the home offers comfortable space for owners and guests. The primary bedroom includes a recently remodeled en-suite bath, while the two additional bedrooms share another beautifully updated bathroom. Outside, a large deck provides plenty of room for dining and entertaining, and the backyard offers space to relax and play without demanding overwhelming maintenance. A detached garage/barn adds valuable storage and versatility. All of this is within walking distance of Ludlow’s shops and dining, with Okemo Mountain Resort just minutes away. A charming village home offering comfort, convenience, and an authentic sense of place. Visit the Okemo real estate community today. Taxes are based on town assessment.

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!

Opportunities like this are rare. Tucked into one of the most desirable locations near Okemo Mountain, this property offers exceptional access to year-round recreation, dining, shopping, and entertainment while avoiding the congestion of the main Access Road. Just under a half mile away, Witalec Road provides a convenient cut-through directly to the Access Road and mountain parking, helping you bypass much of the typical ski traffic. This home is ready for its next chapter and presents outstanding potential for buyers looking to build equity and create a personalized Vermont retreat. While the property does need updating and finishing work, several key improvements have already been started, including a partially finished primary suite with an en-suite bath. This important addition offers a strong foundation for future renovations and gives the next owner the opportunity to complete the space to their own vision and style. The property is also on town water and sewer, making a change of use possible and adding valuable flexibility for future plans. Whether envisioned as a full-time residence, a ski getaway for family and friends, or an investment property in a highly sought after mountain destination, the possibilities are wide open. The location places you just minutes from world class skiing and snowboarding at Okemo, championship golf, lakes, hiking and snowmobile trails, as well as the shops and restaurants of Ludlow. Bring your ideas, tools, and imagination to unlock the full potential of this property. With its unbeatable location, solid start, and renovation upside, this is a rare opportunity to create something truly special in the heart of Vermont’s four-season playground.

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.