Properties Near 990 Main Street Cavendish, VT

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Welcome to The Castle Hill Resort and Spa where you'll find this beautiful turnkey four-bedroom, three-and-a-half-bath condominium with a loft. This unit is the best value in the complex. The renovated kitchen with granite counters and stainless steel appliances is open to the living and dining area. This area has soaring cathedral ceilings and a wall of windows flooding in natural light. A French door leads to the spacious deck, which offers privacy and wooded views, perfect for taking in the Vermont fresh air. Enjoy the flames of the living room gas fireplace while relaxing on the plush sofa after a long day on the slopes. The entire condo has been tastefully decorated by a professional and the included furnishings are in great condition. The spacious primary suite is fit for any king or queen. The primary bath is complete with a two-person jetted tub and a custom-tiled separate shower with a seat. The second bedroom is an en-suite with its own sitting room that can be locked out and rented separately. Upstairs, the bunk room, 3/4 bath, loft area and bonus room provide a great space for guests. The amenities at the Castle include the Aveda Spa, a workout facility with Life Fitness machines, free weights and a cardio room, an in-ground heated year-round salt pool, a hot tub, and tennis and pickleball courts. Enjoy the culinary delight of Chef Fonz who is on premise at the Castle Restaurant and Inn, providing meals fit for a King! Choose this condo as your Vermont retreat and be treated like royalty at the Castle Hill Resort and Spa.
This light-filled contemporary home offers end-of-road peace and quiet privacy yet within walking distance to Ludlow Village shops and restaurants. Enjoy Okemo Mountain views from the great room with vaulted ceilings, cherrywood floors, a floor-to-ceiling brick chimney with wood stove, and walls of glass open to the spacious outside deck. The kitchen offers a granite island with seating that flows into the dining room making it ideal for entertaining. The main-level primary suite provides easy one-level living, while the upper level includes two additional bedrooms, a bath, and a bright loft-style family room with mountain vistas. The lower level includes an attached garage, laundry area and bonus space. Envision yourself having morning coffee on the deck, gathering around the fire after a day of skiing and enough separate space for family and guests to spread out. Quality construction throughout, this home is perfect for those seeking an easy keeper!
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!
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.
This 1850s renovated property located right in the heart of the village adapts perfectly to your lifestyle or investment goals. This home functions seamlessly as a spacious 5-bedroom, 2-bathroom home or is ready to operate as two separate income-generating rental units. The unfinished third floor can easily be converted into additional living space, a master suite, or a bonus room. The spacious attached barn offers incredible storage. This property is just steps away from the local post office and village park and is located just minutes from Okemo Mountain Resort, making it a perfect Winter getaway or a lucrative Airbnb. Quick, direct access to Interstate 91 simplifies travel.
A true farm ready for its next chapter! These grounds have been lovingly tilled, gardened, sown, and harvested; the soil meticulously fed, and the pastures grazed by generations of animals. Hundreds of pounds of produce have been grown in and out of the greenhouse high tunnel. A massive, fixed-rack solar array covers the primary costs of electricity and feeds back into the grid. What is most important on a farm? A beautiful kitchen to serve as the heart of the home. This space features a nearly 10-foot-long granite island with counter-height seating, TWO full-size sinks, a 6-burner-plus-griddle propane stove with a professional hood vent, a French-door refrigerator, and a walk-in pantry. It’s the perfect setup for canning, preserving, or simply gathering to enjoy fresh peaches harvested right from your land. The main floor also offers a laundry room, a beautifully renovated 3/4 bath, and a flexible office/bedroom space. Upstairs, you’ll find three additional bedrooms, another nicely renovated bathroom, and a spacious bonus room (previously a second kitchen) perfect for a studio or playroom or maybe hook up the water and turn it back into a kitchen. Need more room? The walk-up attic features its own subpanel, making future expansion easy, while four mini-splits handle both heating and cooling throughout the home. There is a propane boiler for the baseboards if it gets too chilly outside for mini splits. The massive hay barn easily stores giant tractors, RVs, or heavy equipment, and comes equipped with both power and water. Dreaming of fresh eggs? The resident egg-laying chickens come with the property in their own custom coop! There is direct access to the VAST trail for snowmobiling or a hike in the summer along the huge trail network. With almost everything you need to hit the ground running, this property is a true homesteader’s paradise.
The historic Masonic Temple building is located in the heart of Ludlow Village at the corner of Depot Street and Pleasant Street. This top-floor condo with vaulted ceilings offers the perfect blend of in-town convenience and year-round Vermont adventure. Just steps from local shops, restaurants, and everyday amenities, you’ll love the ease of village living while being only minutes from Okemo Mountain Resort. Unit #3 is a spacious four-bedroom, three-bathroom residence situated on the top floor, offering ample room for gathering with family and friends. The thoughtful layout and renovated kitchen provide both comfort and privacy, making it ideal as a primary residence, vacation getaway, or investment opportunity. This four-unit building also features a shared basement common area, perfect for relaxing or socializing after a day of outdoor activities. Whether you're hitting the slopes, exploring nearby golf courses, enjoying the lakes region, or taking advantage of hiking and biking trails, this location puts you at the center of it all. Experience the charm of village living with unbeatable access to everything Ludlow has to offer, including ski shuttle access across the street! This is your opportunity to own a piece of Vermont in one of its most desirable four-season destinations. Visit the Okemo real estate community today. Taxes are based on the 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. 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!
Nestled between Okemo Mountain and the lakes region, this inviting 5-bedroom home sits on 2 peaceful acres framed by mature trees and an expansive open yard. Filled with warmth and character, the home is a charming reminder of simpler times, offering large sun-filled rooms and generous gathering spaces throughout. At the heart of the home is the open kitchen and family room, where a cozy wood stove creates the perfect setting for relaxing with family and friends. French doors lead to a spacious deck overlooking the beautiful backyard, an ideal spot for morning coffee, summer entertaining, or simply enjoying the peaceful surroundings. The home features five bedrooms, beautiful wood floors rich with history and character, and recent improvements including a newly replaced septic tank by the current owner. With its timeless appeal, spacious layout, and wonderful setting, this property presents an exceptional opportunity to restore and elevate a classic Vermont home to its next chapter.
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.
Three properties are being sold together. Investors, Dreamers, Skiers, Business Owners, Anyone with Ideas and Support...Bring your ideas. Weddings in the barn? Indoor growing? A ski house? A cafe or store? With no zoning there are many possibilities. Pick up where the current owners left off with renovations and make it your own. 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.
Escape to Your Cozy Southern Vermont Sanctuary Nestled in charming Cavendish, VT. This 3 bedroom cabin seamlessly blends rustic character with modern comfort. Inside, gather around the wood burning stove on crisp winter nights, 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. Walk around the house to step into the fully fenced side yard a safe haven for kids and pets to play freely. Unwind around the fire pit in classic Adirondack chairs under the stars. 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. 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.

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