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- Under Contract New Listing!
$225,000 | $100 per sq.ft. | 6 Beds | 2 Baths | Total Sq. Ft. 2254 | Acres: 0.35 VILLAGE OF PROCTORSVILLE IN TOWN OF CAVENDISH VT
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Description:Character and Charm are the two things that best describe this antique village home. This prime location is walking distance to all of the great amenities Proctorsville has to offer. Including Singleton's Store Murdoch's On The Green and Outer Limits Brewery to name a few. This home has been well cared and loved for generations. Although move in ready, this home has it's quirks/character. Fully furnished to include a wood stove in the living room to keep you toasty on a cold winter day. The kitchen is fully equipped, you'll love the butcher block counters and wood cabinetry. Big bright sunny bedrooms, both downstairs and upstairs. There's huge opportunity as well, the upper floor can easily be converted into an apartment for added income. Or use the whole house for extended family and friends. The Cavendish Elementary School is just a short walk down the sidewalk making for a great home for a local family. Endless possibilities and opportunities come take a peek today. The house will be sold as is where is.
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$229,000 | $103 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 2214 | Acres: 2 CAVENDISH VT
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Description:This new to the market home is a must see for location alone: 15 minutes to Okemo gets you skiing all day, or hiking and camping in the state forests. With over 2200 square feet and 3-4 bedrooms, (town has 4 bedrooms, one is accessed by 2 other bedrooms or mudroom could be a bedroom for the count of 4) there is plenty of room for everyone. The living space on the first level is incredible with a 17 foot living room and eat in kitchen of 20 feet. Get away in the family room and cozy up to the propane stove, or retire in the 23' main bedroom. At this price you will want to do some upgrades, but will appreciate the transformation. The 2 acres has a lovely open meadow back yard and some woods to poke about in. You will enjoy the nature and this quiet location. Worth a look for this great price! Sold As Is Sellers will credit buyers $20,000 at closing for repairs and upgrades.
- New Listing!
$260,000 | $208 per sq.ft. | 3 Beds | 1 Baths | Total Sq. Ft. 1248 | Acres: 1.6 CAVENDISH VT
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Description:Welcome to 50 Bates Rd, a charming 1920s Vermont farmhouse perched above the village of Cavendish, offering a country setting with the convenience of being in town. The standout feature is the large covered porch — the kind of welcoming outdoor space that feels from another era and invites you to slow down and take in the setting. This home is ready for updating, but the character is already here: original hardwood floors, a country kitchen, beautiful doors, classic woodwork, period lighting, and built-ins that add both charm and practical storage. Some of the less glamorous but important improvements are already underway, including a new furnace and water heater, allowing the next owner to focus on the more enjoyable parts of renovation and design. The property also offers space for future perennial gardens and a setting with a sense of local history. Just a short drive to Okemo Mountain Resort, area restaurants, shops, and recreation, this is a wonderful opportunity to restore a home with soul in a great village location. Visit the Okemo real estate community today. Taxes are based on town assessment.
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Price Change! reduced by $10,000 down 3% on August 21st 2025
$289,000 | $235 per sq.ft. | 3 Beds | 2 Baths | Total Sq. Ft. 1232 | Acres: 0.26 VILLAGE OF PROCTORSVILLE IN TOWN OF CAVENDISH VT
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Description:This property must be seen in person to be appreciated. Very clean and move-in ready Vermont 3-bedroom, 2-bath home just minutes from Okemo Mountain Resort in Proctorsville Village. Ideal as a low-maintenance vacation retreat or full-time residence, this well-kept home on .26± acres features a new roof and combines comfort and convenience in one of the most desirable areas of the Okemo Valley. Enjoy a spacious living room and bright eat-in kitchen with breakfast nook, and a wonderful enclosed breezeway—the perfect spot to relax or entertain in 3 seasons. The living room offers generous space with picture windows creating plenty of light. The second floor spacious, primary bedroom is equipped with many outlets for charging devices. Two additional bedrooms and a 3/4 bath complete the second floor. House re-built in 70's. The two-car attached garage provides workshop and storage space off the paved driveway. A very neat, clean and dry basement with up newer oil tank, Thermopride furnace and bulkhead doors that open to the breezeway. Enjoy mountain views and a deep yard with space for gardening and winter fun tubing or sledding. Walk to Proctorsville Village for local dining, Singleton’s General Store, or the elementary school. Whether you’re hitting the slopes at Okemo, golfing at Fox Run Golf Course, or simply enjoying Vermont’s four-season beauty, this is rare opportunity to own an affordable home in one of Southern Vermont’s most popular destinations. Motivated sellers encouraging offers.
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$325,000 | $192 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 1696 | Acres: 0.22 CAVENDISH VT
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Description:Opportunity meets flexibility at this charming two-unit property in the heart of Proctorsville. Ideal for an owner who wants a vacation getaway with built-in income potential — or as an easy, turnkey investment — this well-kept duplex offers multiple paths to ownership. The downstairs unit features a three-season porch/mudroom entry, two bedrooms, an open-concept living, dining area, and kitchen, a full bath, and a dedicated laundry/storage room. It comes partially furnished and currently has a lease in place, providing immediate income. Upstairs, the second unit offers two bedrooms, a comfortable open living and dining room or home office, an eat-in kitchen, a full bath, a large three-seasons porch, and a private deck overlooking open meadow views. The upper unit is vacant and ready for personal use or rental. The location is unbeatable — walk to shops, dining, and village amenities in Proctorsville, and enjoy being less than 10 minutes to Okemo Mountain. A rare opportunity to combine lifestyle and investment in one property. Visit the Okemo real estate community today. Taxes are based on the town assessment.
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$495,000 | $148 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 3356 | Acres: 0.15 VILLAGE OF PROCTORSVILLE IN TOWN OF CAVENDISH VT
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Description: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!
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Price Change! reduced by $14,000 down 3% on May 3rd 2026
$525,000 | $228 per sq.ft. | 6 Beds | 2 Baths | Total Sq. Ft. 2304 | Acres: 0.37 CAVENDISH VT
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Description: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.
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Price Change! reduced by $75,000 down 12% on March 29th 2026
$649,000 | $209 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 3100 | Acres: 44.9 CAVENDISH VT
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Description: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!
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$650,000 | $195 per sq.ft. | 3 Beds | 4 Baths | Total Sq. Ft. 3336 | Acres: 13.4 CAVENDISH VT
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Description: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
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$699,000 | $94 per sq.ft. | 0 Beds | 3 Baths | Total Sq. Ft. 7445 | Acres: 3.7 CAVENDISH VT
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Description: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.
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$795,000 | $374 per sq.ft. | 3 Beds | 3 Baths | Total Sq. Ft. 2128 | Acres: 19.06 CAVENDISH VT
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Description:Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral ceiling. Enjoy the warmth of the all-natural wood surroundings while sitting beside the cozy fire from the wood burning stove. There are 3 large bedrooms and 2 1/2 baths. The floors are nicely finished hard and soft wood, with slate tiled floors in the entryway and kitchen. SNOWMOBILE ENTHUSIASTS! The VAST trail is right here, so hop on your sled from your house and go!
- Under Contract
Price Change! reduced by $100,000 down 9% on February 20th 2026
$1,075,000 | $372 per sq.ft. | 4 Beds | 3 Baths | Total Sq. Ft. 2892 | Acres: 12.9 CAVENDISH VT
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Description:Thinking of building your dream home, finding a perfect contractor & designer? Well skip the headaches. Move right in - Here are the keys! Tucked on 12.9 serene acres, custom built in 2024, this 4-bedroom, 3-bathroom amazing home combines expert craftsmanship and design with modern comfort and sweeping mountain VIEWS. Start your mornings with breathtaking vistas and end your evenings with family and friends by the fire. This home offers abundant space for entertaining while maintaining that warm, cozy mountain atmosphere you crave. Every detail reflects timeless design principles. The vaulted living room bathes in natural light through expansive windows, while the open floor plan that seamlessly connects a well-appointed kitchen featuring a large island and stainless steel appliances to the inviting dining and living areas. Step onto the amazing covered deck, unwind in the hot tub, and watch the seasons transform across the panoramic mountain views! Hardwood floors, radiant floor heat, and a propane fireplace create year-round warmth, air conditioning and a standby generator ensure comfort and peace of mind. A finished lower level with full walk-out adds flexibility for guests, family gatherings or additional living space tailored to your needs. Constructed with high quality, low-maintenance materials and thoughtful design, this home delivers both beauty & practicality for years to come. Do not miss this incredible opportunity to own a truly exceptional mountain retreat!!
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$1,300,000 | $681 per sq.ft. | 4 Beds | 2 Baths | Total Sq. Ft. 1908 | Acres: 172.26 CAVENDISH VT
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Description:Did I read that right? 172 acres?! Impeccably renovated farmhouse on +-172 acres - what more could you ask for? ~131 acres of this property are located in Cavendish while the other ~41 are in Reading. Enjoy apples straight from the backyard. Listen and watch the brook babble down by the road and enjoy the peace that comes from this lovely home. All new Marvin Elevate windows, all new appliances, new plumbing, new boiler, new electrical panel, new lighting, new paint, new spray foam insulation, new concrete poured in the basement. No detail was too small. All the work has been done so you can simply move in and enjoy. With 4 bedrooms plus an office there is plenty of space for everyone to feel comfortable. With one bedroom downstairs, it is possible to age in place and have single level living should one want to! Along with the house is an oversized two car two story garage and separate barn. ~15 minutes to the South Woodstock general store, this is the perfect spot to stay nearby but still experience vast amounts of privacy through the land. More exterior photos coming soon. Schedule a private showing.
- Under Contract
$1,499,000 | $421 per sq.ft. | 4 Beds | 4 Baths | Total Sq. Ft. 3560 | Acres: 39.15 CAVENDISH VT
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Description:Tucked discretely off a meandering country road you will find this charming 4 bedroom, 3 and 1/2 bath contemporary home sited on 40 acres of land with miles of groomed trails that include a picnic area on Twenty Mile Stream. The grand living room , anchored by a wood-burning fireplace and lined by a wall of windows , frames views of the giant swimming pond and long range mountain views that include Vermont's own Mt Ascutney. The custom designed kitchen is a chef's dream and the sun-drenched dinning area - with exposures on two sides- provides an elegant setting for intimate gatherings.The deck from the main floor offers expansive spaces for outdoor living with stairs to an upper level enclosed gazebo that gives a 360 degree view of the beautifully landscaped grounds.There are two primary bedrooms , one on the main level with ensuite bath and one on the second level . The second level also has a bedroom that looks out to the mountain views. Lower level is comprised of a game room ,exercise space and bedroom with bath. From the lower level one has access to a 3,000 sq. ft. fenced dog run and hot tub. The 3 car garage with ample storage has room for ATV"s and snow mobiles. Second floor could be finished into living space. Skiing at Okemo Mountain is 12 minutes away. VAST trails are down the road, and Fly fishing on the Black River is some of the best in Vermont. This idyllic property offers serenity for full time living or a delightful second home get away. Call for viewing.
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$1,500,000 | $210 per sq.ft. | 10 Beds | 12 Baths | Total Sq. Ft. 7153 | Acres: 2.4 CAVENDISH VT
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Description:Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space is graced with a stately fireplace, evoking the charm of a bygone era. Five bedrooms offer ensuite baths, each with spa-style finishes, while the owner’s private apartment ensures comfort and privacy. Enjoy central air conditioning, high-speed internet, and cell service—ideal for today’s work-from-home lifestyle. An entertainer’s dream, the lower level reveals an English-style pub complete with a full bar and pool table, opening to an expansive bluestone patio. Step outside to relax in the 6 to 8-person hot tub, gather around the fire pit, or unwind on the gracious covered porch. The estate includes a fully equipped chef’s kitchen designed for restaurant-scale culinary experiences and a beautifully renovated, 3,000-square-foot rustic barn—ideal for hosting events of up to 125 guests. Whether envisioned as a luxury retreat, corporate gathering space, or exceptional venue for weddings and celebrations, the possibilities are endless. Once a thriving bed and breakfast, this remarkable estate is ready for its next steward—whether as a private residence or a luxury hospitality venture.
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