$829,900 $457 per sq.ft. Wells VT Home »


Price Change! Reduced by $20,100 down 2% on August 3rd 2026
2 Beds | 3 Baths |   Total Sq. Ft. 1816  |  Acres: 40.6
Listed on Monday Jul 6, 2026
Description: Attention outdoor enthusiasts! Tucked near the top of the mountain on a quiet deadend dirt road with only one camp beyond, you'll discover the peace, privacy, and adventure that make Vermont so special. Meticulously maintained and custom built by the current owners, this exceptional Ward log home has been lovingly cared for since day one and is ready to welcome its next chapter. The thoughtfully designed living quarters above the impressive 2-story garage showcase quality craftsmanship throughout, featuring granite countertops, custom cherry cabinetry, central air conditioning with a smart thermostat, and a backup generator for year-round peace of mind. Being offered fully furnished, you can start enjoying your Vermont retreat from day one. The property's incredible outbuildings are just as impressive. A massive 30' x 40' three-story garage provides endless space for recreational vehicles, equipment, hobbies, or the ultimate workshop, while a separate bunkhouse offers comfortable accommodations for family and friends. Spanning more than 40 acres across both Wells and Middletown Springs, this remarkable property offers unmatched privacy and endless opportunities to enjoy the outdoors. Paperwork is already in place for a second access road into Middletown Springs, adding flexibility for future use. Once home to miles of ATV trails, the land could easily be restored into your own private network for ATV riding, hiking, hunting or simply exploring. Located in the Town of Wells, where there is no zoning, the possibilities are limited only by your imagination. Whether you envision a private mountain retreat, recreational paradise, family compound, or year-round home, this property is ready to make that vision a reality. Just minutes from the Village of Wells, Lake St. Catherine, the Slate Valley Mountain Bike Trails, only 30 minutes to Manchester, and less than an hour from several premier ski resorts, you'll enjoy four seasons of adventure right outside your door. See Listing Details & 48 images.

$839,000 $621 per sq.ft. Wells VT Home »

150 Ft. of Waterfront on Lake Saint Catherine
3 Beds | 2 Baths |   Total Sq. Ft. 1352  |  Acres: 0.57
Listed on Wednesday Apr 8, 2026
Description: Nestled on the southwest shore of beautiful Lake St. Catherine, which is one of Vermont's best kept secrets, it's lakeshore living at it's best! This picturesque double lot, boasting 150' of lakeshore and over a half acre is accented with the most gorgeous views that you'll ever experience. From the moment that you enter this year round residence built in 1990, you will be enchanted with the beauty of this open concept living where the lake and mountain view fills every corner. Whether you are dining, relaxing, entertaining or cooking in the newly installed 2022 kitchen, it is a slice of heaven. Red birch cabinets, granite countertops, a marble subway tile backsplash, s/s appliances and a large island for prepping your finest meal. This sunfilled room has thoughtful builtins, providing space for your books or finest collectables. The two sliders provides entry to your lake facing deck, a perfect spot for your morning coffee while taking in the glorious sunrise . There are three very comfortable bedrooms including a primary ensuite with luxury bath. The walk-in tile shower, large vanity with Granite countertop and the lake view is everyone's dream. The hardwood floors that flow throughout brings added charm and warmth. If this is not enough, the seller just had built a 24x24 garage with loft and attached is a 16x22 unfinished room providing ample space for vehicles, storage and outdoor toys. The fully poured concrete walk out basement houses the laundry area and a newer hot air furnace provides not only heat but central air. A covered porch the length of house with a Pergola is an added bonus and great for dining, playing cards, board games, reading or an afternoon cocktail. Indulge in four season recreation and embrace the ultimate lakeside lifestyle with peace, serenity and natural beauty. A perfect location to fish, kayak or canoe. This well loved home is ready for its next chapter. Let it be your opportunity. Fully furnished. See Listing Details & 42 images.

$775,000 $132 per sq.ft. West Haven VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 5882  |  Acres: 79.13
Listed on Friday Sep 4, 2026
Description: Step back in time with this extraordinary 222 year old legacy estate - a treasure owned by the same family for more than two centuries. This remarkable property is a rare blend of grandeur and natural beauty along with historical significance. Once part of the Underground Railroad, the property has a fascinating past, and some of its former residents served as Civil War soldiers. The house was also used as the setting for the movie American Gun starring James Coburn with several scenes filmed inside the home. Imagine owning a home that is not only part of local history, but also part of cinematic history. Built in 1804, the magnificent 4/5 bedroom main home has been remarkably preserved - offering timeless architectural details, original craftsmanship, a grand entrance, soaring 11-foot ceilings, 7 gorgeous fireplaces, and two 40' covered porches. Rarely does a home of this vintage come to market in such great condition. The property has been professionally inspected by a licensed real estate inspector, with inspection reports available for review. Complementing the main residence is a renovated 2/3 bedroom guest house or ADU offering an exceptional income opportunity. Rental income easily covers the property taxes for the entire property and more! The guest house is situated a distance away affording privacy to all residents. Set on 79 acres with subdivision potential, the property offers room for farming, recreation, or future development. A gorgeous barn features horse stalls upstairs and a cow area downstairs, along with several additional barns and outbuildings providing flexibility for agricultural, equestrian, or business uses. With its remarkable architecture, extensive acreage, guest house, barns, & fascinating past, this could make an exceptional wedding venue, bed & breakfast, working farm, or family compound. It is extraordinarily rare to find a home of this vintage with so much character in such great condition! Quotes available for heat/ac upgrades. See Listing Details & 60 images.

Under Contract West Windsor VT Home for sale $575,500 $357 per sq.ft.

$575,500 $357 per sq.ft. West Windsor VT Home »


Price Change! Reduced by $24,000 down 4% on August 20th 2026
1 Beds | 2 Baths |   Total Sq. Ft. 1611  |  Acres: 5.15
Listed on Friday Jul 31, 2026
Description: Welcome to the Carriage House, a rustic chic hideaway set on 5.13 acres overlooking a private pond in the bucolic West Windsor countryside. The recent, complete renovation of this exceptional property is truly a work of art, blending refined design with effortless comfort. The open main level is thoughtfully designed for both entertaining and everyday living, with a gourmet kitchen featuring high-end appliances, elegant quartz countertops, and beautiful custom cabinetry flowing seamlessly into a spacious dining and living area. A stylish half bath and a unique climate-controlled pet sanctuary complete the main level, adding an unexpected touch of luxury and convenience to this extraordinary property. The spacious upper-level primary suite offers a serene retreat, complete with a spectacular stone-tiled bath and an inviting elevated reading nook. From the suite, step out onto a private deck overlooking the peaceful landscape and pond. Mini-splits on both levels provide efficient year-round comfort, while both an attached three-car garage and a detached three car barn/garage add exceptional flexibility and endless possibilities. The Carriage House, warm yet sophisticated, will capture your heart! Take in multi-seasonal recreation and the arts just minutes away at Ascutney Outdoors and Brownsville Butcher & Pantry for terrific local dining. Easy access to Woodstock, Killington and Okemo. See Listing Details & 31 images.

New Listing! West Windsor VT Home for sale $675,000 $879 per sq.ft.

$675,000 $879 per sq.ft. West Windsor VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1536  |  Acres: 43
Listed on Friday Sep 11, 2026
Description: An efficient 2-bedroom chalet located in the foot hills of West Windsor. Over the years the sellers have completed a total gut renovation of the interior and exterior of the house. New windows, doors, hardwood flooring, built-ins, remodeled bathrooms and kitchen are just few upgrades to this charming home. A 2-car garage was added with a large heated bonus room above, which can be used as a game/exercise room, or converted into extra living space. The main level is an open floor plan with living, dining, kitchen, primary bedroom and full bathroom. The lower level is outfitted with a walk-out basement along with the main entrance to the home. The finished basement includes a bedroom, full bathroom, laundry room, along with a family room which is heated by a woodstove. Both floors have mini splits for additional heat and air conditioning. The house comes with a full wrap around deck for access to the pool, front sitting deck, and back yard. The barn was originally used as a cider barn which was in disrepair but shored up, insulated and currently being used as a woodworking shop with a wood burning furnace for heat. The new 3-bedroom mound system was installed this year which allows for future growth. The yard around the house and barn are open although most of the 40 acres are wooded with internal trails. Minutes to Brownsville Butcher and Pantry, Ascutney Windsor Trails, 15 mins to Woodstock and I-91 for easy access to the upper valley. See Listing Details & 56 images. Includes a Virtual Tour

$699,500 $331 per sq.ft. West Windsor VT Home »


Price Change! Reduced by $50,000 down 7% on August 20th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2112  |  Acres: 5.01
Listed on Wednesday Jul 29, 2026
Description: Welcome to The Rock House! A beautiful hillside retreat set on a private, lush landscape with captivating views of Mount Ascutney. The home's spectacular great room is the heart of the property, featuring soaring cathedral ceilings, rich hardwood floors, a dramatic floor to ceiling stone fireplace, and walls of windows that flood the space with natural light while showcasing the breathtaking mountain vistas. Thoughtfully designed for both comfortable everyday living and effortless entertaining, this inviting gathering space perfectly captures the warmth, character, and natural beauty that make the Rock House so special. The beautifully updated kitchen features quartz countertops, quality cabinetry, and an efficient layout that makes meal preparation both functional and enjoyable. The spacious main-level primary suite offers a peaceful retreat, complete with an attached sunroom featuring radiant floor heat, an ideal spot to relax year-round while taking in the surrounding landscape. Two additional bedrooms and a three-quarter bath complete the main level, providing comfortable accommodations for family and guests. Privately tucked away on the upper level, an additional ensuite bedroom offers flexibility as a guest suite, home office, or secluded retreat. The exterior is landscaped with two stone patios and level lawn area with fire pit seating area perfect for relaxing and entertaining. Modern comforts and energy efficiency abound with mini-splits, new furnace, solar array, tesla battery, and heated two car garage. Combining timeless architectural appeal with thoughtful updates and an exceptional setting, The Rock House offers a rare opportunity to enjoy Vermont living at its finest.Take in multi-seasonal recreation and the arts just minutes away at Ascutney Outdoors and Brownsville Butcher & Pantry for some terrific local dining. Easy access to Woodstock, Killington and Okemo. Showings to begin at the See Listing Details & 37 images.

Under Contract West Windsor VT Home for sale $775,000 $245 per sq.ft.

$775,000 $245 per sq.ft. West Windsor VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3168  |  Acres: 2.5
Listed on Tuesday Jul 7, 2026
Description: Located in the heart of Sheddsville-West Windsor's earliest settlement, this lovingly stewarded historic Greek Revival Farmhouse imbues the true character of the Vermont vernacular. Improved over the centuries to accommodate modern living, all while preserving the the period detail and charm with original pine plank floors, 6/6 sash windows and hewn beams. The home was well built of solid and sound plank construction, providing insulation throughout. The beautiful Great Room addition is anchored by a handsome wood burning fireplace with custom cherry mantel, and connects to the exterior spaces through French doors stepping out to a covered porch and a spacious deck overlooking a sweeping level lawn, mature maple trees, established perennial beds, and a firepit at the edge of a four-season stream. Open concept eat in kitchen with farmer sink and butcher block counters, formal dining room, library- TV room, study with a half bathroom. Two mudrooms complete the main level. Moving upstairs, there's a generous primary bedroom ensuite with a wood stove, a laundry room, three additional bedrooms and a shared bathroom. Leased Tesla back up battery provides peace of mind in the event of a power outage. The ample three-bay barn can be used as parking, equipment storage, workshop, or for farm animals. Extensive dirt road, and trail systems (ideal for equine interests, hiking, cycling) are just out side your door. Easy access to all recreation, Interstate, Woodstock, Hanover NH. 2.25 Hours to Boston. 4.5 hours to NYC. Showings begin with an Open House on Saturday July 11 from 11:00 to 12:30 See Listing Details & 42 images. Includes a Virtual Tour

$799,900 $355 per sq.ft. West Windsor VT Home »


Price Change! Reduced by $50,000 down 6% on August 24th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 3392  |  Acres: 3.03
Listed on Wednesday Mar 18, 2026
Description: Experience the best of Vermont living in this custom-built home in desirable West Windsor, where thoughtful craftsmanship, energy efficiency, and four-season recreation come together. Designed and built by its original builder, this home offers exceptional quality, low-maintenance living, and comfortable year-round enjoyment. Whether you're searching for a primary residence, a Vermont vacation home, or the perfect mountain retreat, you'll appreciate the generous sleeping spaces that easily accommodate family and guests. After a day of skiing, snowmobiling, hiking, mountain biking, or exploring, gather around the cozy fireplace and soak in the peaceful mountain views that make this property feel like a true escape. Outdoor enthusiasts will love the location, with easy access to Ascutney Outdoors, Mount Ascutney State Park, and the renowned VAST snowmobile trail system. World-class skiing at Okemo Mountain Resort and the charming villages of Woodstock and Brownsville are just a short drive away, making this an ideal home base for every season. A spacious two-car garage provides ample storage for vehicles, outdoor gear, and recreational equipment. Set in one of Vermont's most sought-after communities, known for its scenic beauty, outdoor adventure, and welcoming small-town charm, this exceptional property offers the perfect balance of privacy, convenience, and lifestyle. If you've been dreaming of owning a Vermont mountain home where every season brings a new adventure, this is the one you've been waiting for. See Listing Details & 44 images. Includes a Virtual Tour

$595,000 $231 per sq.ft. Westminster VT Home »


Price Change! Reduced by $1,000 down 0% on September 9th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 3325  |  Acres: 0.4
Listed on Tuesday Aug 11, 2026
Description: Dramatic two-story foyer flaunting elegance and craftsmanship. The kitchen is designed with custom cabinetry, generous workspace, 5burner DCS range, skylight, and dining area. The living room features a beautiful gas fireplace and a Honduran Mahogany entertainment center. oversized Low-E Andersen windows filled w/light. In the evenings, customized recessed lighting. On the first floor is the spacious MB that offers a peaceful retreat with a unique hydrotherapy soaking tub alcove with skylight and power shades. Grand columns invoke luxury and relaxation. An ensuite bathroom includes tiled walk-in shower and double vanity sinks. The second level are wo bedrooms, featuring hard ample closet space, a full bath and a third bonus room that overlooks the foyer. Step into the backyard through the glass, French doors to experience a space that was created for gathering with guest and friends. The covered stone patio includes a built-in Lynx grill, separate gas cooktop, refrigerator, expansive granite countertops, stacked stone finishes, ceiling fan, extensive lighting choices, gas fire pit, and a fountain. With beautiful landscaped grounds, 2 car detached garage with workshop and shed. Also, For buyers seeking additional space, a concrete foundation pad is already in place beside the primary bedroom, and the property previously received Town of Westminster approval for a walk-in closet addition. See Listing Details & 50 images.

$509,000 $202 per sq.ft. Weston VT Home »

Waterfront on Pond _Unnamed
4 Beds | 3 Baths |   Total Sq. Ft. 2526  |  Acres: 7
Listed on Thursday Sep 3, 2026
Description: Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL & MOUND SEPTIC SYSTEM just installed in August 2026. Updated electric makes this house ready for the next steward. The kitchen is authentic and you may choose to update. Situated in the picturesque town of Weston, one of Southern Vermont's most coveted historic villages. The village is home to the iconic Vermont Country Store and the renowned Weston Theater Company. The large swimming pond is spring fed from the babbling brook that boarders the back of the property. A quick drive away find skiing at Okemo Mountain Resort, Bromley, Magic and Stratton, while Summer days can be spent swimming at Hapgood Pond or exploring the West River. Grades 9-12 Have School Choice including Burr and Burton Acadamy. Your piece of Vermont history starts here. Come see this charming Vermont home being sold furnished. Call today! See Listing Details & 43 images.

$645,000 $560 per sq.ft. Weston VT Home »


Price Change! Reduced by $50,000 down 8% on September 6th 2026
3 Beds | 1 Baths |   Total Sq. Ft. 2304  |  Acres: 11.4
Listed on Saturday Aug 29, 2026
Description: Discover classic Vermont living at 74 Moses Pond Road in Weston, set on 11.4 beautiful acres along a quintessential Vermont country road. This warm and inviting three-bedroom home offers a wonderful combination of privacy, character, and convenience in one of southern Vermont's most desirable locations. The property features an oversized barn/garage, providing exceptional space for vehicles, recreational equipment, a workshop, studio, or additional storage. Surrounded by the natural beauty of the Vermont countryside, the setting offers plenty of room to enjoy the outdoors while remaining close to the cultural and recreational attractions that make Weston so special. Enjoy convenient access to the renowned Weston Theater and Kinhaven Music School, along with charming village amenities and year-round activities. Outdoor enthusiasts will appreciate being within easy reach of some of Vermont's premier ski destinations, including Okemo, Killington, Stratton, Magic Mountain, and Bromley. Whether you are searching for a full-time Vermont residence, weekend getaway, or four-season retreat, 74 Moses Pond Road offers an exceptional opportunity to enjoy a peaceful country lifestyle with recreation, culture, and the best of southern Vermont close at hand. See Listing Details & 58 images.

$670,000 $144 per sq.ft. Weston VT Home »


Price Change! Reduced by $29,000 down 4% on August 27th 2026
7 Beds | 6 Baths |   Total Sq. Ft. 4642  |  Acres: 0.15
Listed on Monday Jul 6, 2026
Description: Perfectly situated in the heart of one of Southern Vermont's most picturesque villages. Just a short drive from Stratton Mountain, Okemo Mountain Resort, Bromley Mountain, and Magic Mountain, this beautifully preserved property offers the ideal combination of historic character and modern comfort. Thoughtfully maintained, the home showcases classic New England architecture with warm pine floors, reclaimed barn wood accents, and abundant natural light throughout. Spacious living and gathering areas make entertaining effortless, while intimate sitting spaces provide the perfect setting to relax after a day of skiing, hiking, or exploring Vermont's scenic countryside. The expansive primary suite is a private retreat featuring tranquil river views, a walk-in closet, dressing room, and a beautifully appointed en-suite bath. Each additional bedroom offers its own dedicated bathroom, creating comfort and privacy for family and guests alike. Outside, enjoy mornings on the front patio overlooking the sounds of the river or spend evenings around the backyard fire pit. Located just a short walk from the Village Green, charming shops, dining, and the acclaimed Weston Playhouse, you'll experience the best of village living while remaining close to Southern Vermont's premier ski resorts, golf courses, hiking trails, and outdoor recreation. This property is a timeless treasure, ready to be cherished by generations to come. See for yourself! See Listing Details & 47 images. Includes a Virtual Tour

$695,000 $269 per sq.ft. Weston VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2585  |  Acres: 6.35
Listed on Thursday Aug 27, 2026
Description: Perched above Weston's coveted Dale Road in a private woodland setting, this handsome expanded cape was designed by Raymond Austin, architect of the famed Weston Playhouse. The home exudes graciousness and attention to detail in a living space that offers both cozy warmth and a light and open feeling. Surrounded by country gardens and with a south facing deck and mountain views, the property is a slice of Vermont heaven both inside and out. The first floor has a welcoming mud room with laundry and powder room, a relaxed family room/kitchen with wood burning fireplace, walk-in pantry, and deck access, a formal dining room and spacious living room with gas fireplace, and a private bedroom with ensuite bath. The second floor includes 2 guest bedrooms, one currently used as a home office, sharing a full bath, plus a primary suite with a large bedroom, ensuite bath, and walk in closet. The full dry basement offers plenty of storage space, and the attached 2 car garage will be a special comfort in the winter months. Thanks to fiber optic internet and a standby generator, you'll be able to communicate and work from home while enjoying the peace and quiet of your own Green Mountain retreat. Weston is one of Vermont's most picturesque and vibrant villages, graced with the Weston Theater, The Vermont Country Store, dining at The Hub and The Left Bank, concerts at Kinhaven, and four seasons of outdoor recreation within a short drive to Stratton, Bromley, Magic, and Okemo Mountain resorts. Come see this special property for yourself, and you may well become its next lucky owners! Showings begin September 2. See Listing Details & 40 images. Includes a Virtual Tour

Under Contract Weston VT Home for sale $850,000 $376 per sq.ft.

$850,000 $376 per sq.ft. Weston VT Home »


Price Change! Reduced by $475,000 down 56% on August 22nd 2026
3 Beds | 4 Baths |   Total Sq. Ft. 2913  |  Acres: 5.75
Listed on Tuesday Apr 28, 2026
Description: Renovated in 2024, this timber frame sits on 5.75 pastoral acres. This property offers sunrise views, beautiful sun all day and a peaceful setting with pond on a quiet country road. The house has 3 bedrooms, 3 full baths, and an office. Wide plank original pine floors, open timber frame concept and all new baths with heated floors. Custom white oak cabinets in the kitchen and baths, with professional stainless appliances with stone countertops. Primary bedroom with full bath, pine walls and beams offering a full bar with a drawer refrigerator with microwave. Views of the mountains and the pond from oversized windows. The screened in porch offers morning sun and a beautiful sunrise with direct connect bbq grill. The partially finished lower level offers a gym and storage space. The fresh water pond has a sandy beach. New septic system and whole house generator. The two car garage added in 2024 has radiant heat, corian finish floor , and a timber carport, along with a newly paved driveway. The sunny garden area has an outdoor shower and hot tub with cold plunge are on the granite patio. Come enjoy the pasture, fruit trees, blueberry bushes and 5 acres of fields perfect for animals and gardening. Entire property has electric fence for dog containment. House sits on the corner of Piper Hill rd and Old Tavern rd with stone walls lining both sides of property. Come see this beautiful setting and enjoy one level living at its best! Close to Okemo and Stratton and mins to the Weston village. Owner is a licensed real estate agent. See Listing Details & 50 images.

$895,000 $290 per sq.ft. Weston VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 3086  |  Acres: 6.7
Listed on Thursday Aug 27, 2026
Description: Classic Alpine Chalet with Guest House and Amenities. Embrace the Vermont mountain lifestyle in this four-season retreat, where classic 1970's alpine design meets the beauty of its natural surroundings. More than a private retreat, this property is a gateway to the many pleasures of Southern Vermont, from skiing and snowshoeing in winter to hiking, tennis, gardening, farmers markets, antiquing, galleries, Manchester shopping, the Weston Playhouse and Northshire Bookstore throughout the year. Set on a picturesque property with a private pond, tennis court and delightful gardens, the estate offers peace, privacy and plenty of opportunities to enjoy the outdoors. The main residence was designed to bring the outdoors in, with dramatic cathedral ceilings and expansive walls of glass that fill the rooms with light and frame views of the mountains, gardens and woods. A cozy den with brick fireplace is a comfortable spot to unwind, while a game room offers space for entertaining. There are three spacious bedrooms, including a private en-suite, along with two additional baths, one featuring a jetted tub and private sauna. A massive wraparound deck provides a wonderful place to take in the mountain setting. A split-rail fence creates a courtyard where you will find a curated flower garden, and the tennis court offers hours of play. The separate guest house provides complete privacy and includes a cathedral-ceilinged main room, bedroom and full bath, adding approximately 1,000 square feet of living space not included in the main house square footage or room count. A meandering path winds through the woods to a serene pond. Just 2 miles from Weston Village, 25 minutes to Manchester and within 30 minutes of four ski areas, this is a special Vermont retreat and a wonderful base for enjoying all that the area has to offer in every season. See Listing Details & 50 images. Includes a Virtual Tour

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