$749,000 $498 per sq.ft. Winhall VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2128  |  Acres: 0.85
Saturday Jul 4, 2026
Description: Stratton Mountain Renovated! 4 bedroom 2 bath is located just mins to the mountain . This home has access to all that Stratton has to offer. The Ski shuttle comes right outside your door for easy access to the mountain and your home. Freshly painted inside and out, with a partial renovation just completed. This home just installed all new windows with egress and new doors and sliders. The new large deck is perfect for entertaining and a nice yard for family gatherings. This property was recently hydro seeded with new lawn and a new gravel drive thru driveway. Wood shed included with storage for all the equipment and gear. The living room fireplace is wood burning with a large glass and expanded deck for entertaining. The heating is hot water baseboard making it warm in winter. A interior cedar sauna to enjoy after those long ski days! Large laundry room with new tile floors. This modern home is ready for its new owner. Great rental history for those who may want to rent. See MLS Property & Listing Details & 33 images.

$775,000 $391 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3520  |  Acres: 2.39
Saturday Jun 27, 2026
Description: First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel--quiet and peaceful. Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an inviting and comfortable atmosphere. Recent improvements, including a new roof and new decks, add value and provide great spaces to relax or entertain outdoors. With four large bedrooms and two additional bonus rooms, there's plenty of flexibility. Located just approximately 3 miles from Stratton Mountain, you'll have easy access to year-round activities. In the winter, enjoy some of southern Vermont's best skiing and snowboarding, while the warmer months offer golf, hiking, mountain biking, and a vibrant village with dining, shopping, and events. This property offers space, privacy, and proximity to everything Stratton has to offer. See MLS Property & Listing Details & 38 images.

$795,000 $194 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 4104  |  Acres: 1
Friday Jul 3, 2026
Description: Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping, panoramic mountain views from every single room. Whether you are prepping a meal, lounging by the fire, or waking up in the primary suite, the connection to the landscape is seamless. This home was built for an active, balanced lifestyle, emphasizing connection, wellness, and effortless entertaining. Rise and Align: Start your morning in the dedicated home workout space. Roll out a yoga mat, find your flow with a view of the peaks, or power through a session on the erg and free weights while watching the morning fog lift from the valley. Gather Around: The heart of the home is a dramatic, light-filled great room anchored by a magnificent stone fireplace--the ultimate anchor point for swapping stories after a day on the slopes. Unwind and Reconnect: Pour a drink at the built-in bar, head downstairs to the game area, or step out onto the expansive deck to breathe in the crisp, silent Vermont air. Four Seasons of Adventure: While winter brings world-class skiing just minutes away, the warmer months unlock championship golf, hiking, and the vibrant local culture of Winhall.When the day winds down, the primary suite offers a private retreat, complete with its own crackling fireplace and a balcony made for stargazing through the clear mountain night. It's a space designed to let you recharge deeply before doing it all over again tomorrow. If you've been looking for a home that captures the true essence of Vermont--where modern design meets rugged, natural beauty--25 Benson Fuller Road is waiting. Reach out today to schedule your private tour and experience these views in person! See MLS Property & Listing Details & 38 images. Includes a Virtual Tour

$799,000 $354 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3078  |  Acres: 1.5
Thursday May 21, 2026
Description: Spacious and light-filled four-bedroom home ideally located in desirable Strattonwald, offering both winter and summer enjoyment in a private, peaceful setting. Enjoy convenient access to the Stratton winter shuttle, as well as summer amenities including a private pond and tennis courts. The home features generous living spaces perfect for gathering and entertaining, including a cozy fireplace and a large lower-level family room. Abundant natural light, ample closet space throughout, and a spacious primary suite with a large walk-in closet add to the home's appeal. Red Brook runs peacefully along the back of the property, enhancing the serene surroundings. An oversized garage includes a large unfinished room above, ready for your personal vision or expansion. The home is equipped with a generator for added peace of mind, and the furnace is just two years old. Sellers have completed a building, chimney, water, septic, and pest inspection, and all reports are available to any interested party. Please note: the indoor hot tub is currently not functioning. See MLS Property & Listing Details & 35 images.

$949,000 $223 per sq.ft. Winhall VT Home »

Price Change! Reduced by $30,000 down 3% on July 14th 2026
4 Beds | 4 Baths |   Total Sq. Ft. 5248  |  Acres: 2
Friday Mar 13, 2026
Description: This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with expanded island optimal for entertaining -- grill and wraparound deck just outside the kitchen. The fourth bedroom -- a primary suite with en-suite bathroom -- is on this level. On the walk-out lower level, a game room with pool table and a separate TV room with gas stove offer a getaway before soaking in the hot tub, within earshot of the babbling brook down the hill. Nestled in the coveted community of Strattonwald, this 4-bedroom home offers Stratton shuttle access right from the driveway. Strattonwald's rare swimming pond, sandy beach, tennis/pickleball courts, picnic area, and space to fish and kayak make it one of the area's most preferred communities. Finally -- a renovated 1BR/1BA guest house boasts space for guests, in-laws, your office, or long-term rental income. Just in time to move in, enjoy summer, and get geared up for your first season in your Vermont ski house! Call for your tour soon. See MLS Property & Listing Details & 59 images.

$950,000 $313 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3031  |  Acres: 1.37
Monday Dec 8, 2025
Description: Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton's most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge--or simply hop on the convenient shuttle for effortless access to the slopes--this property offers the best of Stratton living in every season. Step inside to find a spacious, light-filled interior with clean contemporary lines, warm natural materials, and an inviting open layout ideal for gathering with family and friends. Large windows bring the outdoors in, while generous living spaces provide plenty of room to relax after a day on the mountain. With four well-appointed bedrooms, this home comfortably accommodates guests and offers flexible space for work, play, or quiet retreat. Outside, the expansive 1.37-acre lot delivers the privacy and peaceful surroundings you expect from a mountain home, including a covered deck with a hot tub and grill to be able to enjoy year round, all while keeping you close to the heart of the resort. Whether you're seeking a year-round getaway, a winter ski home, or a property with excellent rental potential, 7 Roundtree Road delivers contemporary style, convenience, and Stratton Mountain charm in one exceptional package. See MLS Property & Listing Details & 41 images.

$595,000 $285 per sq.ft. Woodbury VT Home »

Price Change! Reduced by $55,000 down 9% on June 26th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2088  |  Acres: 48.6
Monday Apr 20, 2026
Description: Forty-eight and a half acres of Woodbury homestead has been waiting for you. Hill pasture rolls into mixed softwood forest as you climb the old farm road into the mature maple stand, where the ghost of an old sugarhouse still lingers among the trees. Apple trees, blueberries, organic gardens, trails that invite you to lose track of time. Views of the local hills remind you exactly where you are. This land has been lived on, loved, tended well and it shows. The home sits quietly tucked away from the road, conscientiously sited to let the sun do some of the work. Passive solar design fills the interior with natural light and warmth. The kind that feels authentic rather than forced. Built with intention, the craftsmanship inside rewards a slow look. Sawn tamarack boards, hand hewn timbers, Rutland slate, salvaged Vermont hardwood floors, and custom woodwork sourced from the land itself. Architectural salvage chosen with a discerning eye complements the hand-crafted natural interior elements. Three bedrooms, two full baths, a dedicated office and plenty of common area make the interior spacious and comfortable. There is a stillness about the place that the road noise can't reach. Inside and outside space negotiate here, equally, by design. Two porches, an elevated deck, and a gazebo invite you to linger in the spaces between nature and home. Here the practical and the purposeful coexist in easy harmony. A new high-efficiency LP wall-hung boiler with individual room zones, 4.4kw of roof-mounted solar panels net metering against your electric bill, two EV charging plugs and wiring for a generator. An attached workshop and garage for the projects that never quite finish, plus sheds for wood, and equipment. A second building site was designed for the property about a decade ago adding versatility with an eye toward the future. Woodbury's many lakes and ponds are just a stone's skip away and 'city' amenities in Hardwick, Montpelier, and Morrisville are all within easy reach. See MLS Property & Listing Details & 60 images.

$635,000 $664 per sq.ft. Woodbury VT Home »

1497 Ft. of Waterfront on Lake Greenwood
2 Beds | 1 Baths |   Total Sq. Ft. 957  |  Acres: 3.49
Saturday May 16, 2026
Description: Private island with seasonal cottage and boat launch with 2-story 2-car garage at Greenwood Lake, Woodbury! The 3.3+/- acre island has 1400' of lake frontage according to Town land records. The seasonal cottage is charming and comfortable with a open floor plan and softwood flooring, being sold furnished in "as is" condition with only a few personal items and artwork excluded. First floor bunkroom plus upstairs private bedroom. Also the walk-thru hallway has room for a guest bed. 4-Burner gas range/oven, electric refrigerator, and electric lights makes camping quite civilized! Incinerating propane toilet in the 3/4 bath, however, if you want the camping experience, there is a single-hole outhouse just a short walk into the woods. 12'x40' Floating deck in 3 sections plus decks and dock on either side of cabin. Floating raft. Solar collector with battery bank, plus portable gas generator. Jet pump fills 210+- gallon holding tank with lake water. 2 Tool sheds. Back on the mainland, there's a 0.19+/- acre lot with 97' of water frontage, a 2-story 2-car detached garage built in 2015 with grid power, driveway, and boat launch with dock. Greenwood Lake is a 96 acre minimally developed lake with public boat launch and a maximum depth of 41 feet. Popular for fishing and paddling though water skiing allowed. Private road access off paved state highway, just 5 miles to services in Hardwick Village. Rare offering is ideal for long-term legacy investment and years of enjoyment! See MLS Property & Listing Details & 60 images.

$502,000 $275 per sq.ft. Village of Taftsville in Town of Woodstock VT Home »

Price Change! Reduced by $25,000 down 5% on June 12th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 1824  |  Acres: 0.42
Friday Apr 24, 2026
Description: Step into a rare offering where timeless New England charm meets contemporary comfort. Originally built in 1846 and thoughtfully reimagined, this exceptional Taftsville, Vermont residence is set along Happy Valley Brook, creating a private sanctuary defined by peace, beauty, and understated elegance. Historic character is beautifully complemented by carefully curated upgrades, including energy-efficient heat pumps, enhanced electrical systems, basement insulation, and newer windows--ensuring comfort and efficiency in every season. Recent capital improvements, such as updated siding, a newer drilled well, and new oil and propane tanks, underscore the home's turnkey reliability, while generator-ready capability provides an added layer of confidence. Enjoy a kitchen built for making memories anchored by a newly installed and sleek granite island perfect for connection and celebration. Outdoors, the revitalized grounds invite both quiet relaxation and effortless entertaining, all framed by the natural splendor of this picturesque village setting. Positioned on coveted Happy Valley Road, the property offers a lifestyle as desirable as the home itself--where morning strolls and evening bike rides become part of your daily rhythm. Just minutes from the boutiques, dining, and charm of Woodstock, as well as convenient access to Interstate 89, this location perfectly balances a charming, village-like setting with accessibility. Imagine summer evenings spent beside the gently flowing stream, gathered around a glowing fire under the stars--an experience that captures the very essence of elevated Vermont living. See MLS Property & Listing Details & 48 images. Includes a Virtual Tour

$649,000 $284 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $46,000 down 7% on July 7th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2288  |  Acres: 0.15
Monday May 11, 2026
Description: A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much desired Maple Street neighborhood! Popular Vail Field recreation area is conveniently nearby! For children in Maple Street's Neighborhood, Woodstock Elementary School is just a short walk away. Currently the residence is configured as home to 2 generations of occupants. A ground floor apartment conveniently accessed from 3 sides of the home comfortably provides accommodation for practical single level living. The main entrance is through a spacious 12'x10' mudroom. A great attribute in Vermont winters! On 1 end of a well thought out floor plan is a generously sized bedroom with a nearby bathroom. Midway in the apartment is a nicely appointed kitchen that then leads to an appealing dining area. Through a door off the dining area several steps lead to a laundry room that conveniently has an exit leading out to the rear of the property. A living room off the dining area completes the attractive apartment. Well placed windows throughout this ground floor provide pleasant views and natural light. A spacious 2nd floor apartment, with 2 levels of living space, is accessed through a private doorway on the front exterior of the residence. A flight of stairs leads up to the primary apartment area consisting of a bedroom, a dining room, a living room, a kitchen and a bath. Off the kitchen is a partially finished laundry area and then stairs leading down to a ground level workshop. Above the primary apartment is a useful 2 room attic area and a potential bath. Although this 2nd floor apartment has been a full time residence, a new owner will certainly choose to renovate some components of the apartment. The landscaped lot has much appeal with space for gardens and for relaxing outside. Residents in this neighborhood can enjoy walking to village amenities of shopping, dining and cultural events. A Victorian style home full of enormous potential! Location, location! See MLS Property & Listing Details & 39 images.

$659,000 $207 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $30,000 down 5% on June 25th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3190  |  Acres: 2.94
Friday Feb 20, 2026
Description: Historic Woodstock, Vermont - Spacious Home on Nearly 3 Acres. Welcome to a rare opportunity in the heart of Woodstock, one of Vermont's most picturesque and sought-after villages. This expansive home offers generous living space with many rooms, providing flexibility for a large household, home offices, guest quarters, or the potential to create multiple apartments (buyer to verify local regulations).Inside, you'll find two charming fireplaces that add warmth and character, perfect for cozy Vermont evenings. The home's classic architecture blends timeless appeal with endless possibilities for customization. Set on over 2 acres, the property features a fenced yard ideal for pets, gardening, or outdoor entertaining. A one-car garage adds convenience, while the separate potting shed--complete with electricity and a heater--offers wonderful space for gardening enthusiasts, creative projects, or additional storage. Located just minutes from Woodstock Village, you'll enjoy easy access to boutique shopping, dining, and the renowned Woodstock Inn & Resort and its spa amenities. Vermont's natural beauty surrounds you--world-class skiing, hiking, biking, and year-round recreation make this an exceptional place to unwind, recharge, and truly enjoy life. A unique property with space, charm, and opportunity in historic Woodstock. See MLS Property & Listing Details & 41 images.

$695,000 $304 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $55,000 down 8% on June 5th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 2285  |  Acres:
Wednesday May 20, 2026
Description: Excellent opportunity for residential or office/commercial space with easy access and high visibility on Rt 4 coming into town, Currently configured as office space downstairs (which previously has been living spacce), combined with a separate two-bedroom apartment (with its own access) upstairs. The 1,335 sf lower level (Unit C) is currently a chiropractor's office space and was previously used as natural food store and barber shop. The 950 sf upstairs two-bedroom apartment (Unit D) has been leased out by the month for approx $2,000 per month, and has two separate bedrooms, a kitchen, sitting area, balcony and full bath. Or you could re-combine the two units into a larger 2,285 sf in-town residence or office space. There are 4 dedicated parking spaces for the two units, plus other parking in the rear that is shared with the other two units (A & B) of this commercial condo complex. This is a great opporunity to own a highly visible, move-in-ready building right on Route 4. See MLS Property & Listing Details & 33 images.

$718,500 $433 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $30,500 down 4% on June 1st 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1660  |  Acres: 0.19
Saturday Mar 28, 2026
Description: Great new price! Nestled in the vibrant heart of Woodstock Village, this beautifully renovated residence offers the ultimate "walk-to-all" lifestyle. Stepping inside, newly installed pine flooring guides you through an inviting main level designed for both daily living and effortless entertaining. The cozy living room anchors the home with its warm gas fireplace, while the spacious dining area flows seamlessly into a stunning, expanded kitchen equipped with sleek quartz countertops, and elegant cabinetry. Upstairs, three comfortable bedrooms provide peaceful retreats, highlighted by a versatile sitting room off the primary bedroom that easily transforms into a private study or playroom. Modern peace of mind is built right in, thanks to a new second-floor bath, new energy efficient propane furnace, upgraded 200 AMP electrical wiring, and many more upgrades. Outside, the classic covered porch serves as your front-row seat to the serene village surroundings. Directly across the street, the open green spaces of Vail Field invite you to enjoy playgrounds, ball fields, pickleball/tennis courts or simply walk the dog. Just a short, picturesque stroll away, the very best of Woodstock awaits--from the historic Woodstock Inn and the iconic Village Green to the local elementary school and an array of charming artisan shops, bakeries, and restaurants. For the athlete, this home puts you in the heart of the premier Vermont cycling communities and world class skiing. Complete with a two-car garage with plenty of room to store your outdoor gear, featuring a customizable, partially finished space above, this move-in-ready gem perfectly blends timeless New England charm with modern sophistication. See MLS Property & Listing Details & 46 images.

$785,000 $239 per sq.ft. Woodstock VT Home »

Price Change! Reduced by $30,000 down 4% on June 11th 2026
5 Beds | 4 Baths |   Total Sq. Ft. 3284  |  Acres: 2.84
Tuesday May 12, 2026
Description: This lovely four-bedroom, 2.5-bath cape features a two-car attached garage and a separate 700+/- sq. ft. one-bedroom apartment. The property also includes a separate outbuilding ideal for a workshop or additional storage. The primary living space boasts a modern kitchen with updated cabinetry, granite countertops, and cherry floors. The open-concept family and dining rooms flow into a bright living room equipped with a Woodstock soapstone woodstove, brick hearth, and built-in bookshelves. A three-season porch offers additional space for entertaining. Showings to start May 18, 2026. Open House on May 23, 2026 from 11am to 1pm. The first-floor master suite includes a private full bathroom, two large closets, and a deck. Upstairs, you will find three additional bedrooms, an office/study, and a full bathroom. The separate one-bedroom apartment provides an excellent opportunity for rental income or private guest accommodations. Additional features include a two-car garage and a dog fence/kennel. Located near Mount Tom trails, the home is just five minutes from Woodstock, two minutes from the high school, and twenty minutes from Killington, making it a perfect primary residence or vacation getaway. See MLS Property & Listing Details & 41 images.

$799,000 $399 per sq.ft. Woodstock VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2004  |  Acres: 30.18
Monday Jun 29, 2026
Description: If you've been dreaming of the quintessential Vermont lifestyle, this exceptional property delivers the perfect blend of privacy, charm, and convenience. Nestled on over 30 acres in Woodstock, this classic farmhouse is surrounded by beautiful open fields, mature trees, and peaceful natural beauty. Inside, you'll find a spacious eat-in kitchen that's perfect for gathering with family and friends, while the inviting living room features exposed beams and a cozy wood stove that adds warmth and character. The first floor also offers a primary bedroom with an ensuite bath and the convenience of first-floor laundry. Upstairs are two additional bedrooms, a bonus room, and a separate office or flex space ideal for working from home. Outside, relax on the covered front porch, unwind on the patio, or soak in the hot tub while taking in the scenic surroundings. The classic Vermont barn offers abundant storage, space for vehicles or equipment, and includes an attached chicken coop. The land is truly the highlight, with a picturesque pond, perennial gardens, open pasture, and a mix of wooded acreage offering endless opportunities for recreation, gardening, or simply enjoying the outdoors. All of this is just minutes from Woodstock Village, world-class skiing, shopping, dining, and everything this sought-after region has to offer. See MLS Property & Listing Details & 30 images. Includes a Virtual Tour