$860,000 $210 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 4104  |  Acres: 1
Listed on Saturday Jun 21, 2025
Description: Mountain paradise awaits in this magnificent 5,000 sq ft Winhall retreat! Perched on a private acre with breathtaking, panoramic mountain views, this 4-bedroom, 3.5-bath home is an entertainer's dream and a serene escape. Step inside to discover a grand living room, a cozy family room, and a luxurious primary ensuite bedroom, each featuring a crackling wood-burning fireplace, perfect for chilly evenings. Cathedral ceilings soar, enhancing the spacious feel. The primary suite is a true sanctuary, boasting a spa-like bathroom with double sinks, a jetted tub, a separate shower, and an expansive walk-in closet. Enjoy private balconies directly from your bedroom, offering stunning vistas and a tranquil spot for morning coffee or evening stargazing. Beyond the living areas, this home offers an array of desirable amenities including a stylish bar, ideal for gatherings, and a dedicated exercise room to maintain your wellness routine. Strategically located, this property offers unparalleled access to outdoor adventures. Just minutes from Stratton Resort, you'll enjoy world-class skiing in winter and championship golf in the warmer months. Experience the best of Vermont living with a perfect blend of luxury, comfort, and convenience. Your Winhall dream home awaits! See Listing Details & 38 images. Includes a Virtual Tour

$950,000 $409 per sq.ft. Winhall VT Home »


Price Change! Reduced by $45,000 down 5% on April 20th 2026
5 Beds | 5 Baths |   Total Sq. Ft. 2321  |  Acres: 0.66
Listed on Tuesday Nov 11, 2025
Description: Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite- this mountain chalet has been updated with all the comforts you expect in a luxury getaway. Two wood burning fireplaces , tasteful ambiance with warm wood ceiling and accents. A second family room is designed as a T.V. Room/den with kitchenette/bar for movie night snacks and football game halftime spreads.The floor plan offers bedrooms on each of three levels- ideal for inviting friends and multiple families.Equipped with a well designed mudroom entrance Shuttle picks you up at your driveway and an easy walk home for those who want to close down Grizzlies apres ski and bands.Roads and security fees apply. Stratton Sports Center Bond eligible and property is served by community water and sewer. What are you waiting for? This is beautifully redone and turn key. No need for a project. This mountain residence is ready to go and prime for the winter enthusiast! Stratton Mountain is calling you! See Listing Details & 55 images.

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

4 Beds | 4 Baths |   Total Sq. Ft. 3031  |  Acres: 1.37
Listed on 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 Listing Details & 41 images.

Under Contract Winhall VT Home for sale $975,000 $428 per sq.ft.

$975,000 $428 per sq.ft. Winhall VT Home »


Price Change! Reduced by $24,000 down 2% on March 9th 2026
4 Beds | 4 Baths |   Total Sq. Ft. 2280  |  Acres: 1.42
Listed on Monday Aug 25, 2025
Description: Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 ½ bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at pool and foosball in the game room. A 2-room Primary Wing upstairs is your private oasis, with the remaining 3 bedrooms and 2 baths downstairs for family and guests. A large, tiled mudroom and owners' closet will store your gear after a long day on the slopes. Relax in the outdoor hottub tucked into the private rear patio. 1 car garage. Video included in Listing. Exterior Blink surveillance system. Stratton Road maintenance $1472 annually Water/Sewer fees: $257 quarterly. Original Stratton Bond Can Be Reinstated for $5000. Listing Agent is Owner/Seller See Listing Details & 37 images. Includes a Virtual Tour

Under Contract Winhall VT Home for sale $975,000 $233 per sq.ft.

$975,000 $233 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 4184  |  Acres: 0.98
Listed on Friday Apr 3, 2026
Description: This custom-built contemporary home was designed with large gatherings of family and friends in mind, offering a spacious layout and plenty of room to relax and entertain. You can't beat the location - just minutes to Manchester, Bromley, and Stratton, and nestled in the heart of year-round recreation. The private setting has views of Bromley's trails and is bordered by the National Forest. This well maintained 4-bedroom, 4-bath property features a newly expanded entry area designed to accommodate all your gear with ease. The dramatic open living room boasts hardwood floors, vaulted ceilings, wall-to-ceiling windows, and a fireplace, all filled with natural light.The bright chef's kitchen is seamlessly integrated with the living area and showcases thoughtfully designed cabinetry. High-end appliances include an Electrolux refrigerator, Miele dual wall ovens, a Miele stovetop with hood, and a Fisher & Paykel dishwasher.The primary bedroom suite is conviently located on the main level, with views of the National Forest, generous closet space, and an attached tiled bath with both tub and shower. Upstairs, three additional bedrooms and two baths are arranged to provide privacy and seperation. The lower-level family room offers additional living space with access to the backyard patio. Designed for recreation, this level features a ping pong table, arcade game, and wood-burning fireplace. Additionally there is a bonus room and bath. The large laundry room includes two sets of washer and dryer units, a utility sink, and a built-in drying rack.The designated spa room features a tiled floor, indoor hot tub, and sauna, with access to the back patio and an additional outdoor hot tub. Other notable features include an enclosed porch, multiple decks, a one-car garage, and a whole-house generator. This turnkey home includes new furnishings throughout. See Listing Details & 55 images.

$979,000 $187 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 5248  |  Acres: 2
Listed on 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 Listing Details & 60 images.

Under Contract Winhall VT Home for sale $1,325,000 $390 per sq.ft.

$1,325,000 $390 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3400  |  Acres: 1.83
Listed on Sunday Mar 1, 2026
Description: A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. On the resort shuttle bus route. With 1.83 acres the house has a very private setting in back for the patio, fire pit and hot tub. Unique U-shaped driveway has plenty of room for friends and family. Downstairs family room with kitchenette. Great living space and bedrooms throughout. Quality metal roof sheds snow easily. Two wood burning fireplaces. A must-see property at Stratton. See Listing Details & 43 images.

Under Contract Winhall VT Home for sale $1,399,000 $259 per sq.ft.

$1,399,000 $259 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 5397  |  Acres: 26.9
Listed on Thursday Jan 1, 2026
Description: One-of-a-kind, craftsman-built Vermont log home set on over 26 private acres with breathtaking, long-range mountain views. Tucked away at the dead end of the road, this exceptional property offers rare privacy while remaining close to premier ski mountains and all the dining, shopping, and cultural attractions of Manchester, VT. The land features two picturesque waterfalls and a serene natural setting that feels worlds away. The home showcases expansive windows that flood the interior with natural light, highlighting warm wood tones and timeless craftsmanship throughout. Enjoy outdoor living from the inviting covered front porch or the back deck with pergola--perfect for entertaining or relaxing in nature. Inside, you'll find three wood-burning fireplaces, a spacious game room with bar, sauna and thoughtfully designed living spaces ideal for gatherings or quiet retreats. A three-car garage provides ample space for vehicles and storage, and the home is equipped with an automatic generator for peace of mind and uninterrupted comfort. A truly special Vermont escape. Furnishings may be purchased separately. See Listing Details & 43 images.

$1,399,999 $368 per sq.ft. Winhall VT Home »

6 Beds | 4 Baths |   Total Sq. Ft. 3800  |  Acres: 1
Listed on Monday Mar 23, 2026
Description: Bring the whole household to this great place with lots of room for fun. A 6-bedroom, 4-bathroom Adirondack-style Ski Chalet located in a neighborhood just minutes from the Stratton Mountain Ski Resort, with free door-to-mountain shuttle service on select days. Amenities include four (4) fireplaces, best hot-tub on the market, an in home gym, electric sauna, pool table, SuperChexx Bubble Hockey table, foosball table and corn hole, Sonos entertainment system, and high-speed Wi-Fi and digital cable service. Top of the line WOLF Stove and appliances. 4 years of STRONG rental value. This House checks every box. This is the premier house in the area. Huge owners closet. You have so many options here. See Listing Details & 33 images.

$2,425,000 $535 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 4536  |  Acres: 2.5
Listed on Sunday Feb 8, 2026
Description: SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for comfort and performance, each detail reflects quality craftsmanship-from the sleek finishes to the high performance systems. The handcrafted timber frame great room showcases the natural beauty of the Green Mountains. Defined by soaring cathedral ceilings and exposed natural wood beams, the dramatic wall of stone with wood hearth anchors the space while expansive windows frame breathtaking views, flooding the room with natural light. The designer c hef's kitchen with dedicated scullery is as elegant as it is functional with top tier appliances and and oversized island.A main level en suite primary features views, a walk in closet, and a spa inspired bath, double vanities and glass enclosed tiled shower.A second en-suite primary , occupies its own level with soaring ceilings, upscale tiled bath and peaceful separation from the rest of the residence. The finished lower level walkout provides flexible living with media/game room, and a 4th mega bunk or guest room and bath.The spacious entry welcomes guests, a mudroom and attached 2 car garage provide the spaces needed for Active Mountain Living with a second level expansion room already prepped for future heating, plumbing and electricity.Stone Lodge offers the balance between mountain serenity and the convenience of the Stratton Mountain Resort. Enjoy the comforts of a premier mountain retreat with easy access to year round recreation, dining and everything the area has to offer. Experience adventure , relaxation and the luxury of Stone Lodge! See Listing Details & 11 images.

Under Contract Winhall VT Home for sale $2,999,000 $451 per sq.ft.

$2,999,000 $451 per sq.ft. Winhall VT Home »

6 Beds | 7 Baths |   Total Sq. Ft. 6650  |  Acres: 40.8
Listed on Thursday Feb 13, 2025
Description: Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4 ensuite bedroom, 3 stone fireplaces, huge lodge room w/ large beams and walls of glass and VIEWS VIEWS, VIEWS which is nothing short of EXTRAORDINARY. New gourmet kitchen and baths.PLUS a 2 bedroom/2bath guest house.You'll be captivated by commanding southerly views of Stratton Mountain, surrounding ridge lines and sunset views to the west. This property is without comparison and the last rare parcel of this size near the resort.This will also be your summer retreat with a world of privacy and tranquility. Just minutes to the Base Lodge, you'll come home to endless outdoor fun. Bring your ATVs, snowmobiles and in summer there's a pond and tennis court. Patios, Stonework, outdoor spaces enhance the stunning location. Situated in the heart of everything the region has to offer throughout the seasons. World Class professional theater, theManchester Music Festival, The Dorset Summer Equestrian Festival. Hiking, biking, kayaking, shopping and dining. Fall foliage, first tracks on powder days and the Green Mountain Summers beckon.This one of a kind property is the essence of a true Escape See Listing Details & 56 images.

$389,000 $254 per sq.ft. Woodbury VT Home »


Price Change! Reduced by $10,000 down 3% on March 19th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1530  |  Acres: 11.74
Listed on Monday Jan 12, 2026
Description: Country contemporary home features 4 beds,1-1/2 baths. A main level bedroom,half bath and laundry area walks up to livingroom,dining area and kitchen. Three beds and full bath on second level. Attached one car garage. Attached shed for wood storage. The barn houses small animals, once home to goats and chickens. Located on surveyed 11.7 acres with a path into the woods for walks anytime of the year. Town maintained road drops onto paved Route 14 for an easy commute to the Hardwick,Stowe,and Morrisville areas as well as Montpelier and Barre hubs. All kinds of recreation abound in this location.The home been under good stewardship with added solar roof array,insulation upgrades and heat pump additions. See additional details and Seller improvements attached to listing for full disclosures. The home is ready for the next owner to take to the next level or just come enjoy the country life. See Listing Details & 48 images.

$395,000 $244 per sq.ft. Woodstock VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1617  |  Acres: 0.65
Listed on Wednesday Oct 1, 2025
Description: Classic Vermont farmhouse just minutes from the heart of Woodstock. This charming 4 bedroom , 2 bath home offers the character of a traditional New England property with comfortable , move in ready living spaces. The home features a bright eat-in kitchen, spacious dining room, and a welcoming living room with a wood-burning fireplace--perfect for cozy Vermont evenings. Freshly painted interiors and updated flooring provide a clean , inviting feel while preserving the home's classic farmhouse charm. An attached barn/ garage offers excellent storage and flexible space for outdoor gear , a workshop, or hobby area--ideal for those who enjoy Vermont's year-round outdoor lifestyle. Located just a short drive to the Village Green in Woodstock, the property also provides convenient access to hiking, biking, and skiing at nearby Killington Resort. Whether you are seeking a full time residence or a Vermont getaway , this property offers an excellent opportunity to enjoy one of Vermont's most desirable areas at an attractive price point. Call today for a private viewing. See Listing Details & 47 images.

New Listing! Village of Taftsville in Town of Woodstock VT Home for sale $527,000 $289 per sq.ft.

$527,000 $289 per sq.ft. Village of Taftsville in Town of Woodstock VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1824  |  Acres: 0.42
Listed on 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. Showings begin at the open house on Sunday, April 26th, from 1-3pm. See Listing Details & 49 images. Includes a Virtual Tour

$675,000 $212 per sq.ft. Woodstock VT Home »


Price Change! Reduced by $14,000 down 2% on March 26th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3190  |  Acres: 2.94
Listed on 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 Listing Details & 45 images.

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