Under Contract Winhall VT Home for sale $449,000 $460 per sq.ft.

$449,000 $460 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1460  |  Acres: 0.47
Listed on Thursday May 14, 2026
Description: A Sanctuary for Every Season: Picture the moment you turn off the main road and onto tree-lined Aspen Lane. The frantic pace of the week instantly drops away as you pull into your driveway. Tucked into a lush, wooded lot, this four-bedroom chalet is designed for those who live for the outdoors. Whether you're here to chase the morning light on the slopes of nearby Stratton Resort or to spend a slow summer afternoon exploring the local swimming holes, this home serves as the perfect basecamp for your Green Mountain adventures. Inside, the vibe is cozy. On crisp autumn evenings, the pellet stove becomes the heart of the home, casting a steady warmth that invites long conversations and board game marathons. When the Vermont summer hits its peak, you'll stay perfectly cool thanks to the modern mini-split system--a rare and welcome comfort in a mountain retreat. The expansive deck is your private outdoor dining room, ideal for long weekend brunches or stargazing after a day of hiking. With four bedrooms and 2.5 baths, there is plenty of space for everyone to find their own corner of peace without feeling crowded. A dedicated storage shed means your paddleboards, skis, canoes, and fishing gear are always organized and ready for the next excursion. You can feel the care that has gone into this property. It has been kept in peak condition so that your only job upon arrival is to drop your bags and head outside. From the gear storage to the effortless climate control, every detail has been managed to make your mountain getaways seamless. The mountains are calling, and this chalet is the perfect place to answer. Contact us today to see this Winhall gem in person and start planning your first weekend away. See Listing Details & 32 images. Includes a Virtual Tour

Under Contract Winhall VT Home for sale $495,000 $271 per sq.ft.

$495,000 $271 per sq.ft. Winhall VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1824  |  Acres: 0.4
Listed on Thursday May 28, 2026
Description: Quintessential Vermont charm meets modern comfort in this beautifully updated New England farmhouse just minutes from Stratton Mountain. Ideally located only 1 mile from the Stratton Mountain Access Road and just 1/10 mile to the VAST snowmobile trail, this 4-bedroom, 2-bath home offers the perfect four-season retreat. Rich with character, the home features exposed beams, warm hardwood floors, and a classic cast iron wood stove that creates the ultimate cozy Vermont atmosphere. Thoughtfully modernized while preserving its historic charm, this inviting property blends timeless farmhouse appeal with everyday comfort. Once a gathering place for legendary folk singer Arlo Guthrie, the home carries a unique sense of history and soul. Enjoy easy access to skiing, snowmobiling, hiking, and The Mountain School at Winhall, embracing the classic placement of historic Vermont farmhouses, originally built close to the road for practical year-round access during harsh New England winters. Today, that timeless design translates into effortless convenience with easy in-and-out access and no long driveway to maintain or plow, all while enjoying the beauty and charm of Vermont living. Whether you're searching for a primary residence, weekend getaway, or investment opportunity, this special property captures the very best of Vermont living. See Listing Details & 39 images.

Under Contract Winhall VT Home for sale $749,000 $498 per sq.ft.

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

4 Beds | 2 Baths |   Total Sq. Ft. 2128  |  Acres: 0.85
Listed on 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 Listing Details & 33 images.

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

4 Beds | 4 Baths |   Total Sq. Ft. 3520  |  Acres: 2.39
Listed on 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 Listing Details & 38 images.

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

4 Beds | 4 Baths |   Total Sq. Ft. 4104  |  Acres: 1
Listed on 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 Listing Details & 38 images. Includes a Virtual Tour

New Listing! Winhall VT Home for sale $849,000 $373 per sq.ft.

$849,000 $373 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2878  |  Acres: 1
Listed on Friday Jul 31, 2026
Description: Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lot along a quiet road, this move-in-ready sanctuary offers effortless mountain comfort, high-end entertaining space, and practical updates throughout. Quality architectural details welcome you into a bright main level boasting a spacious kitchen, dining area, and expansive living room centered around a cozy fireplace--perfect for unwinding after a day on the slopes. Designed for active outdoor living, the home features a dedicated ski room right inside the entry from the attached two-car garage to keep your gear organized and dry. Upstairs, comfortable bedrooms offer plenty of space for guests and a fun-filled loft complete with pool and foosball tables. The finished lower level functions as a private second primary suite with generous storage. Outside, year-round enjoyment continues with a covered hot tub and a dedicated fire pit for cool mountain evenings. Offered furnished, this property is ready for immediate use as an alpine getaway or turn-key primary residence. See Listing Details & 32 images.

$910,000 $300 per sq.ft. Winhall VT Home »


Price Change! Reduced by $40,000 down 4% on July 18th 2026
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.

$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
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 & 59 images.

$1,100,000 $342 per sq.ft. Winhall VT Home »

5 Beds | 5 Baths |   Total Sq. Ft. 4453  |  Acres: 1
Listed on Thursday May 21, 2026
Description: Tucked into Stratton Mountain Resort's sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant recent exterior improvements, and the opportunity to personalize the interior aesthetic to your own taste. Encompassing over 4,600 sq. ft. across three finished levels, this expansive mountain home is designed for gathering, relaxing, and enjoying all four seasons in Vermont. Recent exterior improvements have significantly enhanced the home's appearance and overall exterior presentation. Extensive work included reconstruction and upgrading of major exterior sections, along with new windows, roofing, trim, upgraded siding, exterior refinishing, and fresh paint. Complemented by a standing seam metal roof and updated exterior detailing, the home now offers a refreshed mountain exterior with a warm and inviting presence. Inside, the layout is exceptionally functional and inviting. The main level features an open kitchen, dining area, and vaulted living room with fireplace, along with a sunroom, screened porch, stone patio, and private primary suite. A mudroom with half bath off the attached two-car garage adds convenience for ski season and everyday living. Upstairs offers three additional bedrooms, a full bath with double vanity, and an airy loft overlook. The finished walkout lower level is built for entertaining and flexible living, featuring a spacious family room with wood stove and sliders, custom bar area, guest bedroom and bath, additional half bath, laundry, utility areas, and wide hallways throughout. Located just minutes from the slopes, golf course, village, and shuttle access, this is a rare opportunity to own a substantial Stratton mountain home with significant exterior improvements already completed, while still offering the chance to bring your own vision and style to the interior spaces. See Listing Details & 40 images. Includes a Virtual Tour

$1,225,000 $507 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3357  |  Acres: 1.2
Listed on Wednesday May 20, 2026
Description: Located in Stratton Resort's sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of comfort, convenience, and mountain charm. Filled with natural light, the home features four bedrooms and three recently updated full baths, along with hardwood floors, cathedral ceilings, skylights, and a stunning floor-to-ceiling brick fireplace. Recent renovations include updates to the kitchen and carpeting, creating a move-in ready retreat for all seasons. A spacious wraparound deck with hot tub provides the ideal setting to relax after a day on the slopes. The separate family room, complete with an adjacent full bath, offers excellent flexibility and can easily serve as additional sleeping space for guests. Additional highlights include an attached two-car garage and shuttle service access to Stratton's ski slopes, winter activities, Stratton Village, shopping, and dining. Active Stratton Sport Center Bond. See Listing Details & 47 images.

Under Contract Winhall VT Home for sale $1,275,000 $453 per sq.ft.

$1,275,000 $453 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2814  |  Acres: 1.47
Listed on Saturday May 9, 2026
Description: Beautifully renovated in 2023, this 4-bedroom, 2-1/2 bathroom contemporary sits on 1.47 wooded acres with a sweeping circular driveway and genuine privacy -- while still being on the Stratton shuttle route and just minutes from the base lodge on foot. The interior renovation was done right. Radiant heat floors run through the living room and kitchen, with two wood-burning fireplaces anchoring the main living spaces. The kitchen is built for serious use: Top of the line Wolf and Miele appliances, marble countertops and a layout that opens directly to the dining area and forest views. Vaulted wood-plank ceilings and oversized windows keep the spaces light and connected to the setting without trying too hard. The bedroom layout works well for groups or families -- three bedrooms across the main levels plus a top-floor primary suite with loft, two full baths with heated floors and a half bath on the entry level. The two-car heated garage with an electric car charger handles gear and vehicles whether you're coming off the mountain or heading into the fall foliage season. Mechanicals include mini-split cooling, baseboard and radiant heat, community water and septic. Electric roof electric cables were installed for ice protection while security cameras cover the exterior. Walk to the shuttle. Drive to the village in minutes. Own it year-round or use it as the mountain house it was built to be. Your Vermont chapter starts here. Reach out for a private tour. See Listing Details & 32 images. Includes a Virtual Tour

New Listing! Winhall VT Home for sale $1,299,000 $356 per sq.ft.

$1,299,000 $356 per sq.ft. Winhall VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3644  |  Acres: 5.02
Listed on Sunday Jul 26, 2026
Description: Built and thoughtfully expanded by its original owners, this substantial Winhall residence offers the scale and comfort of a true year-round home in a location made for four-season Vermont living. Set on 5.02 acres, the property stands apart for its broad, level, cleared grounds, an uncommon and highly usable setting just minutes from the Stratton Access Road. Inside, 3,644 square feet, four bedrooms, four 3/4 baths, and multiple living areas provide room to gather, work, host, and retreat. The bright formal living room features hardwood floors, detailed millwork, and a classic wood-burning fireplace. The expansive family room addition brings warm mountain character with exposed beams, rich woodwork, abundant windows, radiant floor heat, and a dramatic stone fireplace. Directly above, the newer primary suite creates a private retreat, with the addition served by its own Buderus boiler and radiant heating system. A beautifully appointed kitchen connects naturally to indoor and outdoor dining, while an additional sitting room adds even more flexibility. A two-car garage, dedicated workshop, and covered connection to the house make year-round use especially convenient. Once established as a horse property, the open acreage and barn remain ready for a new chapter, whether for equestrian use, vehicle and recreational equipment storage, a workshop, or memorable gatherings. Approximately 15 minutes from Stratton Resort, 12 minutes from Bromley, 19 minutes from Magic Mountain, 15 minutes from Londonderry, and 19 minutes from Manchester, this is far more than a weekend chalet. It is a gracious, versatile Vermont home designed for full-time living and four-season enjoyment. See Listing Details & 54 images.

$1,399,999 $424 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.

$1,599,000 $393 per sq.ft. Winhall VT Home »

6 Beds | 6 Baths |   Total Sq. Ft. 5568  |  Acres: 1
Listed on Wednesday Jul 8, 2026
Description: Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game rooms, bar, 2 fireplaces and outdoor patio. Interesting architectural features with curved staircase, high ceilings, and light filled spaces. The gourmet kitchen opens to a grand dining room where you can host large dinners on winter weekends and holidays and during those summer golf and hiking excursions. Well designed for large groups, multiple or extended families with 6 bedrooms, 5.5 baths. Custom ski room, attached garage, and Stratton Resort winter shuttle that picks you up at your driveway and delivers you to the Base and Village. Enjoy the use of the Stratton Sports Center and Stratton's 36 hole golf course. This is one of High Meadow's iconic Resort residences with the updated features you look for in your Vermont Mountain Escape. This is a home for all seasons and the Vermont lifestyle you are looking for! Showings Begin Friday, July10th. See Listing Details & 46 images.

$1,990,000 $429 per sq.ft. Winhall VT Home »

6 Beds | 7 Baths |   Total Sq. Ft. 5896  |  Acres: 1.49
Listed on Thursday Jun 4, 2026
Description: Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental flexibility. Handcrafted timber framing creates warmth and character throughout, while four fireplaces including a gas fireplace in the primary suite enhance the home's mountain atmosphere. Designed for gathering, the lower level features a full bar, game room, family room, and wood-burning fireplace, creating an ideal setting for après-ski entertaining. The primary suite serves as a private retreat with a spa-like bath, indoor sauna, hot tub, and oversized shower. Outdoor living is equally impressive. The expansive deck functions as a four-season outdoor kitchen and lounge complete with a covered porch, wood-fired pizza oven, gas grill, and gas fire pit. A landscaped level yard provides additional usable outdoor space, while a second outdoor hot tub extends the home's resort-style amenities. Recent improvements include updated Thermador appliances and a new roof. Additional features include a heated two-car garage and direct access to the Stratton shuttle route. A standout feature is the home's ability to operate as two fully independent residences, each with its own kitchen and laundry. This flexible configuration creates opportunities for personal use, hosting guests, or maximizing rental income throughout the year. See Listing Details & 54 images.

© 2000-2026 Clerkin Agency Real Estate
NEREN Logo
565 Maple Street, White River Junction, Vermont. 05001 802-295-1355
Copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated August 1st, 2026

PLEASE NOTE: Both New Hampshire and Vermont law require brokers and agents to disclose at the “time of first business meeting, prior to any discussion of confidential information”, in New Hampshire’s case, and “first reasonable opportunity”, in Vermont’s case, the nature of the relationships brokers have or may have with customers and clients. Each state requires that a disclosure form be presented to consumers for their review and acknowledgment at the appropriate time. These forms can be accessed here:
VT: VERMONT REAL ESTATE COMMISSION MANDATORY CONSUMER DISCLOSURE FORM
NH: NEW HAMPSHIRE REAL ESTATE COMMISSION BROKERAGE RELATIONSHIP DISCLOSURE FORM