$339,000 $158 per sq.ft. Windsor VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2142  |  Acres: 0.25
Friday Apr 3, 2026
Description: Discover space, flexibility, and everyday convenience in this charming 4-bedroom, 2-bath home in the heart of Windsor. Thoughtfully designed with a spacious floor plan, the main living area features warm hardwood floors and abundant natural light, creating a bright and welcoming atmosphere throughout. The formal dining area flows seamlessly into the living room, perfect for both everyday living and entertaining. A main-level bedroom and full bath, along with convenient first-floor laundry, offer ideal single-level living options or guest accommodations. Upstairs, you'll find three generously sized bedrooms, providing plenty of space for family, guests, or a home office setup. Set on a quarter-acre lot, the property offers ample parking and a detached one-car garage, perfect for storage, hobbies, or a workshop. Centrally located and easy access to town, grab your morning coffee just a short walk away or head to the nearby pond for a relaxing swim. A wonderful opportunity to own a well-located home with space, charm, and versatility in Windsor! See MLS Property & Listing Details & 25 images.

$424,000 $147 per sq.ft. Windsor VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2888  |  Acres: 1.22
Tuesday Mar 24, 2026
Description: A rare piece of Vermont history, thoughtfully preserved for modern living. Dating to 1790, this distinguished brick and frame Colonial stands as a testament to early New England craftsmanship -- and it's ready for its next chapter. Meticulously maintained over the centuries and updated where it counts, this two-story home offers the warmth of wide-plank hardwood and softwood floors, the peace of mind of updated electrical and heating systems, and the curb appeal of a classic standing seam roof and fresh paint throughout. Recent windows flood the interior with natural light while preserving the home's timeless character. Whether you're drawn by the historic details or the practical updates, this property is move-in ready from day one. The kitchen is showstopping with a seamless blend repurposed materials. It exudes character and charm. The attached 1 car garage -- complete with a dedicated storage room/workshop area and a massive open attic accessible from both levels -- offers flexible space for a workshop, studio, or expansion. A property of this age rarely offers this much functional square footage. Positioned conveniently off Exit 9, commuting to the Upper Valley and beyond is effortless. The commercial zoning potential makes this an exceptional opportunity for buyers seeking a live-work arrangement, professional office space, or a savvy investment in one of Vermont's most storied small towns. Historic character. Modern comfort. Extraordinary potential. See MLS Property & Listing Details & 38 images.

$575,000 $240 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2400  |  Acres: 4.48
Wednesday Mar 11, 2026
Description: Perched to capture breathtaking long-range views, this striking ski home offers an unforgettable vantage point of Magic Mountain and Stratton, with Bromley visible to the northwest--a daily reminder that some of Southern Vermont's best skiing and outdoor adventure are just minutes away. With its cool, modern vibe and classic alpine character, the home perfectly blends style, comfort, and mountain living. The main living area is designed to showcase the spectacular scenery, with large windows that frame the surrounding mountains and fill the space with natural light. A wood-burning fireplace anchors the living room, creating the perfect spot to gather after a day on the slopes. Clean architectural lines, warm materials, and thoughtful updates give the home a contemporary yet welcoming feel throughout. Several upgrades and renovations provide comfort and efficiency for years to come. The property also includes a carport, providing convenient covered parking so you won't have to clear snow off your car after a Vermont snowfall, along with space for skis and all the gear that comes with an active mountain lifestyle. Perfectly located just minutes from Bromley Mountain and a short drive to Stratton Resort, this home is ideally positioned for year-round recreation--from skiing and snowboarding in winter to hiking, biking, and golf in the warmer months. An added benefit of this property, if you opt to join, is that a Bromley Bond is available, providing driveway plowing, and garbage pickup services. Whether you are seeking a full-time residence or a retreat, this unique mountain home offers style, views, and an unbeatable Southern Vermont location. Closing to occur on or after June 15. The buyer may elect to close earlier and allow the seller to rent the property back until June 15. This property will transfer unfurnished. See MLS Property & Listing Details & 37 images.

$695,000 $256 per sq.ft. Winhall VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2715  |  Acres: 18.2
Saturday Feb 7, 2026
Description: Classic Vermont farmhouse set on over 18 private acres with Bromley Mountain views, offering timeless character, privacy, and mountain views. This four-bedroom, two-bath home features a striking stone fireplace anchoring the main living space, along with a dedicated library and office--ideal for reading, work, or creative pursuits. Outdoor living shines with a spacious patio and stone firepit, perfect for s'mores, gatherings, and crisp Vermont evenings. The property includes a two-car attached garage and two detached barns, offering flexibility for storage, hobbies, or agricultural use. Rolling open land and wooded acreage create a peaceful, pastoral setting with room to explore. Ideally located just 3 miles from Bromley Mountain and 5 miles to the Stratton Access Road, this farmhouse delivers convenient access to skiing, hiking, and four-season recreation while maintaining the charm and serenity of a true Vermont retreat. The home also features a hot tub, generator, and is being sold furnished for a turnkey experience. See MLS Property & Listing Details & 35 images.

$735,000 $352 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2091  |  Acres: 4.94
Friday Jan 30, 2026
Description: While temperatures outside may be freezing, step inside and take in the incredible views of Stratton while basking in sunlight from the living room of this Vermont home. Located just one mile from the base of the Stratton Access Road and only 20 minutes from Manchester, the setting offers exceptional convenience while remaining peacefully tucked away in the private woods of Winhall. The main living spaces are warmed by a wall of windows, creating a bright and comfortable atmosphere even on the coldest winter days. Vaulted ceilings enhance the light and airy feel, while a large deck provides seamless access to the outdoors and stunning mountain views. The thoughtful layout includes four bedrooms, with two on each level, offering flexibility for family and guests. Two spacious living areas--each with its own fireplace--create inviting spaces for relaxing and entertaining. The lower level features excellent storage with abundant closets and plenty of room for gearing up. Designed for winter living, the wide eaves help keep snow away from the home, and a brand-new standing seam roof offers added peace of mind. While this home is ideal for winter, summer is equally special. Walk up the road to Coleman Hill, one of the area's most picturesque back roads, lined with century-old apple trees and surrounded by hundreds of acres of farmland. Nearby Gale Meadow offers fishing and kayaking, and the Stratton snowmaking pond is just minutes away for swimming and paddleboarding. Enjoy Stratton's 27-hole golf course, local farmers markets, hiking the AT/LT, and all that Vermont living has to offer during the warmer months. For now, while the snow is still here, the property offers quick access to Stratton, Bromley, and Magic Mountain, along with cross-country skiing at Wild Wings. This is an opportunity you won't want to miss. See MLS Property & Listing Details & 39 images.

$795,000 $318 per sq.ft. Winhall VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2500  |  Acres: 2.33
Thursday Apr 16, 2026
Description: Stratton Chalet with INCREDIBLE Mountain Views! Recently renovated this VT mountain retreat is the perfect place to enjoy all seasons in Southern VT. Enjoy the majestic views of the summit from your hot tub and firepit all year long. The interior layout is wonderful for larger groups to gather with an expansive open entertainment area on the ground level including the kitchen, dining and living room, and all of the sleeping quarters separated one level up. The main floor includes a rustic brick wood burning fireplace and dramatic scorched wood high ceilings throughout the entire level. The backdrop of the living room is dominated by those summit views of Stratton. This home is set on over 2 private wooded acres and yet conveniently located on the last shuttle pick up before the base lodge on the Blue Shuttle line. In the summer and fall, you can sleep in until just before your tee time and stroll across the street to the 27-hole championship golf course. No detail has been overlooked on the recent renovations which include a 6-person hot tub, all new Anderson casement windows and sliders, all new flooring, exterior and interior doors, trim, all new bathrooms, sauna, and completely updated kitchen with Danby Marble from a local VT quarry. Offered fully furnished and staged with tasteful neutral decor, just bring your overnight bag and enjoy your mountain home from day one! See MLS Property & Listing Details & 37 images.

$829,000 $296 per sq.ft. Winhall VT Home »

Price Change! Reduced by $20,000 down 2% on March 30th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2797  |  Acres: 1.1
Friday Jan 23, 2026
Description: Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for intimate gatherings during spring blooms or lively celebrations as summer stretches into long, lazy evenings. Step outside onto the deck, where a bubbling hot tub invites you to unwind under the stars, no matter the season. The spacious kitchen is ready for your culinary explorations, from summer barbecues to winter comfort food, making it the heart of your home in every season. Whether you're savoring the vibrant colors of fall, the fresh green of spring, or the serene snowfalls of winter, this Vermont home offers a sanctuary for all seasons. Don't miss your chance to own this four-season gem. Embrace the beauty of Vermont and create memories that will last a lifetime, no matter the time of year! See MLS Property & Listing Details & 37 images.

$849,000 $293 per sq.ft. Winhall VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2897  |  Acres: 1.26
Friday Mar 13, 2026
Description: Nestled in the highly sought-after Forest Farms neighborhood on Stratton Mountain, this beautifully updated 5-bedroom, 3-bath mountain retreat on Sugarbush Drive offers the perfect blend of comfort, style, and breathtaking natural beauty. The home features an open-concept living space designed to showcase the stunning surroundings, highlighted by a dramatic wall of glass that frames gorgeous mountain views and fills the home with natural light. Hardwood floors run throughout the main living areas, complementing the inviting atmosphere. The spacious, updated kitchen is ideal for entertaining, seamlessly flowing into the living and dining areas. Two cozy fireplaces provide warm gathering spaces after a day on the slopes. Upstairs, the private primary suite offers a peaceful retreat set apart from guest rooms, while the home's other four bedrooms and two updated baths provide plenty of space for family and visitors. The lower-level family and game room adds additional living and entertainment space--perfect for movie nights or relaxing après-ski. A generous mudroom entrance makes mountain living easy, providing the ideal drop zone for skis, boots, and outdoor gear. With spectacular views, thoughtful updates, and a prime Stratton Mountain location, this Forest Farms home is an exceptional opportunity for a year-round Vermont getaway or ski-season escape. See MLS Property & Listing Details & 35 images.

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

4 Beds | 4 Baths |   Total Sq. Ft. 4104  |  Acres: 1
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 MLS Property & 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
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 MLS Property & Listing Details & 55 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.

$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
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 MLS Property & Listing Details & 37 images. Includes a Virtual Tour

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

4 Beds | 4 Baths |   Total Sq. Ft. 4184  |  Acres: 0.98
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 MLS Property & Listing Details & 55 images.

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

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 & 60 images.

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

4 Beds | 4 Baths |   Total Sq. Ft. 3400  |  Acres: 1.83
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 MLS Property & Listing Details & 43 images.