You are viewing all listings Homes between $1000000 and $99999999 dollars.
$1,275,000 $227 per sq.ft. West Rutland VT Home »
6 Beds | 6 Baths | Total Sq. Ft. 5616 | Acres: 105.7Listed on Wednesday Jul 8, 2026
Description: Set on approximately 105 acres of picturesque Vermont countryside, this extraordinary property offers exceptional privacy, natural beauty, and the rare advantage of two separate homes--perfectly suited for a primary residence with an entertaining guest house, multi-generational living, or short-term rental opportunity. This one-of-a-kind offering provides space, comfort, and endless four-season recreational potential. The main home is filled with natural light, highlighted by expansive windows that frame the surrounding landscape. Thoughtfully designed for both everyday living and hosting, it features two bedrooms, two and a half baths, and a dedicated office space ideal for remote work. Two inviting living rooms create flexible gathering spaces, while the fully equipped kitchen serves as the heart of the home. Rooftop access offers a unique vantage point to take in sweeping countryside views, and central air ensures year-round comfort. The second home functions beautifully as an entertaining guest house, offering four bedrooms, two and a half baths, an additional kitchen and living room designed for hosting family and friends. A bonus room provides even more versatility for recreation, a game room, gym, or studio. Below the homes, a substantial four-bay garage offers abundant storage for vehicles, outdoor equipment, and seasonal gear. The land itself is a private playground, complete with a pond and expansive acreage to create trails for hiking, snowshoeing, or ATV riding. Enjoy sledding in winter, wildlife watching, and peaceful seclusion in every season. Ideally located near Pico Mountain, Killington Resort, and Okemo Mountain Resort, as well as the charming town of Manchester, the property is approximately three hours to Boston and four and a half hours to New York City. A rare opportunity to own a truly special Vermont retreat offering both lifestyle and investment appeal. See Listing Details & 59 images.
$1,325,000 $519 per sq.ft. West Windsor VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2554 | Acres: 26.72Listed on Wednesday Apr 29, 2026
Description: Farm at Gaelic Crossing is an equestrian property set on 26.72± acres, has dramatic views of Mount Ascutney and, after summer showers, the frequent and magical appearance of rainbows--often even double rainbows--across the wide, open sky. This updated c.1842 New England Cape offers 2,554 square feet of finished living space, including four bedrooms--two conveniently located on the first floor. Wide pine and maple floors run throughout, adding classic farmhouse character. The equestrian amenities are outstanding: a 3,024-square-foot stable with seven spacious stalls, a heated tack room, wash stall, bathroom, and laundry area. The 100' x 200' riding arena features a state-of-the-art, eco-friendly footing made from recycled sneakers, offering outstanding drainage, low dust, and excellent footing. Outdoor facilities also included are a round pen, four grass paddocks, and one dirt paddock. Quiet gravel roads invite walking and riding, with access to the Green Mountain Horse Association trail system. A stream winds along the property's West border, while apple and pear trees provide seasonal bounty. High-speed internet ensures fast connectivity. Ascutney Outdoors, with 40 miles of trails for horseback riding, mountain biking, skiing, and hiking, is nearby, and the popular Brownsville Butcher and Pantry is less than two miles away. (Horses not included) See Listing Details & 46 images. Includes a Virtual Tour
$1,325,000 $729 per sq.ft. West Windsor VT Home »
2 Beds | 2 Baths | Total Sq. Ft. 1817 | Acres: 5.4Listed on Friday Jun 5, 2026
Description: Constructed in 2025, and located in the desirable Rush Meadow region of West Windsor, this impeccably orchestrated Yankee Barn Post and Beam home features superb materials, old world craftsmanship and detailed fit and finish. Custom milled cabinetry and built-ins throughout. The rooms are filled with natural light with stunning bucolic views from every window. The home is centered by a dramatic floating staircase leading to the loft area. Red oak flooring runs throughout. The open concept kitchen is suited with top quality appliances, and a center island with a rich walnut edged yellow birch countertop. The first level Primary ensuite has a dressing room with laundry, and bathroom with a walk in shower and soaking tub. Up the stairs, there's a spacious area for TV Room, or office and a guest bedroom. The walk-out lower basement level is spacious with high ceilings- perfect opportunity for future expansion. The home connects seamlessly to exterior spaces with a stone terrace and a screened porch, both situated to highlight the lovely pastoral views to Mt Ascutney, and beyond. State of the art mechanicals with central AC. Convenient to trail network, all recreation, Woodstock, Hanover NH and Interstate. See Listing Details & 38 images. Includes a Virtual Tour
$1,345,000 $265 per sq.ft. Village of Brownsville in Town of West Windsor VT Home »
7 Beds | 6 Baths | Total Sq. Ft. 5774 | Acres: 5.51Listed on Wednesday Jun 3, 2026
Description: With sweeping views of Mount Ascutney, this exceptional home offers the Vermont lifestyle so many buyers dream of. A place where family and friends gather, traditions begin, and every season brings new adventures. Thoughtfully expanded over time, it blends two living spaces into one inviting home, offering generous room to be together while providing comfort and privacy for everyone. The newer addition features an open concept kitchen, dining, and living area anchored by a custom stone fireplace and dramatic floor to ceiling windows framing the mountain views. A sun-filled deck invites morning coffee, summer entertaining, or cozy après ski evenings. The primary suite is a private retreat with its own deck, ensuite bath, walk in closet, and dedicated office. The original wing offers four additional bedrooms, a kitchen, living area, and its own deck, creating an ideal space for guests or extended family. Whether enjoyed as one expansive residence, configured for private guest accommodations, or explored for its income-producing rental potential, the flexible layout adapts to a variety of lifestyles. Located in the heart of Brownsville. Just minutes from Mount Ascutney's trails and outdoor recreation, and within easy reach of Woodstock, Okemo, Killington, and the Upper Valley, this is a rare opportunity to own a true Vermont retreat where unforgettable memories are made all year long, with the added flexibility of potential rental income when you're away. See Listing Details & 32 images. Includes a Virtual Tour
$1,450,000 $1,066 per sq.ft. West Windsor VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1360 | Acres: 103.1Listed on Tuesday Jun 9, 2026
Description: They say land remembers. On Rush Meadow Road--where rolling fields meet the quiet rhythm of the seasons--there is a place that has been held, cared for, and passed down for over a century. This 103-acre estate is not something that was assembled. It was lived. Worked. Protected. For generations, it operated as a dairy farm, and the land still reflects that stewardship--lush hayfields, a ready-to-tap sugarbush, rich soil for gardening and beautiful solar exposure across every acre. It's the kind of property that continues to give, year after year. At its heart sits a classic Vermont farmhouse with 3 bedrooms and 1.5 baths, grounded by its traditional woodshed ell and surrounded by substantial garage and equipment space. It's practical, authentic, and full of quiet character--equally suited as a full-time residence or a welcoming guest house. To the west, the land opens into sweeping fields with one of the most compelling building sites in the region--long-range views stretching to Mt. Ascutney, expansive and uninterrupted. Whether you envision a private compound, a retreat, or preserving the land as it has been for generations, the setting invites something meaningful. Consider your dream home resting at the height of the land, the beginning to your own heritage. Moments from Brownsville, with easy access to trails across Ascutney Mountain, coffee at local favorites like the Butcher & Pantry, and the culture of Woodstock just 25 minutes down the road, this property offers both connection and complete escape. This is not simply a farm. It is a legacy--waiting for its next chapter See Listing Details & 44 images. Includes a Virtual Tour
$3,250,000 $1,012 per sq.ft. West Windsor VT Home »
Price Change! Reduced by $100,000 down 3% on June 28th 2026
5 Beds | 5 Baths | Total Sq. Ft. 3212 | Acres: 98
Listed on Wednesday Apr 15, 2026
Description: Stately hilltop home built by Silas Banister c.1800, recently undergone a complete restoration. Quality materials & craftsmanship throughout. It has gorgeous views of nearby Ascutney Mountain & long-range views of NH. The property consists of 98 acres made up of fields, hard & softwoods, trails, a large sugarbush (potential for a future boiling operation). Conserved by Upper Valley Land Trust, enrolled in Current Use. The main floor offers a new kitchen which boasts a beautiful 11' quartzite island & counters. Dining & Family Room with soapstone woodstove, Living Room with a new Rumford Fireplace with rod iron & glass doors for efficiency. A large Sunroom with slate floor, more than an entry it's a nice transitional space to enjoy, 3 BR/3 BA and a Sitting area on the 2nd floor with a tranquil view of the back fields. 2 additional BRs and a half bath on the 3rd floor. All new wiring, plumbing, new Bosch propane furnace supplies radiant heat, triple pane, Anderson low-E4 windows, sheetrock, DaVinci slate-like rubber roof & cherry floors. Fully insulated, extremely efficient. Custom built trim, wide baseboards, wainscoting & cabinets. 200+ year old pine boards from the house were used to craft bathroom vanities, 3rd floor stairs & beautiful doors. Outdoor amenities include in ground pool, gardens & lovely stone patio. A large-3600 sq ft former dairy barn with new wiring & FHA furnace & oil tank. Now used as a garage, workshop & abundant storage space offers ENDLESS possibilities! See Listing Details & 60 images.
$1,299,000 $297 per sq.ft. Weston VT Home »
4 Beds | 3 Baths | Total Sq. Ft. 4372 | Acres: 15.1Listed on Monday May 11, 2026
Description: Experience the very best of Vermont living in the charming village of Weston, where every season offers something to enjoy. Spend winter days skiing at nearby Stratton, Magic, Bromley, or Okemo, and warmer months hiking scenic trails, horseback riding, swimming in lakes and ponds, or taking in a performance at the Weston Theater Company. Explore local shops, galleries, and restaurants while enjoying the beauty of one of Southern Vermont's most beloved communities. Whether you're seeking outdoor adventure, a vibrant arts community, or simply the peace and beauty of Vermont, this exceptional property places it all within easy reach. Thoughtfully built and impeccably maintained, this 4 bedroom, 3 bath home reflects exceptional pride of ownership with thoughtful upgrades throughout. Set on a beautifully landscaped property with a private swimming pond, it offers the perfect balance of comfort, privacy, and year round recreation. Designed for gathering, the home features a spacious open kitchen and dining area, inviting living and family rooms, and a generous mudroom ready for skis, hiking boots, and outdoor gear. A first floor den with an adjacent full bath offers flexibility as a guest room or first floor bedroom. Upstairs are four comfortable bedrooms, a dedicated office, and a spacious laundry room. The primary suite is a true retreat with a large walk in closet, oversized bath, soaking tub, and mountain views. A full basement with bulkhead access provides excellent storage and endless potential for a fitness room, workshop, or future finished space. Outside, mature perennial gardens frame the home, while a covered front porch and sun-filled back deck with a hot tub provide the perfect setting to relax and enjoy the mountain views. The private swimming pond completes this exceptional Vermont retreat. Whether you're looking for a full time residence or the perfect four season getaway, this property offers the ideal blend of recreation, comfort, and Vermont charm. See Listing Details & 42 images.
$3,195,000 $635 per sq.ft. Weybridge VT Home »
Waterfront on Pond _Unnamed5 Beds | 5 Baths | Total Sq. Ft. 5687 | Acres: 26.1
Listed on Thursday May 21, 2026
Description: The Drake House is a rare Vermont landmark, nearly two centuries in the making and thoughtfully carried forward by generations of careful stewards. Built in 1825 by Asaph Drake and his wife, this distinguished brick Federal home has long held an important place in the Middlebury area, with later connections to the Morgan Horse Farm, ownership by a Middlebury College president, and listing on the National Register of Historic Places. Most recently purchased in 2023, the 5,030-square-foot home has been meticulously modernized for contemporary living while preserving the character, craftsmanship, and soul that make it irreplaceable. Light-drenched interiors feature original pumpkin pine floors, historic brickwork, marble accents, reclaimed oak flooring, a restored archway, and elevated updates throughout, including a custom kitchen with coffered ceilings, walnut island, Fisher & Paykel dishwasher, and black enamel AGA propane range. Surrounded by approximately 650 acres of conserved land just five minutes from Middlebury village, the property feels deeply private while remaining closely connected to the landscape, with gardens, a pond, outdoor living spaces, and access to the MALT system's 18-mile trail network. Inside, gracious gathering spaces, a parlor with fireplace and beehive/pizza oven, a serene primary wing with office and cedar sauna, and a wine cellar create a home that is both historic and deeply livable. A post-and-beam barn/garage with guest apartment, additional barn, and second driveway complete this beautifully renewed Federal-era retreat, ready for its next chapter. See Listing Details & 34 images. Includes a Virtual Tour
$1,150,000 $583 per sq.ft. Whitingham VT Home »
4 Beds | 1 Baths | Total Sq. Ft. 1972 | Acres: 100Listed on Friday May 22, 2026
Description: Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to the East. The property could easily accommodate a beautiful new build, or else could be rehabbed into a working dairy or gentleman's farm, with privacy and access rare to find. The main house presently features 4 bedrooms, 1 bath, a large kitchen and dining area, den, and walk in pantry. There is an attached two story barn for storage, which leads into the recently built oversized 3 car garage with 12 foot doors, ideal for equipment or classic car storage. From this you can go to the 38x144 large dairy barn with stalls, horse paddocks, and hayloft, or the tremendous oversized dairy barn with 90 stanchions between the two barns, and main room upstairs, which could be converted into amazing space for those with vision. These are the best maintained functioning farm barns I have seen in 20 years. Add to that a full equipment shed, dairy processing area, approx 40 acres of pasture and fields, sugar house, pond, a network of trails, 60 acres of mature woodlands, and an idyllic home site at the crest of the upper field, and you have everything you could possibly want in a true Vermont farm property, with enjoyment and expansion potential for years to come. Recent updates include a new roof on the house, generator, and a full clean out. Don't sleep on this one of a kind opportunity. Property is in Current Use. See Listing Details & 42 images.
$1,400,000 $572 per sq.ft. Wilmington VT Home »
4 Beds | 5 Baths | Total Sq. Ft. 3844 | Acres: 2.38Listed on Sunday Jan 4, 2026
Description: This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an oversized attached two car garage. Buyers who commit early could personalize finishes within the builder's allowances or choose upgrades at their expense. See Listing Details & 16 images. Includes a Virtual Tour
$1,697,000 $701 per sq.ft. Wilmington VT Home »
Waterfront on Lake Raponda4 Beds | 3 Baths | Total Sq. Ft. 2420 | Acres: 1.72
Listed on Tuesday Dec 23, 2025
Description: This vintage renovated waterfront home is being offered for the second time in 40 years. Lake Raponda allows motorized craft, with primarily private beach front, and a small local boat launch and public beach. It is located conveniently down from the Mt Snow Ski Resort, on a quiet road, affording year round enjoyment and solitude. This home has been lovingly maintained, updated, and expanded by the current owners, and features a lodge style quite unique in the area which offers warm charm and Vermont rustic styling perfect for a retreat. Inside you are treated to vaulted ceilings in the main living room with floor to ceiling stone fireplace. There are freshly painted walls and exposed woodwork throughout, a country kitchen with gas stove and basin vintage sink, great light from the many windows and updated lighting, a tremendous great room addition perfect for entertaining with wood stove for ambiance, two main floor suites including a large primary, an upstairs guest suite, a spacious sleeping loft, great storage and closet spaces, a den/tv room ideal as an office or overflow sleeping, and lake views from every bedroom. Outside you'll find a large stone patio with hot tub which leads down to the extensive perennial landscaping and path to the water. There is a boathouse at the lake for lake storage, a large dock, swim platform, and level lawn space for fun in the sun. The home has a detached garage great for off season boat storage or whatever you may need. Updated septic! See Listing Details & 32 images.
$1,975,000 $467 per sq.ft. Wilmington VT Home »
Waterfront on Lake Harriman Reservoir5 Beds | 5 Baths | Total Sq. Ft. 5063 | Acres: 10.08
Listed on Wednesday Jun 10, 2026
Description: Breathtaking Lake and Vermont Forever Wild views from this 10 acre parcel overlooking Lake Whitingham, with deeded lake access. The premiere Old Mill Lane development is host to some of Wilmington's finest homes thanks to large private parcels, extended driveways, exclusive shared lake access and beach area with kayak rack, swimming cove, and easy access to the Village of Wilmington and nearby ski areas of Mount Snow and the Hermitage Club. This 2005 home sits on 10+ acres with tremendous exposure and a serene lake setting. This was a custom architect designed build which is being offered by the original owners. The home features a large open living space with high ceilings and custom mill work throughout, gorgeous wood floors and extensive wide wood moldings, a spacious area which leads to the large screened porch, chefs kitchen with breakfast bar and stainless appliances, all with breathtaking lake and sunset views. There is a main floor guest suite with gorgeous bath and walkin closet, a warm office with built ins which could serve as overflow sleeping, half guest bath, dual main floor entries, and main floor laundry. Up the custom silo staircase is the primary suite with second wood burning fireplace, walk in closet, upscale bath with soaking tub overlooking the view, and private sun deck. There are three more upstairs bedrooms and a large full bath with separate commode. The finished lower level has a large family room space, 4th full bath, and three massive bonus rooms which are insulated and ready to be finished if you want the extra space as bedroom, theater, game room, or gym. This is all complemented by the two car garage, covered front porch, wraparound covered rear porch to entertain while overlooking the scenic vista, extensive landscaping, perennial gardens, stone work, and exposed ledge, extremely private location, and extensive recent updates. This home is ready for immediate enjoyment and turn key use, affording downtime, not upkeep. See Listing Details & 43 images.
$1,998,000 $476 per sq.ft. Wilmington VT Home »
5 Beds | 5 Baths | Total Sq. Ft. 4200 | Acres: 20Listed on Wednesday Jul 1, 2026
Description: Private Vermont Sanctuary with Spectacular Mountain Views. Tucked away on a quiet dead-end road, yet just minutes to Hermitage Club, Mount Snow and downtown Wilmington. Every room offers a view. Direct snowmobile access and walking trails! Set on 20 private acres in the heart of Vermont's Green Mountains, the property features panoramic views of Haystack, Mount Snow, and the spine of the southern Green Mountains. With over 4,200 square feet of thoughtfully designed living space, the interior boasts clean lines, a Primary suite with walk-in closet and spa-like bath. Floating staircase, a large foyer, and a screened-in porch for enjoying warm evenings. Vaulted ceilings, radiant heat throughout, and walls of windows frame the stunning mountain and valley vistas. Open-concept kitchen and dining area with granite countertops, custom cherry cabinets and flooring, large center island, and a massive stone fireplace. Direct access to multi-level decks. Spacious living room with exposed beams and a cozy sitting area with a Projection System and a Custom high-end audiophile Sound system. Oversized heated 3-car garage. Enjoy outdoor living at its best with beautifully maintained flower gardens, open fields, a mature mixed forest, a patio, a hot tub, an outdoor shower, and creek frontage. See Listing Details & 60 images.
$2,100,000 $493 per sq.ft. Wilmington VT Home »
7 Beds | 4 Baths | Total Sq. Ft. 4256 | Acres: 0.55Listed on Wednesday Jun 17, 2026
Description: Stunning contemporary chalet completely renovated in 2016 and located adjacent to the base of the Hermitage Club private ski resort. This gorgeous home sits on a private lot with direct snowmobile trail access, easy access to the ski trails, and direct to the clubhouse. Just a short drive into the village of Wilmington and the area's tremendous lakes. Thanks to the complete overhaul and meticulous maintenance, this home is turn key for immediate enjoyment, with features including an open concept design, large great room with vaulting ceilings and exposed beams, a stone hearth with wood burning fireplace, upscale country kitchen with stainless appliances and granite counters, a secondary wet bar area, sizeable dining table for all your guests, wood floors throughout, a main floor primary suite with walk-in closets and large tiled bath, dual rustic bunk rooms, a lower level guest suite, 7 spacious bedrooms in total, a large family room for great separate entertaining space, movies, and games, as well as an adjacent tv area, and a tremendous mudroom with built in cubbies for all your gear after a day on the trails. There is also a large covered front porch to keep the snow at bay with wood storage, massive hot tub, fenced in dog area, generator, tremendous parking, and nice lawn space without being much to maintain. With proximity like this and creature comforts from home, this makes for a great ski home, as well as a welcome respite from the metropolitan bustle year round. See Listing Details & 33 images.
$2,195,000 $623 per sq.ft. Wilmington VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 3524 | Acres: 0.5Listed on Wednesday May 20, 2026
Description: A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake -- with a private dock -- just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats tend to head for the public-access Harriman Reservoir on the southern end of Wilmington, Raponda remains a predominantly owner-enjoyed lake. The result is noticeably less boat noise and wake, making it equally wonderful for kayaking, paddleboarding, and peaceful summer mornings on the water. The property sits on a generous, nicely sized parcel with sweeping level lawn space, a private yard with fire pit, ample parking, kayak racks, and a private dock -- which transforms into an ice skating destination come winter. Inside the fully remodeled and expanded vintage four-bedroom, four-bath lake house, an open-concept floor plan invites you in with warm wood floors throughout, a living room anchored by a wood-burning stove set in a stone hearth, and a well-appointed kitchen with stainless appliances and island. A relaxing entertainment area with full bath flows into the heated sunroom addition, with expansive windows framing the lake views and opening onto a wraparound deck. A generous mudroom entry handles gear for every season with ease. Upstairs, the primary suite offers wonderful natural light and a luxurious bath, alongside three spacious guest bedrooms, two additional full baths, custom built-in storage, and a lovely office space. The practical upgrades here are just as impressive: efficient mini-split heating and air conditioning, an attached garage for gear storage, an updated septic system, and a private driveway with ample parking. All of it recently completed, the home is completely turnkey -- so all you'll have to worry about is downtime, not upkeep. See Listing Details & 39 images.
