$6,898,000 $1,725 per sq.ft. Wilmington VT Home »

3 Beds | 6 Baths |   Total Sq. Ft. 4000  |  Acres: 11.2
Tuesday Jul 7, 2026
Description: A truly one-of-a-kind estate. Uncompromising quality, timeless design, and exceptional craftsmanship. Every detail has been thoughtfully curated, showcasing impeccable fit and finish. The spectacular main residence features custom stone flooring, reclaimed vintage barn board accents, and a dramatic great room anchored by a massive smooth stone fireplace and walls of glass with natural light. At the heart of the home is a chef's kitchen complete with marble countertops, an oversized center island, walk-in pantry, dual Sub-Zero wine refrigerators, a built-in pizza oven, and a impressive suite of Wolf and Sub-Zero appliances. Designed for year-round enjoyment, the grounds are simply unmatched. Bluestone patios surround the home and lead to a sunken hot tub, cold plunge, a massive BBQ, pergola, children's playscape, and a spectacular post-and-beam open-air pavilion. Gather around the oversized fire pit while enjoying panoramic western sunsets over Haystack Mountain. Private tennis and pickleball courts, complete with a beautifully appointed cabana featuring a half bath, wet bar, and folding glass walls that open directly to the courts. A custom-built carriage house offers four oversized garage bays below for vehicles and seasonal recreational equipment. Above, guests will appreciate a beautifully finished two-bedroom apartment featuring an open-concept kitchen and living area, a gas fireplace, and a full bath--ideal as guest accommodations, an in-law suite, or caretaker's quarters. The professionally landscaped grounds include a paved driveway, beautiful perennial plantings, rolling open field, and stunning views of Haystack Peak. Located just minutes from The Hermitage Club, Mount Snow, golf, skiing, dining, shopping, and all of Southern Vermont's year-round recreational amenities. This is more than a home--it's a legacy estate offering an unparalleled lifestyle where luxury, recreation, and Vermont's natural beauty come together in perfect harmony. See MLS Property & Listing Details & 60 images.

$349,000 $205 per sq.ft. Windham VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1700  |  Acres: 4
Saturday Jul 11, 2026
Description: Set in the quaint village of South Windham, this charming Vermont home offers a warm, comfortable lifestyle with ski areas, outdoor recreation, and four-season adventure all close at hand. Known locally as the "old dance hall," the property is believed to date to around 1900, possibly reflecting an earlier community use that adds an interesting layer to its history. Lovely pine floors bring warmth and character throughout the home, while a Jøtul wood stove in the living room creates a cozy gathering place. A second wood stove in the basement provides efficient whole-house heat during the colder months. The flexible floor plan includes three bedrooms, with two on the main level and one upstairs, making the home well suited as a starter property, retirement home, or peaceful Vermont getaway. The living spaces open to an expansive deck overlooking a generous backyard with a beautiful backdrop of the surrounding hills. A gentle stream meanders through the property, enhancing the quiet setting and creating a wonderful sense of peace. There is ample room for gardens, outdoor projects, or the makings of a small homestead. With 1.5 baths and approximately 1000+ square feet of unfinished attic space offering potential for additional living area, office space, or storage, the home has room to grow and adapt. Full of charm, history, and practical comfort, this is a special opportunity in one of Vermont's most peaceful village settings. See MLS Property & Listing Details & 29 images.

$395,000 $113 per sq.ft. Windham VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 3502  |  Acres: 1.3
Monday Jul 13, 2026
Description: In the heat of it all!! With 4 mountains within in about 1/2 hour, this is the perfect spot to get away for skiing and all the other Southern Vermont treasures. Nestled in a sweet meadow, with a wee bit of forest, this home is a perfect home base with plenty of room for everyone. With a lovely flat yard, huge private back deck and large above the ground pool, there are lots of options for entertaining. The guest suite has a private entrance or can be open to the main house. It would work well as a potential rental (check with the town), x generation starter, or an in home caretaker suite. Snug up to the cozy fireplace or wood stove on the crisp winter nights, hunt for fireflies in summer, breathe the clean crisp air of fall. You can't go wrong here. See MLS Property & Listing Details & 31 images.

$299,000 $260 per sq.ft. Windsor VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 1152  |  Acres: 6.8
Monday Jun 22, 2026
Description: Embrace the ultimate Vermont lifestyle with this 1950s ranch, perfectly situated on 6.8 sprawling acres of versatile land at 466 Esty Lane in Windsor. Combining nostalgic mid-century charm with extraordinary future potential, this property is an absolute dream for investors, developers, or anyone looking to build their ideal country homestead. The existing home offers 1,152 square feet of single-level living space, featuring two comfortable bedrooms, one full bathroom, and a full basement providing excellent storage or workshop space. While the house requires renovation, it boasts solid bones and a layout ready for your personal touch. For those desiring more space, the structure is suited to easily add a second-floor expansion, allowing you to maximize the footprint and capture beautiful scenic views.The true crown jewel of this property is the expansive acreage. With 6.8 total acres at your disposal, there is incredible potential to subdivide the land into two additional separate lots. Adding to this investment appeal, the land layout accommodates separate entrance possibilities for the new potential lots, ensuring future privacy and ease of access. Nature lovers will be captivated by the extensive river frontage running right along the property line, complete with idyllic spots perfect for a private summer swimming area or peaceful afternoon relaxation by the water's edge.Location is everything, and this property delivers. Nestled on a quiet, serene dirt road, you will enjoy complete peace and privacy while remaining just a short drive close to downtown Windsor's shops, dining, and historic amenities. Outdoor enthusiasts will rejoice knowing that Mount Ascutney is less than five miles away, offering fantastic alpine skiing, snowboarding, and winter recreation right in your backyard, alongside summer hiking. Whether you choose to renovate the existing ranch, expand upward, or pursue the subdivision, 466 Esty Lane offers an unmatched canvas. See MLS Property & Listing Details & 60 images.

$1,399,000 $350 per sq.ft. Windsor VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 4000  |  Acres: 4.96
Tuesday Jun 16, 2026
Description: "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two porches: one open air and one screened-in, with views into the New Hampshire hillsides. Inside, the house is open and bright with a wonderful flow throughout. The large living room features a wood-burning fireplace and plenty of windows streaming in lots of natural light. The formal dining room, with built-in cabinets and a second wood burning fireplace, connects to the kitchen which is open to the family room. A beautiful spindle staircase with oversized steps leads you upstairs to the four bedrooms, including the primary with an ensuite bath and an attached office. The main guest/children's bedroom features a magnificent turret style sunroom taking in views of the Connecticut River, and a second set of stairs leads back down to the mudroom. The full basement offers plenty of storage and all the utilities. The large 2 story garage offers room for 4 vehicles and plenty of storage on the 2nd floor. This unique property presents a rare opportunity to own a special homestead in the Windsor area, just minutes from downtown shopping and restaurants. See MLS Property & Listing Details & 50 images. Includes a Virtual Tour

$675,000 $306 per sq.ft. Winhall VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2204  |  Acres: 0.85
Wednesday Jun 24, 2026
Description: This is not your average chalet. Tucked in the quiet Stratton View neighborhood, just 1 mile from the base of the Stratton Access Road, this 3-bedroom, 2-bath home offers the warmth and character of a classic Vermont chalet with updated systems, thoughtful improvements, and the things you have been looking for but can't seem to find: two living spaces and a garage -- actually, two garages. Offered furnished and in immaculate condition, this is a home you can enjoy from day one. The great room features soaring ceilings, a wood-burning stove, beautiful beams, and flat-sawn balusters that add to the alpine feel. A recent two-story addition adds a one-bay garage and a large second living room with vaulted ceilings, creating an impressive gathering space. High-quality modern materials and systems, including a standing-seam roof, efficient mini-split heating and cooling, and cedar shakes, were used in the construction of this addition. Beyond the addition, the rest of the home has been thoughtfully modernized over time, including drainage around the house, improved insulation, updated mechanicals, an updated electrical system including a 200-amp electrical panel, stainless steel flue liners, a whole-house water filtration system, renovated kitchen and baths, a drilled well, modern septic components, and years of thoughtful site work. With a large mudroom that makes organizing gear easy and a great-sized laundry room that helps keep the house running and orderly, this home functions beautifully as either a primary residence or a vacation home. Step outside onto the deck, outfitted with a new awning, and take in the views of the pond. In addition to the new one-bay attached garage, there is a detached oversized 2-car garage measuring approximately 21' x 26', as well as a shed, so there is plenty of space to store vehicles and gear, or have a workshop. Located in the desirable town of Winhall with school choice. Make it your home and start enjoying Vermont this summer. See MLS Property & Listing Details & 49 images. Includes a Virtual Tour

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

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

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

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

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

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

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

6 Beds | 6 Baths |   Total Sq. Ft. 5568  |  Acres: 1
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 MLS Property & Listing Details & 46 images.

$1,650,000 $575 per sq.ft. Winhall VT Home »

3 Beds | 4 Baths |   Total Sq. Ft. 2872  |  Acres: 1
Wednesday Jul 1, 2026
Description: Your Ultimate Vermont Mountain Retreat Awaits! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is the perfect year-round escape - crafted for adventure, relaxation, and making lasting memories in every season. Whether you're hitting the slopes in winter, hiking through summer trails, or soaking in the stunning fall foliage, this property delivers! Plus, it's only a 10-minute drive to Manchester, where you'll find excellent dining and local shops. Step inside the main house to a soaring great room with exposed beams, a dramatic stone fireplace, and lodge vibes that scream cozy comfort. At the heart is a chef's kitchen that opens to a bright sunroom and dining area, ideal for gathering with family and friends. Fireplaces throughout, plus a game-packed entertainment zone with pool table, shuffleboard, arcade games, TVs, and a wet bar bring endless fun indoors. With 3 bedrooms, 2 bonus rooms and 3 bathrooms, there's room for everyone to relax in comfort. But that's not all - this expansive property also includes a 2,250 sqft guest house with an open kitchen, 1.5 baths, covered porch, and an epic downstairs arcade/bar. Outside is a private playground for all ages: fire pit, hot tub, full outdoor kitchen with fireplace, TV, and grills. Enjoy the pond, playground, horseshoes, and a court for basketball, pickleball, or badminton. Whether you're carving fresh powder, basking in summer nights or soaking in Fall colors - this is Vermont living on a whole new level! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$359,000 $250 per sq.ft. Woodbury VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1436  |  Acres: 0.64
Tuesday Jul 7, 2026
Description: Welcome to 114 West Woodbury Road in beautiful Woodbury, Vermont--a peaceful country retreat offering privacy, comfort, and easy one-level living. This well-maintained 1,436-square-foot home features 2 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and entertaining. Tucked away at the end of a dead-end road, this property is surrounded by open conservation land, creating a serene setting with abundant wildlife and year-round natural beauty. Outdoor living is a highlight, with a spacious screened-in porch, a stone patio perfect for relaxing or gathering with friends, and a private deck off the primary bedroom where you can enjoy your morning coffee overlooking the peaceful surroundings. Additional features include a detached shed and workshop, providing plenty of space for hobbies, storage, or outdoor equipment. Outdoor enthusiasts will appreciate the property's close proximity to the VAST trail system, offering easy access to Vermont's renowned snowmobile trail network. Despite its tranquil setting, the home is conveniently located with a short commute to both Morrisville and Montpelier, making it an ideal balance of rural privacy and accessibility. See MLS Property & Listing Details & 49 images.

$495,000 $362 per sq.ft. Woodbury VT Home »

Waterfront on Pond _Unnamed
3 Beds | 2 Baths |   Total Sq. Ft. 1368  |  Acres: 10.6
Monday Jul 6, 2026
Description: A Vermont Lifestyle Property with Surprises Around Every Corner! So much more than just a home, this unique property offers the space and versatility to live, work, gather, and explore. The inviting 3-bedroom farmhouse was moved back onto a new full foundation and renovated inside and out in the early 1990s, blending classic farmhouse charm with important updates. Inside you will find an eat-in kitchen that opens nicely into the dining and living areas, full bath, 3 bedrooms upstairs with 1/4 bath~ creating a warm and welcoming space to call home. The massive garage/barn opens the door to endless possibilities. The owner has run a successful repair shop in this fully insulated, wood-heated space that includes a car lift and air compressor, making it ideal for a continued workspace, hobbies, equipment, storage, or future ventures. Beyond the home and garage is where this property truly sets itself apart. A small barn and level pasture area offer the opportunity for horses, smaller farm animals, or homesteading. Continue along the gravel drive and discover a private retreat created for relaxing and gathering, complete with a spacious pavilion that doubles as RV winter storage, two storage sheds, a sleeping cottage, and a stone fire pit perfect for evenings under the stars. Travel farther into the land to find a hidden pond that has provided years of summer enjoyment. With some clearing, this peaceful setting could be opened back up to capture more sunlight and beautiful views overlooking the gathering field below. The adventure continues into the back acreage with wooded terrain, hiking opportunities, and an ATV-accessible trail leading toward a level area near the top. From workspaces to recreation, animals to quiet escapes, this is a property designed to be enjoyed in every season. There is more than meets the eye-a property you need to explore! Bring your ideas and discover all the possibilities waiting here! See MLS Property & Listing Details & 36 images.

$400,000 $302 per sq.ft. Woodstock VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 1324  |  Acres: 0.51
Friday Jul 10, 2026
Description: Once an old school house, this home features stone walls, beautiful gardens, and a nice level yard with a stone patio. The year-round brook cascades over rocks and winds along the back side of the property. A covered porch leads inside, where the main floor offers an eat-in kitchen, a large living room and a dining area with French doors to the outside. There are also two bedrooms, an office with stairs to the basement, a full bath with laundry, and a mudroom. The 2nd floor attic, with a large dormer, offers many possibilities for additional space but requires installing stairs and building out the open area. The basement houses utilities and allows for significant storage. The house needs a few updates but has lots of potential and is a wonderful investment opportunity or a great way to get into a starter home in the Woodstock area. It is conveniently located just minutes from Woodstock Village and only a few miles from the Kedron Valley Inn, the South Woodstock Store, and the Green Mountain Horse Association. See MLS Property & Listing Details & 32 images.

$465,000 $205 per sq.ft. Woodstock VT Home »

2 Beds | 3 Baths |   Total Sq. Ft. 2268  |  Acres:
Sunday Jun 21, 2026
Description: Spacious, immaculate, and beautifully maintained Federal-style brick townhouse located in the prestigious village of Woodstock, often recognized as one of America's most beautiful small towns. Three finished levels, the larger size residence of 24 homes. Surrounded by mature woods, perennial gardens, & maple trees. A peaceful setting just minutes from Woodstock Village. The Woodstock Farmers' Market is located at the end of the street. Outdoor enthusiasts will appreciate being less than one mile from trailheads leading into Marsh-Billings-Rockefeller National Historical Park, as well as nearby aqueduct and cycling trails. Killington Resort is approximately 20 minutes away. Gorgeous hardwood floors. The first level features a flexible room with pocket doors that can be used as guest bedroom, home office, studio, den, providing exceptional versatility for today's lifestyle. The spacious floor plan lives more like a single-family home, with generous room sizes, abundant natural light, and a deluxe wood-burning fireplace. Additional features include: Full bathroom on each level Oversized private deck Covered bridge in town Brand new dryer Updated electrical and plumbing 2019 furnace This Property is conveyed subject to the Woodstock Community Trust Local Deeds covenant, a copy of which is attached to this listing. See MLS Property & Listing Details & 31 images.