$1,995,000 $520 per sq.ft. Weston VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3839  |  Acres: 105.8
Thursday Aug 28, 2025
Description: Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house preserves the historic character of an early 19th-century English barn with the addition of a two bedroom apartment on the main level. A short walk from the house, is a handsome post and beam bank barn. The three level barn includes a six-stall stable, three bay garage for equipment, and an inviting entertaining space on the top floor. Surrounding the buildings are stone walls, extensive perennial gardens and apple trees. An 1.5-acre spring-fed swimming pond with a sandy beach is stocked with trout and bordered by open fields and woodlands. A conservation easement with the Vermont Land Trust allows for the potential subdivision and construction of one additional residence. Located just minutes from the award-winning Weston Theater Company and year-round recreational opportunities such as hiking on the Long Trail and skiing some of Vermont's best at Okemo, Magic, Stratton, Bromley and Viking Nordic Center. See MLS Property & Listing Details & 37 images. Includes a Virtual Tour

$275,000 $138 per sq.ft. Whitingham VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2000  |  Acres: 4.7
Thursday Sep 18, 2025
Description: 4 bedroom 2 bath home located on 4.7 acres. Has a ground level access. Level parking and garden spots. There are huge White Pine trees surrounding this home. Showings delayed until September 29, 2025 to allow for cleaning. License to Sell is needed and in progress, Expected in October. See MLS Property & Listing Details & 3 images.

$380,000 $163 per sq.ft. Whitingham VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2336  |  Acres: 12.8
Tuesday Feb 3, 2026
Description: Charming and character-filled 1835 post-and-beam Craftsman. This inviting five-bedroom, two and-a-half-bath home blends antique appeal with cozy comfort. A covered porch offers the perfect place to enjoy summer breezes, the sound of rainstorms, and peaceful evenings, while the deck is ideal for gathering with friends and family. Inside, wood floors and exposed hand-hewn beams highlight the home's craftsmanship. The open living and dining area features a brick fireplace with woodstove insert, creating a warm and welcoming setting on cold winter nights. The second floor offers five bedrooms, two baths, a cozy den, and a tucked-away upper-level retreat--ideal for reading, writing, or quiet reflection. Set on 12.80 acres, the land offers endless possibilities, ideal for a hobby farm, pastures for horses or cows, or growing your own vegetables. A vintage barn and storage shed, ready for restoration, adds to the property's timeless rural appeal. See MLS Property & Listing Details & 45 images. Includes a Virtual Tour

$399,000 Whitingham VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 0  |  Acres: 10.9
Monday Jul 21, 2025
Description: New home under construction. Siding painted and installed, plumbing and electric is roughed in. Roof is completed. Anderson windows. 4 bedrooms to be installed.. The well is drilled and needs to be hooked up. Situated on 10.9 acres with large White Pine and Cherry Trees. Mountain stream in the rear of the property. This will be a 4 bedroom home with 3 full baths, 1 on each of the three levels. Planned for a stone fireplace. Prepped for decks on the east and west sides of the House. Septic plan is designed by a Vermont Licensed Engineer to be built, area is cleared for the system. There is Timber on the property estimated at 15,000 board feet of volume. Close to Wilmington and Dover, Lake Whitingham, Burrington Brook. Deerfield River, North River, Burrington Brook, Haystack Club Golf and Ski and Mount Snow Resort. See MLS Property & Listing Details & 12 images.

$625,000 $248 per sq.ft. Williamstown VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2520  |  Acres: 8.3
Wednesday Apr 15, 2026
Description: Thoughtfully designed and impeccably maintained, this custom-built farmhouse offers the perfect blend of comfort, quality, and Vermont country living. From the moment you arrive, the inviting covered front porch sets the tone for relaxed mornings, quiet evenings, and effortless entertaining. Inside, you'll find a bright, open layout with warm wood floors, natural light, and well-proportioned living spaces. The kitchen flows seamlessly into the main living area, creating an ideal setup for everyday living and gatherings. Cathedral ceilings, natural woodwork, and a smart, functional design give the home both character and ease. Spacious bedrooms provide comfort and privacy, while wide hallways, first-floor laundry, and accessible features support true single-level living. A standout feature is the accessory apartment above the garage, offering excellent flexibility for guests, extended family, or additional income. A whole-house generator provides added peace of mind, ensuring comfort and functionality year-round. Set on over 8 acres with land on both sides of the road, the property preserves its own views and sense of space into the future. Enjoy open fields, gentle terrain, and a setting that feels private and peaceful, yet remains just minutes to Barre, Montpelier, shopping, and I-89 . A rare opportunity to enjoy quality construction, functional design, and a lifestyle that's becoming harder to find. See MLS Property & Listing Details & 40 images.

$299,000 $171 per sq.ft. Wilmington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1750  |  Acres: 1.1
Monday Aug 11, 2025
Description: A solid home in a great location in Wilmington Vermont! Currently set up as a duplex. Live in one and rent the other or have family close by! Add internal stairs and use as one! This is a classic Chalet with the ease of a metal roof, large deck, 2 bedrooms and a full bathroom upstairs along with a cathedral ceiling, cute sleeping loft and built ins! The lower level is 2 bedrooms and a full bathroom with large combined kitchen/living and dining room. There is a large wood shed and an even larger garage/shed/barn. Enjoy your days on the oversized front deck and your evenings by the fire pit! The wooded area behind the home is great for exploring! So close to the local towns, ski areas, lakes and ALL! See MLS Property & Listing Details & 32 images.

$329,000 $302 per sq.ft. Wilmington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1088  |  Acres: 1.34
Wednesday Feb 25, 2026
Description: Charming country cape just outside the village of Wilmington on a spacious corner parcel with easy access off Rte 9. This lovely home could be a great full time residence or vacation retreat, thanks to a great price, great bones, recent upgrades, and nearby lakes, skiing, villages, and Molly Stark State Park right across the street. The house has a bright south facing living room, country kitchen with breakfast table and functional space, two main floor bedrooms and a full tiled bath, 2 upstairs bedrooms and a half bath, wood floors throughout, a full basement entry level with tiled bonus space, laundry room, and mudroom entry, and large deck to take in the scenery. There is a detached studio shed for whatever creative outlet you may want, multiple storage sheds, a second driveway to the outbuildings, a lower grassy area leading down to the beaver brook, and nice winter exposure over nearby fields. Recent upgrades include an updated roof, charming Vermont stone walls, updated drainage around the home, and fresh paint. Truly a unique opportunity at a rare price. See MLS Property & Listing Details & 24 images.

$379,000 $197 per sq.ft. Wilmington VT Home »

6 Beds | 2 Baths |   Total Sq. Ft. 1920  |  Acres: 0.72
Thursday Jun 26, 2025
Description: Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate 3 bedroom, totally renovated, units. This would be a wonderful multi-generational home, two family purchase, use one unit - rent one unit. Wheeler Farm view of pasture and mountain ranges. Exterior garden shed. Plenty of parking, an amazing view and waiting for you! See MLS Property & Listing Details & 43 images.

$399,000 $188 per sq.ft. Wilmington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2128  |  Acres: 0.49
Wednesday Apr 15, 2026
Description: Thoughtfully maintained 4-bedroom, 2-bath Chimney Hill chalet offering a warm, inviting feel with natural wood finishes, open-concept design, woodstove and features that capture the essence of Vermont living. The main living areas are bright, comfortable and welcoming, with easy flow to a deck overlooking surrounding mountain ridgelines--an ideal setting for both quiet mornings and relaxed entertaining. The home is designed for comfort and ease, featuring an oversized mudroom entry, full laundry area, and a layout that accommodates both everyday living and extended stays, of extended groups! A lower-level family room and additional overflow sleeping space provide flexibility for hosting and creating room for everyone without sacrificing privacy. Outdoor features include a fire pit area, large storage shed for recreational gear, and ample parking for vehicles, boats, or snowmobiles--making it easy to enjoy everything the area has to offer in every season. Located within the desirable Chimney Hill community, owners enjoy access to a wide range of amenities including indoor and outdoor pools, hot tub, fitness center, tennis and basketball courts, ice skating rink, stocked fishing pond, picnic areas, and direct access to multiple trailheads. Just minutes to Mount Snow Resort and Hermitage Club, as well as nearby golf and Lake Whitingham with a marina and boat rentals. This property offers a well-rounded four-season lifestyle. Boating, skiing, golfing, hiking, shopping, dining, snowmobiling or just deep relaxation and escape are all within reach from your new home base in the Vermont mountains. See MLS Property & Listing Details & 37 images.

$435,000 $324 per sq.ft. Wilmington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1344  |  Acres: 0.44
Friday Aug 29, 2025
Description: Amazingly private cul-de-sac, the nicest location in Chimney Hill! 4 Bedroom 2 Baths, Livingroom with wood stove and a wall of windows to let the outdoors in! Hot Tub on multi-tiered deck. Beautiful wooded lot to explore, garden shed and garage. Live the Resort lifestyle on Chimney Hill's 1,200-Acre Resort Campus, with 550-Acres owned in common by the Homeowners Association. Numerous multi-use trail system for biking, hiking, snowmobiling, 3 areas with tennis courts, seasonal pickleball and ice skating, year-round swimming at the Exclusive Members-Only Club House , indoor and outdoor in-ground pools, hot tub, fitness room, arcade room, small child playroom, community room, table tennis, basketball, fully-equipped kitchen for HOA members use, outdoor grill by the outdoor pool, along with a playground for young children, and members lounge. Plus, world class skiing and shredding just minutes away, golf, boating, fishing, paddleboarding, unique shops, fine dining, flea markets, festivals, music, and all the Deerfield Valley and Southern Vermont have to offer! Own this winter don't rent!!! See MLS Property & Listing Details & 50 images.

$449,000 $236 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
4 Beds | 3 Baths |   Total Sq. Ft. 1900  |  Acres: 0.32
Wednesday Oct 1, 2025
Description: Time to start living the dream with your very own getaway in Chimney Hill! Little Bend Haven is a short walk to the Clubhouse, at the end of the road, with a wood burning fireplace, family room, open concept living, dining and kitchen, with deck, and three levels of living and sleeping spaces. Main level has a mudroom for gear, bedroom and full bath, kitchen/dining, deck with a babbling brook below, and living room with wood-burning fireplace for taking the chill off. Second level has two bedrooms and a half bath. Lower level has a family room with a gas fired stove for added warmth, full bath and guest room. Furnishings included! Enjoy all the amenities Chimney Hill offers including pickleball, tennis, hiking, biking, cross country skiing, ice skating, sledding, our exclusive member-only Clubhouse located at 2,000' in elevation on our 1,200 Acre Resort Campus and features indoor and outdoor heated pools for year-round swimming, hot tub, fitness room, arcade room, playroom, community room, fully-equipped kitchen, playground, and on-site management. World Class skiing and shredding are minutes away, as well as fine dining golf, boating, shopping, music, breweries, distilleries, wineries, antiques, flea markets, festivals, the Green Mountain National Forest, and more! See MLS Property & Listing Details & 60 images.

$499,000 $223 per sq.ft. Wilmington VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 2240  |  Acres: 1.1
Friday Mar 21, 2025
Description: Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear shed. Inside is a vaulted great room with natural wood throughout, large windows for natural light, a wood burning stove with brick hearth, kitchen with breakfast bar and stainless appliances, main floor primary bedroom with en suite full bath, two guest rooms and another full bath, a first story family room recently renovated with gas fireplace, large bunk room with attached bath, fifth bedroom with half bath, and large entry mudroom for all your snowy equipment. The home offers ample space for groups, but is intimate and cozy enough for less. A true Vermont style getaway. See MLS Property & Listing Details & 28 images.

$675,000 $268 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2516  |  Acres: 0.46
Monday Feb 23, 2026
Description: Beautiful upscale chalet in the Chimney Hill community just a short drive from the Mount Snow ski resort and the village of Wilmington. This meticulously maintained turnkey home has been extensively renovated and upgraded, and sits on a private lot along a quiet side road with direct access to nearby snowmobile trails. Inside, a gorgeous great room features vaulted ceilings, exposed natural woodwork and beams, wood floors throughout, and abundant natural light from large windows -- creating a warm and inviting Vermont mountain feel. A wood-burning fireplace with floor-to-ceiling stone hearth anchors the living space. The updated kitchen includes custom cabinetry, stainless appliances, and quartz countertops. The main level also offers a primary suite with full bath and jetted tub, two additional bedrooms, a full bath with tiled shower, and a functional mudroom entry designed for four-season gear. A cozy loft above provides ideal office or reading space. The fully finished lower level features a spacious family room with game area and wet bar, an additional sleeping area, and a third full bath with tiled shower. Outside, enjoy a large deck for entertaining, an outdoor hot tub for relaxing after a day on the trails, fire pit area, and a generous driveway with ample parking. A nearby overflow parking area accommodates snowmobile trailers or boats in the summer months. Chimney Hill amenities include indoor and outdoor pools, clubhouse, theater, fitness center, hot tub, basketball court, tennis courts, and winter ice skating, with optional services such as plowing and trash removal -- allowing for downtime, not upkeep. Septic system is sized for three bedrooms. Lower-level sleeping area does not have legal egress. See MLS Property & Listing Details & 37 images.

$749,000 $253 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $20,000 down 3% on March 23rd 2026
4 Beds | 4 Baths |   Total Sq. Ft. 2964  |  Acres: 0.5
Wednesday Feb 18, 2026
Description: Turnkey mountain retreat with style, space, and serious four-season fun--welcome to Chimney Hill living at its best. This beautifully crafted 4 bedroom home offers 4 full tiled baths and approximately 3,000 sq ft of warm, inviting living space on 3 levels designed for gathering, relaxing, and making memories. The open concept main level delivers instant wow factor with soaring cathedral ceilings, rich natural woodwork, gorgeous wood flooring, and a stunning timber frame beam. A dramatic south-facing wall of windows floods the home with natural light, while the stone-faced woodburning fireplace creates the perfect après-ski atmosphere. The kitchen is built for entertaining with granite countertops, a large seating island, stainless appliances, and abundant cabinetry. You'll also find a custom bar area, full bath, ensuite bedroom, and easy access to both the covered front porch and new back deck with hot tub. Upstairs offers two spacious, light-filled bedrooms and a full tiled bath. The lower entry level is built for real mountain living with radiant heat throughout, a showpiece tiled mudroom with cubbies, benches, shelving, and storage baskets, plus a laundry room with counters, cabinets, and sink. A full tiled bath with double sinks, bonus room with proper egress window, and a massive den/game room featuring pool table, darts, basketball setup, ping pong, living area, custom art, and sliding barn door complete the space. Outside, enjoy the new huge back deck with hot tub, ski lift chair feature, and additional rear deck space, plus covered front porch and outdoor lockable ski storage. The home is tastefully furnished throughout and features central vacuum & smart features for interior/exterior lights, thermostats, hot tub, keyless entry. Chimney Hill offers true four-season amenities including a clubhouse w/ indoor/outdoor pools, hot tub, sauna, fitness room, game room, etc. Haystack hiking trail is a short walk away. Septic system is designed for 3 bedrooms. See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

$799,000 $258 per sq.ft. Wilmington VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 3091  |  Acres: 1.05
Monday Nov 3, 2025
Description: Multi-Family & Commercial Opportunity in Wilmington, Vermont Set on 1.05 acres just outside Wilmington village, this versatile property offers two recently renovated apartments totaling five bedrooms, each with its own two-car garage perfect for owner occupancy, rental income, or staff housing. The main building features updated interiors with modern kitchens, stylish baths, and new flooring throughout, combining contemporary finishes with a convenient, low-maintenance layout. The property has also been upgraded with a brand-new five-bedroom septic system, providing peace of mind and long-term value. Behind the main residence sits a spacious three-bay garage with a full upper level, ideal for a workshop, contractor space, or additional storage. A smaller outbuilding nearby offers even more flexibility for tools, recreational gear, or seasonal items. Whether you're seeking an investment property, a home with income potential, or a commercial space with ample storage, this Wilmington location offers endless possibilities just minutes from Mount Snow Resort, Lake Whitingham, and the shops and dining of downtown Wilmington. On the MooVer Route See MLS Property & Listing Details & 41 images.