$589,000 $247 per sq.ft. Whiting VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 3556  |  Acres: 11.17
Thursday Aug 20, 2026
Description: Set on 11.17 beautifully cared-for acres with sweeping pastoral views, this versatile Whiting property is ideal for buyers seeking a homestead, flexible living space, and potential income generation. The thoughtfully maintained grounds offer an appealing blend of open, gently sloping acreage, established outdoor spaces, a large pond, a 4-stall barn with an additional bay, and a chicken coop! The property is completely ready for animals, gardening, recreation, or small-scale farming. Recent improvements include new doors, replaced front and back composite decks, driveway work, and improved drainage, adding everyday function and long-term peace of mind. A huge parking pad in front of the house provides plenty of room for vehicles, equipment, trailers, or recreational toys, with potential for a future shop or additional outbuilding opportunity. The pond serves as a peaceful focal point, enhancing the property's natural beauty, privacy, and year-round enjoyment. The comfortable four-bedroom home offers nearly 2,400 square feet of above-ground living space, with the option for single-level living and two additional second-floor bedrooms plus a full bath. A nearly 1,200-square-foot walk-out accessory space adds even more flexibility, complete with its own kitchen, bedroom, bath, and living are well suited for guests, extended family, work-from-home needs, or possible rental income. Practical features include an oversized attached two-car garage, automatic whole-house generator, standing seam roof, and vinyl siding for added peace of mind. Inside, a gas fireplace and pellet stove complement traditional baseboard oil heat, offering multiple heat sources for the Vermont seasons. Well kept, functional, and full of possibility, this property is a rare opportunity for buyers who want usable land, natural beauty, extra space, and a lifestyle with options. See MLS Property & Listing Details & 44 images. Includes a Virtual Tour

$599,000 $253 per sq.ft. Whiting VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2368  |  Acres: 10
Saturday Aug 15, 2026
Description: Nestled on 10 beautiful acres in a peaceful country setting, this well-built 1990s home offers generous living space, privacy, and an easy commute to both Middlebury and Rutland. With 5 bedrooms and 2.5 bathrooms, the functional layout is ideal for comfortable family living and effortless entertaining. The large kitchen features an island, dining area, and sliding doors that open to a brand new deck perfect for enjoying the outdoors. From the kitchen, step into a cozy den warmed by a pellet stove, or flow into the expansive living room complete with a red brick wood-burning fireplace. Convenience is built into the main level with a laundry room, mudroom, and half bath, along with direct access to the attached two-car garage. Upstairs, the primary suite includes its own private bathroom, complemented by four additional bedrooms and a full bath. Recent updates include a new oil furnace, new oil tank, new flooring throughout, fresh interior paint in select areas, updated toilets, and a new vanity. A spacious home, a serene setting, and thoughtful updates make this your new Vermont home! See MLS Property & Listing Details & 55 images.

$325,000 $271 per sq.ft. Whitingham VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1200  |  Acres: 2
Wednesday Aug 26, 2026
Description: Enjoy the best of Vermont country living in this bright, 3-bedroom, 1-bath home set on 2+/- mostly wooded level acres just off Route 100. The property offers plenty of room to relax, play, garden, and enjoy the outdoors. A covered porch provides a welcoming spot to take in the peaceful surroundings. Inside, the home features a spacious open kitchen, living, and dining area with a large primary bedroom, Its own private deck with hot tub. Two additional bedrooms, and a full basement offering plenty of storage. Recent improvements include fresh interior paint. Outdoor enthusiasts will love the location, with nearby VAST snowmobile trails, Lake Whitingham/Harriman Reservoir just minutes away for boating and fishing, and Mount Snow approximately 20 minutes away for skiing, snowboarding, hiking, mountain biking, and golf. Downtown Wilmington, with its shopping, dining, and local amenities, is only about 10 minutes away. Only 30 minutes to MASS MoCA. The oversized detached 2-car garage offers plenty of room for vehicles, recreational equipment, and toys, plus a full upper level for storage or future use. With easy access from Massachusetts, Connecticut, New York, and southern Vermont, this property makes an excellent year-round residence, vacation getaway, or Vermont retreat. Move-in ready and priced to sell. Come enjoy everything Mount Snow, Deerfield Valley has to offer! See MLS Property & Listing Details & 34 images.

$349,000 $395 per sq.ft. Whitingham VT Home »

Waterfront on Pond _Unnamed
2 Beds | 1 Baths |   Total Sq. Ft. 883  |  Acres: 10
Sunday Aug 2, 2026
Description: Utter privacy from this 10 acre log home retreat, with easy access to nearby lakes, skiing, and trails. This charming 2 bedroom log home has been lovingly maintained by the current owners and is a perfect manageable getaway. The level woodlands features extensive trails ideal for atvs, hunting, or exploration. The property includes a portion of a large pond at the rear currently with Blue Heron nests and abundant wildlife. Just down the road is access to Lake Whitingham for nearby public access large lake enjoyment, and a public boat launch is not far either. Drive up into the country village of Wilmington for shopping and dining, and 10 mins further for skiing at the Mount Snow ski resort. The home itself features a wraparound porch including a large screened in section for three season enjoyment. There is a vaulted living room space which also includes the dining area, and basic kitchen which could easily be upgrades. The main floor also features a large bedroom with great light, as well as a full bathroom. The second floor is a large sleeping loft. Natural woodwork abounds to ensure you know you are in Vermont. There is also a full unfinished basement for great storage or further finishing potential. Add to this a three bay storage building for toys, a log play fort, and fiber internet, and you have everything you need to enjoy your new home away from home. See MLS Property & Listing Details & 26 images.

$595,000 $404 per sq.ft. Whitingham VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2401  |  Acres: 72.6
Tuesday Aug 4, 2026
Description: Private 72 acre playground with 3 bedrooms, 3 bath log cabin. Lots of room to play, including a VAST trail in the rear. A great covered porch makes for enjoying the privacy just out side to large kitchen/living/dining room, or downstairs outside the equally large family room. Plenty of room for guests and a large barn or outbuildings for all your Vt outdoor stuff. Lake Whitingham is minutes down the road for boating and fishing. Wilmington shopping & dining, and even golfing & skiing is just to the north. Easy drive from down south or hit The Deli on your way from Brattleboro. Lots of outdoor fun for friends & family! See MLS Property & Listing Details & 20 images.

$599,000 $255 per sq.ft. Whitingham VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2350  |  Acres: 41.1
Wednesday Aug 5, 2026
Description: This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman Reservoir and not far from skiing and villages. Truly an ideal location for anyone looking for a Vermont retreat, hobby farm, country getaway, or whatever your heart may desire. The home itself has been renovated with contemporary stylings including a gorgeous open concept great room with exposed original woodwork and wood burning custom fireplace, a gorgeous chefs kitchen with stainless appliances and quartz counters, a family room with second wood burning fireplace, main floor primary suite with tiled full bath and media room, four upstairs bedrooms and a second full bath, wood floors and beautiful furnishings throughout, a main floor mudroom entry for gear, and more. The 1840s barn has a stone faced concrete block foundation and direct access to the fields with a brook running along the southwesterly property boundary. There is a 12x12 garden house & a 12x16 shed. The fields are tiered with beautiful old trees, stone outcroppings and spectacular mountain views. You must see this if you are looking for a Quintessential Period Vermont Farm. See MLS Property & Listing Details & 29 images.

$271,500 $192 per sq.ft. Williamstown VT Home »

2 Beds | 1 Baths |   Total Sq. Ft. 2144  |  Acres: 15.7
Friday Aug 28, 2026
Description: This property is located near VT-14, with access to local shops, restaurants, convenience stores, recreational areas, and other community establishments in Williamstown. Nearby destinations include Limehurst Lake Campground and businesses along Main Street and Business Center Road. Property details should be independently verified by the buyer. The property will be offered through an upcoming auction. See MLS Property & Listing Details & 7 images.

$298,800 $267 per sq.ft. Williamstown VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 1120  |  Acres: 0.3
Thursday Aug 27, 2026
Description: Beautifully restored post-and-beam Cape tucked into the hillside in Williamstown, Vermont, offering the warmth and historic character of an older New England home alongside thoughtful modern updates. Original hand-hewn timbers run throughout the main living spaces, while fresh finishes and abundant natural light keep the home bright, warm, and comfortable. Major improvements include a brand-new Bosch heating system, on-demand hot water, new plumbing, updated electrical, and new hardwood flooring throughout. The result is a home that feels character-rich and comfortably up to date. At the heart of the home is a welcoming kitchen framed by exposed beams and featuring soft sage cabinetry, butcher block countertops, stainless steel appliances, generous workspace, and ample storage. The kitchen flows easily into the adjoining dining and living areas, where substantial exposed timbers, multiple windows, and an electric fireplace create a cozy focal point. Just beyond, the enclosed three-season sunroom is lined with windows and offers a peaceful place to relax or take in the surrounding greenery. The main level also includes a dedicated laundry area, convenient storage, and a beautifully updated full bathroom with a tiled tub and shower. Upstairs are two generously sized bedrooms. The spacious primary bedroom offers natural light, views toward the surrounding hills, a new walk-in closet, and a brand-new half bath. The second bedroom offers flexibility for guests, a home office, or additional living space. Outside, established perennial gardens surround the home, including a charming picket-fenced deck just off the kitchen. A large covered porch offers room for outdoor dining and lounging, while the lower-level covered patio and private backyard provide even more space to enjoy the Vermont setting. Thoughtfully restored, warm, and full of personality, 67 Pleasant Street blends historic character, modern updates, and inviting indoor-outdoor living. See MLS Property & Listing Details & 25 images.

$419,900 $251 per sq.ft. Williamstown VT Home »

1 Beds | 1 Baths |   Total Sq. Ft. 1673  |  Acres: 15
Wednesday Aug 12, 2026
Description: Tucked away on 15± private acres, 316 Stellar Road is the kind of place that makes you want to slow down and stay awhile. Spend your mornings on the wraparound porch with a cup of coffee, then head out to explore the trails that wind throughout the property. Whether you're looking for a year-round home or a weekend getaway, you'll appreciate the peace, privacy, and connection to nature this property offers. Inside, the home features an open living area, one bedroom, a full bath, a spacious loft, and an attached garage, creating a comfortable space that's easy to make your own. If you've been looking for your own slice of Vermont, this just might be it. See MLS Property & Listing Details & 47 images.

$249,900 $114 per sq.ft. Wilmington VT Home »

2 Beds | 2 Baths |   Total Sq. Ft. 2184  |  Acres: 0.02
Wednesday Aug 5, 2026
Description: Located in the heart of Wilmington, this charming two bedroom, one and a half bath home offers an excellent opportunity to create something truly special. Just a short walk to shops, restaurants, and everything downtown has to offer, the location is hard to beat. The home features an attached garage with potential unfinished space above, offering endless possibilities for expansion, a home office, studio, or additional living area. Fidium high-speed fiber internet is already available on site, making it ideal for remote work or streaming. Connected to town water and sewer, the property offers added convenience and potential for future improvements, subject to local permitting and applicable town approvals. A new furnace was installed in May 2026, providing peace of mind for the next owner. Lovingly owned by the same family for the past 30 years, this home is ready for its next chapter. Being sold as is, it presents a wonderful opportunity for buyers with vision to update, personalize, and build equity in a highly desirable village location. All measurements are approximate, please conduct your own due diligence if important. See MLS Property & Listing Details & 27 images.

$299,000 $231 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1296  |  Acres: 1.4
Friday Aug 14, 2026
Description: NEW 2025 MANUFACTURED HOME ON 1.4 ACRES IN WILMINGTON! Enjoy the perfect blend of privacy, convenience, and value in this immaculate 3-bedroom, 2-bath double-wide manufactured home offering approximately 1,300 square feet of comfortable one-level living. Set on 1.4+/- acres on a quiet dead-end road, this property offers a peaceful setting while remaining just a short drive to downtown Wilmington and all that Southern Vermont has to offer. Inside, you'll find a bright, spacious open-concept layout with a comfortable living room, well-appointed kitchen with plenty of cabinet and counter space, dining area, and a generous primary bedroom with a private ensuite bath. Two additional bedrooms provide plenty of room for family, guests, a home office, or hobbies. With its modern construction, easy one-level floor plan, and move-in-ready condition, this home is an excellent choice for a year-round residence, vacation getaway, or affordable mountain retreat. Outside, the 1.4-acre property provides plenty of room for gardening, outdoor dining, recreation, or simply enjoying the surrounding woods and privacy. The location is hard to beat, close to Wilmington's shops and restaurants, Harriman Reservoir for boating and swimming, Lake Raponda, Haystack Golf Club, hiking and biking trails, and just a short drive to Mount Snow for winter skiing and year-round activities. If you're looking for a new, spacious, low-maintenance home in Southern Vermont without the price tag of a traditional site-built home, this one deserves a look. Spacious, immaculate, private, and move-in ready, come see all this 2025 home has to offer! See MLS Property & Listing Details & 49 images.

$349,000 $204 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 1712  |  Acres: 0.59
Wednesday Aug 26, 2026
Description: Woodsy and charming ski chalet just a short drive from the village of Wilmington and Harriman Reservoir, and 10 minutes to the Mount Snow ski resort. This home sits on a private wooded lot, nestled in the Chimney Hill community with easy access thanks to a circular driveway, and just down the hill from the amenities building. The home has been partially updated and cared for and features a large living room with exposed woodwork, great natural light from the large windows, a wood burning stove and brick hearth, spacious dining area which leads into the large kitchen, media room which could serve as a main floor bedroom, large mudroom entry with ample gear storage and full bath, and spacious deck for entertaining. The upper level has 4 vaulted bedrooms as well as a second full bathroom. There is a full walkout lower level for tremendous expansion potential. Featuring the tremendous Chimney Hill amenities including indoor and outdoor pools, remodeled clubhouse with hot tub, gym, game room, theater, basketball court, tennis courts, fishing pond, winter ice skating, overflow parking lots for boats and snowmobile trailers, and direct snowmobile trail access, as well as a la carte maintenance, for easy downtime, not upkeep. See MLS Property & Listing Details & 19 images.

$354,900 $283 per sq.ft. Wilmington VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1586  |  Acres: 0.75
Sunday Aug 2, 2026
Description: Welcome to 21 Big Bend Loop in Wilmington, VT, where mountain charm, year-round adventure, and peaceful surroundings come together. Tucked among the trees, this chalet-style home offers the perfect escape, whether you're looking for a full-time residence, a weekend getaway, or an investment property in one of Southern Vermont's most desirable recreation areas. Step inside through the spacious mudroom, the perfect place to kick off your boots after a day on the slopes or hiking the trails. The warm and inviting interior features comfortable living spaces, a finished basement that provides extra room for guests, a game room, home office, or cozy movie nights, and a layout designed for making memories. Outside, the deck is freshly remodeled, creating an even better space to relax and take in the beautiful wooded views. Enjoy your morning coffee surrounded by nature, unwind after a day of adventure, or entertain friends in your own private mountain retreat. One of this property's unique advantages is the additional lot located directly across the street, offering exciting possibilities for future owners. Whether you envision building a garage, creating additional parking, or simply holding the land for future use, it's a valuable bonus that adds flexibility and long-term potential. Located just minutes from Mount Snow and a short distance to other nearby ski areas, this home puts four-season recreation right at your fingertips. Spend your winters skiing and snowboarding, then enjoy mountain biking, hiking, golf, lakes, breweries, restaurants, and charming downtown Wilmington throughout the warmer months. No matter the season, adventure is always close by. Speaking of close by, the Clubhouse with indoor and outdoor pools, hot tub, game room, tennis courts, gym, etc is only a short walk away! If you've been dreaming of a Vermont getaway with room to grow, beautiful surroundings, and an unbeatable location, 21 Big Bend Loop is ready to welcome you home. See MLS Property & Listing Details & 59 images.

$449,000 $374 per sq.ft. Wilmington VT Home »

Waterfront on Lake Raponda
3 Beds | 2 Baths |   Total Sq. Ft. 1200  |  Acres: 1.15
Tuesday Aug 25, 2026
Description: Priced to sell, on the Hill, End of the Road, Double Lot, built in 2024, Attached Garage, 3-bedroom 2 baths, Primary Suite with Ensuite Bath, Woodstove, Gas Cook Stove, Furnished, and Move-in Ready! Start enjoying all the amenities Chimney Hill offers within its 1,200-Acre Campus. Truly the most complete All-Season Resort in the Deerfield Valley with its exclusive members-only Clubhouse located at 2,000' on the Hill, featuring year-round swimming, new hot tub, fitness room, arcade room, playroom, community room, fully equipped members kitchen, reading nook, après ski lounge, 3 tennis court areas plus basketball court, extensive multi-use trail system, snowmobiling, ice skating, pickleball and tennis, stocked fishing pond, hiking, biking, and more! Plus, the Deerfield Valley offers world class skiing and shredding literally minutes away, fine and casual dining, unique shopping, escape room, mini, disk, and traditional golf, kayaking, canoeing, pontoon and sail boating, paddleboarding, the Green Mt National forest, antiques, flea markets, breweries, wineries, distilleries, music, theater, equestrian events, and so much more! See MLS Property & Listing Details & 47 images.

$520,342 $494 per sq.ft. Wilmington VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1521  |  Acres: 0.58
Monday Aug 3, 2026
Description: Perched atop Chimney Hill, this 3-bedroom, 3-bathroom home is perfectly suited as a vacation retreat or a primary residence, offering fantastic indoor and outdoor entertaining spaces. Enter the main level via the newly expanded staircase and deck. Inside, a spacious tile entryway provides ample room for gear and clothing storage. The sunken living room, with stone fireplace, flows seamlessly into the open-concept dining area and kitchen, where a deck extends your living space for seasonal enjoyment. A main-floor bedroom with a private balcony and a full bathroom rounds out this level. Upstairs, you'll find a bright, spacious bedroom with another private balcony and an en-suite bathroom. Additionally, a lofted bonus room that easily doubles as an office, media nook, or extra sleeping space. The walkout basement adds further versatility, featuring a third bedroom with an en-suite, a large den, with wet-bar, perfect for lounging, games, or fitness equipment, and a laundry room equipped with a workbench for DIY projects or gear maintenance. Outside, the property is as impressive as the interior, featuring thoughtfully landscaped grounds. Recent updates include a Generac whole-house generator, Mitsubishi mini-split, fiber optic internet service, and septic system improvements including a new riser and D-box. Chimney Hill is a recreationist's dream, offering access to indoor and outdoor pools, tennis/pickleball courts, ice skating, and direct trail access to Haystack Summit, all with low HOA fees. See MLS Property & Listing Details & 39 images.