$275,000 $172 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.

$299,900 $177 per sq.ft. Village of Jacksonville Village in Town of Whitingham VT Home »

Waterfront on River East Branch Deerfield River
4 Beds | 2 Baths |   Total Sq. Ft. 1696  |  Acres: 0.6
Thursday Apr 30, 2026
Description: Classic Jacksonville Village farmhouse filled with warmth, character, and thoughtfully curated spaces that feel straight out of a charming country inn. Exposed beams, high ceilings, wide-plank wood flooring with period details, built-ins, and inviting gathering spaces create an atmosphere that immediately feels comfortable, relaxed, and lived in the very best way. Kick off your shoes, curl up with a book, and enjoy the historic and classic charm this home offers both inside and out. The flexible floor plan includes 4 bedrooms and 2 baths, with the current owners utilizing both second-floor bedrooms as a primary wing and an expansive suite-style retreat. A separate guest wing offers two additional bedrooms, bonus space for overflow, and a full bath, creating privacy and versatility for guests, extended family, or work-from-home needs. Mudroom entry and full laundry add everyday practicality to the home's timeless appeal. Formal dining room, formal sitting room, and expansive great room with skylights. Outside, enjoy a covered farmer's porch, fire pit area, mature perennial gardens, ample parking on .60 acres, and the peaceful sounds of the East Branch of the North River flowing through the heart of Jacksonville Village. A large powered shed/outbuilding offers excellent storage and workshop space, while also presenting exciting potential for use as an artist studio, hobby space, or flexible bonus area. Standing seam metal roof, drilled well, and public sewer add important modern infrastructure to the historical and charming features. Conveniently located to Mount Snow , the Deerfield Valley, downtown Wilmington, lakes, hiking, skiing, and year-round recreation in beautiful Southern Vermont. Only 15 minutes to Massachusetts and 25 minutes to Interstate 91 for an easy commute to work, home, or play. See MLS Property & Listing Details & 48 images.

$349,000 Whitingham VT Home »

Price Change! Reduced by $120,000 down 34% on April 30th 2026
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.

$349,000 $134 per sq.ft. Whitingham VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2596  |  Acres: 1
Tuesday May 26, 2026
Description: This charming chalet on one acre is surrounded by enchanting gardens, with a peaceful stream providing a soothing natural backdrop. Over the years, the seller has lovingly planted thousands of daffodils and day lilies, along with a beautiful mix of perennials, annuals, flowering shrubs, and potted plants that line the walkways, gazebo, and hillside below the home. The original chalet has been expanded with two substantial additions, creating a flexible floor plan featuring a spacious main-level living room with a woodstove and a private primary bedroom or study above, plus a separate dining nook (good for expanding the kitchen). Enter through the welcoming kitchen and dining area, where oak flooring and a wood-burning fireplace create warmth and character. Glass patio doors fill the space with natural light and open to an expansive deck overlooking the lush gardens--an ideal setting for relaxing or entertaining. Located on a town-maintained gravel road, Chapel Hill Road is home to a mix of year-round residences and vacation getaways. Enjoy nearby Lake Sadawga for kayaking, canoeing, and fishing, or head to Lake Whitingham for swimming, sailing, waterskiing, and more. Conveniently located within easy driving distance of MASS MoCA. See MLS Property & Listing Details & 30 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 & 56 images. Includes a Virtual Tour

$429,000 $138 per sq.ft. Whitingham VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 3100  |  Acres: 3
Friday May 15, 2026
Description: OPEN HOUSE SUNDAY, MAY 17th, 11AM to 1PM Set on 3 peaceful acres near Lake Whitingham and Lake Sadawga, this spacious 4+ bedroom, 2.5 bath Colonial-style home offers a comfortable and versatile floor plan with room for everyone. Pull into your attached 2-car garage and enter through the mudroom with closets and storage for gear, or enter through the front formal entrance looking into the main living areas with high ceilings, wood floors, and great natural light.The comfortable living room with a wood stove flows into the open kitchen, which features a great workspace and a breakfast bar. The dining area accesses the new back deck overlooking the manicured lawn. Catch a glimpse of Harriman Reservoir from the deck and watch epic sunsets to the west over the lake and mountains. The family room for informal fun or media space is also located on the first floor.The second floor offers generously sized bedrooms, including a spacious primary suite with a full bath, along with three additional bedrooms and a 2nd large shared bathroom with double sinks. Laundry is conveniently located on the same level as the bedrooms for added everyday ease.The third floor adds even more flexibility with a bonus sleeping room and expansive overflow space ideal for recreation, office use, home gym, media room, hobbies, guests, or additional hangout space, depending on your needs.Outside, enjoy mature perennial gardens, stone walls, and usable lawn space in a peaceful setting on a paved dead-end road shared by only a few homes. A 1-year-old above-ground pool is included in the sale, a perfect summer setup to complement Vermont's warm-weather season with boating ( boat launch just down the road), swimming, hiking, and recreation around lakes just moments away. Space, location, acreage, ample bedrooms and baths, garage, and well-maintained...don't miss it! See MLS Property & Listing Details & 40 images.

$1,150,000 $583 per sq.ft. Whitingham VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1972  |  Acres: 100
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 MLS Property & Listing Details & 42 images.

$549,000 $229 per sq.ft. Williamstown VT Home »

Price Change! Reduced by $76,000 down 14% on June 8th 2026
4 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 relaxed Vermont country living. From the moment you arrive, the inviting covered front porch sets the tone for quiet mornings, evening sunsets, and easy entertaining. Inside, the home features a bright, open layout filled with natural light, warm wood floors, cathedral ceilings, and beautifully crafted natural woodwork. The kitchen flows seamlessly into the main living area, creating a space that feels both comfortable and refined. Wide hallways, first-floor laundry, and a spacious primary suite on the main level support true single-level living and everyday convenience. Designed with ease in mind, the home offers true single-level living with the added flexibility of guest or extended-stay space above the garage. A major bonus is the apartment above the garage, ideal as an income-producing accessory apartment, private guest suite, home office, or in-law apartment. A whole-house generator provides added peace of mind year-round. Set on over 8 acres with land on both sides of the road, the property protects its own views and sense of privacy into the future. Enjoy rolling fields, peaceful surroundings, and a setting that feels worlds away while remaining convenient to Barre, Montpelier, shopping, and I-89. A rare opportunity to enjoy quality construction, flexibility, privacy, and a Vermont lifestyle that's becoming harder to find. See MLS Property & Listing Details & 40 images.

$349,000 $233 per sq.ft. Wilmington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1500  |  Acres: 2
Friday May 15, 2026
Description: Tucked away on two private acres in a peaceful wooded setting, this four bedroom two bath chalet offers the perfect balance of seclusion and convenience. The lower level welcomes you with a practical mudroom/laundry area, three comfortable bedrooms, and a full bath. Upstairs, the main living space features vaulted ceilings, a striking wall of windows, and a cozy wood-burning fireplace that creates a warm, inviting atmosphere. The open dining area flows into a fully equipped kitchen with new stainless steel appliances, making it perfect for entertaining. This level also includes a spacious fourth bedroom and a full bath. Step outside to enjoy the beautiful wraparound front deck with built-in bench seating--perfect for relaxing or gathering with friends--while the carport below adds convenience and protection from the elements. Additional home upgrades include new lighting fixtures and dimmer switches, updated blinds throughout, kitchen faucet set and cabinet handles, main living space programmable thermostat, sliding door screens and locksets, and bathroom vanities, cabinets and fixtures. Located just around the corner from Lake Raponda's public beach and only minutes to Mount Snow for year-round recreation. Only a short drive to the shops and restaurants of downtown Wilmington, and Brattleboro is 20 minutes away. Whether you're seeking a full-time residence or a weekend retreat, this property captures the best of Vermont lake and mountain living. See MLS Property & Listing Details & 24 images.

$379,000 $395 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 $375 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.

$425,000 $351 per sq.ft. Wilmington VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2345  |  Acres: 2
Thursday May 21, 2026
Description: Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for gatherings or quiet evenings, while the functional kitchen and dining room combination provides a practical space for meals and entertaining. From the dining room sliding door, access the deck, perfect for al fresco dining or soaking up the sun while overlooking the expansive backyard. Behind Door Number 1, off the living room, discover two comfortable bedrooms and a full bath. Behind Door Number 2, a stairway leads to a full, finished basement, where a versatile recreation room can be customized to suit your needs, whether it be a home theater, game room, or additional living space. The basement also includes the fourth bedroom, a ¾ bath, a practical utility room, and a storage area, with the ease of a walk-out to the backyard from this level. Behind Door Number 3, adjacent to the kitchen/dining area, lies the primary bedroom with a full ensuite bathroom, offering a peaceful retreat for rest and relaxation. This home is not only perfect as a primary residence with easy access to schools, a thriving Main Street, and area activities, but also holds potential as a second home or investment property, just minutes to ski resorts, golf courses, and Harriman Reservoir for swimming and boating. Located within the Beaver Brook Association, residents benefit from comprehensive road maintenance, snow plowing, and sanding services. Don't miss the opportunity to make this beloved home your own, enjoying the serene setting and convenient amenities it has to offer. See MLS Property & Listing Details & 59 images. Includes a Virtual Tour

$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.

$439,000 $314 per sq.ft. Wilmington VT Home »

Price Change! Reduced by $56,000 down 13% on May 13th 2026
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.

$489,000 $357 per sq.ft. Wilmington VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2070  |  Acres: 0.61
Wednesday May 13, 2026
Description: Spacious ski chalet in the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. Just down from the rec center and clubhouse sits this well maintained home with easy access, ample parking, a level back yard, and nice privacy, yet with all the conveniences of community living. The interior has a vaulted open concept living space with natural light and large windows, natural woodwork throughout, a kitchen with stainless appliances and breakfast bar, a spacious dining area open to the living room with gas fireplace and brick hearth, a main floor bedroom and full bath as well as a large mudroom for all your gear, 2 upstairs bedrooms including a large bunk room with great closet space, as well as a second full bath recently renovated, a finished walkout lower level with games, additional sleeping space, and ample room to spread out. There is also a large storage and utility room for seasonal storage or owner lock out space. There is a garage shed outside for snowmobile, a fire pit, and large entertaining deck. This comes with all the great Chimney Hill amenities including road maintenance, community water, clubhouse with indoor and outdoor pools, hot tub, game room, theater, playground, tennis courts, basketball, gym, and more. There are also a la carte services including plowing, sanding, and trash pickup. A truly unique spot that affords Vermont charm and serenity, with easy management. See MLS Property & Listing Details & 33 images.