Whitingham Vermont Real Estate

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.

Charming cottage just up from the MA border in Whitingham Vermont. This lovely home sits on a 4 acre parcel with great lawn space, easy paved road access, and a pastoral setting with adjacent nearby farmland and large parcels. The home has been well maintained and features an open kitchen, dining, and living space on the main floor, with full bath. The second story features a large primary bedroom, 2 guest bedrooms, and a half bath. There is a full unfinished basement with great storage space, laundry, and a full walkup staircase. A tremendous primary home or Vermont retreat.

Escape to the beauty of Southern Vermont with this newly built chalet, offering comfort, flexibility, and year-round recreation. Situated just minutes from Lake Sadawga and Town Hill Park, this property is ideal as a full-time residence, vacation home, or investment getaway. The well and septic system were installed in Spring 2026, providing peace of mind and a strong foundation for future enjoyment. The interior is ready for your personal touch, with the opportunity to build a kitchen tailored to your lifestyle or utilize the thoughtfully designed kitchen plans already created by the builder. Enjoy the warmth and charm of chalet-style living, surrounded by the natural beauty of the area and endless outdoor activities throughout every season. Whether you're boating, fishing, hiking, snowmobiling, skiing, or simply relaxing in a peaceful setting, this property offers something for everyone. Being sold partially furnished, this move-in-ready retreat allows you to start enjoying Vermont living right away while adding your own finishing touches. A rare opportunity to own a newly constructed getaway with major infrastructure already in place and the flexibility to make it uniquely yours.

Discover the perfect Vermont four-season retreat in this architecturally unique round home, set on a picturesque 1-acre corner lot in Southern Vermont. Offered fully furnished and move-in ready, this 1,840-square-foot, 3-bedroom, 2-full-bath property is ideal as a year-round residence, vacation home, or turnkey getaway. The welcoming lower level features three comfortable bedrooms, a spacious full bath with a jetted soaking tub, tiled floors, and a glass-enclosed shower, along with a convenient utility room. Upstairs, abundant natural light fills the open-concept living area where the kitchen, dining, and living spaces flow seamlessly together. A cozy wood-burning fireplace creates the perfect gathering place after a day of skiing, hiking, snowmobiling, or exploring the surrounding lakes and trails. A second full bath on the main level adds convenience for both everyday living and entertaining guests. Step outside to enjoy multiple outdoor living spaces, including a sunny second-floor deck, covered patio, established perennial gardens, and a storage shed. The mostly open lot offers space to relax, entertain, and enjoy the peaceful surroundings. Ideally located just 8 minutes from Jacksonville Village, 10 minutes from Harriman Reservoir (Lake Whitingham), 8 minutes from Lake Sadawga, and 17 minutes from Wilmington, this property provides convenient access to some of Southern Vermont's most sought-after recreation destinations. Enjoy skiing at Mount Snow and Berkshire East, boating and fishing on nearby lakes, hiking the Catamount Trail, paddling the Deerfield River, and exploring the VAST snowmobile trail network. With high-speed fiber internet available and all furnishings included, this distinctive home offers the perfect combination of comfort, character, and year-round adventure. Whether you're seeking a mountain getaway, recreational base camp, investment opportunity, or full-time residence, this turnkey Vermont property is ready to enjoy from day one.

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.

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.

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.

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.

3 Bed, 3 Bath, 9+ Acres and exceptionally well cared for country retreat! Lovingly maintained & thoughtfully reimagined by the same owners for more than 20 years, every improvement has been made with care & purpose. The result is a home that feels warm, welcoming, effortlessly comfortable & beautifully connected to its surroundings. Set on 9± acres of rolling fields, mature woods & groomed walking trails, the property begins to tell its own story of Vermont living. Well manicured, planned perennial gardens, split rail fence, stonewalls and stonework, arbor, broad lawns, charming footpath, winding over natural stone & wooden bridges to your year-round brook! A converted barn with power and water is an inspiring studio, yoga retreat, or creative workspace, complete with an antique plunge sink, the perfect place to rinse vegetables gathered from the garden. Inside, 3 bedrooms, 3 baths, primary suite with a classic clawfoot soaking tub, a den, and thoughtfully updated living spaces. Four-zone mini-splits provide efficient heating, air conditioning & dehumidification. Wildlife is a regular visitor here, from deer, fox & wild turkey to soaring birds of prey. In the evening, gather something fresh from the garden, pick a bouquet, and head back to the house to linger over dinner on the deck and gaze at the mountain views! Welcome the next day with coffee as the sun rises over the surrounding hills. Take a stroll down the footpath to the brook or kick off your shoes and climb into a hammock with a book. This isn't simply a home; it's an invitation to slow down. It's the kind of home, property, and lifestyle that reminds you why you came to Vermont in the first place.

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!

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.

Outstanding contemporary farmhouse set on 5.3 acres of private, level acres, offering the perfect blend of comfort, space, and functionality. This well-maintained home features an open-concept first floor with a spacious great room highlighted by a cathedral ceiling. The main level also includes one bedroom and full bath, along with a convenient mudroom and laundry room. The custom maple kitchen cabinets boast updated countertops, and the newer flooring runs throughout the first floor. The home's efficient Buderus boiler provides five heating zones for year-round comfort, with radiant heat running through the kitchen and bath for added comfort on those chilly mornings. The unfinished basement has separate rooms for potential finishing, along with a workspace for the handy or craftsperson. The oversized 30x30 two-car garage with loft provides exceptional storage space. A covered wraparound porch offers the perfect place to relax and enjoy the peaceful surroundings, and the open deck off the rear for sunny days to relax or entertain. Conveniently located near a local park with a ballfield and playground. We are just a short drive to wonderful Vermont skiing and many 4 season activities. Whitingham Dam is a quick drive for your boating pleasure. This is country living with easy access to community activities all on your own 5.3 acre parcel.

What a gem! This absolutely meticulously maintained 2015 farmhouse sits just up from Lake Sadawga and Harriman Reservoir on a private 2 acre parcel off a paved road. The curb appeal is beyond what most can dream of with gorgeous perennial gardens, split rail fencing, ample yard space, and total privacy. Features include a beautiful open floor plan with large living room and family room, beautiful floors throughout, gorgeous chefs kitchen with breakfast far and pantry, spacious dining area, great natural light thanks to plenty of windows, a main floor primary suite with walk in closet, main floor den or office space, additional full guest bath, four separate upstairs rooms to do with as you see fit, and 2 full guest baths, all with tremendous space and closets, a finished sewing room in the full lower level and tons of extra storage or finishable space, central heat and air conditioning. Less obvious features include a high end septic system, quality construction and energy efficiency, an oversized two car garage, full covered front porch and back deck for entertaining, garden shed, and covered rear storage area. Enjoy the property year round thanks to a spacious level lawn, walking trails, nearby town field, and access to lakes, nearby snowmobile trails, country villages or ski resorts, still just a short drive to Mount Snow. Septic sized for 3 bedrooms full time use.

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.