Whitingham Homes for Sale

Welcome to Whitingham, Vermont – a hidden gem nestled in the heart of Windham County. Known for its breathtaking natural beauty and tight-knit community, Whitingham offers a serene escape from the hustle and bustle of city life. With its picturesque landscapes, rolling hills, and tranquil lakes, this charming town is perfect for those seeking a peaceful retreat or a vibrant place to call home.

Whitingham is steeped in rich history, with quaint architecture that tells the story of its past. The town is surrounded by lush forests, making it a haven for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply taking in the stunning views, Whitingham provides endless opportunities for adventure. The nearby Harriman Reservoir is a popular spot for boating and swimming, while the surrounding trails are perfect for exploring year-round.

Currently, there are a variety of homes for sale in Whitingham, catering to diverse tastes and budgets. From cozy cottages that exude charm to spacious family homes with modern amenities, you’re sure to find the perfect fit for your lifestyle. Many properties boast stunning views and easy access to nature, allowing you to fully embrace the beauty of Vermont living.

In Whitingham, you’ll not only find a home, but also a welcoming community that values connection and collaboration. With local events and activities throughout the year, you’ll quickly feel right at home. Discover the magic of Whitingham and explore the opportunities that await you in this enchanting Vermont town!

Newest Whitingham Homes for Sale

$325,000

3 Beds ⋅ 1 Baths ⋅ 5106844 MLS

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!

639 Wilmington Cross Rd, Whitingham

$599,000

5 Beds ⋅ 2 Baths ⋅ 5103454 MLS

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.

9282 Vt Rte 100, Whitingham

$595,000

3 Beds ⋅ 3 Baths ⋅ 5103309 MLS

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!

783 Wilmington Cross Rd, Whitingham

$349,000

2 Beds ⋅ 1 Baths ⋅ 5102973 MLS

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.

443 East Rd, Whitingham

$419,000

3 Beds ⋅ 3 Baths ⋅ 5100538 MLS

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.

2843 Burrington Hl, Whitingham

$629,900

3 Beds ⋅ 2 Baths ⋅ 5093664 MLS

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.

187 Poverty Row, Whitingham

$349,000

4 Beds ⋅ 2 Baths ⋅ 5091213 MLS

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 and is 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.

985 Chapel Hill Rd, Whitingham

$299,000

3 Beds ⋅ 2 Baths ⋅ 5090926 MLS

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.

2448 Burrington Hill Rd, Whitingham

$1,150,000

4 Beds ⋅ 1 Baths ⋅ 5090460 MLS

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.

2245 Burrington Hill Rd, Whitingham

$335,000

5 Beds ⋅ 3 Baths ⋅ 5075630 MLS

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.

1033 Burrington Hill Rd, Whitingham

$225,000

4 Beds ⋅ 2 Baths ⋅ 5061887 MLS

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.

2173 Rte 8a, Whitingham

$309,000

3 Beds ⋅ 2 Baths ⋅ 5058111 MLS

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.

1192 Chapel Hill Rd, Whitingham

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