Whitingham Real Estate

Welcome to Whitingham, Vermont – a hidden gem nestled in the picturesque Windham County. This charming town, known for its breathtaking natural beauty and tight-knit community, offers a serene escape from the hustle and bustle of city life. With a population of just over 1,000 residents, Whitingham embodies the essence of small-town living, where neighbors become friends and the pace of life slows down just enough to savor each moment.

Surrounded by the stunning Green Mountains, Whitingham is a paradise for outdoor enthusiasts. With an array of recreational opportunities, including hiking, fishing, and skiing, residents can immerse themselves in the great outdoors year-round. The nearby Harriman Reservoir provides a perfect spot for boating and swimming during the warm summer months, while winter brings opportunities for cross-country skiing and snowshoeing on the town’s scenic trails.

Whitingham is also rich in history, with charming architecture and landmarks that tell the story of its past. The town center features quaint shops and local eateries, where you can experience the warm hospitality of the community. The annual events and festivals celebrate local culture and traditions, making it easy for newcomers to feel at home.

Whether you’re seeking a peaceful retreat, a place to raise a family, or a vibrant community to call your own, Whitingham offers a unique blend of tranquility and adventure. Explore the beauty and charm of this Vermont treasure – your dream home awaits in Whitingham!

Newest Listings in Whitingham

$199,000

3 Beds ⋅ 1 Baths ⋅ 5113644 MLS

Looking for an affordable home with a little personality? You've found it in this colorful 3-bedroom, 1-bath home in the historic village of Whitingham, Vt. Set on 0.10 acres along a quiet, paved street with town sewer, the home is surrounded by some of Southern Vermont’s best lakes, including Sadawga Lake and Harriman Reservoir. Step inside through the French doors that separate the mudroom from a flexible living space that can become a dining room, home office, sitting area, or whatever works best for you. The first floor also includes the full bathroom, laundry area, and primary bedroom with a walk-in closet. The kitchen features an eat-in island for casual dining and opens to a spacious great room, where a large picture window brings in plenty of natural light. Bold colors throughout give the home a fun, playful energy and make each room feel a little different from the next. Keep the color, tone it down, or make it completely your own. Upstairs, two additional bedrooms continue the home's bright and bold personality. A door off the living area leads to the fenced backyard, where you can relax and enjoy the sounds of nearby Sadawga Brook on the front porch of the shed, which can be used for storage, a workshop, or play space. Major systems have been recently updated including the well pump and pressure tank (new in 2016), furnace (new in 2021) and water heater (new in 2024). The home is just 13 minutes to Wilmington, 16 minutes to Hogback Mountain’s 100-mile view, 23 minutes to Marlboro, 25 minutes to Mount Snow, and roughly 40 minutes to Brattleboro to the east and Greenfield, Mass., to the west.

105 School St, Whitingham

$599,000

3 Beds ⋅ 3 Baths ⋅ 5113061 MLS

OLD BARN. NEW LUXURY. YOUR PRIVATE SOUTHERN VERMONT ESCAPE. There’s something special about a home that feels completely different from anything else—and this beautifully transformed barn conversion is exactly that. Originally an old barn, this stunning 3-bedroom, 2.5-bath home has been thoughtfully reimagined with sophisticated modern finishes, an inviting open-concept layout, and all the comforts of contemporary living both inside and out, while still preserving the character and soul of its original structure. Set on nearly 12 private acres, this is more than a home—it’s a lifestyle. Spend summer afternoons enjoying your own private pond, enjoy peaceful mornings surrounded by nature, gather with friends and family in the spacious open living areas, or simply get away from the pace of everyday life and enjoy the privacy and tranquility that Southern Vermont has to offer. An amazing opportunity to own a truly distinctive Vermont retreat.

679 Burrington Hill Rd, Whitingham

$219,000

5111500 MLS

17+/- Acres of Vermont Country Living in Jacksonville. Discover the possibilities on this beautiful 17+/- acre parcel in the charming village of Jacksonville. With frontage on both Parsons Road and Gates Pond Road, the property features a wonderful mix of open, south-facing pastureland and wooded areas, offering plenty of room for horses, farming, gardens, recreation, or creating your own Vermont family retreat. The rolling open land is well suited for animals and outdoor activities, with a year-round brook adding to the property's natural appeal. A woodshed and former milk house remain on the property, adding character and potential for future use. The existing septic system from the former 5-bedroom home is also in place, subject to verification and approval by a Vermont-licensed engineer. Water is provided by a deeded spring, locally known for its excellent-tasting water. Parsons Road is a quiet, tree-lined country road, while the property is just a short walk from the village and general store, making it easy to enjoy the convenience and charm of Jacksonville. Outdoor recreation is abundant throughout the area, including hiking, boating, fly fishing, snowmobiling, skiing and more, with Mount Snow and the surrounding Deerfield Valley just a short drive away. Whether you're looking for a small farm, an equestrian property, a recreational retreat, or a place to build your Vermont home, this property offers an exceptional opportunity to create something of your own. A special property with open land, water, privacy and village convenience, ready for someone with the vision to bring its next chapter to life

292 Parsons Rd, Whitingham

$59,000

5107817 MLS

Warranty Deed, 4 Bedroom Septic Permit, Roughed-in Drive, Great location!! Build your dream home on this surveyed 5.66 acre lot with deeded rights to Ryder Pond! A great location for primary or vacation living, situated between down town Wilmington VT and Greenfield MA with easy access to scenic Rt 100. Lakes, ski resorts and out door recreation abound with Mount Snow Resort, Lake Whitingham, Lake Sadawga, Lake Raponda and Molly Stark State Park all close by. To stick closer to home, access the snowmobile trails right from your property or take a walk across the street to fish or kayak in Ryder Pond. Accessible from Murdock Lane or Rt 100, power at street. Roughed in driveway. Permit for 4 bedroom waste water system included in sale.

4 Murdock Ln, Whitingham

$309,000

3 Beds ⋅ 1 Baths ⋅ 5106844 MLS

Enjoy the relaxed pace of Vermont country living in this bright and inviting 3-bedroom, 1-bath home set on 2+/- mostly wooded, level acres just off Route 100. With plenty of room to relax, garden, play, and enjoy the outdoors, this property offers a wonderful setting for a year-round home, vacation getaway, or Vermont retreat. A covered front porch welcomes you home, while the private deck and hot tub off the spacious primary bedroom provide a great place to unwind and enjoy the peaceful surroundings. Inside, the open kitchen, living, and dining area creates a comfortable gathering space, complemented by two additional bedrooms and a full basement with abundant storage. Recent improvements include fresh interior paint and basement waterproofing and insulation by Northern Basement Systems. Outdoor recreation is right at your doorstep, with nearby VAST snowmobile trails and Lake Whitingham/Harriman Reservoir just minutes away for boating and fishing. Mount Snow is approximately 20 minutes away for skiing, snowboarding, hiking, mountain biking, and golf. Downtown Wilmington, with its shops, restaurants, and local amenities, is about 10 minutes away, and MASS MoCA is approximately 30 minutes away. The oversized detached 2-car garage provides plenty of space for vehicles, recreational equipment, and all your Vermont toys, with a full upper level offering additional storage or potential for future use. Conveniently located for an easy getaway from Massachusetts, Connecticut, New York, and southern Vermont, this property offers the space, location, and flexibility to enjoy all that the Deerfield Valley has to offer. Come take a look, you may find this is the Vermont getaway you've been waiting for!

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

$95,000

5100022 MLS

Discover the perfect setting for your Vermont getaway or future home on this beautiful 4-acre lot located at the end of a quiet dead-end road with direct access to a private pond. The gently sloping, wooded landscape offers privacy, natural beauty, and an ideal mix of mature trees and usable terrain for your vision. A Vermont wastewater permit is already in place, making it even easier to start planning your build. Enjoy year-round recreation right from your doorstep, with opportunities for hiking, snowmobiling, gardening, and relaxing in the peaceful surroundings. Spend weekends exploring the area's charming antique shops, scenic back roads, and local attractions. Just minutes from Wilmington and Dover, you'll find shopping, restaurants, cafes, golf, Lake Whitingham for boating and fishing, and everyday conveniences, while nearby Mount Snow and The Hermitage Club provide outstanding skiing and four-season outdoor activities. Despite its tranquil setting, the property is easily accessible from major metropolitan areas including Boston and New York City, making it an ideal destination for weekend escapes or full-time living. Whether you're dreaming of a cozy cabin or a custom mountain retreat, this exceptional property offers the privacy, convenience, and Vermont lifestyle you've been looking for.

00 Ryder Pond Rd, Whitingham

$629,900

3 Beds ⋅ 2 Baths ⋅ 5093664 MLS

ATTENTION BUYERS! Think you can't afford this great property? Think again! Call me about a 5.99% interest rate to get you into this dream home! 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

$279,000

5090898 MLS

Lovely pastoral parcel of land in Whitingham Vermont with mountain views. This parcel sits conveniently on the MA border for easy access into the Deerfield Valley or Heath area. The 45 acre parcel is about half pasture and half mature woodlands, with easy access of the quiet country road, old stone walls, views of the mountains to the west, and a serene setting.

Lot 0 Saddada, 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

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