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314 Vt Route 112, Whitingham
$89,000
3 Beds ⋅ 2 Baths ⋅ 5116450 MLS
Discover the charm and potential of this 3-bedroom, 2-bath antique home located in the Village of Jacksonville. Full of character and ready for renovation, this fixer-upper offers an opportunity to restore and make it your own. Conveniently connected to town sewer, this property is ideal for buyers looking to bring new life to a classic home and create something special. Showings begin 11/10/2026!

314 Vt Route 112, Whitingham
146 Plumb Rd, Whitingham
$350,000
3 Beds ⋅ 2 Baths ⋅ 5116434 MLS
Enjoy comfortable one-floor living in this 3-bedroom, 2-bathroom single-family home set on a beautiful acreage parcel with a spacious, private yard. There’s plenty of room to relax, garden, and enjoy the outdoors. Outdoor features include an enclosed gazebo with electric and TV hookups, a garden shed, and a back porch perfect for enjoying the peaceful surroundings. The impressive 4-bay garage offers plenty of room for vehicles, equipment, and hobbies. Looking for even more living space? The basement offers great potential to be finished, with an existing bathroom and fireplace already in place. Additional features include a whole-house Generac generator for added peace of mind. A wonderful opportunity to enjoy privacy, space, and the convenience of single-level living!

146 Plumb Rd, Whitingham
221 Pratt Rd, Whitingham
$875,000
3 Beds ⋅ 3 Baths ⋅ 5115853 MLS
This handsome Cape, built by green builder David Powell, is set on 18 private acres of stunning countryside featuring long-range views, open meadows, stone walls, and walkways. South-facing and super-insulated, the home combines classic character, thoughtful design, and comfortable living. A large studio/workshop with radiant heat and abundant storage adds versatility. The formal entry features a coat closet and handsome staircase with an Oriental carpet runner. The living room offers hardwood floors, a large brick fireplace, exposed beams, and crown molding, with an arched entry to the formal dining room, where generous windows frame beautiful views. The spacious eat-in kitchen features cherry cabinetry, soapstone countertops and backsplash, an island, breakfast bar, and dining area with sliders to the rear yard. The first floor also includes a slate-floored mudroom connecting to the laundry room, family room, and oversized heated garage with workshop space. A peaceful private library, also suitable as a first-floor bedroom, has an adjoining three-quarter bath. Added in 2002, the impressive great room features built-in cabinetry and shelving, expansive windows, Italian porcelain flooring, recessed lighting, and a mini-split for air conditioning. Sliders open to a wonderful covered porch and fieldstone patio, ideal for relaxing and entertaining while enjoying the tranquil setting. Upstairs are 3 bedrooms, including a light-filled primary suite with three closets and an ensuite bath, plus two guest bedrooms sharing a full bath. Above the garage, a spacious bonus family room offers skylights and extensive storage, perfect for recreation, hobbies, or a home office. Additional features include a generator, underground utilities, and a Buderus boiler. This exceptional property offers a rare combination of architectural charm, energy-conscious construction, flexible living spaces & spectacular land - a wonderful opportunity to enjoy private country living at its finest!!!

221 Pratt Rd, Whitingham
195 Vermont Route 112, Whitingham
$269,000
2 Beds ⋅ 2 Baths ⋅ 5115663 MLS
Set on 1.5 acres in the heart of Jacksonville, this charming 1860 farmhouse offers a wonderful blend of historic Vermont character, flexible living space, and small-town convenience. With 2 bedrooms, 2 three-quarter baths, and 1,624 square feet of finished living space, the home features beautiful natural light, hardwood floors, warm woodwork, and a versatile floor plan with opportunities to adapt or expand to suit your needs. The main level offers a spacious kitchen with warm wood cabinetry, a walk-in pantry, inviting dining and living areas, a bonus room, first-floor laundry, and a three-quarter bath. Upstairs, you'll find two bedrooms and an additional three-quarter bath. A covered front porch and enclosed porch provide inviting spaces to unwind, while a pellet stove, forced-air heating, and mini-split heating and cooling offer comfort throughout the seasons. Outside, the property truly shines with its picturesque yard, mature apple trees, historic stone walls, established gardens, open lawn, and ample space for outdoor enjoyment. Whether you envision tending to gardens, gathering with friends and family, or simply enjoying the beauty of the changing Vermont seasons, this setting offers plenty of possibilities. Despite its peaceful country atmosphere, the property enjoys the convenience of an in-town location, with the local general store, gas station, post office, library, all nearby. Outdoor enthusiasts will appreciate the proximity to the southern end of Lake Whitingham, Berkshire East, Mount Snow, Prospect Mountain, the Catamount Trail, and VAST snowmobile trails, providing access to year-round recreation. Conveniently situated for travel to Brattleboro, Wilmington, North Adams, and Greenfield, this property offers an appealing combination of Vermont charm, outdoor adventure, and everyday accessibility. Whether you're seeking a primary residence or a relaxing Vermont getaway, this classic farmhouse is ready for its next chapter.

195 Vermont Route 112, Whitingham
148 Lone Pine Rd, Whitingham
$415,000
3 Beds ⋅ 2 Baths ⋅ 5115033 MLS
Charming Vermont Retreat with Easy Access to Outdoor Recreation! Nestled among the trees in the peaceful town of Whitingham, this inviting 3-bedroom, 2-bath home offers a wonderful blend of privacy and comfort. Inside, vaulted ceilings create an open, airy atmosphere, adding character and a sense of spaciousness to the living areas. Low-maintenance cedar shake siding adds to the home's Vermont charm, while a screened-in porch and sun deck provide inviting spaces to relax, entertain, or simply enjoy the peaceful wooded surroundings. A small barn/workshop offers additional space for hobbies, projects, or storage of outdoor recreational equipment. Located just a short distance from the snowmobile trail, and less than 4 miles from Lake Whtingham, this property is ideally situated for those who enjoy exploring Southern Vermont's four-season recreation. Whether you're looking for a year-round residence or a weekend getaway, this property offers an appealing combination of comfort, privacy, and the Vermont lifestyle.

148 Lone Pine Rd, Whitingham
105 School St, 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
679 Burrington Hill Rd, 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
639 Wilmington Cross Rd, Whitingham
$249,000
3 Beds ⋅ 1 Baths ⋅ 5106844 MLS
Discover the charm of Vermont country living in this bright and inviting 3-bedroom, 1-bath home situated on approximately 2 mostly wooded, level acres just off Route 100. Offering an appealing combination of privacy, space, and convenience, this property is ideal for a year-round residence, weekend getaway, or four-season Vermont retreat. A welcoming covered front porch invites you inside, where an open kitchen, living, and dining area creates a comfortable gathering space for family and friends. The spacious primary bedroom features access to a private deck and hot tub, perfect for relaxing after a day enjoying Vermont's outdoors. Two additional bedrooms and a full basement provide flexibility and plenty of storage. Recent improvements include fresh interior paint and professional basement waterproofing and insulation by Northern Basement Systems. A standout feature is the oversized detached 2-car garage, offering ample space for vehicles, snowmobiles, boats, recreational equipment, and all your Vermont toys. The full upper level provides additional storage or potential for future use. Outdoor recreation is close at hand, with nearby VAST snowmobile trails and Lake Whitingham/Harriman Reservoir just minutes away for boating, fishing, and exploring. Mount Snow is approximately 20 minutes away for skiing, snowboarding, mountain biking, hiking, and golf. Downtown Wilmington, with its shops, restaurants, and local amenities, is just 10 minutes away, while MASS MoCA is approximately 30 minutes away. Conveniently accessible from Massachusetts, Connecticut, and New York, this property offers an affordable opportunity to enjoy everything Southern Vermont has to offer. With 2 acres, a spacious garage, recent improvements, and a new asking price of $249,000, there's plenty to appreciate here. Come take a look and imagine making this your own Vermont getaway!

639 Wilmington Cross Rd, Whitingham
9282 Vt Rte 100, 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
783 Wilmington Cross Rd, 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
187 Poverty Row, 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
985 Chapel Hill Rd, 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
1033 Burrington Hill Rd, Whitingham
$315,000
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
292 Deer Hill Rd, Whitingham
$325,000
2 Beds ⋅ 2 Baths ⋅ 5072025 MLS
Tucked amongst trees with a great deck. This rural location is not far from great skiing, shopping and all kinds of great dining and entertainment. Over an acre of mostly wooded lot. Property is occupied. No drive by's please..

292 Deer Hill Rd, Whitingham
2173 Rte 8a, 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
442 Mcmillan Rd, Whitingham
$324,000
4 Beds ⋅ 2 Baths ⋅ 5052510 MLS
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.

442 Mcmillan Rd, Whitingham
233 Poverty Row, Whitingham
$699,000
5 Beds ⋅ 4 Baths ⋅ 5047890 MLS
What a gem, totally turn key and furnished ready to go! 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.

233 Poverty Row, Whitingham

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