Whitingham Homes under $500,000

Welcome to Whitingham, Vermont – a hidden gem nestled in the picturesque Windham County. Known for its stunning landscapes and a close-knit community, Whitingham offers a unique blend of rural charm and modern conveniences. With its serene lakes, lush forests, and rolling hills, this quaint town is perfect for nature lovers and those seeking an escape from the hustle and bustle of city life.

Whitingham is home to a variety of recreational activities, including hiking, fishing, and skiing, making it an ideal location for outdoor enthusiasts year-round. The town’s rich history and vibrant community spirit are evident in its local events and festivals, where neighbors come together to celebrate the beauty of their surroundings.

For those considering a move to Whitingham, you’ll be delighted to discover that there are beautiful homes available for under $500,000. Whether you’re looking for a cozy cabin, a charming farmhouse, or a contemporary family home, Whitingham has a diverse selection of properties to suit your needs and budget. With its affordable real estate options, you can enjoy the tranquility of country living without breaking the bank.

Living in Whitingham means embracing a lifestyle that values community, nature, and simplicity. With its stunning scenery and welcoming atmosphere, it’s no wonder that so many are drawn to this enchanting town. Explore the possibilities of calling Whitingham home, and experience the perfect blend of comfort, adventure, and small-town charm.

Newest Whitingham Homes under $500,000

$368,000

4 Beds ⋅ 2 Baths ⋅ 5114079 MLS

Welcome to this lovingly maintained country property situated on 5.5 acres in Whitingham, Vermont. Offering a wonderful combination of open pasture, wooded acreage, and privacy, this property has so much to offer. The two-story home has been thoughtfully cared for by its long-time owners and features abundant natural light throughout the main living level. A delightful sunroom provides additional living space with direct access to the deck, perfect for enjoying the peaceful surroundings. A walk-out basement adds flexible space with access to the front yard. Outside, you’ll find beautiful open fields, wooded areas, and a spacious two-story barn in excellent condition, complete with electricity and versatile space for storage, vehicles, hobbies, or potential equestrian use. A two-car garage with storage above is located across the road. Additional highlights include a new septic system installed in 2024, two water sources consisting of a drilled well and an original spring-fed system with an updated metal cistern, and a whole-house generator for added peace of mind. Enjoy the privacy and peaceful surroundings of country living, just five miles from downtown Wilmington. Conveniently located near Mount Snow, Harriman Reservoir, Lake Raponda, rivers, hiking trails, and golf courses, offering endless opportunities for four-season recreation. With its inviting home, beautiful acreage, useful outbuildings, and picturesque Vermont setting, this is a property offering room to live, grow, and enjoy country living for years to come.

1287 Wilmington Cross Rd, 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

$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

$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

$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

$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

$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

$299,000

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

$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

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