Browse All Waitsfield VT Historical Properties for Sale

Nestled right in the heart of the Mad River Valley, this Waitsfield gem perfectly blends classic Vermont charm with modern comfort. From the moment you arrive, the covered front porch welcomes you with open arms, offering the ideal spot to sip your morning coffee and take in the fresh mountain air. Step inside to a warm, sun-lit interior featuring gorgeous vintage hardwood floors that tell a story of timeless craftsmanship. The thoughtfully designed layout includes a private primary suite, providing a peaceful sanctuary to unwind at the end of the day. For those who love to entertain or simply soak in nature, the large back deck overlooks a serene mountain landscape and includes access to a beautiful shared pond. Behind the scenes, a fully spray-foamed insulated basement ensures peace of mind through every New England season. Location is everything, and this property delivers the ultimate Vermont lifestyle. Enjoy world-class outdoor adventures right out your front door, with immediate access to alpine skiing at nearby Sugarbush and the legendary, skier-owned Mad River Glen. Whether you are mountain biking, hiking the Long Trail, or kayaking the Mad River, recreation is a daily luxury. Best of all, you can easily commute to regional employment hubs, with Montpelier less than 35 minutes away and Burlington just about an hour by car. This is more than a home; it is your gateway to the very best of Vermont. Open house this weekend Sunday 7/5 11am-1pm

1069 E Warren Rd, Waitsfield

$260,000

2 Beds ⋅ 1 Baths ⋅ 5094053 MLS

Bright, open, and inviting, this beautifully renovated two-story condominium offers the perfect blend of comfort, style, and convenience. Gleaming hardwood floors, oversized windows that fill the space with natural light, and a thoughtfully updated kitchen create a truly turnkey opportunity. Ideally located within walking distance of historic Bridge Street, you'll enjoy easy access to local shops, restaurants, and the refreshing waters of the Mad River. Commuters will appreciate the central location, with convenient access to the Mad River Valley, Waterbury, Montpelier, and Burlington. Whether you're seeking a full-time residence, weekend retreat, or investment opportunity, this property places you just minutes from all the recreation and amenities the Mad River Valley is known for, including Sugarbush Resort and Mad River Glen.

4125 Main St Unit 6, Waitsfield

$1,250,000

5 Beds ⋅ 3 Baths ⋅ 5091698 MLS

The very essence of Vermont represented in a historic, classic farmhouse. Valley-wide views from Sugarbush Resort to Camel's Hump and beyond. Just down a scenic gravel road abutting the iconic Von Trapp Dairy Farm and Greenhouse. Modern appointments that honor and reinforce traditions created over 200 years. Watch a glorious sunrise in the morning, and sunset evenings from the covered side porch while neighbors stroll, bike, and horseback ride along the Common Road (a local treat). Gourmet kitchen with ample counters, custom crafted cabinetry, and a large pantry area fit for the most discerning of chefs. Mudroom entry with built-in benches, closets, and cabinetry, and direct entry from the 2-car garage. Open plan living and dining room offers furniture placement options. The main floor features a beautiful Count Rumford style fireplace, and several rooms that could function as home office, library, or bedroom. The graciously sized upper-level bedrooms, one of which features another Count Rumford style fireplace, offer incredible westerly views of the mountains. Don't miss the finished top floor that's currently used as a workout space and TV Room with direct exterior access. The doors from the pantry and mudroom lead to a private Bluestone patio with a nearby babbling brook, just perfect for entertaining and outdoor relaxation.

609 Common Rd, Waitsfield

$575,000

4 Beds ⋅ 2 Baths ⋅ 5087947 MLS

Nestled in the heart of the Mad River Valley, this property is more than just land and buildings it’s a chance to shape your dreams. Here, the tranquil flow of the Mill Brook sets the soundtrack, while the sweeping views of Wu Ledges remind you daily of the beauty that surrounds you. For those seeking a home, it offers privacy, gardens bursting with color, a welcoming fieldstone patio, and the shade of mature trees. Imagine mornings with coffee in hand, the sounds of water drifting through the air, and evenings spent under starlit skies. It’s not just a place to live, it’s a place to breathe. For those with a vision, the property is already steeped in history and success. For over 25 years, its walls have carried the warmth of healing, serving as a beloved massage therapy practice. It's not in the process of being converted back to a single family home, with a new kitchen being installed. And the future is wide open—recent rezoning has approved the addition of up to four more dwelling units. Whether you dream of creating a wellness retreat, an inspiring community hub, or a residential haven with rental opportunities, the foundation is already here. Step outside and you’ll find yourself perfectly positioned—walking distance to the Mad River Path, restaurants, shops, the new Recreation & Mountain Biking Hub. Just a short drive brings you to the legendary slopes of Sugarbush Resort and Mad River Glen. This is more than property, it's a canvas.

5677 Main St, Waitsfield

$1,050,000

9 Beds ⋅ 8 Baths ⋅ 5086610 MLS

Prime opportunity for an investor, a homeowner or an aspiring inn-keeper, this immaculate 9 bedroom & 10 bath home has been lovingly updated with modern heating and cooling, energy efficient updates and a timber-framed solar canopy that powers it all. This historic farmhouse is located in the heart of the Mad River Valley, perched on a hillside by the eponymous Mad River, close to shops, schools, skiing, swimming, hiking and biking - everything you love Vermont for, this gem has everything you're looking for, and a few things you've only dreamed of. Large enough for a huge family gathering, perfect for a multi-family investment, and so full of charm it could shine as that quintessential Vermont inn. This property has been a private home, a successful B & B, and most recently as a highly productive investment property, with good financials to back up the asking price. The interior features 9 bedrooms, each featuring mini-split heating and cooling, multiple bedrooms with ensuite bathrooms, a variety of interior living spaces including 2 fireplaces, a formal dining room, fantastic kitchen, family room, living room, a large multi-teared rec room for games, media or just curling up with a good book. The exterior features comfortable green spaces, a beautiful garden, mountain views, a solar canopy with parking/EV charging for multiple vehicles and a 2BR/2BA caretaker/innkeeper/owners cottage. Located along Vermont's Scenic Byway, this Mad River Valley home is close to every attraction Vermont has to offer, perfectly situated to draw in your friends and family. This beautiful property begs to be filled with guests, laughter, feet on the hearth to warm by the fire, skis by the door, and muddy shoes on the porch. Stop scrolling the real estate listings. Stop dreaming. Stop waiting until tomorrow. Start living the dream today. Slide into the good life in the Green Mountains of Vermont. Come home for good, to the Mad River Valley.

1460 Main St, Waitsfield

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Waitsfield Historical Real Estate

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