The 6 Most Expensive Mountain Towns in Vermont to Buy a Second Home

Vermont’s proximity to Boston, Montreal, and New York City makes it a popular spot for escaping the city. Ski resorts, waterfalls, and hiking trails paired with quaint shops and farm-to-table restaurants make the mountain towns hot destinations. Around 17% of Vermont’s homes are second homes and provide the picturesque setting and clean air that vacationers love.

Zillow places Vermont’s average home price at $388,868 as of October 27, 2023. Home prices have increased by approximately 5% in 2022 and 2023. Plus, it only takes about 10 days to get an offer, which means buyers must act fast.

Homes in some of Vermont’s mountain towns are often well over that average. If you’re looking for a vacation home in these towns, expect to pay at least $500,000. Explore the six most expensive mountain towns in Vermont to buy a second home and the average price of a home in that area.

6. Weston ($511,272)

Centered in the southern part of Vermont, Weston abuts the Green Mountain National Forest. A canal in the West River splits the town into two parts: Weston and The Island, a section that once housed sawmills, tanneries, a grist mill, and a variety of specialty professions including blacksmiths and shoemakers.

Weston Playhouse Theater opened in 1935, and the Vermont Country Store opened in 1946. Both the Weston Theater Company and the Vermont Country Store draw visitors. The town boasts a picturesque town green, complete with a bandstand, and the Weston Priory is home to Benedictine Monks who welcome guests to their priory and gardens.

While land is your most affordable option in Weston, contractors are in short supply. It can take months to get on a plumber’s, electrician’s, or carpenter’s schedule. While the average home price is $511,272, our findings were that for the handful of homes available in town, you’re going to spend $800,000 or more on a second home.

5. Waitsfield ($565,032)

Waitsfield is tucked in a valley near Mount Ellen, Roxbury State Forest, Sugarbush Resort, and Camel’s Hump. Ski resorts in Stowe and Sugarbush are within easy reach, but there are many other attractions in Waitsfield Common, which is the historic town center and home to the Von Trapp Farmstead Farm Store, where they sell dairy products from the Von Trapp family’s cows. Yes, this is the famous family from the movie “The Sound of Music.”

Take the Waitsfield Covered Bridge across Mad River to the historic district. This side of the river is home to area healthcare services, the village grocer, and a variety of restaurants. A Sip of Sunshine is one of the state’s popular local IPAs and is served at Lawson’s Finest Liquids.

While the average home price is $565,032, homes in good shape are well over $1 million. If you’re okay with a fixer-upper in need of major renovations and repairs, it’s possible to get a second home in Vermont for less than $300,000.

4. Manchester ($591,277)

When it comes to Vermont towns with a bit of everything, Manchester is at the top of the list. It’s home to designer outlet stores like Armani and Michael Kors. There are historic sites like President Abraham Lincoln’s son’s manor home, Hildene Farm. Arts plays an important part in this town, as it’s home to the Southern Vermont Ballet, Southern Vermont Arts Center, and several annual music festivals. Fine dining and area skiing and hiking are other activities.

Vacation homes in this popular getaway have an average price of $591,277, but there are more affordable options if you’re okay with a smaller condo or townhome. For larger stone mountain homes and historic houses in the village, expect to pay over $1 million.

3. Stratton ($639,543)

For a quintessential Vermont mountain town that’s popular for skiing, hiking, and fishing, choose Stratton. Summer hiking to points like the Stratton Fire Tower in the Green Mountain National Forest is a favorite pastime. The Appalachian Trail meets Vermont’s Long Trail in Stratton, which makes it easy to reach other towns along the Long Trail. Anglers find plenty to do, too, as the 86-acre Grout Pond offers camping and fishing for bluegill, smallmouth bass, and yellow perch.

Much of the housing in Stratton is at the ski resort and focuses on condos and townhomes. The average home price is $639,543, and it’s hard to find anything less than that without buying land and building your own Vermont vacation home.

2. Dorset ($714,066)

The town of Dorset often feels like a step back in time with a main street (Route 30) lined with a general store, deli, pottery store, bakery, inn, and bed and breakfast. Plus, Manchester is close by for additional dining and shopping opportunities.

Dorset drew the attention of John Jacob Astor’s unmarried granddaughter Cecelia deNottbeck. She used family money to purchase a 74-acre farm in Dorset and had a stone tower erected on her land. The Pinnacle Tower still stands and is a popular stop along the forest’s hiking trails.

Even reasonably-sized family homes in Dorset sell for over $1 million. It’s easy to understand why Dorset is the second most expensive mountain town in Vermont for second homes. With an average price of $714,066, Dorset is known for its natural beauty. It’s also home to a former marble quarry that’s now a popular at-your-own-risk swimming hole.

1. Stowe ($944,528)

Adjacent to the Mount Mansfield State Forest, Stowe is a skier’s dream destination. Stowe Mountain Resort has 116 trails on Spruce Peak and Mount Mansfield. Year-round fun awaits with an abundance of restaurants and shops, breweries including the eco-friendly award-winning Alchemist, and plenty of hiking and biking trails. Waterbury is right down the hill and offers more restaurants, shops, and the famous Ben and Jerry’s Factory for tours and free samples.

Stowe is the most expensive mountain town in Vermont for buying a second home, and it’s well known that many of the area’s homes are vacation getaways. With an average price of $944,528, you might find a small condo for less than $400,000, but it’s often a condo with basic amenities and far less than 1,000 square feet of living space. It’s not uncommon to see homes topping $20 million in this area.

The Most Expensive Mountain Towns in Vermont

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