6 Best Places to Buy a Winter Home in the U.S.

Whether you dream of flip-flops and shorts or packing up your skis and snowboards and heading for the slopes, there are many great destinations in the U.S. where you can escape from or enjoy winter. Here are six to consider—three in warm climates and three in cold. 

1. Anna Maria Island, FL

This barrier island in South Florida is just 7 miles long and 1.5 miles wide. Ron Smedley, who lives in Cincinnati, OH, and bought a vacation house there in 2007, says, “Anna Maria Island is the perfect place to escape the hustle and bustle of our busy lives and rest our toes in the sand. The island is what ‘Old Florida’ used to be." 

There is an ordinance that no structure can be built higher than the tallest palm trees, so you don’t have huge high-rise condos dotting the beach, just great views of the crystal-clear water. Numerous restaurants offer seafood right off fishermen’s boats. 

When Smedley and his family visit, they spend most of their time at the beach, where, he says, “It’s not surprising to see manatees, dolphins, stingrays, and plenty of other wildlife while we’re looking out at the water.” 

According to Zillow, the median home value for Anna Maria Island is $1.41 million as of June 30, 2021, and home values have gone up more than 24% over the past year. 

2. Beaufort, SC 

Beaufort (pronounced Byew-fort, and not to be confused with Beaufort, NC, pronounced Bow-fort) is a great destination for anyone looking for a temperate climate during the winter. Located in South Carolina Lowcountry, the "winters are very mild and allow for plenty of outdoor recreation—inshore fishing is popular as are trips to the nearby beaches, golf, biking, and tennis,” says Edward Dukes, a lifelong resident and managing partner in Lowcountry Real Estate.

Chartered in 1711, Beaufort sits on the Intracoastal Waterway between Charleston and Savannah, each just a short drive away. Hunting Island, 15 miles from town, offers an “amazing beach, bike paths, and a canal for kayaking, paddle-boarding, and fishing,” says Dukes.

He recommends buying a vacation house right in the town, which is rich with history and Lowcountry architecture and culture and an easy walk to dinner, shopping, and the USCB Center for the Arts. You can also buy properties in nearby gated golf and beach communities and, if you like boating, you can buy in a neighborhood with a community dock. 

Homes in Beaufort have a median value of $262,764 as of June 30, 2021, on Zillow. Home values have risen 11.8% over the past year, making the market “very hot,” according to Zillow. 

3. Phoenix, AZ

Encompassing Scottsdale, Paradise Valley, and Mesa, the Phoenix area makes outdoor living in the middle of winter easy and fun with plenty of sunshine, little rain, and mild temperatures. Combine golfing, hiking, tennis, biking, and swimming with visits to the Phoenix Art Museum or the Heard Museum dedicated to Native American art and history, or to a performance by the Phoenix Symphony, Ballet Arizona, or the Arizona Opera. 

Phoenix was hit hard during the housing crisis, but the housing market has now fully recovered. According to Troy Reeves, owner of the Reeves Team, "While housing prices have had growth at a slightly faster than average pace over the last few years, it is mainly fueled by the fact that prices previously were too low and we have been catching up to where we need to be all along." 

The median home value in Phoenix is $350,077 as of June 30, 2021, and values have gone up 27.4% over the past year, according to Zillow.

4. Jackson Hole, WY

Jackson Hole Mountain Resort took first place in the Ski Magazine list of top ski resorts in 2019, and the magazine continues to heap praise on the town. It also makes frequent appearances at the top of Forbes' annual rankings of Top 10 Ski Resorts in North America.

But downhill skiing is only one choice for getting outside: You can ski cross-country on groomed tracks or into the national parks and forests, snowmobile around nearby Yellowstone National Park, take a sleigh ride through the National Elk Refuge, dogsled, helicopter ski, snowshoe, and ice skate. Because 97% of Jackson Hole’s land is currently permanently protected from development, properties on the remaining 3% are pretty scarce. As a result, dollar volume and transactions are extremely high. 

Kelli Ward, an associate broker at Jackson Hole Real Estate Associates and Christie's International Real Estate, says that “Wyoming is one of the friendliest states in the U.S. for people relocating for the purposes of…trusts and overall asset protection.” But “that is just a bonus to some who want to be in Jackson Hole for the beauty of the land.”

That is apparent as soon as you fly into the area airport: It is the only airport in the U.S. located in a national park, and passengers get a look at “huge views of the Tetons, which are absolutely breathtaking” even before their plane has landed, says Ward.

As of June 2021, the median home value listed in Jackson Hole is $2.1 million, trending up 55.6% year-over-year, according to Realtor.com.

5. South Lake Tahoe, CA

Lake Tahoe is huge—71 miles around—with ski areas on its north end (in Nevada) and its south end (in California). The South Shore is the livelier of the two, according to Dan Spano, who went there to ski 30 years ago and never left. According to Spano, a broker with Sierra Sotheby's International Realty, the south end is also somewhat more affordable.

“People are attracted to Lake Tahoe because it’s one of the most beautiful places on Earth and the winters are mild compared to resorts in the eastern part of the U.S.,” says Spano. At the Heavenly Mountain Resort area, you can ski two states in one day and enjoy what Spano says is the best snow-making equipment in the area. 

The real estate market in Tahoe is “very strong,” says Spano. “San Francisco Bay Area residents doing well financially are buying second or even third homes before prices go out of sight.” 

The median home value in South Lake Tahoe is $624,632 as of June 30, 2021, up 40.8% over the past year, according to Zillow.

6. Okemo Mountain Resort, Ludlow, VT

Okemo is routinely included in OnTheSnow.com's Best Family Resort in America rankings—so if you’re looking for a family vacation destination, this might be it.

According to Bonnie MacPherson, director of public relations at the resort, Okemo gets this top rating because the family who owns the operation understands that “families are looking for activities they can enjoy together on and off the slopes.” 

The resort boasts options for skiers of every level, available from the top of each chair with 46 miles of trails, 667 skiable acres, and thanks to snowmaking equipment that covers 98% of the mountain, a “weatherproof” ski vacation. Okemo is a three-hour drive from Boston and just under five hours from New York City. 

According to Zillow, the median listing price in Ludlow, Vermont, is $376,021 as of June 2021, trending up 10.4% over the past year.

The Bottom Line

Whether you like to escape the snow or have fun in it, there are many great destinations to find the perfect winter home. In addition to price, climate, and activities, decide if you will rent out your home when you’re not there. If so, it's a good idea to consider destinations that have plenty to offer year-round.