The 10 Most Expensive Towns to Buy a Second Home in the U.S.

The United States is rife with expensive vacation towns from the beach to the mountains and everything in between. The vast majority of the most expensive towns to buy a second home in the U.S. are on the east and west coasts. Please continue reading to learn where they are and how much the average homes in these towns cost!

1. Southampton, New York

Celebrities flock to Southampton, New York, to relax in their second (or third or fourth) homes. That makes it the most expensive town to buy a second home in the U.S. The median property value in Southampton is a whopping $2 million, more than eight times larger than the national average of $244,900. Furthermore, the median household income in Southampton supports that median property value, sitting at $135,405.

During the Covid-19 pandemic, these numbers grew in Southampton as wealthy people sought to escape city living. Between 2020 and 2021, the median property value increased by nearly 25%, from $1.61M to $2M. Likewise, Southampton’s population grew from 3,301 to 4,380, a 32.7% increase. Its median household income of $135,405 increased by about $10,000 from 2020.

2. Sag Harbor, New York

Unsurprisingly, the Hamptons boast some of the most expensive vacation towns to buy a second home in the U.S. Sag Harbor, located about 10 miles from Southampton, also has a high median property value of $1.43 million. Sag Harbor has a median household income of $111,518.

This Hamptons town also provided an escape during the Covid-19 pandemic, seeing a population increase of 26% between 2020 and 2021. Today, about 2,500 people live full-time in Sag Harbor.

Over the years, many celebrities and writers have had or currently have homes in Sag Harbor, including Ellen Pompeo, Paul Simon, Jimmy Buffett, Christie Brinkley, John Steinbeck, Vince Clemente, Julie Andrews, and Richard Gere.

3. Carmel-by-the-Sea, California

The third most expensive town to buy a second home in the U.S. is Carmel-by-the-Sea, California. It has a median household income of $100,365 and a median property value of $1.54 million, over six times larger than the national average. Just over half of the people living in Carmel-by-the-Sea own their homes.

This west coast beachfront town was rated one of the most dog-friendly towns in the country. There are a lot of beaches and trails where dogs are permitted to run and play off-leash. In addition to amazing beaches and golf courses, there are many reasons why someone might want to buy a second home in Carmel-by-the-Sea. One of those reasons might include the art scene in town, which is rife with galleries, studios, and antique stores that represent the works of master artists, both local and international.

4. Park City, Utah

Park City, Utah, has a median property value of $1.37 million, making it one of the most expensive towns in the U.S. to buy a second home. That median property value is more than five times the national average. The median household income of $121,701 supports that steep median property value.

During Covid-19, like many other towns on this list, Park City saw its median property value increase. In 2020, the median property value was $1.1 million; by 2021, it saw a 25% increase.

People who like to ski enjoy visiting or living in Park City because it is home to two world-class ski resorts: Deer Valley and Park City Mountain. Thus, it is common for skiers to choose Park City as their vacation home!

5. Montauk, New York

Montauk, New York, is located at the top of the South Fork peninsula of Long Island. It is a village known for its beaches, the Montauk Point State Park, Camp Hero State Park, and the iconic Montauk Point Lighthouse. It is one of the most expensive towns to buy a second home in the U.S., with a median property value of $995,400.

Between 2020 and 2021, Montauk saw a 20% increase in its population and a 33% increase in its median household income, which currently sits at $135,927.

And a fun fact: celebrities including Julianne Moore, Robert De Niro, and Ralph Lauren have homes in Montauk!

6. East Hampton, New York

Yet another Hamptons town on this list, East Hampton, New York, is one of the most expensive towns in the U.S. to buy a second home. The median property value is $2 million, which is the same as it was in 2020. This is over eight times larger than the national average of $244,900. The median household income in East Hampton is $122,763.

Over the years, East Hampton has been a getaway home to many celebrities, including Jerry Seinfeld, Katie Couric, Robert Downey, Jr., Ina Garten, Jon Bon Jovi, Martha Stewart, Steven Spielberg, and Beyoncé and Jay-Z.

7. Naples, Florida

Flying south a bit, Naples, Florida, has a median property value of $1.4 million and a median household income of $125,306. These stats make Naples one of the most expensive towns to buy a second home in the U.S. Unlike many of the towns on this list, Naples saw a decrease in population between 2020 and 2021. The population there declined from 21,750 to 19,187, a nearly 12% drop. Its median household income, however, grew by 6% during that same period.

Naples offers famous white sandy beaches, sprawling golf courses, and many water activities, including water sports, boating, and fishing. It also has a thriving arts and culture scene.

8. Vail, Colorado

For those who prefer mountains to beaches, Vail, Colorado, provides a perfect escape… but only for those who can afford it! Vail is one of the most expensive towns in the U.S. for buying a second home. It has a median property value of $729,000 and a median household income of $100,417. Like Naples, Vail saw a drop in population between 2020 and 2021; similarly, it decreased by 13%. Its median household income, however, increased by 21.5%.

People who enjoy winter activities love Vail because of its skiing and snowboarding scenes. However, there is more to Vail than winter sports. There are many great restaurants, a thriving arts and culture scene, and outdoor activities in the summer.

9. Avalon, New Jersey

Avalon, New Jersey, located on Seven Mile Island in Cape May, is one of the most expensive towns in the U.S. to buy a second home. The median property value is $1.43 million, which increased by more than 14% between 2020 and 2021.

It has a small year-round population of about 1,400 people, which increases to about 45,000 people during the summer.

10. Chatham, Massachusetts

It would be impossible to list the most expensive towns to buy a second home in the U.S. without mentioning Cape Cod, Massachusetts. Chatham is a popular vacation spot for people who live in New England and those who enjoy traveling there from across the country. Between 2020 and 2021, the median property value of $1.15 million increased by 12.6%.

Over the years, several famous people have owned homes in and near Chatham, including Harry Connick, Jr., Taylor Swift, Meg Ryan, and John F. Kennedy.

Like many other towns on Cape Cod, Chatham is famous for its seafood, boating, fishing, beaches, and shopping.