The 5 Most Expensive Mountain Towns in Oregon to Buy a Second Home

Oregon Map
klenger/iStock via Getty Images

Written by Alyssa Shea

Published: December 9, 2023

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There’s a reason why Oregon is such a popular choice for people looking to buy a second home! The beautiful mountains, forests, rivers, and parks are desirable for people of any age. Outdoor enthusiasts enjoy hiking and skiing, too. There’s also no sales tax, and the nightlife is incredibly enticing! If you’re into wine or beer, this is the state for you, as Oregon is known for its wineries and breweries. Are you looking for another home in one of Oregon’s mountain towns? Here are the most expensive towns to buy a second house.

1. Bend

An aerial view of the Bend, Oregon Whitewater Park

Bend is located to the east of the Cascade mountain range.

There’s a reason why over 100,000 people reside in Bend. And that number only grows! At 3,623 ft above sea level, this town boasts over 150 days of clear skies per year. The numerous craft breweries and various restaurants also bring plenty of foodies to the area. Bend is right by Mount Bachelor, The Three Sisters volcanic peaks, and Mount Jefferson. More people want to buy a home here than there are homes available for sale, making it a seller’s market.

Averages for the AreaPrices
Median home listing price$850,000
Median price of sold homes$734,000
Median home value$728,807

2. Ashland

Emigrant Lake County Park offers camping near Ashland, Oregon

You can enjoy year-round camping at Emigrant Lake Park near Ashland.

Sixteen miles north of the California border is the mountain town of Ashland, OR. With a population of just over 20,000, homeowners head outdoors to enjoy hiking trails, rafting on the Rogue River, and other recreations. Plenty of people also head to the area for the Oregon Shakespeare Festival, which was started in 1935 by a teacher at Southern Oregon University. In 2019, the festival had an attendance of approximately 360,000 people! Right now, the real estate market is considered to be a seller’s market because so many people are looking to buy here.

Averages for the AreaPrices
Median home listing price$600,000
Median price of sold homes$565,000
Median home value$543,830

3. Sandy

Mount Hood in Autumn

Oregon residents consider Sandy the gateway city to Mount Hood.

People seeking recreational opportunities are sure to enjoy Sandy, OR. This beautiful town is located in the foothills of the Cascade Mountain Range and is a hotspot of activity! If you’re a foodie, you’re in for a treat! There are plenty of local cafes and longtime staples of the area. Everyone heads to Mount Hood as often as possible, as there’s something to do in every season! Fishing, biking, hiking, and many other outdoor opportunities await you here.

Averages for the AreaPrices
Median home listing price$568,000
Median price of sold homes$497,000
Median home value$500,000

4. Joseph

Wallowa Lake in eastern Oregon near Joseph, Oregon

Ice fishing is a popular activity once Wallowa Lake freezes over in the winter.

This picturesque town is called “the Little Switzerland of America” for a reason! Located at the base of the Wallowa Mountains, the area’s beauty is striking. The interesting name came about for an exceptional reason. It was to honor Chief Joseph of the Nez Perce tribe, who was a strong leader and advocate for his people. If you enjoy hiking trails, river rafting, and more lake activities, this town is right for you! Don’t forget to check out the art galleries, too! This town is famous for its unique, western-themed bronze sculptures.

Averages for the AreaPrices
Median home listing price$625,000
Median price of sold homes$540,000
Median home value$484,657

5. Enterprise

Horseback riding trail

There are plenty of trails to choose between for horseback riding in Enterprise.

The last entry on the list is yet another excellent option for outdoor enthusiasts and recreationists! Hunting, biking, horseback riding, and fishing are just some of the fun things to do in Enterprise, OR. Again, breweries and food options are popular, so you won’t have to go without in this area. It’s just six miles away from Joseph, so you have easy day-trip options, too. The area has a lot less action when it comes to tourists, so this could be a more laid-back area for you. We can thank the bronze foundry for all the beautiful bronze art pieces in the local area!

Averages for the AreaPrices
Median home listing price$574,000
Median price of sold homes$332,500
Median home value$400,521


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About the Author

I'm a 36-year-old mother of 2 and military wife. I have 2 dogs and a cat that I'm thoroughly obsessed with. When I'm not writing for work, I'm writing as a hobby. You can find me knee deep in a pile of books or way too invested in a video game.

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