La Grande

If you’re looking for affordability, charm, access to the Blue Mountains, and a strong sense of community, Kenzie Carlstrom of RE/MAX Key Properties in Bend recommends La Grande. She calls it a “hidden gem” in Eastern Oregon, and says its historic district is particularly popular, thanks to its “classic homes with character and larger lots.” The average home value in La Grande is $277,988, and, given the fact that it’s home to Eastern Oregon University, Carlstrom says it’s ideal for anyone looking to invest in rental properties.

“La Grande is an appealing option for those seeking a slower pace of life, stunning natural surroundings, and lower home prices than many other Oregon cities,” she says. “Plus, it’s the easiest four-hour drive to Portland; hop on I-84, and that’s it for your weekend city fix.”

Bend

It’s not hard to understand why Bend has a competitive housing market; Jen Dillard, CEO and founder of the JDRE Team affiliated with Real Broker, calls it a “paradise for outdoor enthusiasts, offering year-round recreation from skiing at Mt. Bachelor to hiking, biking, and paddling down the Deschutes River.” Carlstrom adds that Bend has recently experienced a “strong demand for single-family homes,” which she credits to “remote work trends, the local biotech industry, and the city’s vibrant craft beer scene,” as well as its “excellent schools and year-round recreation.”

Dillard says that prices have “cooled slightly from pandemic highs,” but inventory remains on the lower end. Per Zillow, the average home price in Bend is over $733,000. Still, if you can find a home within your budget, you’ll enjoy all the adventure and modern amenities, including riverfront restaurants and live music venues, that Bend has to offer.

Salem

Anyone envisioning a classic Pacific Northwest lifestyle without the high prices associated with Portland should have Salem on their shortlist. While the capital of Oregon has a somewhat competitive housing market, Zillow records the average home value as $428,744—19 percent lower than Portland’s.

Whether you’re buying or renting, Salem is the type of place where there’s always something to do. The historic Elsinore Theatre hosts live music, comedy, and theater performances, and the Hallie Ford Museum of Art, which is part of Willamette University, has a series of rotating and permanent exhibitions to explore. And if you prefer to spend your free time outside? You’ll have your pick of nearby trails for biking, running, or walking.

Newberg

There’s a high chance that oenophiles looking to invest in real estate will be swayed by this next statement. “Newberg is the gateway to wine country, and I liken it to buying real estate in Sonoma or Napa 50 years ago,” says Shannon Janssen, a Coldwell Banker Global Luxury Property Specialist and real estate broker affiliated with the Portland office of Coldwell Banker Bain. “The topography is stunning with a mix of rolling hills, farmlands, and vineyards, and the town itself has a quaint little downtown with excellent restaurants and a variety of tasting rooms.”

Located just south of Portland, Newberg is a more affordable option for those who want to be within driving distance of Oregon’s most populous city. According to Janssen, buyers are usually “able to find starter homes under $500,000,” and, simultaneously, Newberg “offers the kind of large acreage view properties that luxury buyers are looking for.”

Roseburg

“The Umpqua Valley’s rolling vineyards, mild climate, and outdoor recreation create an idyllic place to call home,” Carlstrom tells Travel + Leisure. Of all cities in this Southern Oregon region, though, her top recommendation is Roseburg, a destination she says has a hefty dose of small-town charm. “Melrose and Hucrest are among the most desirable neighborhoods, offering a mix of newer homes, historic estates, and riverfront properties,” she says, noting that the real estate market is growing, “with ample opportunities for return on real estate investments.” In Hucrest, the average home value is around $438,000, while the average home value in Melrose is $614,630.

As a Roseburg resident, you’ll have outdoor activities at your doorstep, whether you’re interested in hiking, rafting, or even wine tasting. Carlstrom notes the proximity to the coast is another perk; in just over 1.5 hours, you can be walking along the beach and taking in an amazing sunset.

Hood River

“Nestled in the Columbia River Gorge, Hood River and the Hood River Valley is a paradise for outdoor enthusiasts, windsurfers, hikers, and wine drinkers, and it, hands down, has the most picturesque landscapes,” says Carlstrom. Unfortunately, though, she says Hood River’s appeal and its “small-town, close-knit community” have created a tight real estate market, largely driven by high demand for second homes. But, she says, the town’s “farm-to-table scene, craft breweries, and easy access to Portland” still make it a top place to live in the state.

Dillard echoes her sentiment, sharing that there are also great schools and a lovely downtown lined with boutique shops, cafes, and restaurants. She says the most desired homes are typically found in downtown Hood River, the Westside of Hood River, and The Heights area—and you can expect to pay a pretty penny. Home prices in Hood River continue to increase; as of March 2025, the average home value is $694,592.

Cedar Mill

If you’re thinking about relocating to a suburb of Portland, consider Cedar Mill. “It’s closer to downtown Portland than any other suburb in Washington County, yet it feels like a different universe since the two are separated by Forest Park,” says Janssen. “It’s friendly, safe, unpretentious, and has a small-town feel with a weekly farmers market, its own library, and numerous locally owned businesses.”

Its list of green flags continues with relatively low property taxes (Oregon property taxes are capped at 1.5 percent) and highly rated schools. That said, she explains that home values have seen “consistent and steady growth for years and are about 53 percent higher than the greater Portland Metro average.” Zillow estimates the average home value in Cedar Mill is currently just over $835,000.

Three Rivers​

Living in a big city isn’t for everyone; some prefer to live where they can prioritize spending time outdoors, preferably by a river. If that rings true for you, Kristen Butz, principal broker at Sunriver Realty, suggests checking out Three Rivers, an area named after the three rivers that flow through it. “Three Rivers is located south of Bend​​, southwest of Sunriver, and north of La Pine. The community comprises a diverse group of neighborhoods with varying price ranges,” she explains. Three Rivers is technically an unincorporated area, so you may find that you need to drive into Bend or a larger city for some things, but you don’t need to go far to enjoy the natural beauty this part of Oregon is known for. “From bird watching and boating to neighborhood gatherings, Three Rivers is a wonderful place to call home,” Butz adds.

Portland

There are both pros and cons to moving to Portland, but for some, the positives may outweigh the high cost of living, traffic, and crime rates. After all, it is one of the greenest cities in the U.S., it attracts a vibrant, creative community, and the job market is home to major employers including Nike, Adidas North America, and Columbia Sportswear. Additionally, the access to all kinds of outdoor recreation—rivers, beaches, and mountains—is hard to beat.

Granted, the real estate inventory tends to run low, and the average home value in the city is $531,463. While those looking to invest in real estate may have to be patient, renting is also an option. With average rent estimated to be $1,700, Portland is a solid choice for anyone who wants a mix of city amenities and a relaxed, outdoorsy lifestyle.

Hillsboro

“The epicenter of the ‘Silicon Forest,’ Hillsboro has a lot more to offer than most realize and isn’t just about working at Intel,” says Janssen. Located on the west side of the Portland Metro area in the Tualatin Valley, Hillsboro has a strong job market; several large companies—including Applied Materials, Epson, and Thermo Fisher Scientific—join Intel in calling the city their home.

The average home value in Hillsboro comes in around $538,00, and Janssen specifically recommends looking at the Orenco Station neighborhood. She nods to its local farmers market, restaurants, shops, and access to the light rail system, and says that its “abundance of small to midsize townhomes and condos that cater to a low-maintenance, car-free, and carefree lifestyle” tend to appeal to both first-time home buyers and retirees.