Discover the Charm and History of Oakland, Oregon

A hidden gem in Douglas County with deep roots and real estate potential

When most people think of real estate in Douglas County, towns like Roseburg might be top of mind—but just 20 minutes up the road sits a truly special place: Oakland, Oregon. With deep historical roots, incredible charm, and growing potential for homeowners and investors alike, Oakland offers a rare blend of past and present.

We recently sat down with Mary Gilbert, lead broker at The Mary Gilbert Group of Keller Williams Southern Oregon, to talk about what makes this small town so uniquely appealing.

A Walk Through History

Did you know Oakland was the first city in Oregon to be placed on the state historic register back in 1968? It was later added to the National Register of Historic Places, and when you stroll through downtown, it's easy to see why.

Oakland’s main street spans just two blocks, but it’s lined with some of the best-preserved brick commercial buildings from the 1880s and 1890s in the entire state. The town feels like a movie set, and it has actually served as one! Films like Fire in the Sky and Grand Tour: Disaster in Time were both filmed in Oakland’s historic core.

Timeless Businesses That Tell a Story

Oakland is home to Stearns Hardware, one of the oldest continuously operating hardware stores in the West. It’s been family-run since the 1880s - through world wars, the Great Depression, and the rise of online shopping. That kind of continuity and community loyalty is rare and speaks volumes about the people who call Oakland home.

“This town has heart,” Mary explains. “If you value small-town life, history, and a sense of connection, you’ll feel right at home here.”

From Turkeys to Tasting Rooms

Oakland’s story doesn’t stop with historic buildings. In the early 1900s, it earned the nickname “Turkey Capital of the U.S.” due to its thriving poultry industry. Today, that agricultural tradition has evolved, Oakland is now part of the Umpqua Valley wine region. Local tasting rooms have popped up in beautifully repurposed historic buildings, including one particularly creative space in an old bank vault.

Quirky Traditions and Community Spirit

Small-town doesn’t mean boring in Oakland. The town hosts a number of whimsical events throughout the year, including Potato Bingo on St. Patrick’s Day and a Fourth of July Parade that’s been known to feature everything from farm animals to camels. Add in 50‑cent hot dogs, bounce houses, and hometown pride, and you’ve got a community that’s as fun as it is welcoming.

Why Oakland Real Estate Stands Out

For buyers and investors, Oakland represents a rare opportunity in today’s market. According to Mary:

“You can still find homes with historic character—real wood floors, wraparound porches, original details—at more affordable prices than in other parts of Oregon.”

The town also supports creative development. With zoning that allows for mixed-use properties, many of Oakland’s historic downtown buildings are ideal for entrepreneurs looking to open a boutique, gallery, or café while living upstairs or nearby.

Plus, Oakland’s Historic Preservation Commission helps maintain the authenticity and value of these properties long term—a huge draw for buyers who want to invest in a town that honors its roots while looking ahead.

A Small Town with Big Personality

If you’re searching for a place where you can slow down, connect with your neighbors, and live surrounded by charm, Oakland is worth a closer look. With its blend of history, creativity, and strong community values, it’s one of those rare places where lifestyle and investment go hand in hand.

Ready to Explore Homes in Oakland?

Whether you’re dreaming of a historic fixer-upper, a turnkey cottage, or even a commercial space downtown, The Mary Gilbert Group is here to help. Our team has deep knowledge of the Douglas County market, and we’d be honored to help you find a place to call home.

📍 Visit us at 2658 NE Stephens Street, Roseburg
📞 Call 541‑371‑5500
🌐 Browse listings anytime at www.marygilbert.com