Windermere Van Vleet & Associates Inc. has been a trusted name in Southern Oregon real estate since 1955. What began as a small two-room office—built by a group of brokers including Bob Van Vleet and Leo Zupan, where marketing meant walking down the street in Ashland and stopping into each storefront to build relationships with local shop owners and residents—has grown into a regionally respected brokerage with more than 100 brokers and four offices in Medford, Ashland, Jacksonville, and Eagle Point as well as a satellite presence on the South Oregon Coast and Grants Pass.

Still locally owned and operated by the Zupan family—now three generations strong—Windermere Van Vleet continues to thrive by holding fast to its original mission: to put people before profit and relationships before transactions.

At the heart of the company today are John and Devin Zupan, a father-son team whose leadership embodies three generations of dedication to relationships, integrity, and community in a beautiful blend of deep-rooted experience with forward-thinking vision.

Their commitment to family values, professional excellence, and community connection shapes the culture of the company and inspires the agents they support. Under their stewardship, Windermere Van Vleet has remained a place where real estate feels like home and agents feel like family.

At Windermere Van Vleet, real estate is more than just a business—it’s a family tradition. Our legacy of client-centered service is matched only by our dedication to agent success. We believe that when agents are respected, supported, and part of a meaningful culture, they thrive—not just in business, but in life. That’s why we’ve built a workplace where collaboration, innovation, and heart drive everything we do. Our agents don’t just work here—they belong here.

As part of the broader Windermere Real Estate network, which spans 9 states and includes more than 300 offices and 6,500 brokers, we combine the strength of a regional powerhouse with the personal care of a boutique agency. Whether helping buyers relocate from California, serving lifelong local clients, or guiding first-time homebuyers, we provide the tools, technology, and relationships to make every step of the journey feel like home.

If you’re looking for a brokerage where you’re more than a number—where success is measured in people, not just production—Windermere Van Vleet & Associates is the place to call home. Built on relationships. Rooted in Southern Oregon. All in for you.