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 in Ashland—founded by a group of brokers including Bob Van Vleet and Leo Zupan, where marketing meant walking down N. Main street 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 Southern Oregon Coast and Grants Pass.

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.

“We thrive by putting people before profit and relationships before transactions.”

Windermere Van Vleet offers more than just real estate services—it offers a culture where agents feel like family and clients are genuinely cared for. We measure success by the strength of our relationships, not production numbers. As part of the Windermere Real Estate network spanning nine states and includes more than 300 offices and 6,500 brokers, we combine the power of a regional brand with the warmth of a locally rooted legacy.

If you’re looking for a place to grow your career, serve your community, and be part of something meaningful, our family at Windermere Van Vleet says: “Welcome Home”!