Aubre Cheshire

Bend

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About Aubre Cheshire

I’ve been helping people buy and sell homes in Central Oregon since 2006, but to me, real estate has never really been about sales. It’s about people, timing, transitions, and trust.

Over the last 20 years, I’ve had the privilege of stepping into people’s lives during some of their most meaningful and vulnerable moments. I’m often one of the first to hear about a new baby, a marriage, a divorce, a loss, a fresh start, or a long-awaited dream finally taking shape. I don’t take that lightly.

I approach this work with an open heart, a calm presence, and the belief that people deserve to be met exactly where they are. My role isn’t to push or convince—it’s to guide, advise, problem-solve, and help people navigate big decisions with honesty and clarity.

As a fourth-generation Central Oregonian with deep roots in Bend and Redmond, I bring a perspective that goes beyond market stats. I understand the lifestyle, the nuances of the neighborhoods, and how much “home” can shape a person’s life. My background in business and property management also gives me a practical, big-picture approach whether someone is buying their first home, investing, downsizing, or starting over.

About 95% of my business comes from referrals and repeat clients, which is something I’m incredibly grateful for. Many of my clients become long-term relationships, and there’s nothing more meaningful to me than being trusted through multiple chapters of someone’s life.

Outside of real estate, I’m usually spending time with my young son, exploring the outdoors and enjoying everything Central Oregon has to offer.

If you’re thinking about buying, selling, investing—or simply want a thoughtful conversation about the market—I’m always happy to connect.

An impressive 95% of Aubre’s business is built on referrals, underscoring her commitment to providing personalized service and cultivating lasting relationships with her clients.

Outside of real estate, Aubre enjoys spending time with her energetic young son. They love biking, hiking up hills, and going on adventures "hunting for bugs."

If you’re looking for a dedicated partner in your real estate journey, Aubre would love to connect. Feel free to reach out!

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