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Denny Osborn, Broker
REALTOR®, ABR, e-PRO, RSPS
(541) 771-1578
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About Denny Osborn, Broker, ABR, e-PRO, RSPS

After 20 years in Bend real estate, I’ve learned something simple: people don’t need more hype — they need clarity, patience, and someone who will truly listen.

I work with buyers and sellers who want thoughtful guidance before making one of the biggest financial decisions of their lives. Whether you’re purchasing your first home, relocating to Bend, downsizing, or preparing to sell a place filled with memories, my role is to help you understand the market clearly and move forward with confidence.

Serving Bend, Redmond, and the surrounding areas, I focus on steady preparation, realistic pricing, and smart strategy. For sellers, that means positioning your home carefully and protecting your equity. For buyers, it means evaluating opportunities honestly and helping you make strong, informed offers. In both cases, the goal is the same: clear information, steady communication, and decisions that feel right long after closing.

Many clients tell me they simply want an agent who will be direct, responsive, and grounded in experience. I’ve built my business around exactly that — realistic expectations, open conversations, and guidance shaped by navigating multiple market cycles here in Bend.

Whether you’re buying, selling, or simply exploring your options, I’m here to help you sort through the noise and make a confident decision that fits your next chapter.

If clarity, steadiness, and honest advice matter to you, we’ll work well together.

Customer Reviews

  • Melissa W

    Denny was absolutely fantastic to work with. From the very beginning, he made us feel comfortable and supported throughout the entire process. He was never pushy and always gave us the space to make... read more

  • Karl V

    It was a real pleasure to meet and work with Denny through the entire process. It was a truly pleasant experience and a successful outcome for me and would recommend his service to anyone any time .

  • Bransen Hayes
    Buyer

    Denny was great to work with. He was easy to get a hold of and was happy to answer any question that I had.

  • Lisa Jones
    Buyer

    We appreciated the help and advice from Denny Osborn of Bend Premier Estate, while buying our home. He was very professional, answered every call and concerns quickly. Denny was always upbeat and enco... read more

  • Leslie and Laura Camacho
    Seller & Buyer

    We've worked with Denny since 2007. He was so patient with us
    as we toured almost every house for sale in Bend over the next 3
    years. Finally, in 2011, we found our perfect home and he helpe... read more

  • Darla Kennedy
    Seller & Buyer

    Denny far exceeded my expectations and went above and
    beyond!

Denny's Blog

Acreage Sellers: What You Need to Know Right Now

Acreage properties around Bend still get attention. Space, privacy, flexibility—it's what a lot of buyers are looking for. But selling acreage right now isn't the same as selling a home in town. ... read more

Acreage Purchases: What Buyers Often Miss

Acreage properties around Bend have a strong pull. More space. More privacy. Room for shops, animals, or just a quieter lifestyle. And for a lot of buyers — especially those relocating — it feel... read more

3 Questions Every Relocation Buyer Should Ask Before Moving to Bend

Every year I talk with buyers who are relocating to Bend, Oregon. Many of them have spent time visiting, fallen in love with the scenery, and are excited about making Central Oregon home. But relocat... read more

3 Questions Every Relocation Buyer Should Ask Before Moving to Bend

Every year I talk with buyers who are relocating to Bend, Oregon. Many of them have spent time visiting, fallen in love with the scenery, and are excited about making Central Oregon home. But relocat... read more

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/29/2026. The listing information on this page last changed on 04/29/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 04/29/2026 6:35:36 AM EST) or RMLS (last updated Wed 04/29/2026 1:50:17 AM EST) or COAR/MLSCO (last updated Wed 04/29/2026 1:31:19 AM EST). Real estate listings held by brokerage firms other than Bend Premier Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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