Meet Jaclyn Oakland, 

Jaclyn Oakland

Your Bend Oregon Real Estate Expert

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portraitJaclyn
Realtor®

Jaclyn Oakland

With over 15 years in the real estate industry and 6 years as a licensed Realtor in Bend, I bring a 360° perspective to every transaction. Over 190+ closed sales and $200M+ in closed volume means I am experienced and knowledgeable with all aspects of your sale and allows me to anticipate potential challenges before they arise and keep every detail moving smoothly toward closing. My job is to ensure every step of the process is seamless. Whether looking to Buy, Sell, or Invest in Central Oregon Real Estate, rest assured that my experience and dedication to each and every client allows me to anticipate challenges before they happen and guide you through the details with confidence.

What sets me apart is not just my professional expertise but the values I bring to my work. I believe that real estate is about more than contracts and closings. It is about people, relationships, and helping clients achieve their goals in one of life’s most important milestones. My clients know me for my attention to detail, strong communication, and commitment to being available whenever they need me.

Living and working in Bend allows me to combine my love for this community with my professional skills. I know the neighborhoods, the market trends, and the lifestyle that makes Central Oregon so special. Whether you are relocating, investing, buying your first home, or preparing to sell, I provide personalized guidance tailored to your unique needs.

I also take pride in staying connected long after the keys change hands. Many of my clients become friends, and I enjoy being a trusted resource for contractors, lenders, designers, and local services that make settling into a home easier.

At the heart of my business is a simple promise: to treat every client with honesty, respect, and care. Real estate can feel complicated, but with the right partner, it can also be rewarding and even fun. I am honored to be that partner for so many families in Bend, and I look forward to being that partner for you. 

Hear What My Clients Have to Say

"We had an amazing experience purchasing our first home ever with Jaclyn! We found the perfect match very quickly with her help. She made the process easy for us and took the time to answer and questions we had. I would highly recommend Jaclyn for your next endeavor!"
"Jaclyn was so great to work with! We were from out of town, so we had limited time to look at houses and were unfamiliar with the area. Jaclyn did a wonderful job of selecting homes to look at, setting up several appointments according to our availability, and helping us learn the area. She also guided us through the home-b
"Jaclyn Oakland is an exceptional real estate agent in the Bend, Oregon area. We’ve worked with her on multiple home purchases and sales, and she has delivered outstanding results every time. She is incredibly detail-oriented, communicates clearly and proactively, and always goes above and beyond to make sure every aspect of
"Jaclyn Oakland with Cascade Sotheby’s in Bend is a true professional in the Central Oregon real estate market. She has a deep understanding of the Bend housing market and does a fantastic job helping buyers and sellers navigate every step of the process. Jaclyn is incredibly responsive, detail-oriented, and genuinely cares
"Jaclyn Oakland is everything you hope for in a real estate professional and more. She brings a level of integrity, market knowledge, and attention to detail that immediately sets her apart. From start to finish, she is organized, responsive, and genuinely committed to her clients’ best interests. What really stands out abo
"I highly recommend Jaclyn Oakland with Cascade Sotheby’s International Realty. Jaclyn is the definition of professionalism in real estate. She is knowledgeable, dedicated, and truly passionate about her work. She brings a high level of expertise to every interaction and consistently demonstrates integrity, strong communica
Client Success Stories

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