Jenna (Jacobsen) Swain is a top-producing real estate broker and co-founder of Ninebark Real Estate, a boutique firm rooted in community, integrity, and a deep understanding of the Central Oregon lifestyle. A lifelong local and graduate of Sisters High School, Jenna has spent her entire life in Central Oregon, bringing an unmatched level of market knowledge and personal connection to Bend, Tumalo, Sisters, Redmond, Prineville, and the surrounding areas.
Growing up on a ranch, raising cattle and grass hay, Jenna developed a deep appreciation for the land and the lifestyle that defines this region. She also spent years traveling throughout the Northwest competing with her horses, giving her firsthand experience and insight into equestrian properties, ranch operations, and the unique needs of buyers and sellers in this space. This background is not just part of her story - it’s a true value-add for her clients navigating ranch, land, and horse property transactions.
With over $100M in closed real estate volume and ranking in the top 5% of REALTORS® in Central Oregon, Jenna has built her business on results, relationships, and a reputation for guiding clients through every step of the process with clarity and confidence.
Jenna specializes in residential, ranch and horse properties, acreage, and investment real estate throughout Central Oregon. Whether it’s navigating zoning, evaluating land potential, or positioning a property for maximum value, Jenna brings a strategic and informed approach to every transaction - always with the goal of securing the best outcome for her clients.
Known for her strong negotiation skills, clear communication, and hands-on service, Jenna is deeply committed to delivering a seamless and elevated client experience. Her approach is both professional and personal - built on trust, attention to detail, and a genuine passion for helping people achieve their goals.
What Jenna loves most about Central Oregon is the lifestyle it offers - the stunning mountain views, endless opportunities to explore lakes and rivers, quiet moments camping under the stars, and a community where people are genuinely kind and welcoming. Having grown up and built her life here, she brings an authentic perspective that resonates with both locals and those looking to call this special place home.
At the core of her business is a belief that real estate is more than a transaction - it’s about walking her clients home.
Who is Jenna?
As both a real estate broker, coach, and brokerage owner, I help agents at every stage build businesses that actually work—for their goals, their lifestyle, and their future. Whether you’re just getting started or ready to scale, I’ll show you how to turn your passion into a powerful, profitable, and sustainable career.
For clients, that same level of strategy, dedication, and experience translates into a thoughtful, results-driven approach to buying and selling—ensuring you feel confident, supported, and positioned for the best possible outcome every step of the way.
Because this isn’t just about selling homes—it’s about stepping into your potential, creating real impact, and building a business and life that genuinely excites you every day.
I am excited to meet you!
I would love the opportunity to serve you!
No more random marketing or hoping for referrals. It's time to run your real estate practice like the business it is.
Build efficient systems that scale
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Convert prospects into committed clients
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Stand out in your local market
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Create predictable lead generation
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Through my proven framework, you'll learn how to:
I transform ambitious realtors into successful business owners by providing the systems, strategies, and support you need to consistently attract clients, close deals, and build a real estate business of YOUR dreams.
The Real Estate Growth Lab: Your Blueprint to a Thriving Practice
The Real Estate Growth Lab: Your Path to Success is dedicated to igniting real estate growth by providing a transformative coaching experience that helps individuals to achieve extraordinary results.
The Real Estate Growth Lab: Your Path to Success
I know the doubts, fears, and challenges because I’ve lived them. I also know the incredible freedom, success, and joy that come when you push past them. Whether you’re just starting out or looking to grow your real estate business, I’m here to guide you, inspire you, and show you how to create the life and career you’ve always dreamed of.
The early days were tough - terrifying, even. Waiting weeks or months for that first sale felt endless, and every new client brought both excitement and anxiety. But I made a decision early on: there was no option but success. I committed to shifting my mindset, building systems, and getting crystal clear on my goals.
Fast-forward, I sold 35 million in my first two years in real estate and to this day have now sold over 100 million. The life I have now - flexible, fulfilling, and filled with opportunity - is a world apart from where I started. And the best part? I can barely remember my life before I took that leap because this journey has been so transformative.
Now, I’m here to help you do the same.
Let’s take the leap together!
I took the traditional path at first - high school, community college, university. I earned my bachelor’s degree in Diagnostic Medical Sonography and landed what I thought was my dream job at the local hospital in my hometown. At first, it felt like success. But week after week, the long hours, endless on-call shifts, and grueling 60+ hour work weeks started to wear me down.
Growing up, my father was a custom home builder, developer and investor, so real estate was always in the background of my life. One day, I decided I wanted something different. I realized no one was going to hand me the life I dreamed of, so I made the decision to leap into real estate - and I’ve never looked back.
I couldn’t shake the feeling that this couldn’t be it for me - that there had to be something more.
Here is My Story
(Click to read more!)
Fun Facts
I’ve been fortunate to travel to 24 countries, and explore the world. Immersing myself in different cultures is one of my greatest passions and it fills my soul.
My happiest moments are spent on horseback, relaxing on a sun-soaked beach, or adventuring around the world with my best friend—my husband.
My dogs are my world! I’m a proud fur-mom to two amazing border collies, Kimber Rae and Sadie Jo, and one large Maine Coon Cat - Louis V, who bring endless joy to my life.
I thrive on competition and embrace new challenges - it’s what keeps me motivated and inspired. Pushing myself to grow, learn, and improve every day fuels my passion for both personal and professional success. But beyond my own growth, I find true fulfillment in helping others achieve their goals. Mentoring has always been a passion of mine, and there’s nothing more rewarding than guiding and supporting others on their journey to success. I’m driven by the pursuit of excellence, always striving to be my best self and continuously raising the bar.
I’m blessed to call beautiful Sisters, Oregon, my home. Every morning, I wake up to breathtaking views of Faith, Hope, and Charity - the iconic Three Sisters Mountains. Surrounded by trails, lakes, rivers, and 9 Mountains, I truly live in a slice of heaven on earth.
When I was 18, I spent two months solo backpacking through Europe, and it was an experience that completely transformed me. I discovered so much about myself and gained a deep appreciation for the incredible beauty and diversity this world has to offer. What struck me the most was the rich history and how passionately other countries preserve it, allowing us to step back in time and experience it firsthand.
Most weekends, you’ll find me showing homes, writing contracts, and hosting open houses. But outside of real estate, my life has always been deeply rooted in the rodeo world. From managing social media for rodeo events to timing competitions across the country, it’s a passion that has been a part of me for as long as I can remember.
I also have a deep love for the outdoors - especially here in beautiful Central Oregon, where I’m lucky to call home. Whether it’s playing pickleball, paddle boarding, camping, or chasing the next adventure, I’m always up for something new. My husband and I love to travel as often as we can, but we also enjoy working on our own little slice of heaven - our property just outside of town. Keeping up with a few acres is a job in itself, but we wouldn’t have it any other way. And through it all, our two Border Collies are right by our side, joining us on every adventure possible!
In addition to my passion for real estate, I co-own a brokerage - Ninebark Real Estate - alongside my business partner. We have an office in Sisters and Bend.
Together, we take great pride in supporting and mentoring a team of 37 talented brokers.
