Today we’d like to introduce you to Cheyenne Conner.
Hi Cheyenne, please kick things off for us with an introduction to yourself and your story.
I got my start in real estate working for a custom home builder in Arizona, where I fell in love with homes, design, and the entire building process. That experience really sparked my passion for real estate and helping people find a place to truly call home. Shortly after, my husband commissioned in to the Army and from there the military lifestyle ultimately shaped the direction of my career in a big way.
When we were stationed in Washington State, I decided to pursue my real estate license. The process definitely challenged me. I actually had to take the exam seven times because the national portion kept getting me — but I was determined to make it happen. Once I finally passed, I jumped right in and got my first deal within two months. All of this was during COVID, what a market to jump into!
Of course, military life meant moving shortly after getting started, so about six months later we relocated and I had to completely restart and earn a new license in South Carolina. Despite starting over, I was able to sell 10 homes and earn two referrals within my first year there. Then we received orders again and moved to the Savannah, Georgia area, where I continued growing my business while practicing in both Georgia and South Carolina. During my third full year in real estate there, I sold 17 homes through networking, referrals, and building genuine relationships.
A few years into my career, my husband deployed, and I took a small step back professionally while still continuing to help clients buy and sell homes. Being a military spouse myself has really shaped how I approach real estate. I understand firsthand how overwhelming it can feel to constantly move, learn a new area, figure out where everything is, and try to make an unfamiliar place feel like home.
That’s why I’ve always wanted to be more than just a real estate agent to my clients. I want to be someone they can trust — someone honest about the home, the area, the lifestyle, and whether it truly fits their needs. Especially for military families, a home is so much more than just a house. These are the places where families create memories, celebrate milestones, endure deployments, and build their lives, whether they’re there for two years or ten.
I also became passionate about helping military families build generational wealth through homeownership because I know how easily that community can sometimes be overlooked or taken advantage of. Since I live this lifestyle too, it’s incredibly meaningful to help other families navigate those transitions and find a place that genuinely feels like home.
We all face challenges, but looking back would you describe it as a relatively smooth road?
My real estate career has been anything but a smooth road. Between constantly shifting markets, learning entirely new areas quickly, and navigating military life and frequent moves, there have been a lot of challenges along the way. Every time we received new orders, it felt like I had to pause everything I had built and then immediately figure out how to rebuild it all over again in a completely different place.
At times, that uncertainty has been exhausting, but it also created a level of determination and resilience in me that I don’t think would’ve existed otherwise. Real estate takes a tremendous amount of hard work, consistency, and persistence. Of course, luck can help, but I’ve learned very quickly that I can’t rely on luck alone. There were definitely moments early in my career where I questioned whether I should keep going at all.
One of the hardest parts has honestly been trying to build a business while constantly moving. In real estate, people always say “your network is your net worth,” and for many agents, their network has been built over decades in the same hometown or city. Meanwhile, I’ve often moved somewhere where the only person I knew was my husband. I’d sit in masterminds surrounded by agents who had deep roots and lifelong connections in one place, and my experience looked completely different.
Because of that, I had to learn how to build relationships quickly, network intentionally, and adapt fast. Sometimes I was already networking before we even moved just to prepare myself. It taught me how to connect with people genuinely and how to rebuild from the ground up more than once.
While it’s been difficult, I truly believe those experiences shaped me into a stronger person and a better agent. It taught me resilience, adaptability, and how to keep showing up even when things feel uncertain. If you want something badly enough, you keep working for it — even when the path isn’t easy or guaranteed. And even through the struggles, the lessons and growth along the way have been invaluable.
Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I specialize in helping military families, first-time homebuyers, and relocating clients navigate the home buying and selling process with confidence. Because I’m a military spouse myself, I understand firsthand how stressful and emotional moving can be especially when you’re trying to make huge financial decisions while balancing deployments, timelines, uncertainty, and starting over in a completely new place.
What I’m really known for is being relationship-focused and honest. I never want clients to feel like just another transaction. I genuinely care about helping people find a home and community that fits their lifestyle, goals, and future. I’m the type of agent who will tell clients the truth, point out concerns, help them understand the area, and make sure they feel comfortable every step of the way. I want people to feel like they have someone in their corner, not just someone unlocking doors.
I’m also very adaptable because of my background. Having to restart my business multiple times in different states taught me how to build connections quickly, communicate well, and truly understand people’s needs. It’s made me incredibly driven and resourceful.
What I’m most proud of is building a successful business despite constantly moving and having to start over. Growing my business through relationships, referrals, and repeat clients means a lot to me because it shows people genuinely trusted me during some of the biggest decisions of their lives. I’m especially proud to help military families build stability and generational wealth through homeownership because I know how important that can be for our community.
I think what sets me apart is that I don’t just understand relocation professionally — I live it personally. I know what it feels like to arrive somewhere new and try to make it feel like home, and I bring that understanding into every client relationship.
What’s next?
Right now, the biggest change in my life is our recent move to Portland, Maine. Honestly, at first I wasn’t sure if I wanted to restart my real estate career again for the fourth time in just five years, but the more time I spend here, the more excited I become about this next chapter.
I’ll be taking my Maine real estate exam soon, and I’m definitely keeping my fingers crossed everything goes well so I can continue doing what I love, helping people navigate major life transitions and find a place that truly feels like home.
What makes this move different is that I genuinely love Maine and the lifestyle here. The outdoors, the community, the slower pace, and the overall quality of life have really inspired me. I’m excited not only to help military families relocate here, but also to help people who are looking for a lifestyle shift and a deeper connection to nature, adventure, and community.
My hope is that this becomes a long-term home for my husband and me after military life, where we can really build a beautiful life together. Professionally, I’m looking forward to continuing to grow my business, build meaningful relationships, and create a brand that blends real estate, relocation, lifestyle, and the outdoors in an authentic way.
Hopefully very soon I’ll be able to help people with all of their home buying and selling needs here in Maine and help them fall in love with this place the same way I have.
Contact Info:
- Website: https://Cheyennestarconner.exprealty.com
- Instagram: _cheyenneconner & cheyenne.inmaine
