Kevin Osborn

Born and raised in Michigan, I first discovered North County San Diego in 2014—and it didn’t take long to feel at home. The coastal lifestyle, vibrant community, and year-round sunshine made a lasting impression. Today, my wife Anna (a proud Encinitas native), our two dogs Rusty and Penny, and I are lucky to call Leucadia home.
After earning my degree in Accounting from the University of Notre Dame, I began my career as a CPA with a Big 5 public accounting firm in Chicago. While the experience was invaluable, I was driven to find a more balanced and meaningful path. That led me to spend a year with Habitat for Humanity DC—an experience that deeply shaped my perspective and sparked a lasting passion for homeownership, as well as building and renovation.
I went on to spend 20 years in the sports industry, working with some of the world’s most recognized brands. Along the way, I built a diverse skill set across finance, analytics, sales, and marketing—always focused on delivering results and creating strong, lasting relationships.
Real estate is where all of these experiences come together. It’s not just about buying or selling property—it’s about guiding people through one of the most important decisions of their lives with confidence, clarity, and trust.
As a Senior Real Estate Specialist, I’m passionate about helping seniors and their families navigate the transition of downsizing with care, clarity, and confidence. I understand that these decisions often involve both practical considerations and deep emotional ties, and I take pride in being a steady, patient guide for everyone involved. Whether I’m working directly with clients or partnering with adult children supporting their parents, my focus is on creating a thoughtful, well-paced process where every question is answered and every concern is respected.
I’m proud to be part of the team at Swell Property and to serve this incredible community. Whether you’re buying, selling, or simply exploring your options, I’m here to be a dedicated, knowledgeable, and collaborative partner every step of the way. I look forward to earning your trust.