Hi, I'm Tracy Chacksfield

For some, real estate is a career. For me, it’s always been a lifelong calling.
A born go-getter from California, I started my professional journey in Santa Fe, NM in property management. Before long, I pivoted to commercial asset management, taking me to Chicago. For nearly 25 years, I worked with both private and institutional investors throughout the Midwest and Southeast, overseeing virtually every aspect of their multi-million-dollar real estate portfolios, including the management of capital projects, budgets, financials, new developments, branding, marketing, and teams. Throughout my consistent growth, one goal remained paramount – to maximize value and help investors make the most of their real estate ventures.

Tracy Chacksfield Realtor
Tracy Chacksfield - Middle Keys, FL Real Estate

Residential real estate is my passion, and it shows
Outside of work, I became the go-to person for real estate advice within my inner circle of family and friends. I was recognized for my passion for residential real estate. Whenever someone wanted to buy, sell, or renovate a home, they would call me for my brass-tacks knowledge, time-tested insights, and general level-headedness to help them navigate the process.

Working in the Florida Keys has been a dream
As consistent as my career growth was, so too were my trips back and forth between a home in Chicago and my beloved island getaway on Key Colony Beach. So, when it was time for a life and career change, there was no question about what I would do or where I would go: Residential real estate in the Florida Keys. I moved permanently to the island and got to work.

My analytical skills and strong work ethic have been influential in securing decisive collaborations that better serve my clients
My decision to relocate was met with an invitation to partner with one of the top real estate professionals in the Middle Keys, Karen Raspe. Having represented me in the purchase and sale of two homes in Key Colony Beach, Karen recognized my professional and analytical skills, as well as my strong Midwest work ethic. We both felt our collaboration would be very successful, and it was. Together, we had a record-breaking first year, with more than 40 transactions and $45 million in sales. We continue to join forces to connect our clients with their ideal properties in the distinct and colorful communities here in the Keys, with a focus on the Middle Keys.

I live life to the fullest and want my clients to as well
When I’m not working, I like to unwind by spending time on the water with family and friends, relaxing at Inch Beach, sampling my husband’s culinary creations, walking with my beloved dogs, Massi and Addie, and venturing off to Italy as often as I can.

Tracy Chacksfield
What they say about me

Client Testimonials