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Expertise that elevates every decision.

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Meet Tracy Chacksfield

For some, real estate is a career. For me, it’s always been a lifelong calling.

Real estate has always been more than a career—it’s been a constant presence in my life. Before shifting to residential sales, I spent nearly 25 years in commercial real estate asset management while living in Chicago, overseeing multi-million-dollar portfolios for private and institutional investors across the Midwest and Southeast. During that time, I built a skillset around strategic planning, financial clarity, and long-term value—all of which now shape how I help residential clients make confident, well-informed decisions.

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Residential real estate is my passion, and it shows.

While my professional foundation was in commercial real estate, my passion was always residential. Friends and family routinely came to me for candid advice on buying, selling, or renovating—drawn to my grounded approach and ability to see the bigger picture. Eventually, that passion brought me to the Florida Keys, a place I had long considered a second home.

Working in the Florida Keys has been a dream.

Now based full-time in Key Colony Beach, I bring a strategic, analytical lens to residential real estate in the Middle Keys. In just my third year, I earned the Berkshire Hathaway HomeServices Chairman’s Circle Platinum award, placing me among the top 1% of BHHS agents worldwide. That recognition reflects what I continue to deliver—measurable results, trusted guidance, and a strong commitment to protecting my clients’ best interests.

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I live life to the fullest and want my clients to as well.

Real estate is part of my everyday life—in work and at home. My husband, now retired, spent his career as a commercial real estate developer, so conversations about markets and properties are second nature to us. When I step away from business, you’ll usually find me with a good book, enjoying time with our dogs, Massi and Addie, or planning our next trip to Italy.

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Aspire to live inspired.

Joshua L.

Joshua L.

It's been a little over two years since my wife and I first met Tracy when she helped make our dreams come true. We had gotten married in the Keys and then discovered Key Colony Beach, the most perfect little community. We star...
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Lisa C.

Lisa C.

Tracy is a fantastic realtor! She is extremely knowledgeable, very responsive and truly a pleasure to work with. A true professional that I would absolutely recommend to anyone looking for a home in the Keys.
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Phyllis

Phyllis

Tracy is very professional with a friendly approach to business. She takes time to understand your concerns and do her best for you.
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Katie M.

Katie M.

A little over a year ago, my husband and I sold our home in Denver and moved to the Florida Keys! It was time for us to slow down, simplify our lives, get out of the snow, smell the ocean salt and live the "island life". Findin...
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Jerry S.

Jerry S.

Tracy is the Best of the Best! Her professional real estate skills are the best I have found in Florida Keys! She is a prompt, professional, knowledgeable, honest, transparent, easy going, real estate agent who has great commun...
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Harley J.

Harley J.

I had the privilege of being represented by Tracy both as a buyer and seller, I can confidently attest to her exceptional skills and unwavering commitment. Tracy’s easy going style may be disarming, but it conceals a formidable...
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Chris H.

Chris H.

Tracy is what you wish for in a Realtor. We started looking for a place 2 years ago. She knew exactly what we were looking for and only sent us the properties that fit our specs. In the age of spamming and overselling, Tracy wa...
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Melissa M.

Melissa M.

Tracy was recommended to us by friends. We knew from the first conversation that she was a perfect fit to help us find our dream Marathon home. Being out of town buyers went from stressful to relaxed with her expertise and dire...
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Scott R.

Scott R.

My wife and I recently sold our home in Key Colony Beach, and we couldn’t have asked for a better experience. Tracy is not only the best realtor we’ve worked with but also incredibly professional from start to finish. What we a...
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Brian D.

Brian D.

Tracy is the most professional workaholic I want and sold a home with her. She knows the ins and outs of the keys knows professionals to assist in any project and keeps giving advice after sales.
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Find your next dream home.

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Where island charm meets strategic expertise.

If you’re ready to buy, sell, or invest in the Keys, you need a trusted and knowledgeable real estate partner who understands the market and has a strong network. I’ll take the time to understand your needs and confidently guide you to the right opportunities.

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