Tracy Chacksfield

Tracy Chacksfield

Sales Associate
9141 Overseas Hwy
Marathon, FL 33050


Why the Florida Keys?

“I like to call it Island Alchemy. Sounds like the perfect title of a Carl Hiaasen book or Jimmy Buffett song, right?!” says Tracy, “it’s a place to unplug, relax, meet some colorful characters, breathe in salty air, experience beautiful natural surroundings and enjoy year-around warm weather!” 

Originally from California, Tracy began her career in commercial real estate in Santa Fe, NM, which in turn took her to Chicago, IL where she spent 23 successful years in asset management. During her time in Chicago, Tracy oversaw extensive real estate portfolios, throughout the Midwest and Southeast, for both institutional partners and private investors. All through her career, Tracy evaluated properties, guided, managed, and advised owners on achieving their real estate investment goals.

After years spent going between homes in both Chicago and Key Colony Beach, Tracy decided to permanently trade in snow boots for sandals, city living for island living, and commercial real estate for residential real estate. Tracy had the good fortune to hit the ground running when one of the top agents in the market, Karen Raspe, invited Tracy to partner with her, resulting in a record first year together of over $45,000,000 in sales and more than 40 transactions. Upon making Key Colony Beach her home base, Tracy recalls with laughter, “I pulled into town late one Sunday night, Karen called that Tuesday, ‘Ready to start?’ and by Saturday I was already assisting Karen at an open house.”  To this day, Karen and Tracy continue to partner, providing superior results and excellence in service for their clients.

Patient, genuine and committed to her clients’ success, Tracy offers invaluable insight into the nuances of the various communities in the Keys, with a focus on the Middle Keys. Representing Keys homeowners and future homeowners, Tracy is committed to listening to her clients’ needs and utilizing her strong negotiating skills to ensure a successful transaction. She also has a knack for numbers, an eye for interior design and seeing potential in every property. Clients and fellow agents appreciate her work ethic, business acumen, and easy-going style.

When Tracy’s not holding an open house or searching for the ideal property for a client, she enjoys relaxing at Inch Beach with a good book, hosting friends for a nice meal (prepared by her husband.... he cooks, she cleans!), exploring Italy and spending time with her pups, Massi and Addie.


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Agent Listings


Listing ID604607
Total Baths2
Full Baths2
SqFt 1,232
Acres 0.190
SubdivisionSea crest (50.5)
Designed to capture the natural beauty of the Florida Keys within the shores of Marathon, this nearly new property features sweeping views of the Atlantic's aquamarine waters. Outdoor living is at...
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