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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.

Sold Properties

1001 W Ocean Drive Unit: 1-204

1001 W Ocean Drive Unit: 1-204

2 Beds | 2 Baths | 1,343 Sq.Ft.

1158 Bulevar De Palmas

1158 Bulevar De Palmas

6 Beds | 4 Baths | 3,090 Sq.Ft.

201 E Ocean Drive Unit: 3-107

201 E Ocean Drive Unit: 3-107

2 Beds | 2 Baths | 1,034 Sq.Ft.

230 10Th Street

230 10Th Street

2 Beds | 2 Baths | 960 Sq.Ft.

7047 Harbor Village Drive Unit: and dock #30

7047 Harbor Village Drive Unit: and dock #30

4 Beds | 3 Baths | 1,320 Sq.Ft.

480 E 105th Street Ocean

480 E 105th Street Ocean

3 Beds | 2 Baths | 1,188 Sq.Ft.

304 109th St Ocean

304 109th St Ocean

2 Beds | 2 Baths | 1,248 Sq.Ft.

755 W Ocean Drive Unit: 3

755 W Ocean Drive Unit: 3

1 Beds | 1 Baths | 675 Sq.Ft.

1133 W Ocean Drive Unit: 35

1133 W Ocean Drive Unit: 35

2 Beds | 3 Baths | 1,750 Sq.Ft.

521 11Th Street

521 11Th Street

2 Beds | 3 Baths | 1,247 Sq.Ft.

755 W Ocean Drive Unit: 7

755 W Ocean Drive Unit: 7

1 Beds | 1 Baths | 675 Sq.Ft.

755 W Ocean Drive Unit: 5

755 W Ocean Drive Unit: 5

1 Beds | 1 Baths | 675 Sq.Ft.

29842 Journeys End Road

29842 Journeys End Road

2 Beds | 2 Baths | 1,040 Sq.Ft.

1001 W Ocean Drive Unit: 2-106

1001 W Ocean Drive Unit: 2-106

2 Beds | 2 Baths | 1,352 Sq.Ft.

1047 68th Street

1047 68th Street

2 Beds | 2 Baths | 1,232 Sq.Ft.

11340 6th Avenue Ocean

11340 6th Avenue Ocean

2 Beds | 2 Baths | 1,400 Sq.Ft.

12411 Overseas Highway Unit: 35A

12411 Overseas Highway Unit: 35A

2000 Coco Plum Drive Unit: 1202

2000 Coco Plum Drive Unit: 1202

1 Beds | 2 Baths | 792 Sq.Ft.

200 13th Street

200 13th Street

200 - 210 11Th Street

200 - 210 11Th Street

3 Beds | 3 Baths | 1,534 Sq.Ft.

201 9th Street

2 Beds | 2 Baths | 1,049 Sq.Ft.

201 E Ocean Drive Unit: 209

201 E Ocean Drive Unit: 209

2 Beds | 2 Baths | 1,121 Sq.Ft.

220 4th Street

2 Beds | 2 Baths | 1,155 Sq.Ft.

240-250 11th Street

240-250 11th Street

4 Beds | 4 Baths | 2,151 Sq.Ft.

246 Guava Avenue

246 Guava Avenue

3 Beds | 2 Baths | 1,198 Sq.Ft.

25 Sadowski Causeway

25 Sadowski Causeway

2 Beds | 2 Baths | 900 Sq.Ft.

441 10th Street

441 10th Street

2 Beds | 2 Baths | 885 Sq.Ft.

491 10th Street

491 10th Street

3 Beds | 3 Baths | 1,923 Sq.Ft.

501 E Ocean Drive Unit: 22

501 E Ocean Drive Unit: 22

2 Beds | 2 Baths | 1,001 Sq.Ft.

501 E Ocean Drive Unit: 9

501 E Ocean Drive Unit: 9

2 Beds | 2 Baths | 1,001 Sq.Ft.

540 11Th Street

540 11Th Street

2 Beds | 2 Baths | 1,061 Sq.Ft.

540 12th Street

540 12th Street

2 Beds | 2 Baths | 1,636 Sq.Ft.

57547 Gibson Street

57547 Gibson Street

3 Beds | 1 Baths | 952 Sq.Ft.

581 11th Street

581 11th Street

3 Beds | 2 Baths | 1,624 Sq.Ft.

590 11th Street

590 11th Street

2 Beds | 2 Baths | 1,141 Sq.Ft.

601 W Ocean Drive Unit: 401A

601 W Ocean Drive Unit: 401A

2 Beds | 2 Baths | 1,234 Sq.Ft.

6099 Overseas Highway Unit: 40E

6099 Overseas Highway Unit: 40E

1 Beds | 1 Baths | 485 Sq.Ft.

630 10th Street

630 10th Street

3 Beds | 2 Baths | 1,558 Sq.Ft.

65 Sea View Avenue

65 Sea View Avenue

3 Beds | 2 Baths | 2,140 Sq.Ft.

65 Tingler Lane

65 Tingler Lane

2 Beds | 2 Baths | 1,232 Sq.Ft.

73 7th Street

2 Beds | 2 Baths | 915 Sq.Ft.

74 7th Street

2 Beds | 2 Baths | 915 Sq.Ft.

755 W Ocean Drive Unit: 8

755 W Ocean Drive Unit: 8

1 Beds | 1 Baths | 675 Sq.Ft.

76 7th Street

2 Beds | 2 Baths | 1,185 Sq.Ft.

799 W Ocean Drive Unit: 301

799 W Ocean Drive Unit: 301

2 Beds | 2 Baths | 1,650 Sq.Ft.

846 E Copa D Oro

846 E Copa D Oro

3 Beds | 2 Baths | 2,670 Sq.Ft.

Aspire to live inspired.

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...

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.

Phyllis

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

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...

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...

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...

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...

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...

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...

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.

Find your next dream home.

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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Contact Details

Tracy Chacksfield

Phone

(305) 912-2177

Email

[email protected]

Address

9141 Overseas Hwy Marathon FL 33050

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By providing Tracy Chacksfield your contact information, you acknowledge and agree to our Privacy Policy and consent to receiving marketing communications, including through automated calls, texts, and emails, some of which may use artificial or prerecorded voices. This consent isn’t necessary for purchasing any products or services and you may opt out at any time. To opt out from texts, you can reply, ‘stop’ at any time. To opt out from emails, you can click on the unsubscribe link in the emails. Message and data rates may apply.