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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.
$740,000
1158 Bulevar De Palmas

1158 Bulevar De Palmas

6 Beds | 4 Baths | 3,090 Sq.Ft.
$2,750,000
201 E Ocean Drive Unit: 3-107

201 E Ocean Drive Unit: 3-107

2 Beds | 2 Baths | 1,034 Sq.Ft.
$600,000
230 10Th Street

230 10Th Street

2 Beds | 2 Baths | 960 Sq.Ft.
$790,000
7047 Harbor Village Drive Unit: and dock #30

7047 Harbor Village Drive Unit: and dock #30

4 Beds | 3 Baths | 1,320 Sq.Ft.
$1,400,000
480 E 105th Street Ocean

480 E 105th Street Ocean

3 Beds | 2 Baths | 1,188 Sq.Ft.
$572,500
304 109th St Ocean

304 109th St Ocean

2 Beds | 2 Baths | 1,248 Sq.Ft.
$565,000
755 W Ocean Drive Unit: 3

755 W Ocean Drive Unit: 3

1 Beds | 1 Baths | 675 Sq.Ft.
$480,000
1133 W Ocean Drive Unit: 35

1133 W Ocean Drive Unit: 35

2 Beds | 3 Baths | 1,750 Sq.Ft.
$690,000
521 11Th Street

521 11Th Street

2 Beds | 3 Baths | 1,247 Sq.Ft.
$1,695,000
755 W Ocean Drive Unit: 7

755 W Ocean Drive Unit: 7

1 Beds | 1 Baths | 675 Sq.Ft.
$485,000
755 W Ocean Drive Unit: 5

755 W Ocean Drive Unit: 5

1 Beds | 1 Baths | 675 Sq.Ft.
$515,000
29842 Journeys End Road

29842 Journeys End Road

2 Beds | 2 Baths | 1,040 Sq.Ft.
$680,000
1001 W Ocean Drive Unit: 2-106

1001 W Ocean Drive Unit: 2-106

2 Beds | 2 Baths | 1,352 Sq.Ft.
$640,000
1047 68th Street

1047 68th Street

2 Beds | 2 Baths | 1,232 Sq.Ft.
$750,000
11340 6th Avenue Ocean

11340 6th Avenue Ocean

2 Beds | 2 Baths | 1,400 Sq.Ft.
$1,100,000
12411 Overseas Highway Unit: 35A

12411 Overseas Highway Unit: 35A

| 11.11 Sq.Ft.
$159,000
2000 Coco Plum Drive Unit: 1202

2000 Coco Plum Drive Unit: 1202

1 Beds | 2 Baths | 792 Sq.Ft.
$465,000
200 13th Street

200 13th Street

9,400 Sq.Ft.
$1,300,000
200 - 210 11Th Street

200 - 210 11Th Street

3 Beds | 3 Baths | 1,534 Sq.Ft.
$1,580,000
201 9th Street

201 9th Street

2 Beds | 2 Baths | 1,049 Sq.Ft.
$832,250
201 E Ocean Drive Unit: 209

201 E Ocean Drive Unit: 209

2 Beds | 2 Baths | 1,121 Sq.Ft.
$585,000
220 4th Street

220 4th Street

2 Beds | 2 Baths | 1,155 Sq.Ft.
$775,000
240-250 11th Street

240-250 11th Street

4 Beds | 4 Baths | 2,151 Sq.Ft.
$1,650,000
246 Guava Avenue

246 Guava Avenue

3 Beds | 2 Baths | 1,198 Sq.Ft.
$405,000
25 Sadowski Causeway

25 Sadowski Causeway

2 Beds | 2 Baths | 900 Sq.Ft.
$515,000
441 10th Street

441 10th Street

2 Beds | 2 Baths | 885 Sq.Ft.
$862,000
491 10th Street

491 10th Street

3 Beds | 3 Baths | 1,923 Sq.Ft.
$1,160,000
501 E Ocean Drive Unit: 22

501 E Ocean Drive Unit: 22

2 Beds | 2 Baths | 1,001 Sq.Ft.
$800,000
501 E Ocean Drive Unit: 9

501 E Ocean Drive Unit: 9

2 Beds | 2 Baths | 1,001 Sq.Ft.
$777,500
540 11Th Street

540 11Th Street

2 Beds | 2 Baths | 1,061 Sq.Ft.
$875,000
540 12th Street

540 12th Street

2 Beds | 2 Baths | 1,636 Sq.Ft.
$1,325,000
57547 Gibson Street

57547 Gibson Street

3 Beds | 1 Baths | 952 Sq.Ft.
$565,000
581 11th Street

581 11th Street

3 Beds | 2 Baths | 1,624 Sq.Ft.
$2,000,000
590 11th Street

590 11th Street

2 Beds | 2 Baths | 1,141 Sq.Ft.
$1,025,000
601 W Ocean Drive Unit: 401A

601 W Ocean Drive Unit: 401A

2 Beds | 2 Baths | 1,234 Sq.Ft.
$435,000
6099 Overseas Highway Unit: 40E

6099 Overseas Highway Unit: 40E

1 Beds | 1 Baths | 485 Sq.Ft.
$340,000
630 10th Street

630 10th Street

3 Beds | 2 Baths | 1,558 Sq.Ft.
$1,200,000
65 Sea View Avenue

65 Sea View Avenue

3 Beds | 2 Baths | 2,140 Sq.Ft.
$1,500,000
65 Tingler Lane

65 Tingler Lane

2 Beds | 2 Baths | 1,232 Sq.Ft.
$1,450,000
73 7th Street

73 7th Street

2 Beds | 2 Baths | 915 Sq.Ft.
$715,000
74 7th Street

74 7th Street

2 Beds | 2 Baths | 915 Sq.Ft.
$705,000
755 W Ocean Drive Unit: 8

755 W Ocean Drive Unit: 8

1 Beds | 1 Baths | 675 Sq.Ft.
$499,000
76 7th Street

76 7th Street

2 Beds | 2 Baths | 1,185 Sq.Ft.
$860,000
799 W Ocean Drive Unit: 301

799 W Ocean Drive Unit: 301

2 Beds | 2 Baths | 1,650 Sq.Ft.
$1,375,000
846 E Copa D Oro

846 E Copa D Oro

3 Beds | 2 Baths | 2,670 Sq.Ft.
$1,910,000
View All

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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Khris R.

Khris R.

Tracy was an absolute pleasure to work with and her expertise in the local market was invaluable. She went above and beyond her duties as a realtor by overseeing repairs and adding her personal touch to the home to make sure it...
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Katie W.

Katie W.

Tracy was such a great realtor for us. I say us because she had to negotiate the fine line between aged parents and their desire for a quick and easy sale of their condo that they no longer used. Tracy was so kind and patient b...
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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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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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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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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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Phyllis K.

Phyllis K.

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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Luz & Jeff F.

Luz & Jeff F.

Tracy is the best real estate agent hands down! She just helped us sell our condo in Key Colony Beach and we couldn't be happier with the results. Tracy had our property under contract in less than 5 days and the final sale exc...
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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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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 bought 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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Larry F.

Larry F.

Tracy was the most professional and knowledgeable realtor I’ve ever worked with . The buying process was very easy, organized and on schedule. Everything worked out wonderfully for a quick close. I would highly recommend Tracy.
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Cliff V.

Cliff V.

Our friend, who is a real estate agent in Ohio, was staying at our place in Key Colony when she met Tracy at an open house. Knowing we were considering selling, she highly recommended Tracy based on their conversation—and hirin...
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Tully D.

Tully D.

I listed both my condos in Key Colony Beach with Tracy and she had them both sold within a week. Due to her professionalism and hustle I highly recommend her service.
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Carlos O.

Carlos O.

You can count on Tracy to make it happen! Highly recommend!
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Find your next dream home.

Browse Homes

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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