Turning real estate dreams into “Pleasant” realities with honest guidance, responsive communication, and unwavering commitment.
I spent much of my childhood vacationing on Sanibel Island, Florida, trading cold winters for warm, sandy beaches. During one of those trips, my grandmother made the decision to relocate permanently to Florida, which ultimately shaped my family’s move. I relocated from upstate New York to Florida at the age of ten, and it immediately felt like home. I later attended the University of South Florida in Tampa, where I earned my Bachelor’s degree in Communication. While living in Tampa, I also met my former husband, and together we began building our life.
For seven years, I worked as an insurance fraud investigator. I investigated motor vehicle accidents, evaluated their legitimacy, and negotiated settlements—work that required attention to detail, research, and analytical thinking. During that chapter of my life, I also became a mother to my two children, Grayson and Ellison.
Life shifted when my ex-husband received a job offer in North Carolina. We relocated, and for a brief time I stayed home with the kids. While I treasured that year, I realized I missed adult conversation and intellectual stimulation. I discovered a love for working with children and found the perfect balance in teaching. I spent seven years teaching pre-K, a role I truly loved and one that allowed me to be present with my kids while doing meaningful work.
During those years in North Carolina, we invested in real estate and purchased/sold properties. That experience introduced me to the industry and allowed me to learn the business from the inside out. What started as an investment became a genuine interest—and then a calling.
As time went on, I found myself returning to Florida more and more. I would pack up the car, visit friends and family for long weekends, and drive back to North Carolina. Those trips became frequent enough that I couldn’t ignore what was surfacing: I missed Florida deeply, and it was calling me home.
When COVID allowed my ex-husband to work remotely, I convinced him to move back. I also told my parents, who had relocated north to be closer to their grandchildren. To my surprise—and relief—they were thrilled. We all missed Florida. I sold my home and theirs, and together we drove south.
That move was both literal and symbolic of more changes ahead. I became a substitute teacher, but my heart wasn’t in it. I kept thinking about real estate. Every career I had held shared a common thread—research, communication, organization, and care. Real estate felt like the place where all of those skills could finally come together. I earned my real estate license in 2021 and transitioned into the industry full-time.
At the same time, I faced the difficult truth that my marriage was no longer working. Choosing divorce wasn’t easy, especially when nothing was “wrong” on the surface, yet I wasn’t fully happy. Honoring that truth came at a cost: some friends didn’t understand, and I lost relationships.
At nearly 40 years old, I found myself ending a twenty-plus-year partnership while building a new career from the ground up. I’d never been on my own, and that season tested me—but it also forced me to become self-reliant, a gift I carry with me every day.
Today, I’m excited for what’s ahead. Grayson and Ellison are now 14 and 12, and competitive soccer keeps us traveling often. I love working out (I transformed my garage into a gym), spending time with my family, traveling—especially internationally—and giving back through volunteering with veterans’ foundations.
Real estate is more than a profession to me. It is a reflection of my personal journey and a passion rooted in understanding change, transition, and the true meaning of home. Having experienced these moments firsthand, I bring empathy, authenticity, and dedication to every client relationship.
What truly sets me apart is connection. I take the time to listen, ask thoughtful questions, and fully understand my clients’ goals so I can serve them with intention and clarity. I pride myself on being highly accessible and responsive, knowing that timely communication is essential not only in real estate, but in life. Earning my broker license is a reflection of my commitment to excellence and continuous growth.
With a strong focus on ongoing education and up-to-date market knowledge, I guide my clients confidently through every step of the process. Real estate can feel overwhelming, but my role is to simplify it, advocate fiercely, and provide trusted guidance along the way. I treat my clients like family, leading with integrity, care, and a genuine desire to help them succeed.
Sincerely,
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Kara Pleasant
Broker-Associate
Direct (239) 699-6382
pleasant.kara@gmail.com
karasells-swfl.com

