Kris Kennedy Top real estate agent in Winter Park

Kris Kennedy

Compass
11 Years of Experience
(43)
$25M
Total Sales Last Year
11
Years of Experience
65
Recent TransactionsTransactions from the last 3 years
$762.5K
Average Price Point

    Service Areas

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    About Kris Kennedy

    Kris Kennedy is widely recognized as one of the top real estate agents in Orlando, known for his strategic approach to luxury home sales, new construction, and high-end resales. As one of the founding real estate sales teams to partner with Compass in Winter Park, FL, Kris has helped shape the modern standard for premium real estate service in Central Florida.

    Kris's business is built on three pillars that consistently drive results:

    • Strong client and friend referrals earned through trust, performance, and long-term relationships

    • Top organic rankings on Yelp, where he is frequently recognized as a leading Winter Park realtor

    • Educational real estate resources on YouTube, where he breaks down the Orlando market, new construction insights, and buyer/seller strategy

    Proven Success in Orlando Real Estate Since 2015

    Since 2015, Kris has built a track record of success in Orlando real estate sales and marketing. He thrives in the areas that matter most to clients-strategic marketing, pricing, and negotiation-because each property and situation requires a tailored, skill-driven approach.

    A Realtor Who Understands the Process Personally

    Having relocated multiple times and actively invested in real estate himself, Kris understands the emotional and logistical challenges that come with buying or selling a home in Orlando. This firsthand experience fuels his commitment to making every transaction smooth, informed, and stress-free.

    Clients consistently choose Kris for his:

    • Exceptional personalized service

    • Tenacious work ethic

    • Professionalism and clear communication

    • Ability to simplify complex decisions

    These qualities set him apart in a competitive market and have earned him a loyal client base across Winter Park, Orlando, and surrounding communities.

    A Background Rooted in High Performance

    Before real estate, Kris built a successful career as a sport performance coach, working with elite organizations including:

    • United States Tennis Association

    • IMG Academy

    • Louisiana State University

    • New York University

    This background sharpened his discipline, communication skills, and ability to perform under pressure, traits that now directly benefit his real estate clients.

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    Specialties

    • Sellers
    • Buyers
    • Residential Property

    Awards

    • Five Star Award Image
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