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Real Estate Agents in Kissimmee, FL

7 best Real Estate Agents in Kissimmee, FL that specialize in real estate investments. Updated August 31, 2025. See agent reviews, ratings, and investment specialties.

  • Judson Osbon's profile image

    Judson Osbon

    RE/MAX Prime Properties

    Residential

    Commercial

    5.0 stars
    13 Reviews
    56 forum posts

    Residential

    Commercial

    Investor-friendly agent specializing in Long-term rentals, buy & hold, small multi-family, house-hacking, BRRRR and mobile-home parks. I am NOT currently taking new clients for fix & flip or Short Term Rentals. Minimum price point $300k. I bought my first home when 23 years old and I house hacked for years (long before the term existed) by renting the two additional bedrooms. Years later I met my would be wife and she promptly chased my roommates off. Ultimately, I totally flipped the hous... view more
  • Tyler Gibson's profile image

    Tyler Gibson

    GPG Team

    Residential

    5.0 stars
    81 Reviews
    1379 forum posts

    Residential

    The GPG Team is your go-to real estate partner for building wealth, finding the perfect home, or making a smooth sale. We specialize in working with both buyers and sellers—from first-time house hackers to seasoned investors—offering personalized guidance and clear strategy every step of the way. Whether you're planning your first purchase, scaling a portfolio, or preparing to sell, our mission is to simplify the process, maximize your results, and help you reach your financial goals through ... view more
  • Jadel M Patterson's profile image

    Jadel M Patterson

    Keller Williams Advantage Realty Realty

    Residential

    5.0 stars
    78 Reviews
    8 forum posts

    Residential

    HOUSE HACK/BUY & HOLD LONG-TERM RENTALS/SHORT-TERM RENTALS/CO-LIVING/PADSPLITS! Taking care of people. That´s what I love to do. I always thought I´d be a doctor or physical therapist, so I went to college and got an Associate of Science in Pre-Physical Therapy Studies and then a Bachelor of Science in Biology with a minor in Chemistry. These degrees gave me a framework for how to think analytically, and developed patience and perseverance in me. After college, I joined the United States Army... view more
  • Danae Pitcher's profile image

    Danae Pitcher

    Florida Resort Realty

    Residential

    5.0 stars
    5 Reviews
    36 forum posts

    Residential

    I have worked in the Central Florida real estate market for over 20 years. I specialize in Vacation Homes sales and Investment Properties in the most popular tourist destination in the world. I have been a top producer since 2005 with millions of dollars in sales annually and have extensive knowledge of the market. My attention to detail and willingness to go above and beyond for my clients is what has enabled me to enjoy a successful career in real estate. I align myself with some of the top... view more
  • Matthew Lamoreaux's profile image

    Matthew Lamoreaux

    Matthew Lamoreaux Realtor

    Commercial

    Residential

    22 forum posts

    Commercial

    Residential

    I'm passionate about real estate and have first hand experience in investing. Specialties: Fix & flip, buy & hold, STR, MTR, and house hacking. Retired Veteran (Marine Corps/ US Army), passionate about family (to include pets), friends, helping others, travel, fitness, and finding you the perfect home for you and your needs. view more
  • Cristina Perez's profile image

    Cristina Perez

    Cristina Properties

    Residential

    5.0 stars
    70 Reviews

    Residential

    I specialize in investment properties, with a keen focus on the short-term rental market. My journey in real estate is driven by a deep-rooted passion for empowering and guiding clients from around the globe discover the lucrative opportunities that Florida's market offers. I pride myself on aligning with some of the top companies in the business. From contractors ready for small repairs or major renovations to short-term rental management companies who can maintain your home and optimize ... view more
  • James McQuade's profile image

    James McQuade

    Jim McQuade - Broker - Author - Mentor

    Residential

    5.0 stars
    128 Reviews

    Residential

    Jim McQuade is a top Short-Term Rental (STR) agent in Central Florida, with extensive experience and industry connections. Ranked in the Top 5% in Florida for Customer Satisfaction and Top 10% in the U.S. A Ramsey Trusted ELP and consistently a Top 5 ELP in Florida. Recognized as a BiggerPockets Preferred Agent as well as a Rabbu Preferred Agent, specializing in investment properties. Originally from Philadelphia, Jim has lived in Central Florida for over 30 years. He is dedicate... view more
Showing 1 - 7 of 7 Kissimmee Agents

How to Find Investment Properties in Kissimmee, FL


For real estate investors, finding the right REALTOR® or real estate agent is crucial for successful investments in Kissimmee, FL—whether you're looking at residential or commercial properties in the Kissimmee area. Working with real estate agents in Kissimmee will give you an understanding of market trends for the surrounding areas when buying or selling properties.

Identifying the right investment property to generate rental income requires time, energy, and patience. While real estate agents can assist in this search, it's essential to choose the right one who is familiar with the specific areas of Kissimmee, FL. Not all agents have a strong understanding of investment properties, so it's essential to find investor-friendly ones to ensure you achieve your desired profits.

What Is an Investor-Friendly Real Estate Agent?

Not all real estate agents know the features investors need when purchasing rental properties. Some real estate agents work primarily with buyers looking for a primary residence. These buyers have many different needs than real estate investors. Primary residence real estate agents focus on features primary homebuyers need for their family versus considering after-repair value, the local rental market, or renovation costs. An investor-friendly agent understands the business side of purchasing rental properties and will help investors find properties that not only meet their budget but also help them achieve their investment goals.

You need a real estate agent with the pulse on everything real estate-related, including off-market properties, rental income, demand, renovation, the local market, and overall costs.

Finding a good rental property requires a lot of help from many professionals to make it work. It takes a village to invest in real estate.

Testimonials

"It was great and easy. I received emails and calls from two of the agents almost immediately"

Drew N.

"The agent seemed to be very knowledgeable and thorough"

Jonathan M.

"Found two great and professional agents very quickly. Literally no complaints and way better than googling it"

Tommy H.

"I received communication almost right away regarding my inquiry"

Wendy M.

"The easy way to connect and find the people of interest"

Euviel L.

"I found a few agents from several options available, thank you!"

Jordan D.

"It was great and easy. I received emails and calls from two of the agents almost immediately"

Drew N.

"Very simple. Contacted 2 different agents, got quick responses. I think I chose a great agent, my property is listed for sale. I'm happy so far!"

Michael B.

"Quick response. Willingness to connect and search for target homes."

Richmond M.