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Real Estate Agents in Winter Park, FL

4 best Real Estate Agents in Winter Park, FL that specialize in real estate investments. Updated March 14, 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, fix & flips, BRRRR and mobile-home parks. I do not work in STR. 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 house while living in it over 10 years. Being ... view more
  • Matthew Lamoreaux's profile image

    Matthew Lamoreaux

    Matthew Lamoreaux Realtor

    Commercial

    Residential

    10 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
  • James McQuade's profile image

    James McQuade

    Jim McQuade - Broker - Author - Mentor

    Residential

    5.0 stars
    95 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
  • Garrett Elrod's profile image

    Garrett Elrod

    Garrett Elrod and Tyler Labod

    Residential

    Commercial

    5.0 stars
    38 Reviews

    Residential

    Commercial

    Ranked #1 in Orlando for maximizing investor ROI view more
Showing 1 - 4 of 4 Winter Park Agents

How to Find Investment Properties in Winter Park, FL


For real estate investors, finding the right REALTOR® or real estate agent is crucial for successful investments in Winter Park, FL—whether you're looking at residential or commercial properties in the Winter Park area. Working with real estate agents in Winter Park 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 Winter Park, 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.