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Property Management, Perfected.
Maximum Earnings. Minimum Stress.
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Central Florida Property Management

Let us manage your Winter Park Rental Property

Having a successful Winter Park rental property requires a lot of time, effort, experience and knowledge. Let us save you that time, effort and frustration that comes with gaining that experience.

As a full service Winter Park property management company, our team is responsible for taking care of all aspects of managing your rental(s).

How much rent can you get for your investment?

Our market analysis helps landlords and us make data-informed decisions about their rental property, including rate estimates and other information so they can invest and manage their investment property more wisely.

  • Get Optimized Rental Value for Your Property
  • Gain Crucial Insight into Current Market Conditions
  • Determine Your Cashflow from Monthly Rental Value

Get In Touch With Us

Not Sure What You Can Charge For Your Rental?

Find Out Now With Our Free Rental Analysis Report! No Obligations, Just Free Information.

$1,400

The average rent for a one bedroom rental in Winter Park, FL.

$1,850

The average rent for a two bedroom rental in Winter Park, FL.

$2,350

The average rent for a three bedroom rental in Winter Park, FL.

$?

Fill out the form to the
left to find out what you
should be charging.

Prices shown are estimates only, showing the median rate in a range of pricing for that type of single-family home. Current rental prices will vary based on actual property location, property condition and market fluctuations.

Why Choose Wilson Management Group

Why Hire Us Vs. Self-Managing

You’ll make more money – and spend less time maintaining your investment.

Some people assume that property management is expensive - but that’s not the case at all. You will actually make more money in the long run due to better quality tenants that stay longer and less damage or repairs to deal with.


Eliminate the constant run around & stress.

It is a full time job dealing with repairs, complaints, collecting rent and coordinating vendors. Transferring these responsibilities to a good property manager allows you to enjoy the benefits without spending all your free time working.


Better screening process = better tenants.

Because of our application tools and extensive resources, we can screen more tenants, and with more filters, ensuring you get the best renter for your investment. We often have a waiting list of potential renters and our eviction rate is extremely low.

Free Consult

Our Client Reviews Speak For Themselves

2023-03-02

"Can’t say enough good things about this company! We worked specifically w Mrs. Spano and would recommend - her work ethic is above and beyond!"

Jill Wirka

2022-10-19

"Simply the best property management company we have worked with. I am a contractor/vendor for Wilson Management and have witnessed for 22 years the dedication to their property owners and vendors the same! Managers such as Mr. Lionel Hebert make a huge difference!!"

Arman Hedayat

2023-05-01

"David is great. Would recommend to anyone looking for property. Makes you feel like more than a number."

Lindsey Dugger

2023-06-14

"I have used Wilson Mgt to oversee my Florida property for the past 12 years and can honestly say they have done a magnificent job. They have handled tenant screening, occupancy marketing, property maintenance, and more. Always professional and eager to serve. Lionel, the property manager assigned to me, is the best. He always gets the job done and exceeds my expectations every time. Today I needed photos taken to renew my landlord property insurance. Within a couple of hours, Lionel sent me complete set taken today. There may be a lot of competition out there, but no one could ever convince me to change from Wilson."

John Lee
Winter Park Property Management

Discover Winter Park

The city of Winter Park is located in Orange County, FL and was founded as a resort community by northern business magnates in the late 19th and early 20th centuries. Today it houses a population of just over 30,000 with a median household income of $80,500, median home rental costs of $1,372 per month and a median house value of $470,800. 

The historic downtown area, Park Avenue, is a robust mixture of civic buildings, upscale retail, fine dining, art galleries, a private liberal arts college (Rollins College), world class museums, a park, and a train station, all with the feel of a European Village.

Orange County Public Schools is the eighth-largest school district in the nation and the fourth-largest in Florida. U.S. News & World Report Best High Schools rankings has Winter Park High School ranked #84 out of Florida high schools, #7 in Orlando, FL metro area, and #3 in Orange County Public Schools.