Property Manager - 200 Unit Community | Winter Park, FL | Semoran Blvd
Classet · Winter Park, Florida, United States · Posted Jul 8, 2026
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RENT PROSPER is Hiring a Property Manager!
Job Type: Full-Time | On-Site
Salary: $55,000–$65,000 base + monthly performance bonus up to 20%
Schedule: Monday–Friday, 8:30 AM – 5:00 PM
Location: Winter Park Woods - 349 Scottsdale Square, Winter Park, FL 32792
Start Date: Within 2–4 weeks
Please submit an updated resume with your application.
This Isn't a Corporate Property Management Job. That's the Point.
If you're burned out on red tape, tired of waiting weeks for simple decisions to get approved, and ready to actually feel the impact of your work — keep reading.
Rent Prosper is a locally owned and operated Orlando property management company. We're not Greystar. We're not RPM. We're not Lincoln. We're not McKinley. We're a team of about 40 people.
Our owners Josh, Dan, and Kimia show up every single day. They work right alongside the team, they know everyone by name, and when a decision needs to get made — it gets made fast. No corporate delays.
We're growing. We have an immediate opening for a proven Property Manager to lead a residential community of under 200 units in the Orlando area.
The Role
You'll be the person running the show. Day-to-day operations, resident relationships, leasing, and partnering with your team, Leasing Professional, Maintenance Supervisor, and Technician, to keep things running well.
This property is part of a growing portfolio. As our client adds units and expands, there's real room to grow with us.
Here's a big perk most managers don't get: The HOA handles all exterior building maintenance, grounds, and amenities. That's completely off your plate — so you can stay focused on your residents and your team.
What you'll be doing day to day:
Building strong relationships with residents and keeping them happy
Leasing vacant units — from first contact all the way through move-in
Overseeing work orders and staying in sync with your Maintenance Supervisor
Managing vendors and keeping projects on track
Keeping accurate records, lease files, and financial reporting in Yardi
Working professionally alongside the HOA
Weekly check-ins and reporting to our Regional Manager
Why Rent Prosper
We know you have other options. Here's what's different about us:
Our owners are here. Josh, Dan, and Kimia work in the business every day. They know your name. They back their managers. Decisions happen fast — no long approval chains, no waiting on someone two states away.
We recognize our people. Every quarter we bring the whole company together for an all-staff meeting. We go over how things are going and we hand out real recognition awards — for top Google reviews and for people who live out our core values. It's not just talk.
Our Christmas party has cash prizes. We do a holiday presentation and then go bowling — where every team member earns cash for every strike their teammates roll. It's loud, competitive, and something everyone looks forward to.
When you do well, you get paid more. Our monthly performance bonus program is based on leasing results, resident retention, and key metrics. Top performers can earn an additional 10–20% of their salary on top of their base pay.
We're growing and you can grow with us. We've gone from 20 to 40+ team members and we're not slowing down. The right person has real upward opportunity here.