Property Manager - 200 Unit Community | Winter Park, FL | Semoran Blvd

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.

Requirements

• Proven experience as a Property Manager or Community Manager at a residential apartment or condo community
• Solid working knowledge of Yardi — you need to be comfortable on day one
• Strong leasing AND retention skills — this role needs both equally
• Experience managing vendors and working alongside a maintenance team
• Comfortable working with an HOA in a professional and collaborative way
• Valid driver's license
• Able to pass a pre-employment background and driving record check
• Strong written and verbal communication skills
• Someone who leads independently and doesn't need to be micromanaged
  

Benefits

• Base Salary: $60,000-$70,000 per year
• Monthly Performance Bonus: Up to 10–20% of salary based on leasing, retention, and key metrics
• 5-Star Service Bonus: Extra recognition when your residents love where they live
• Health Insurance: Up to $500/month company contribution toward the plan of your choice
• Dental Insurance: Complimentary coverage provided
• Life Insurance: Complimentary $25,000 policy
• PTO: 10 days to start — grows after year 2 and again after year 5
• Paid Holidays
• Birthday Bonus
• Work Anniversary Bonus
• Quarterly all-staff events with recognition awards
• Annual holiday party with team cash prizes
  

***Please submit an updated resume with your application.***

About RENT PROSPER

Rent Prosper is a locally owned property management company based in Orlando, FL. We manage single-family rentals and multifamily residential communities across Central Florida. Over the past few years we've grown from 20 to 40+ team members and we're continuing to expand.

Our Google reviews reflect the standard we hold ourselves to. We care about how we treat our residents and we care just as much about how we treat our team.

If you're a proven property manager who's ready to stop being a number at a big company and start making a real difference — we want to talk to you.