Location: Cypress Pointe, 4180 Versailles Dr, Orlando, FL 32808
On-Site Role | Full-Time | 200-Unit Property
Pay Rate: $28 – $31/hour
Schedule: Monday–Friday, 8:30 AM – 5:00 PM
Cool Perk: No Grounds, Trash, or Exterior Duties
Rent Prosper is seeking an experienced Maintenance Supervisor to lead our on-site team at a residential property in the Rosemont / Lake Orlando area.
If you’re a skilled hands-on leader with a strong background in HVAC, plumbing, electrical, and appliance repair, this is your chance to join a tight-knit, growth-oriented company that values work-life balance, teamwork, and reliability.
We pride ourselves on providing top-tier service to our residents through loyalty, reliability, problem-solving, integrity, and continuous improvement—the core of The Rent Prosper Way.
Oversee and perform maintenance on residential HVAC systems (10+ years old), plumbing, appliances, and electrical systems.
Manage unit turnovers: inspect, scope, repair, and prepare units for new tenants.
Complete daily work orders using a property management system (e.g., Yardi or AppFolio).
Maintain accurate logs of time, materials, receipts, and before/after photos.
Communicate professionally with residents and team members.
Submit weekly maintenance reports to the management team.
Ensure safety and quality standards are met on all maintenance projects.
Maintenance Scope Includes:
HVAC: Troubleshooting, full system repairs, and replacements (coils, compressors, fans, etc.)
Appliances: Installation and repair of stoves, refrigerators, washers/dryers, microwaves
Plumbing: Repairs and replacements for sinks, toilets, valves, water heaters, disposals
Electrical: Fixtures, fans, switches, receptacles, and appliance wiring
General: Drywall, touch-up painting, carpentry, and make-readies
Requirements
Valid driver’s license
Comfortable with pre-employment background screening
10+ years of maintenance experience (plumbing, electrical, appliances, make-readies)
7+ years of residential HVAC troubleshooting, repairs, and installations
5+ years of leadership experience managing an on-site maintenance team
EPA Certification
Benefits
Competitive Pay for a Small Property: $31hr
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
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.
