Demo

Property Manager

Cypress Key Property Management
Winter Haven, FL Full Time
POSTED ON 9/12/2026
AVAILABLE BEFORE 1/9/2027

PROPERTY MANAGER

Central FloridaFull-Time | In-Office Position

ABOUT US

Cypress Key Property Management is a growing Central Florida property management company currently overseeing approximately 60 residential and commercial properties. We are expanding our third-party management portfolio and are looking for an organized, motivated Property Manager to oversee daily operations and help support our continued growth.

POSITION SUMMARY

The Property Manager will manage the day-to-day needs of our residential and commercial portfolio, including owner and resident communication, leasing, maintenance coordination, inspections, recordkeeping, and new-property onboarding.

This is a hands-on, in-office position for someone who can work independently, solve problems, stay organized, and provide dependable service to owners and tenants.

KEY RESPONSIBILITIES

  • Oversee the daily management of approximately 60 residential and commercial rental properties.
  • Serve as a primary contact for property owners and tenants.
  • Respond to questions, maintenance requests, lease matters, and property concerns.
  • Coordinate rental listings, inquiries, showings, applicant screening, leases, renewals, move-ins, and move-outs.
  • Monitor rent payments, lease expirations, notices, vacancies, and tenant balances.
  • Coordinate repairs among owners, tenants, and vendors.
  • Obtain estimates and approvals and follow work orders through completion.
  • Conduct or coordinate curbside, quarterly, annual, move-in, and move-out inspections.
  • Document property conditions with photographs and written reports.
  • Maintain leases, work orders, inspections, payments, and communications in our CRM.
  • Maintain accurate owner, tenant, property, vendor, and maintenance records.
  • Assist with lease violations, nonpayment notices, and eviction-related documentation when needed.
  • Help develop procedures, checklists, and workflows.
  • Respond to prospective property owners and assist with onboarding new properties.
  • Support owner retention, referrals, and portfolio growth.
  • Follow applicable fair housing, leasing, privacy, and property management requirements.
  • Provide regular portfolio and operational updates to company leadership.

REQUIRED QUALIFICATIONS

  • Previous experience in property management, leasing, maintenance coordination, or a related field.
  • Strong organizational, communication, and time-management skills.
  • Ability to manage multiple properties, responsibilities, and deadlines.
  • Professional and patient approach to owner and resident concerns.
  • Basic understanding of residential leasing and property maintenance.
  • Strong problem-solving skills and ability to work independently.
  • Comfortable using property management software, spreadsheets, email, and cloud-based systems.
  • Valid driver’s license, reliable transportation, and ability to visit properties throughout Central Florida.
  • Ability to complete applicable background and employment screenings.

PREFERRED QUALIFICATIONS

  • Two or more years of residential and/or commercial property management, leasing, or real estate operations experience.
  • Experience with property management software.
  • Experience coordinating maintenance vendors and property inspections.
  • Knowledge of the Central Florida rental market.
  • Experience with lease violations, nonpayment notices, and the residential / commercial eviction process is preferred but not required.
  • Property management sales or business-development experience is helpful but not required.

PHYSICAL REQUIREMENTS

The employee must be able to perform the essential functions of the position, with or without reasonable accommodation. The position may require:

  • Sitting and working at a computer for extended periods.
  • Standing, walking, bending, reaching, kneeling, or climbing stairs during property inspections.
  • Walking through occupied and vacant properties, including outdoor areas and uneven surfaces.
  • Occasionally lifting or carrying up to 25 pounds.
  • Driving to properties and appointments throughout Central Florida.
  • Working outdoors for limited periods in typical Central Florida weather conditions.

SCHEDULE AND WORK ENVIRONMENT

This is a full-time, in-office position and is not remote or hybrid. The role includes office work, property visits, inspections, vendor coordination, and occasional business-development activities.

Some evening, weekend, or after-hours availability may occasionally be required for property emergencies or leasing needs.

COMPENSATION

  • Competitive salary based on experience.
  • Performance incentives may be available based on portfolio growth and new third-party properties.
  • Compensation and benefits will be discussed during the interview process.

TO APPLY

Please submit your résumé along with a brief description of your property management, leasing, real estate operations, or maintenance-coordination experience.

We are an equal opportunity employer. Employment decisions are based on qualifications, experience, performance, and business needs.

Pay: $45,000.00 - $60,000.00 per year

Benefits:

  • Paid time off

Work Location: In person

Salary : $45,000 - $60,000

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