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With over 45 years of experience, Winterwood, Inc., is a leading property management company dedicated to providing safe and affordable housing. Founded in 1979, Winterwood manages over 14,000 apartments in 340 communities across 8 states, specializing in affordable housing.
OUR PEOPLE, FIRST.
At Winterwood, Inc., our staff is the foundation in our work to provide services to our clients, our residents, and our neighbors. Our People, First is more than our mission statement. It is how we approach every challenge and serve every customer. We are glad you are here and thank you for your interest in starting a career at Winterwood, Inc.
To explore our current job openings, simply click on the job title below and apply today!
Career Opportunities
Winterwood, Inc. is hiring for the role of Lifeguard. The Lifeguard is responsible for ensuring the safety and enjoyment of our pool patrons. Position Details Location: The Monroe Apartments - 940 University Woods Drive, New Albany, IN 47150 Pay Rate: $18.00 per hour Stay Bonus: $500 (for those who stay till the end of the pool season) Job Type: Temporary/Seasonal (40 hours per week)…
Winterwood is seeking dependable, safety-conscious individuals to join our team as Pool Attendants. The Pool Attendant ensures a clean, safe, and welcoming pool environment while delivering excellent service to residents and guests. Position Details: Location: 1804 Russell Lee Drive, Louisville, KY 40211 Pay Rate: $18.00 per hour Job Type: Temporary/Seasonal (Part-time, up to 24 hours/week)…
Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of one of our residential properties. In this key role, you’ll be responsible for ensuring the property runs efficiently, maintaining high standards, and providing exceptional support to our residents. Strong computer proficiency and excellent communication skills are essential to…
Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of one of our residential properties. In this key role, you’ll be responsible for ensuring the property runs efficiently, maintaining high standards, and providing exceptional support to our residents. Strong computer proficiency and excellent communication skills are essential to…
Staff Accountant
Accounting
Lexington, KY
Accounting
Winterwood, Inc. is seeking an experienced, motivated and detail oriented individual to fill the role of Staff Accountant to join our corporate office in Lexington, KY. The Staff Accountant is responsible for maintaining the books of accounting for a portfolio of properties under Winterwood’s management. The Staff Accountant is considered part of the property team and is responsible for ensuring…
Utilities Accounts Payable Associate
Accounting
Lexington, KY
Accounting
Winterwood, Inc. is seeking a highly organized and detail-oriented Utilities Accounts Payable Associate to join our dynamic Accounting team. This position is responsible for the daily coding of vendor invoices and phone contact for Accounts Payable. We’re looking for candidates with strong customer service experience and a solid background in administrative tasks. The ideal candidate will…
Accounts Payable Intern
Administrative
Lexington, KY
Administrative
Winterwood, Inc. is seeking a motivated Accounts Payable Intern to join our Accounting team. This is a hands-on opportunity to gain real-world experience supporting Accounts Payable operations, vendor management, and financial processes in a collaborative office environment. Job Type: Temporary (potential for long-term employment) Schedule: Part-Time | Flexible (Mon–Fri, 8:30 AM – 5:00 PM)…
Office Assistant
Administrative
Lexington, KY
Administrative
Winterwood, Inc. is seeking a reliable and detail-oriented Office Assistant to support the day-to-day administrative operations of our property management team. This role is ideal for someone who thrives in a fast-paced environment, enjoys helping others, and takes pride in keeping an office organized and running smoothly. Position Details: Location: Parkway Manor - 431 Rogers Road P-2…
Recertification Specialist
Administrative
Louisville, KY
Administrative
Winterwood, Inc. is hiring for the role of Recertification Specialist. The Recertification Specialist will be responsible for completing all annual recertifications, ensuring compliance with federal, state, and local regulations related to public housing, tax credit, and equal opportunity housing guidelines. The ideal candidate will be detail-oriented and committed to performing all duties with…
Maintenance Technician
Maintenance
Central City, KY
Maintenance
Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 8:00 AM to 4:30 PM Compensation:…
Maintenance Technician
Maintenance
Elkton, KY
Maintenance
Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 7:00 AM to 3:30 PM Compensation:…
Maintenance Technician
Maintenance
Frenchburg, KY
Maintenance
Winterwood, Inc. is hiring for the role of part-time Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Part-time (24 hours per week) Work Schedule: Monday, Wednesday, Friday 8:00 AM-4:30 PM Com…
Maintenance Technician
Maintenance
Lebanon, KY
Maintenance
Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Location(s): Springdale - 109 Armory Hill, Springfield, KY 40069 (24 units) Marion Centennial - 560 Maple…
Maintenance Technician
Maintenance
Louisville, KY
Maintenance
Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property(ies). Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 8:30 AM to 5:00 PM Compensation:…
Maintenance Technician
Maintenance
Nicholasville, KY
Maintenance
Winterwood, Inc. is hiring for the role of part-time Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Part-time (20 hours per week) Work Schedule: Monday, Wednesday 8:00am-4:30pm Friday 8:00am…
Maintenance Technician
Maintenance
Sellersburg, IN
Maintenance
Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of three properties located in the Sellersburg-Jeffersonville, IN area. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Full-time (40 hours per week) Work Schedule:…
Maintenance Technician
Maintenance
Stanton, KY
Maintenance
Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 8:00 AM - 4:30 PM Compensation: $20.00…
Maintenance Technician
Maintenance
Tompkinsville, KY
Maintenance
Winterwood, Inc. is hiring for the role of part-time Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Part-time (16 hours per week) Work Schedule: Monday and Thursday 8:00 AM-4:30 PM Compensat…
Part-Time Maintenance Tech
Maintenance
Warfield, KY
Maintenance
Winterwood, Inc. is hiring for the role of part-time Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Part-time (24 hours per week) Work Schedule: Monday, Wednesday, Friday 8:00 AM-4:30 PM Co…
Marketing Manager
Management
Lexington, KY
Management
Winterwood, Inc. is seeking a highly organized and strategic Marketing Manager to lead marketing operations, branding initiatives, and portfolio-wide campaign execution across our communities. This role partners closely with operational leadership to drive occupancy, strengthen brand presence, and ensure consistent execution of marketing strategies across properties. Travel in this role is…
Property Manager
Management
Lawrenceburg, KY
Management
Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of three residential properties in the Lawrenceburg-Versailles, KY area, totaling 106 units. In this key role, you’ll be responsible for ensuring the property runs efficiently, maintaining high standards, and providing exceptional support to our residents. Strong computer proficiency…
Property Manager
Management
Warfield, KY
Management
Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of one of our residential properties. In this key role, you’ll be responsible for ensuring the property runs efficiently, maintaining high standards, and providing exceptional support to our residents. Strong computer proficiency and excellent communication skills are essential to…
Leasing Agent
Property Management
Louisville, KY
Property Management
Winterwood, Inc. is hiring for the role of Leasing Agent. The Leasing Agent is responsible for the leasing and marketing of the property, and ensures target occupancy is maintained at all times. Ideal candidates will have excellent customer service skills and proficiency with computers. Position Details: Location: The Stratton Apartments - 333 Whispering Brook Drive, Louisville, KY 40229…
Multi-Site Property Manager
Property Management
Sellersburg, IN
Property Management
Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of three of our residential properties located in the Sellersburg-Jeffersonville, IN area, totaling 312 units. In this key role, you’ll be responsible for ensuring the property runs efficiently, maintaining high standards, and providing exceptional support to our residents. Strong…
Property Manager
Property Management
Clintwood, VA
Property Management
Winterwood, Inc. is seeking a detail-oriented part-time Property Manager to oversee the day-to-day operations of one of our residential properties. In this key role, you’ll be responsible for ensuring the property runs efficiently, maintaining high standards, and providing exceptional support to our residents. Strong computer proficiency and excellent communication skills are essential to…
Property Manager
Property Management
Louisville, KY
Property Management
Winterwood, Inc. is seeking a detail-oriented part-time Property Manager to oversee the day-to-day operations of our residential property(ies). In this key role, you’ll be responsible for ensuring the property runs efficiently, maintaining high standards, and providing exceptional support to our residents. Strong computer proficiency and excellent communication skills are essential to succeed in…