.png)
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 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…
RealPage Administrator
Administrative
Lexington, KY
Administrative
Winterwood, Inc. is seeking a qualified and motivated RealPage Administrator to join our team at our corporate office in Lexington, Kentucky. The RealPage Administrator is responsible for reviewing, supporting, and implementing new processes and modules within OneSite Accounting. This role requires a strong understanding of the platform and how interconnected modules (such as Leasing & Rents)…
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 Tech
Maintenance
Versailles, 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: Part-time (24 hours per week) Work Schedule: Monday, Wednesday and Friday 8:00 AM-4:30 PM Compens…
Maintenance Tech
Maintenance
Warfield, 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:…
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…
Property Maintenance Tech
Maintenance
Georgetown, KY
Maintenance
Winterwood, Inc. is hiring for the role of Property Maintenance Tech. The Property Maintenance Tech is responsible day-to-day maintenance operations and physical appearance of our residential 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: 8:00 AM to 4:30 PM…
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…
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
Campbellsville, KY
Property Management
Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of two residential properties located in the Campbellsville-Springfield, KY area. 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…
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…