.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, 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…
Apartment Maintenance Technician
Maintenance
Calvert City, KY
Maintenance
Apartment Maintenance Technician – $18.00/hr. + $250 Sign-On Bonus Calvert City, KY | Part-time (25 Hours/Week) Winterwood, Inc. is hiring for the role of Apartment Maintenance Technician. The Apartment Maintenance Technician is responsible for day-to-day maintenance operations and physical appearance of the property. What We Offer $18.00 per hour $250 Sign-On Bonus (Rehires are eligible…
Apartment Maintenance Technician
Maintenance
Carrollton, KY
Maintenance
Winterwood, Inc. is hiring for the role of Apartment Maintenance Technician. The Apartment 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 (37.5 hours per week) Work Schedule: Monday-Friday, 8:00 AM-4:00 PM Com…
Apartment Maintenance Technician
Maintenance
French Lick, IN
Maintenance
Winterwood, Inc. is hiring for the role of part-time Apartment Maintenance Technician. The Apartment 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. This Is a Part-Time Role – Full-Time Availability Will Not Be Considered Job Details: Job Type:…
Apartment Maintenance Technician
Maintenance
Frenchburg, KY
Maintenance
Winterwood, Inc. is hiring for the role of part-time Apartment Maintenance Technician. The Apartment 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. This Is a Part-Time Role – Full-Time Availability Will Not Be Considered Job Details: Job Type:…
Apartment Maintenance Technician
Maintenance
Hopkinsville, KY
Maintenance
Apartment Maintenance Technician | $18.00-$20.00/hr. | $250 Sign-On Bonus Hopkinsville, KY | Part-time (20 Hours/Week) Winterwood, Inc. is hiring for the role of Apartment Maintenance Technician. The Apartment Maintenance Technician is responsible for day-to-day maintenance operations and physical appearance of the property. What We Offer: $18.00-$20.00 per hour based on experience $250…
Apartment Maintenance Technician
Maintenance
Lawrenceburg, KY
Maintenance
Apartment Maintenance Technician – $20.00/hr. + $250 Sign-On Bonus Lawrenceburg, KY | Part-Time (24 hours per week) | 3 days a week Winterwood, Inc. is hiring for the role of part-time Apartment Maintenance Technician. The Apartment Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of the property. Ideal candidates will have prior experience in…
Apartment Maintenance Technician
Maintenance
Lexington, KY
Maintenance
Apartment Maintenance Technician – $20.00/hr. + $500 Sign-On Bonus Lexington, KY 40508| Full-Time | Monday–Friday, 8:00 AM–4:30 PM Winterwood, Inc. is hiring for the role of Apartment Maintenance Technician. The Apartment Maintenance Technician is responsible for day-to-day maintenance operations and physical appearance of the property. What We Offer: $20.00 per hour $500 Sign-On Bonus…
Apartment Maintenance Technician
Maintenance
Paris, KY
Maintenance
Apartment Maintenance Technician – $23.50/hr. + $500 Sign-On Bonus Lexington, KY-Paris, KY area | Full-Time | Monday–Friday, 8:00 AM–4:30 PM Winterwood, Inc. is hiring for the role of Apartment Maintenance Technician. The Apartment Maintenance Technician is responsible for day-to-day maintenance operations and physical appearance of the property. What We Offer: $23.50 per hour $500…
Apartment Maintenance Technician
Maintenance
Vanceburg, KY
Maintenance
Part-Time Apartment Maintenance Technician – $18.00/hr. + $250 Sign-On Bonus Vanceburg, KY | Part-time (29 Hours/Week) Winterwood, Inc. is hiring for the role of part-time Apartment Maintenance Technician. The Apartment Maintenance Technician is responsible for day-to-day maintenance operations and physical appearance of the property. What We Offer $18.00 per hour $250 Sign-On Bonus…
Groundskeeper
Maintenance
Lexington, KY
Maintenance
Winterwood, Inc. is hiring for the role of Groundskeeper. The Groundskeeper will play a vital role in ensuring that the grounds of the community are attractive, orderly, and healthy. If you have a passion for outdoor work and take pride in maintaining an inviting and well-kept environment that enhances the community’s appeal, we want to hear from you! Position Details: Job Type: Full-time (40…
Groundskeeper
Maintenance
Louisville, KY
Maintenance
Winterwood, Inc. is hiring for the role of Groundskeeper. The Groundskeeper will play a vital role in ensuring that the grounds of the community are attractive, orderly, and healthy. If you have a passion for outdoor work and take pride in maintaining an inviting and well-kept environment that enhances the community’s appeal, we want to hear from you! Position Details: Job Type: Full-time (40…
Janitor
Maintenance
Louisville, KY
Maintenance
Winterwood, Inc. is hiring for the role of Janitor. The Janitor plays a key role in maintaining the daily cleanliness, curb appeal, and physical condition of the apartment community. This position combines routine custodial duties with basic light maintenance—to ensure a safe, clean, and welcoming environment for all residents. Position Details: Job Type: Full-time (40 hours per week) Work…
Lead Maintenance Technician
Maintenance
Louisville, KY
Maintenance
Winterwood, Inc. is hiring for the role of Lead Maintenance Technician. The Lead Maintenance Technician is responsible for maintaining day-to-day maintenance operations and physical appearance of the property, with additional leadership responsibilities for the maintenance team. Job Details: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday, 8:00 AM-4:30 PM Compensation:…
Maintenance Technician
Maintenance
Bloomington, IN
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: Mon, Wed, Fri 8:00am to 2:30pm Compensation:…
Maintenance Technician
Maintenance
Crestwood, 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: $23.00 per…
Maintenance Technician
Maintenance
Frankfort, 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: **HIRING MANAGERS: PLEASE FILL IN THE BLANKS BELOW** Job Type: Full-time 40 hours per week) Work Schedule (Days…
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
Hopkinsville, 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 per…
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. Job Details: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 8:00 AM-4:30 PM Compensation: $22.00-$25.00 per hour based on experience What We Offer: Sign-On Bonus: $500 (Payable on…
Maintenance Technician
Maintenance
Russellville, 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: $21.00…
Maintenance Technician
Maintenance
Shelbyville, 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. This Is a Part-Time Role – Full-Time Availability Will Not Be Considered Job Details: Job Type: Part-time (24 hours…
Property Maintenance Technician
Maintenance
Lebanon, KY
Maintenance
Property Maintenance Technician – $18/hr. + $500 Sign-On Bonus Lebanon, KY/New Haven, KY area | Full-Time | Monday–Friday, 8:00 AM–4:30 PM Winterwood, Inc. is hiring for the role of Property Maintenance Technician. The Property Maintenance Technician is responsible for day-to-day maintenance operations and physical appearance of the property(ies). What We Offer $18.00 per hour $500…
Property Manager
Management
Bloomington, IN
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…
Assistant Property Manager
Property Management
Corbin, KY
Property Management
Winterwood, Inc. is hiring for the role of part-time Assistant Property Manager. The Assistant Property Manager will support the overall operations of the property, under the general direction of the Property Manager. Position Details: Job Type: Part-time (20-24 hours per week) Work Schedule: Monday, Wednesday and Friday 8:30 AM to 5:00 PM Compensation: $18.00 per hour What We Offer: …
Assistant Property Manager
Property Management
Hazard, KY
Property Management
Part-Time Assistant Property Manager Position – Only Part-Time Candidates Will Be Considered Winterwood, Inc. is hiring for the role of part-time Assistant Property Manager. The Assistant Property Manager will support the overall operations of the property, under the general direction of the Property Manager. Position Details: Job Type: Part-time (20 hours per week) Work Schedule: Mon…
Floating Assistant Property Manager
Property Management
Georgetown, KY
Property Management
Part-Time Floating Assistant Property Manager Position – Only Part-Time Candidates Will Be Considered Winterwood, Inc. is seeking an adaptable, detail-oriented part-time Floating Assistant Property Manager to join our team. In this dynamic, multi-site role, you will travel across a portfolio of properties to support day-to-day operations, ensure high occupancy, and deliver exceptional service…
Property Manager
Property Management
Campbellsville, KY
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
Florence, KY
Property Management
Property Manager – $21.00/hr. + $500 Sign-On Bonus Florence, KY/Warsaw, KY area | Full-Time | Monday–Friday, 8:00 AM–4:30 PM 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…
Property Manager
Property Management
Frankfort, KY
Property 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…
Property Manager
Property Management
Harrodsburg, KY
Property 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…
Property Manager
Property Management
Hopkinsville, KY
Property 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…
Property Manager
Property Management
Louisville, KY
Property 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…
Property Manager
Property Management
Morganfield, KY
Property 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…