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 motivated and customer-focused Leasing Agent to join our team. The Leasing Agent is responsible for the leasing and marketing of residential properties, while maintaining target occupancy levels. The ideal candidate will have strong customer service skills and be comfortable using computer systems. Position Details: Job Location(s): The Hemingway Apartments -…
Winterwood, Inc. is hiring for the role of Maintenance Technician. The Lead Maintenance Technician is responsible for maintaining 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: $20.00 per hour What We Offer: Sign-On Bonus: $500 (Payable on first…
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 (32 hours per week) Work Schedule: Monday-Friday 8:00 AM-4:30 PM Compensation: $25.00…
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)…
Lexington, KY
Construction
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Winterwood, Inc. is seeking qualified Construction Technicians to join our team. Under the general supervision of the Construction Superintendent, the Construction Technician will assist with project execution by performing a variety of hands-on tasks at job sites. This role involves general labor and construction support, with an emphasis on carpentry. The ideal candidate will have basic…
Lexington, KY
HVAC
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Winterwood, Inc. is seeking two qualified HVAC Installers to join our team. The primary responsibility of the HVAC Installer is to perform skilled skilled installation, and alteration of heating, ventilation, air conditioning, and refrigeration systems and related equipment and facilities. This position may perform preventative maintenance and routine servicing of equipment. Travel

Maintenance Tech

Maintenance
Stanton, KY
Maintenance
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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…
Charlotte, NC
Maintenance
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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; 8:30 am - 5:00 pm Compensation:
Cynthiana, KY
Maintenance
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Winterwood, Inc. is hiring for the role of Maintenance Technician in the Cynthiana-Falmouth, KY area. The Maintenance Technician will be responsible for day-to-day maintenance operations and physical appearance of two properties totaling 55 units. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Full-time (40 hours per week) Work
Frenchburg, KY
Maintenance
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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
Georgetown, KY
Maintenance
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Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician 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 (Monday-Friday)…
Hartford, KY
Maintenance
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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-3:30 PM Compensation:
Huntington, WV
Maintenance
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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, plus on-call Compensation
La Grange, KY
Maintenance
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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: 8:00 AM-4:30 PM, Monday-Friday Compensation: $21.00…
Nicholasville, KY
Maintenance
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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 properties. 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-430 PM Compensation: $20.00 per…
Scottsville, KY
Maintenance
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Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible day-to-day maintenance operations and physical appearance of two properties. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Full-time (32 hours per week) Work Schedule: Mon, Tues, Wed and Thur 8:00 AM-4:30 PM Compensation:
Tompkinsville, KY
Maintenance
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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
Wilmore, KY
Maintenance
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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
Irvine, KY
Maintenance
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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 and Friday 8:00 AM-4:30 PM…
Lexington, KY
Maintenance
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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: Property Name/Address: Coolavin Apartments - 551 West 6th Street, Lexington, KY 40508 (104 units) Job Type:
Nicholasville, KY
Management
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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…

Floating Property Manager

Property Management
Louisville, KY
Property Management
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Winterwood, Inc. is seeking a proactive, detail-oriented Floating Property Manager to oversee the day-to-day operations of our residential properties. In this key role, you’ll be responsible for ensuring the properties run 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
Lexington, KY
Property Management
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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: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 8:30 AM-5:00 PM…

Leasing Agent

Property Management
Louisville, KY
Property Management
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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: Property Name/Address: The Hemingway Apts. - 3309 River Chase Ct., Louisville, KY…

Property Manager

Property Management
Campbellsville, KY
Property Management
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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
Danville, KY
Property Management
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Winterwood, Inc. is seeking a proactive, detail-oriented 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…

Property Manager

Property Management
Frankfort, KY
Property Management
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Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of two 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
Glasgow, KY
Property Management
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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
Lexington, KY
Property Management
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Winterwood, Inc. is seeking a 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 succeed in this…

Property Manager

Property Management
Madison, IN
Property Management
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Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of two residential properties, in the Madison-Versailles, IN area, totaling 72 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 and…
Paris, KY
Property Management
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Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the day-to-day operations of three residential properties in Paris, KY totaling 70 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 and excellent communication…

Property Managers

Property Management
Clintwood, VA
Property Management
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Winterwood, Inc. is seeking a proactive, detail-oriented Property Manager to oversee the daily operations of two residential communities located in the Clintwood, VA and Jenkins, 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…

Recertification Specialist

Property Management
Charlotte, NC
Property Management
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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…