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 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…

Receptionist

Administrative
Huntington, WV
Administrative
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Winterwood, Inc. is seeking a Receptionist/Front Desk Office Assistant to join our team. In this role, you will be a key point of contact for residents and visitors, providing exceptional service by greeting guests, answering phone calls, and performing a variety of administrative tasks to support the property’s operations. The ideal candidate will demonstrate attention to detail,
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
Barbourville, KY
Maintenance
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Winterwood, Inc. is hiring for the role of Maintenance Technician. The Maintenance Technician is responsible for day-to-day maintenance operations and physical appearance of two properties totaling 78 units. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Properties: Catron Square Apartments - 200 First Street, Barbourville, KY 40906 (46…

Maintenance Tech

Maintenance
Central City, 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:

Maintenance Tech

Maintenance
Louisville, 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: Positions available in the following zip-codes: 40202, 40299 and 40219 Job Type: Full-time (40 hours per week) …
Berea, 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 (37.5 hours per week) Work Schedule: Monday-Friday 8:00 AM - 4:30 PM Compensation:
Frostproof, FL
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: Elkhorn Apartments - 37 Elkhorn Drive, Frostproof, FL 33843 Job Type: Part-time (24 hours per week) …
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…
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: Job Type: Full-time (40 hours per week) Work Schedule: 8:00 am-4:30 pm Monday-Friday Compensation: $23.00…
Flemingsburg, 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…

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: Property: Coolavin Apartments - 551 West 6th Street, Lexington, KY 40508 Job Type:

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: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 8:30…

Leasing Agent

Property Management
New Albany, IN
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…

Property Manager

Property Management
Abingdon, VA
Property Management
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Winterwood, Inc. is hiring for the role of Property Manager. The Property Manager is responsible for the overall operation of the property. In this vital role, you'll ensure everything runs smoothly while using your strong computer and communication skills to support tenants and maintain property standards. Position Details: Job Type: Part-time (24 hours per week) Work Schedule: Monday…

Property Manager

Property Management
Barbourville, 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 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…

Property Manager

Property Management
Versailles, IN
Property Management
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Winterwood, Inc. is hiring for the role of Property Manager. The Property Manager is responsible for the overall operation of the property. Position Details: Property: Gaslight Square - 319 Gaslight Drive #100, Versailles, IN 47042 Job Type: Part-time (21 hours per week) Work Schedule: Mondays and Fridays, 8 hours. Wednesdays, 5 hours Compensation: $20.00 per hour, plus monthly cell…