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 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:
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…
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

Janitor

Maintenance
Huntington, WV
Maintenance
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Winterwood, Inc. is hiring for the role of Janitor. This position is under the general direction of the Regional Manager or Maintenance Supervisor and is responsible for the daily upkeep and overall appearance of the property/facility. Position Details: Job Type: Full-time (40 hours per week) Work Schedule: Monday-Friday 8:00 AM-4:30 PM Compensation: $15.00-20.00 per hour based on…

Maintenance Tech

Maintenance
Hindman, 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 a 36 unit apartment complex located in Hindman, KY. Ideal candidates will have prior experience in apartment or property maintenance. Job Details: Job Type: Part-time (24 hours per week) Work Schedule: 8:00…
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 (40 hours per week) Work Schedule: Monday-Friday 8:00 AM-4:30 PM Compensation:
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
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 three small residential properties, totaling 82 units. 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…
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:
Hickman, 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: Indian Hills Village - 305 Bernal Ave., Hickman, KY 42050 Job Type: Full-Time (40 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: Monday-Friday 8:00 AM-4:30 PM Compensation: $20.00 per…
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…
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: Location: The Hemingway Apartments - 3309 River Chase Ct., Louisville, KY 40218 Job Type: Full-time (40 hours per…
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…
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:

Leasing Agent

Management
Jeffersonville, IN
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 one of our properties located in Jeffersonville, IN, 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

Leasing Agent

Management
Louisville, KY
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 two properties (one located in Fairdale, KY and the other one in Louisville, KY), 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:

Leasing Agent

Management
Louisville, KY
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 two properties, and ensures target occupancy is maintained at all times. Ideal candidates will have excellent customer service skills and proficiency with computers. Position Details: Property Names/Address: Indigo at the Park & Woodland Hills - 518 Iroquois Garden…
Harlan, 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…
Harrodsburg, KY
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 Harrodsburg, KY. 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…
La Grange, KY
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. 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…
Lawrenceburg, KY
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 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…

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
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 Stratton - 333 Whispering Brook Drive, Louisville, KY 40229…

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…

Leasing Agent

Property Management
Shelby, NC
Property Management
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Winterwood, Inc. is hiring for the role of part-time Leasing Agent. The Leasing Agent is responsible for the leasing and marketing of two properties in Shelby, North Carolina, and ensures target occupancy is maintained at all times. Ideal candidates will have excellent customer service skills and be proficient with computers. Position Details: Job Type: Part-time (24 hours per week) Work

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
Lexington, KY
Property Management
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Winterwood, Inc. is looking for a proactive, detail-oriented Property Manager to oversee the daily operations of our 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: Property Managed: Coolavin Apartments - 551 West 6th Street, Lexington, KY 40508…

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…

Property Manager

Property Management
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 Manager

Property Management
Tompkinsville, 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 consisting of 24 units, located in Tompkinsville, KY. 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…