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 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…
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: Properties: Oakridge Apartments: 500 Pin Oak Court…
Winterwood, Inc. is looking for a proactive, detail-oriented Property Manager to oversee the daily operations of three small properties in the Lebanon-New Haven, KY area. In this vital role, you'll ensure everything runs smoothly while using your strong computer and customer service skills to support tenants and maintain property standards. Position Details: Job Type: Full-time (40 hours per…
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 hiring for the role of HVAC Apprentice. In this hands-on, entry-level position, you will assist licensed HVAC Technicians with the installation, troubleshooting, maintenance, and repair of heating, cooling, and ventilation systems on construction projects. This role is designed to provide valuable on-the-job training and real-world industry experience. Job Type: Full Time…
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

Groundskeeper

Maintenance
Lexington, KY
Maintenance
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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: Property: Alcove at…

Groundskeeper

Maintenance
Louisville, KY
Maintenance
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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: Property: Donerail…

Groundskeeper

Maintenance
Richmond, KY
Maintenance
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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: Properties: Kit Carson…
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:

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) …

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: Location: Park DuValle - 1804 Russell Lee Drive, Louisville, KY 40211 Job Type: Full-time (40 hours per week) …

Maintenance Tech

Maintenance
Versailles, 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: Part-time (20 hours per week) Work Schedule: Monday and Tuesday 8:00 AM-4:30 PM; Friday 8:00…
Bardstown, 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: Properties: Colonial Woods Apts.: 232 Marvin Downs, Bardstown, KY 40004 (24 units) Birch Trace Apts.: 1100…
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: Location: Sycamore Station Apts. - 7156 Barrington Dr., Charlotte, NC 28215 Job Type: Full-time 40 hours per…
Georgetown, Versailles, 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: Properties: Arbor Place: 220 Clifton Road C, Versailles, KY 40383 Elk River: 101 Rykara Path, Georgetown, KY…
Sturgis, 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: Ashmoor Apartments - 301 North Kelsey St., Sturgis, KY 42459 Job Type: Part-time (24 hours per week) …
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) …
Gate City, VA
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…

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:

Property Management

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
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
Brandenburg, 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: Properties: Cedar Ridge: 649 Westport Rd., Elizabethtown, KY 42701 Langdon I…

Property Manager

Property Management
Lexington, KY
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 Name/Address: Arlington Lofts Apts. - 1003 North Limestone, Lexington, KY 40505 Job Type: Full-time 40 hours per week Work Schedule: M-F 8:30am-5pm Compensation: $22.00 per hour, plus monthly cell phone reimbursement of…

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…

Recertification Specialist

Property Management
Louisville, KY
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…

Recertification Specialist

Property Management
Louisville, KY
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…