Winterwood, Inc Jobs Hiring Now
Winterwood, Inc is hiring for 29 open roles on Migrate Mate as of July 16, 2026, concentrated in business operations and business development. Migrate Mate updates Winterwood, Inc's live openings daily. Winterwood, Inc is a regional property management company operating residential communities across Kentucky and Indiana.
Find Winterwood, Inc JobsOverview
Winterwood, Inc hiring data on Migrate Mate, as of July 16, 2026.
- Open jobs
- 29
- Top team
- Business Operations
- Seniority
- Mid to senior level
- Work type
- 0% remote or hybrid
- Top location
- Lexington
Open Roles at Winterwood, Inc
Showing 25 of 29+ Winterwood, Inc jobs
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 succeed in this position.
Position Details:
- Job Type: Full-time (40 hours per week)
- Work Schedule: Monday-Friday 8:00 AM to 4:30 PM
- Compensation: $19.00-$20.00 per hour based on experience
What We Offer:
- Sign-On Bonus: $500 (Payable on first paycheck. Rehires are eligible if their separation period has been 1 year or more).
- Monthly cell phone reimbursement of $100.
- 401(k) plan with matching.
- Health, dental, vision, life and disability insurance.
- Paid time off (vacation, sick leave, holiday pay).
- Referral program.
- Opportunities for advancement and more!
Key Responsibilities:
- Lead leasing efforts and implement effective marketing strategies to attract new residents.
- Monitor and forecast upcoming move-outs to maintain optimal occupancy rates.
- Conduct thorough applicant screenings to assess eligibility.
- Showcase available units to prospective residents with professionalism.
- Ensure compliance with HUD, Rural Development, Tax Credit, Public Housing, and Conventional Housing standards.
- Complete all necessary leasing paperwork while adhering to compliance guidelines.
- Manage rent collection and ensure timely deposits.
- Assigns maintenance work orders and ensures timely follow-up upon completion.
- Conduct unit inspections and prepare for state inspections.
- Handle evictions and oversee annual recertifications.
- Proactively investigates and addresses tenant complaints and concerns.
- Collaborate effectively with staff, residents, vendors, and other stakeholders.
Qualifications:
- Proven experience in property management required.
- Experience in affordable housing preferred.
- Strong computer proficiency and the ability to manage multiple tasks efficiently.
- Exceptional communication and customer service skills.
- Ability to work well both independently and as part of a team.
- A stable work history demonstrating reliability.
- Valid driver’s license and willingness to travel for training.
- Successful completion of a pre-employment drug screening and criminal background check.
If you are ready to take on this rewarding opportunity and make a difference in our community, we encourage you to apply today!
Winterwood, Inc. is a growing family-owned property management company with over 40 years of experience in the industry. We achieve our mission and vision of Our People, First by living out our values each and every day with customer service.
Winterwood, Inc. is proud to be an Equal Opportunity Employer
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 succeed in this position.
Position Details:
- Job Type: Full-time (40 hours per week)
- Work Schedule: Monday-Friday 8:00 AM to 4:30 PM
- Compensation: $19.00-$20.00 per hour based on experience
What We Offer:
- Sign-On Bonus: $500 (Payable on first paycheck. Rehires are eligible if their separation period has been 1 year or more).
- Monthly cell phone reimbursement of $100.
- 401(k) plan with matching.
- Health, dental, vision, life and disability insurance.
- Paid time off (vacation, sick leave, holiday pay).
- Referral program.
- Opportunities for advancement and more!
Key Responsibilities:
- Lead leasing efforts and implement effective marketing strategies to attract new residents.
- Monitor and forecast upcoming move-outs to maintain optimal occupancy rates.
- Conduct thorough applicant screenings to assess eligibility.
- Showcase available units to prospective residents with professionalism.
- Ensure compliance with HUD, Rural Development, Tax Credit, Public Housing, and Conventional Housing standards.
- Complete all necessary leasing paperwork while adhering to compliance guidelines.
- Manage rent collection and ensure timely deposits.
- Assigns maintenance work orders and ensures timely follow-up upon completion.
- Conduct unit inspections and prepare for state inspections.
- Handle evictions and oversee annual recertifications.
- Proactively investigates and addresses tenant complaints and concerns.
- Collaborate effectively with staff, residents, vendors, and other stakeholders.
Qualifications:
- Proven experience in property management required.
- Experience in affordable housing preferred.
- Strong computer proficiency and the ability to manage multiple tasks efficiently.
- Exceptional communication and customer service skills.
- Ability to work well both independently and as part of a team.
- A stable work history demonstrating reliability.
- Valid driver’s license and willingness to travel for training.
- Successful completion of a pre-employment drug screening and criminal background check.
If you are ready to take on this rewarding opportunity and make a difference in our community, we encourage you to apply today!
Winterwood, Inc. is a growing family-owned property management company with over 40 years of experience in the industry. We achieve our mission and vision of Our People, First by living out our values each and every day with customer service.
Winterwood, Inc. is proud to be an Equal Opportunity Employer
Job Roles at Winterwood, Inc
Working at Winterwood, Inc
Winterwood, Inc's 29 open roles are mid to senior level, and about 0% are remote or hybrid. The most active teams are business operations, business development, and electrical engineering. Winterwood, Inc is a regional property management company that operates residential apartment communities, with roles spanning on-site maintenance, leasing, property management, and accounting. Most Winterwood, Inc roles are based in Lexington, with some in Jeffersonville and Bowling Green.
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Browse jobs by roleWinterwood, Inc Jobs: Frequently Asked Questions
How many jobs is Winterwood, Inc hiring for right now?
Winterwood, Inc is hiring for 29 open roles on Migrate Mate as of July 16, 2026, updated daily, concentrated in business operations and business development. Positions span on-site maintenance, property management, and accounting functions across its residential portfolio.
What kinds of roles does Winterwood, Inc hire for?
The most active teams are business operations, business development, and electrical engineering. Winterwood, Inc regularly hires for property managers, maintenance technicians, assistant property managers, and staff accountants, including bilingual and multi-site roles. Most postings are mid to senior level, with a mix of full-time and part-time positions across its residential communities.
Are Winterwood, Inc jobs remote or in-person?
Mostly on-site. About 0% of Winterwood, Inc's open roles on Migrate Mate are remote or hybrid as of July 16, 2026, with the rest based in Lexington. Each Winterwood, Inc listing shows its work location so you can filter before applying.
How do I apply to a job at Winterwood, Inc?
Find a Winterwood, Inc role on Migrate Mate, then follow the listing through to Winterwood, Inc's own application portal to submit your materials. Winterwood, Inc manages its own hiring process directly, so applications go to their internal team.
Does Winterwood, Inc hire entry-level?
Most of Winterwood, Inc's open roles on Migrate Mate are mid to senior level as of July 16, 2026. Entry-level openings are limited. Check individual Winterwood, Inc listings for stated experience requirements.
Where is Winterwood, Inc hiring?
Most Winterwood, Inc roles are based in Lexington, with some in Jeffersonville and Bowling Green, and about 0% offer remote or hybrid work as of July 16, 2026. Migrate Mate shows the location on each listing.