Weekend Property Manager Jobs in Trumbull, CT (NOW HIRING)

Property Manager

Location: Stratford, CT
Reports To: CEO / Ownership
FLSA Status: Exempt or Non-Exempt, depending on final structure

About the Role

We are seeking a highly capable, proactive Property Manager to oversee the day-to-day operations of a portfolio of residential and commercial properties in Connecticut. This is a hands-on role for someone who takes ownership, communicates exceptionally well, and can keep multiple moving parts organized in a fast-paced environment.

The ideal candidate is a self-starter with excellent attention to detail, strong judgment, and the ability to learn quickly. This person must be comfortable balancing tenant relations, leasing, maintenance coordination, vendor management, and compliance responsibilities while also handling occasional administrative tasks such as invoice entry, paperwork, and bank deposits when needed.

This is an excellent opportunity for someone who thrives in an entrepreneurial environment, is flexible and solutions-oriented, and wants to play a meaningful role in improving property performance and day-to-day operations.

Key Responsibilities

Property Operations

• Oversee the daily operations of assigned residential and commercial properties to ensure they are well-maintained, responsive to tenant needs, and operating efficiently.

• Conduct routine property inspections to maintain standards for safety, cleanliness, presentation, and preventive maintenance.

• Assign, monitor, and close out work orders, ensuring repairs are completed thoroughly and on time.

• Coordinate with maintenance personnel and third-party vendors to ensure quality work and strong follow-through.

• Maintain accurate, organized records of maintenance activity, repairs, vendor communications, and operational issues.

• Travel regularly between Connecticut-based properties.

Leasing and Tenant Relations

• Manage leasing activity from start to finish, including advertising vacancies, conducting showings, screening applicants, and preparing lease documentation.

• Oversee move-ins and move-outs, including inspections and related documentation.

• Build and maintain strong tenant relationships through clear, professional, and timely communication.

• Respond promptly and effectively to tenant concerns, service requests, and day-to-day property issues.

• Enforce lease terms, policies, and operational procedures consistently and professionally.

Administrative and Financial Support

• Prepare, maintain, and organize leases, notices, compliance records, and other property documentation.

• Assist with budgeting, expense tracking, and reporting.

• Review vendor invoices for accuracy and process them appropriately.

• Handle occasional administrative and operational support tasks, including invoice entry, filing, and bank deposits.

• Collect rents, monitor delinquencies, and issue notices as needed.

• Help ensure that property files, reports, and records are accurate, current, and audit-ready.

Compliance and Risk Management

• Help ensure all properties remain in compliance with applicable local, state, and federal requirements.

• Maintain documentation related to insurance, incidents, risk management, and property compliance matters.

• Support emergency response procedures and assist with after-hours issues when necessary.

Qualifications

• High school diploma required; associate’s or bachelor’s degree preferred.

• 2+ years of property management experience in residential, commercial, or mixed-use properties preferred.

• Working knowledge of leasing, property operations, tenant relations, and compliance requirements.

• Experience with property management platforms such as DoorLoop, Yardi, AppFolio, or Buildium. DoorLoop experience is a plus.

• Excellent verbal and written communication skills.

• Strong organizational and time management skills.

• High attention to detail and commitment to accuracy.

• Ability to manage multiple priorities and projects at once without losing follow-through.

• Comfortable working independently, taking initiative, and solving problems in real time.

• Fast learner who can quickly adapt to new systems, properties, and operational needs.

• Flexible and willing to step in wherever needed to support the business.

• Valid driver’s license and reliable transportation required.

What We’re Looking For

The strongest candidates for this role will be:

• Self-starters who do not need constant direction

• Highly detail-oriented and organized

• Strong communicators, both in person and in writing

• Comfortable juggling multiple priorities in a fast-paced environment

• Adaptable, resourceful, and flexible

• Willing to handle both core property management responsibilities and occasional administrative tasks

• Calm under pressure, responsive, and solutions-focused

• Professional in dealing with tenants, vendors, and ownership

Why This Role Stands Out

This is not a passive property management role. It is an opportunity to join a growing operation where your work will have visible impact. You will work closely with ownership, help improve systems and execution, and play an important role in keeping the portfolio running smoothly and professionally.

For the right candidate, this role offers meaningful responsibility, variety in day-to-day work, and the opportunity to grow with the business.

Working Conditions

• Combination of office and field work

• Frequent travel between properties in Connecticut

• Occasional evening or weekend availability for showings, emergencies, or urgent property needs

• On-call responsibilities required

To apply, please submit your resume along with a brief note describing why you are a fit for this role and how you stay organized while managing multiple priorities in a fast-paced environment.