Join our team

Maine Street Property Management is a family-owned business in Wells, Maine.
We are a dedicated, hardworking, tight knit team striving to exceed our client’s expectations every day.
Consider joining us today!  

Property Manager – Long-Term Rentals & Condo Associations
40 Hours Per Week | Salaried Position
Monday–Friday
Starting Salary: $65,000+ (commensurate with experience)

Join our innovative and fast-growing property management company based in Wells, Maine. We specialize in tech-forward solutions and offer year-round services including long-term rentals, vacation rentals, and condo association management. We’re looking for an organized, motivated, and personable Property Manager to oversee long-term rental and condo association properties while also helping to grow our portfolio through sales, marketing, and client acquisition efforts.


Responsibilities

Long-Term Rentals

  • Communication & Conflict Resolution: Foster positive tenant relationships, address concerns, and mediate disputes.

  • Lease & Leasing Management: Manage leases from execution to renewal, including marketing, showings, and screening.

  • Rent Collection: Ensure timely payments and manage delinquencies professionally.

  • Maintenance & Turnovers: Oversee move-in, move-outs, make-ready processes and schedule routine maintenance with vendors and internal teams.

  • Tenant Education: Keep tenants informed about policies, procedures, and property resources.

Condo Association Management

  • Governance & Compliance: Enforce bylaws and ensure state/local compliance.

  • Financial Oversight: Assist with budget development and manage fee collection and reporting.

  • Board Support: Organize meetings, prepare materials, record minutes, and follow up on board directives.

  • Community Engagement: Maintain strong communication with owners and vendors to resolve issues and improve community satisfaction.

  • Administrative Duties: Maintain thorough and accurate documentation and stay informed on industry best practices.

Sales, Marketing, and Client Acquisition

  • Promote and sell our property management services to potential owners and associations.

  • Develop and implement marketing strategies for company services and rental listings.

  • Network, attend local events, and maintain relationships to drive new business.

  • Collaborate with leadership on growth initiatives, pricing, and client retention.

  • Track leads, conversions, and sales metrics to measure growth and effectiveness.


Requirements

  • High school diploma (Bachelor’s degree preferred).

  • 2+ years of experience in property management or a related field.

  • Strong communication and customer service skills.

  • Proficient with Microsoft Office, property management software, and social media tools.


Values

  • Highly organized and detail-oriented.

  • Growth-minded and process-driven.

  • Personable and compassionate.

  • Trustworthy, professional, and reliable.


Benefits

  • Flexible Work Environment – While we maintain a culture of responsiveness beyond traditional office hours, we also offer flexibility and trust our team to manage their time effectively.

  • Unlimited PTO Policy – Take the time you need to rest, recharge, and handle life outside of work.  We believe in working hard and enjoying life just as much. 

  • Health, Dental, and Vision Insurance – Great policies to keep you and your family supported- 70% company paid.

  • $50/Month Cell Phone Reimbursement – Offset the cost of using your personal phone for work.

  • 100% Company-Paid Policies for Short-Term Disability, Long-Term Disability, and Life Insurance.

  • Annual Performance-Based Bonuses – Be rewarded for your contributions and achievements each year.

  • Use of Company Vehicle During Work Hours – For site visits, inspections, and errands.

  • Beautiful Office Space – Enjoy a luxury workspace located in Wells, Maine, with state-of-the-art technology.

  • Energetic, Motivated Team Environment – Be part of a collaborative, supportive group that values innovation and initiative.


Why Join Us?

We foster a collaborative, forward-thinking environment where innovation, accountability, and growth are top priorities. If you’re ready to take the next step in your property management career and want to help shape the future of a growing company, we want to hear from you. Apply today to join us in Wells, Maine!

Please fill out the form below or email a cover letter and resume to employment@mainestreetpm.com to apply.

Skye Oullette

Owner / CEO

Skye is the CEO of Maine Street Property Management. She founded the company after leaving the corporate world, where she built a successful career as a consultant and project manager. Under her leadership, Maine Street has grown into a leading property management firm, known for its expertise and commitment to excellence.

Skye and her husband, Joe, are passionate about real estate, and experienced property investors, actively expanding their extensive portfolio of residential and commercial rental properties in the Wells area. From hands-on, sweat equity renovations in their investing early days to now having a full maintenance staff and overseeing multi-million dollar renovation projects, Skye and Joe have built a reputation as industry experts in real estate investment, property rehabilitation, and large-scale renovations. Skye has made it Maine Street’s mission to help real estate investors tap into this wealth of knowledge and continue building their portfolios with confidence.
 

As a licensed Real Estate Broker with Anne Erwin Sotheby’s International Realty in York, Skye is a real estate expert.  Her focus is 100% on running Maine Street, so she rarely is active in the sales world these days, however she strongly collaborates with her colleagues at Anne Erwin to provide comprehensive real estate services—from deal analysis and negotiation to purchase—seamlessly transitioning into full-service property management.

Outside of work, Skye enjoys spending time with her family and their dog, Charlie. She has a passion for flower gardening and loves taking in the beauty of Maine’s beaches.