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Trusted Property Management in Oak Harbor, WA
Established in 2022, Windermere Property Management has become a trusted leader in real estate services across Whidbey Island. Our team specializes in connecting property owners with qualified tenants while providing comprehensive management solutions tailored to individual needs. With offices in Oak Harbor and Coupeville, we leverage deep local market knowledge to deliver exceptional service from Deception Pass to the entire island region. Our experienced professionals offer end-to-end property management including maintenance coordination, tenant screening, and financial administration. We maintain strong relationships with local vendors to ensure quality service delivery while prioritizing transparent communication with all stakeholders. Our commitment to personalized attention is demonstrated through 24/7 availability for urgent matters and regular property status updates.

The management team brings decades of combined experience in real estate operations, supported by a proven track record of successful property placements. We utilize modern technology platforms for seamless communication and documentation while maintaining a human-centered approach to client relationships. Our services extend to commercial property management and specialized HOA solutions, adapting to each community's unique requirements. Client testimonials consistently highlight our responsiveness, expertise, and ability to handle complex property situations with professionalism. This combination of local expertise, technological capability, and personalized service establishes us as industry leaders in the region.
Services
Property Management Tenant Screening HOA Management Rental Services Commercial Properties Maintenance Coordination
Details
  • Year established: 2022
Highlights and features
  • We offer 20+ years of combined local real estate expertise
  • Our team provides 24/7 emergency response availability
  • We implement a proprietary tenant screening process
  • We maintain 100% transparent financial reporting systems
  • Our services include customized HOA management solutions
What people say
Professional staff Prompt service Great experience Highly recommend 24/7 availability
Services
Property Management
Our comprehensive property management services cover maintenance coordination, financial administration, and tenant relations. We provide customized solutions for residential and commercial properties across Whidbey Island. Our local expertise ensures optimal property performance and tenant satisfaction.
Tenant Screening
We implement rigorous tenant screening processes including background checks, credit evaluations, and rental history verification. Our system ensures property owners receive qualified tenants while maintaining fair housing compliance throughout the selection process.
HOA Management
Specialized HOA management services include financial administration, vendor coordination, and community communication. We tailor solutions for condominiums, single-family communities, and large-scale associations while maintaining local regulatory compliance.
Rental Services
Full-service rental management covers property marketing, tenant placement, and lease administration. Our local market expertise ensures competitive pricing and optimal tenant-owner matching across Whidbey Island properties.
Commercial Properties
We manage commercial property portfolios with specialized leasing strategies and tenant relations. Our services include market analysis, lease negotiation, and property maintenance coordination for business spaces in Oak Harbor and surrounding areas.
People
Jason McFadyen
Managing Broker
With over 15 years in real estate, Jason leads our property management team. He specializes in Whidbey Island market dynamics and has successfully managed hundreds of residential and commercial properties.
Jennifer McGlothlin
Property Manager
Jennifer brings 10 years of property management experience. Her focus on client communication and problem-solving has earned multiple service awards from local real estate associations.
Questions
What property types do you manage?
We manage residential homes, condominiums, commercial properties, and HOA communities across Whidbey Island.
How do you screen tenants?
Our process includes credit checks, criminal background screening, rental history verification, and income evaluation.
What areas do you serve?
We specialize in Whidbey Island properties from Deception Pass to Coupeville, including Oak Harbor and surrounding communities.
How are maintenance requests handled?
Emergency requests receive immediate attention. Non-urgent issues are addressed within 24-48 hours by vetted local contractors.
Can owners access account information online?
Yes, our secure portal provides 24/7 access to financial statements, maintenance records, and property documents.
What sets you apart from competitors?
Our local expertise, personalized service approach, and proven track record of successful property placements distinguish us in the market.
Reviews (5)
Christopher Reed
Jun 28, 2022 Report
We rented a home from Windermere that developed several serious leaks from multiple bath and laundry room fixtures. We spent nearly six months in a home with only one functioning toilet out of three, no bathroom sinks, and no wall for the bathroom with a working toilet. that was in the master bedroom. The issue was never fixed even though they have made public statements via social media that it was rectified for us.

We rented from Windermere for nearly seven years, with only one late rent payment, during the COVID-19 pandemic. Late. not missed. What came of all this? Well because I stood up for my family's rights. they sued us for nearly $9000. Stay tuned for updates following the small claims case, as well as photos once the case is closed. My advice: you're better off renting a home from Bernie Madoff or living in a van. Under a bridge. Down by the river.
David Smith
Mar 19, 2022 Report
Applied and was approved for a apartment but they refused to provide me with a copy of the lease unless I paid a non-refundable holding fee first. I don't know if this is illegal but it is definitely unethical!
Christian Holeman
Feb 17, 2022 Report
Absolutely awful. Please avoid this company. It will save you a lot of time, trouble, and money. I hardly have the time to explain all the issues we have with our home, but nothing gets resolved and maintenance issues go unaddressed for MONTHS despite multiple reminders to the agent. Please take your business somewhere else, so you can find a secure home for your family.
Jeremy M.
Nov 02, 2021 Report
Charged for rekey of house when all keys were turned in and also charged for chimney clean when we never used chimney. Charged for water filter for fridge that was always bad as well. We cleaned house before move out still got charged for cleaning in amount of $571. I don't understand how this is okay?
Blair Johnson
Jun 26, 2021 Report
Renting from Windermere Oak Harbor has been the single most stressful and time-wasting experience I have gone through in my 4 years of living in Oak Harbor. While living in one of their properties, they were slow to respond to maintenance requests for the apartment (requiring multiple maintenance requests before taking action), gave no heads-up when building maintenance was being performed, and seemingly weren't able to answer their phones during business hours.

After moving out, Jacklyn Allen was slow to respond to e-mails, leaving my roommate and I in the dark about the status of our moving-out inspections and processing. Two and a half months after turning in our keys, we received what little was left of our security deposit and a non-specific receipt totaling more than $900 for "wall repairs" (that weren't required) and "removal of items" (we left nothing behind in the apartment). But, maybe Ms. Allen is just a poor property manager and ours is an isolated experience. If you are active duty military, do not rent from this company. I really wish it was possible to leave a half-star review.