The Truth About HOA Special Assessments on Maui in 2026

If you’ve been looking at condos on Maui lately, you’ve probably heard the words “special assessment” come up more than a few times.

Honestly, for many buyers, it’s become one of the biggest concerns in today’s condo market.

And I get it.

Nobody wants to buy a condo only to get hit with a massive unexpected bill a few months later.

The reality is special assessments are not automatically a bad thing — but buyers absolutely need to understand what they are, why they happen, and how they can impact ownership costs before buying a condo on Maui.

I’ve personally seen buyers panic the second they hear the word assessment, while other buyers completely ignore it and fail to ask the right questions.

Like most things in real estate, the truth is usually somewhere in the middle.

What Is a Special Assessment?

A special assessment happens when a condo association needs additional money beyond regular HOA dues to cover major expenses or projects.

These can include things like:

• Roof replacements
• Plumbing upgrades
• Structural repairs
• Elevator modernization
• Fire safety compliance
• Exterior painting
• Hurricane or storm damage
• Insurance shortfalls
• Deferred maintenance projects

Sometimes assessments are relatively small.

Other times they can become substantial depending on the size of the project and financial health of the association.

Why Are Special Assessments Becoming More Common on Maui?

Honestly, several things are colliding at once right now.

We’re seeing:

• Rising insurance costs
• Older condo buildings aging
• Increased construction costs
• Stricter reserve funding expectations
• Deferred maintenance issues surfacing
• Higher labor and material costs in Hawaii

A lot of Maui condo buildings were built decades ago, and many associations are now dealing with large-scale maintenance projects that simply can’t be postponed forever.

And living on an island doesn’t make maintenance cheaper.

Salt air, humidity, sun exposure, and tropical weather all accelerate wear and tear on buildings — especially oceanfront properties.

Insurance Is a Huge Part of the Conversation

This has probably become one of the biggest drivers behind HOA fee increases and assessments lately.

Insurance costs across Hawaii have increased dramatically over the past several years, and many condo associations are struggling to keep up with rising premiums.

I’m seeing buyers pay far more attention now to:

• master insurance policies
• reserve studies
• pending litigation
• deferred maintenance
• financial statements
• reserve funding percentages

than they were even a few years ago.

And honestly, they should be.

If you haven’t already read it, our article on
The Hidden Costs of Owning a Condo on Maui in 2026

goes deeper into many of the ownership costs buyers often overlook.

Older Buildings Aren’t Always Bad Investments

This is something I think gets misunderstood a lot.

Just because a building has an assessment doesn’t automatically mean it’s a bad property.

Sometimes it actually means the association is finally addressing major projects properly.

I’ve seen extremely well-run associations choose to aggressively improve:

• plumbing systems
• roofing
• structural integrity
• exterior maintenance
• fire safety systems

to protect long-term property values.

In some cases, I’d actually rather see a proactive association than one constantly delaying maintenance to artificially keep HOA fees low.

Cheap HOA Fees Can Be Misleading

A lot of buyers initially get excited when they see unusually low HOA dues.

But honestly, sometimes that can actually be a red flag.

Low dues can occasionally mean:

• underfunded reserves
• deferred maintenance
• postponed repairs
• lack of long-term planning

I’ve personally seen buyers focus only on finding the lowest monthly dues without fully understanding the financial condition of the building itself.

That can become dangerous long-term.

A healthy association with strong reserves is often much more important than simply having the cheapest HOA fees.

Questions Buyers Should Be Asking

This is where having a good local agent matters.

When buyers are evaluating condos on Maui, I always think they should ask questions like:

• Are there pending special assessments?
• Is the association adequately funded?
• Are major repairs coming soon?
• Has deferred maintenance become an issue?
• Are insurance costs rising significantly?
• Is there pending litigation?
• How healthy are reserves?

Those answers can tell you a LOT about the overall condition of a condo association.

Vacation Rental Condos Have Additional Layers

This becomes even more important in vacation-rental-friendly complexes.

Some resort-oriented condo communities have:

• higher operating costs
• heavier wear and tear
• more staffing expenses
• increased insurance exposure
• stricter maintenance expectations

At the same time, many buyers still strongly want these properties because of their location and income potential.

If you’re exploring Maui vacation rental ownership, I’d also recommend reading:
Can You Still Buy a Legal Airbnb on Maui in 2026?

Maui Condo Buyers Are More Educated Today

One thing I’ve definitely noticed lately is buyers are becoming much more educated about condo ownership.

A few years ago, many buyers focused almost entirely on:

• purchase price
• views
• rental income
• location

Now buyers are digging much deeper into:

• HOA financials
• insurance exposure
• reserve studies
• long-term maintenance planning
• future assessments

And honestly, that’s a good thing.

Final Thoughts

I think one of the biggest misconceptions buyers have is assuming special assessments automatically mean a condo is a bad investment.

That’s simply not always true.

Sometimes assessments happen because associations are finally addressing important long-term maintenance projects the right way.

The key is understanding:

• why the assessment exists
• how financially healthy the association is
• whether maintenance has been properly managed
• what future costs may look like

The buyers who usually do best on Maui are the ones who fully understand the overall financial picture before closing escrow.

And in today’s market, that matters more than ever.

About the Author

Todd Hudson is a Maui real estate agent, real estate investor, and leader of The 808 Team at Keller Williams Realty on Maui. Todd specializes in Maui condos, vacation rental properties, luxury homes, and helping mainland buyers understand the realities of owning property in Hawaii.

Having worked with buyers and sellers throughout Kihei, Wailea, Kaanapali, and South Maui, Todd closely follows HOA trends, insurance changes, vacation rental regulations, and Maui condo market conditions.

📱 808-344-3584
📧 Todd@the808team.com

The 808 Team Maui Real Estate