Watch the full conversation with Misti Padilla, Linda Kawakami, and Chelsea Fernandez in the video below.

Considering a move to Hawaii or investing in island real estate? Choosing between a condo vs. single family home in Hawaii is one of the most important decisions you’ll make. In this episode of Living in Hawaii, local experts Misti Padilla (Big Island), Linda Kawakami (Oahu), and Chelsea Fernandez (Maui) dive deep into the pros, cons, and price points of both property types across the islands.

Island-Specific Real Estate Insights

Each island has its own personality—and price tag. From oceanfront condos in Waikiki starting at $5M to charming single-family homes in Pearl City under $400K, the cost of living in Hawaii is all about location, lifestyle, and long-term goals.

  • Oahu: High-rise condos with luxury amenities dominate urban areas, while family homes in suburbs like Kaneohe offer more space and privacy—but at a premium.
  • Maui: Scenic condos near the beach in Wailea can cost over $2M, while inland areas like Wailuku offer larger homes and acreage at more affordable prices.
  • Big Island (Hawaiʻi): Still the most affordable island, with options ranging from entry-level condos in Kona to rural estates in Waimea. Expect to pay more the closer you are to the coast.
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HOA Fees, Maintenance, and Hidden Costs

The hosts unpack critical financial considerations like HOA (Homeowners Association) fees, which can range from a few hundred to over $1,500/month depending on amenities. While condos offer convenience (no yard work, shared maintenance, amenities), they may have stricter rules, especially around pets and upgrades.

In contrast, single family homes come with more freedom—but also more responsibility. Think roof replacements, landscaping, and insurance premiums, which can be high on older homes.

Investment Potential and Lifestyle Fit

If you’re eyeing short-term vacation rentals (STRs), this episode also breaks down the evolving legal landscape, especially in Maui and Oahu where zoning laws restrict where STRs are allowed. Overall, single family homes tend to appreciate more in value, but condos can be a smart first step toward building a real estate portfolio.

Real Stories, Real Advice

This episode isn’t just about numbers. The hosts share personal stories—from first-time condo purchases to dream-home wishlists—to highlight the heart behind the homebuying process in Hawaii. Whether you’re a young buyer like Misti’s 21-year-old son or a seasoned investor, there’s something here for everyone.

Final Takeaway

The bottom line? There’s no one-size-fits-all answer. Your decision depends on your budget, lifestyle, family needs, and long-term plans. That’s why it’s so important to work with local experts who understand the nuances of Hawaii real estate.

Ready to explore your options? Connect with the team at Living in Hawaii and let us help you navigate your path to island homeownership.

Aloha—and happy house hunting!

 

 

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