Client Story-Buying a Second Home Before Retirement in Kailua Kona

What does it really look like to buy a home in Hawaiʻi before you’re ready to live here full time?

In this video, we sit down in Kailua-Kona with a homeowner who did exactly that. Brad and his family purchased a condo in The Pines — a detached condo community in the heart of Kona — with the long-term goal of retiring here, while still working and living part of the year on the mainland.

This conversation gives a real, honest look at what it’s like to keep one foot in Hawaiʻi and one foot in your current life.

We talk about:

• Why they chose to buy now instead of waiting for retirement
• How they balanced finances between two homes
• Renovating a property from a distance
• Why they chose not to rent it out
• Managing projects when visiting only a few times a year
• HOA living vs. a single-family home
• Concerns about pricing, maintenance, termites, and island logistics
• Healthcare, family, and job considerations that keep people from moving full time
• How owning here changes your relationship with Hawaiʻi compared to being a visitor
• Volunteering, community involvement, and building connections before living here permanently

They share what surprised them, what was harder than expected, and why they feel buying early — even years before retirement — was the right move for their family.

If you’ve ever thought about purchasing a second home in Hawaiʻi, creating a future retirement place, or slowly transitioning your life to the islands, this video will help you understand the realities, trade-offs, and rewards.

We also talk about how different housing types in Kona — including detached condos like The Pines — can offer lower maintenance while still giving you space, privacy, and ocean views.

If you have questions about relocating, buying part time, or planning ahead for retirement in Hawaiʻi, we’re happy to help guide you through the options and connect you with people who’ve already done it.

Interested in a showing or more info? Contact details are below.
Mahalo for watching — like, subscribe, and follow 365Hawaii for more Hawaiʻi home tours and neighborhood insights.

If you’ve been on the fence about buying in Hawaii, this could be your best chance to get a great deal before rates change again. Let’s find your dream home in paradise!

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