Kauaʻi Real Estate Insights

Market updates, buyer and seller guides, and neighborhood perspectives from someone who lives and works here.

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Wailua Homesteads Kauaʻi — mauka living on the East Side
Kauaʻi Neighborhood Guide — East Side
Wailua Homesteads, Kauaʻi: Mauka Living on the East Side
Elevation, privacy, and valley views — just minutes from Kapaʻa. Here's what daily life looks like in one of the East Side's most sought-after mauka neighborhoods.
By Kristine Dugan  ·  April 2026
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North Shore vs South Shore Kauaʻi — Hanalei Bay and Poʻipū
Kauaʻi Buyer’s Guide — North Shore vs. South Shore
North Shore vs. South Shore Kauaʻi: Which Side Is Right for You?
Most buyers are already predisposed to one side before they realize it. Here's what actually drives the decision: commute realities, pricing, golf, and what daily life looks like on each side of the island.
By Kristine Dugan  ·  April 2026
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Buying a vacation rental on Kauaʻi — aerial view of Hanalei Bay
Kauaʻi Vacation Rentals — VDA Zoning & TVR Licensing
Buying a Vacation Rental on Kauaʻi: What VDA Zoning and TVR Licensing Mean for Investors
Kauaʻi created dedicated vacation rental zones in 1982 — decades before most of Hawaiʻi started regulating short-term rentals. Here's how VDA zoning and TVR licensing work, and what investors need to know.
By Kristine Dugan  ·  March 2026
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Kauaʻi real estate complexity — buyer's guide
Kauaʻi Buyer’s Guide — Market Complexity
What Makes Kauaʻi Real Estate More Complex Than Most Markets
TVR zoning, AG land restrictions, cesspools, flood zones, coastal setbacks, leasehold — what every serious Kauaʻi buyer needs to understand before making an offer.
By Kristine Dugan  ·  March 2026
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Can AI replace a real estate agent on Kauaʻi?
Real Estate & Technology — Kauaʻi Market
Can AI Replace a Real Estate Agent? What Kauaʻi Buyers and Sellers Should Know
AI tools can help with research — but Kauaʻi real estate involves zoning, negotiation, and legal complexity that require experienced professional representation. Here's what the data actually shows.
By Kristine Dugan  ·  March 2026
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Is now a good time to buy a home on Kauaʻi?
Kauaʻi Market Report — 2025 Data · 2026 Outlook
Is Now a Good Time to Buy a Home on Kauaʻi?
Prices pulled back 11% in 2025 — but they're still up 97% over ten years. Here's what the data says about buying on Kauaʻi right now, by neighborhood, and what it means heading into 2026.
By Kristine Dugan  ·  February 2026
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Why Kauaʻi housing supply is shrinking
Kauaʻi Housing Supply — Long-Term Trends
Why Kauaʻi's Housing Supply Is Shrinking — And What It Means for You
Available homes on Kauaʻi dropped 50% in a decade. Here's why — geography, TVR conversions, second homes — and what it means if you're renting or planning to buy.
By Kristine Dugan  ·  January 2026
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Selling your home on Kauaʻi in 2025
Kauaʻi Seller Guide — 2026
Selling on Kauaʻi in 2026: What the Data Says About Pricing, Buyers, and Timing
Inventory rose 13% in 2025 — but well-priced homes sold in 79 days. Here's what sellers need to know about pricing, who's buying, and how to position your property.
By Kristine Dugan  ·  January 2026
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Kauaʻi Market Update →