Finding Paradise Again: How Persistence Secured the Perfect Second Home in Hawaii
For many, Hawaii is a dream destination. For this client, it was home once before, and the pull of the islands never faded. After previously living and selling in Hawaii, he knew he wanted to return, this time to purchase a second home that truly embodied everything he loved about island living.
What followed was a journey of strategy, resilience, and trust. Ultimately, we secured his dream home below asking price in one of Hawaii’s most desirable gated communities
This wasn’t just any second home purchase.
The buyer’s must-haves were clear:
Panoramic views
Privacy and quiet
Architecturally interesting design
A secure, gated community
And most importantly… a deep pool
Having already experienced Hawaii living, he understood the lifestyle and culture deeply. He wasn’t browsing casually. He was searching for something specific, something exceptional.
When the perfect home hit the market, it immediately attracted attention. The seller received multiple offers. We submitted a strong offer, but we weren’t in primary position. In fact, we weren’t even accepted as backup. It was a devastating moment.
But instead of walking away, we did what experienced, credible agents do: we stayed engaged. Maintaining communication with the listing agent kept the relationship warm, and ensured that if anything shifted, we would be top of mind.
And it did.
When the accepted buyer cancelled, we were the first call. We moved swiftly into contract. Persistence made the difference.
Because the buyer’s primary residence is on the mainland, much of the search process was virtual. We conducted extensive virtual tours and narrowed the search to three primary neighborhoods based on his goals. From there, we pinpointed the one community that aligned perfectly.
This preparation paid off. When the right home became available in that specific neighborhood, the buyer was confident enough to make a quick decision, even before seeing it in person.
Behind the scenes: we studied the comps carefully, gave a strategic offer approach, researched listings in depth and called agents for additional insight, and ensured the buyer fully understood market conditions, inventory levels, and pricing trends.
In a market where desirable homes are still moving quickly and attracting multiple offers, this buyer:
Secured his dream property
Purchased below asking price
Obtained negotiated concessions
Closed with confidence
The home checked every box: views, privacy, gated security, architectural character — and yes, the deep pool.
Desirable properties still move fast. Multiple offers are common in sought-after neighborhoods.
Not being accepted initially doesn’t mean it’s over. Deals fall apart. Persistence matters.
Preparation creates power. When buyers deeply understand a neighborhood, association rules, pricing trends, and market conditions, they can act decisively.
Credibility wins contracts. Relationships between agents matter more than many realize.
Credibility kept us top of mind. Research secured the concessions. The buyer’s trust in my guidance is what ultimately brought this transaction to a successful close.
Do your research. Market conditions shift constantly. Stay informed.
Understand inventory and pricing trends. Knowledge reduces hesitation.
Work with a trusted, well-connected agent. Results don’t happen by accident.
In competitive markets, expertise isn’t optional. It’s essential.
Whether you’re relocating, investing, or purchasing a second home, strategy and persistence can make all the difference.
If you're considering making Hawaii your next chapter (even part-time) let's create a plan that positions you to win.
Specializing in mid-century, modern Hawaii homes, her desire to broaden the scope of the service has been successfully achieved as a 5-time award winner of the Top 100 agents in Hawaii by Hawaii Business Magazine.
