A Home with Heart: Helping the DeSimone Family Find Their Whidbey Retreat
One of the greatest joys of being a real estate broker is when the work becomes about so much more than bedrooms, bathrooms, and square footage. It becomes about people, about families, and about creating space for life’s most meaningful moments.
Earlier this year, I met Tim and Rachel DeSimone when Tim reached out with some questions about my listing. We clicked right away, and soon after, they decided to hire me as their buyer’s agent. Their dream was to find a second home — a retreat where their two young boys could connect with nature, and where they, as a family, could make memories together.
But their story carried a deeper, more emotional layer. When Rachel was 39 weeks pregnant, they learned that their youngest, just two years old, had cancer. The past year+ has been a battle filled with treatments, hospital visits, and the courage only parents in that situation can truly understand. As Rachel and Tim shared their vision for a Whidbey Island home, it was clear this wasn’t just about real estate. It was about finding a refuge. A place of peace, restoration, and joy — close enough to the region’s best hospitals, but far enough away to feel like an escape.
Rethinking the Vision
At first, the search was daunting. The type of home they pictured in their heads was likely two or three times their budget — if it existed at all. This is where I believe real estate becomes a mix of detective work, intuition, and deep listening. I spend a lot of time focusing not just on the look of a house, but on the feeling and the lifestyle it supports.
I often find myself meditating on what my buyers are truly telling me. Not the exact paint color or the size of the garage, but the heart of it: What does this home need to provide for their lives?
The Serendipity of a Tour
A few times a month, our office tours each other’s listings. It’s a way to get feedback from colleagues and to see homes we might otherwise overlook. One July morning, I walked into a colleague’s new listing, and something clicked.
It wasn’t just the high-quality construction or the immaculate upkeep. It was the feeling. The warmth. The care that radiated from the space. The sellers, a couple in their late 70s, were ready to downsize and wanted a simple, hassle-free sale. They had priced the home reasonably, and it was clear it offered tremendous value.
I immediately texted Tim and Rachel: “I know this isn’t what you thought you were looking for — and you might think I’m crazy — but I really think you should take a look.”
They hesitated at first, but curiosity grew. About 10 days later, they stepped inside for the first time, and just like I had, they felt it instantly. This was home.
More Than They Imagined
The DeSimones not only purchased the house, but also the furnishings and even the vacant lot next door. Even better, the property sits waterfront to the lagoon, right across the street from the ocean, and includes access to a large pool. For two adventurous little boys, that means endless opportunities to explore island living — from splashing and swimming to discovering wildlife and sandy shores.
At the final walkthrough, I got teary-eyed reading the sellers’ thoughtful notes, sharing how they had freshly washed the linens and towels so everything would be ready for the DeSimones’ arrival. That level of care set the tone for what this house truly is: an invitation to rest, recharge, and build new memories.
When I checked in after their first night, their response was simple but powerful: “Better than expected.”
Why This Work Matters
This experience reminded me why I love what I do. Real estate isn’t about transactions — it’s about transformations. It’s about listening deeply, thinking creatively, and guiding people toward a home that supports their lives in ways they may not have even imagined.
For the DeSimones, this house is more than a retreat. It’s a sanctuary. A place of healing, joy, and togetherness. And for me, it’s a reminder that the right home really can feel like a warm hug.
To all the fun times ahead! Cheers to you DeSimone Family! 🥂🍾
~Kristen