For those who see Sarasota as more than a vacation spot, finding the right second home is about timing, relationships, and knowing where to look. Waterfront properties in this market don’t often trade hands, and when they do, it’s rarely a public affair. That’s where John Parker comes in.
With years of experience navigating Sarasota’s upscale and second‑home market, Parker blends deep local knowledge with a knack for recognizing value others might overlook. His network extends into the circles where the most sought‑after properties are quietly discussed long before they hit any listing service. Buyers who work with Parker aren’t just shown homes—they’re introduced to opportunities they might never have known existed.
In this conversation, Parker shares how he approaches the Sarasota market, the qualities that make a second home a lasting investment, and why his approach focuses as much on lifestyle fit as it does on closing the deal.
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What makes Sarasota such a strong market for second‑home buyers?
Sarasota offers a mix that’s hard to find anywhere else. We have pristine beaches, a thriving arts scene, excellent dining, and an overall quality of life that appeals to people looking for more than just a place to vacation. It’s also well‑connected—easy to get here from other major cities—so owners can enjoy it year‑round or come for quick getaways.
The real draw, though, is the lifestyle. People don’t just buy here for the property; they buy into the idea of Sarasota as a place where they can truly relax and live on their own terms.
How do you gain access to properties that don’t hit the public market?
It’s a mix of trust and long‑term relationships. Many of Sarasota’s best properties are owned by people who value privacy. They’re not interested in public showings or open houses. Over the years, I’ve built connections with homeowners, attorneys, financial advisors—people who know when a property might quietly be available.
Because I respect that privacy, those same people are willing to call me when it’s time to talk about selling. My clients benefit from that trust by getting first look at homes that never make it online.
What do you advise buyers to look for in a Sarasota second home?
It starts with location, but not just in the traditional sense. Waterfront is obviously prime, but even within that category, some stretches hold their value better than others. Then it’s about functionality—does the home fit how you plan to use it?
If it’s primarily for family gatherings, you want space for everyone to stay comfortably.
If it’s more of a couple’s retreat, maybe the focus is on luxury finishes and a great view. I also encourage clients to think about the upkeep. A second home should be a joy to own, not a constant project.
How do you help buyers see beyond the immediate purchase and into the long‑term value?
I take them through both market history and future projections. We look at how similar properties have appreciated over time and what’s happening in the neighborhood now. Are there new amenities being built? Any changes to zoning or environmental regulations?
The goal is to make sure they’re buying something that will still be desirable—and marketable—10 or 20 years from now. That’s especially important for a second home, where resale might not be the immediate focus but is still part of the bigger picture.
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What’s your guiding principle when matching a buyer with a Sarasota second home?
A second home should enhance your life, not complicate it. I work to make sure the property fits not only the client’s budget and investment goals but also their lifestyle and vision for how they’ll spend their time here.
If it’s the right home, it will feel like a natural extension of who they are and how they want to live. When that’s the case, you’ve done more than close a deal—you’ve helped someone secure a place that will hold meaning for years to come.
