Darin Chaffee

Hi, I’m Darin Chaffee— I grew up in a small town in Northeast Pennsylvania and spent my early adulthood living in different places along the East Coast. After going through some challenging life events, I knew I needed a fresh start—and something about San Diego called to me. The lifestyle, the energy, and the sense of possibility here gave me exactly the reset I was looking for. Now, I’m proud to call San Diego home and passionate about helping others find the place that feels like home for them, too.

Before real estate, I built a career in hospitality and project management—industries rooted in service, detail, and human connection. That experience shaped how I approach real estate today: I’m not just here to open doors; I’m here to be a trusted guide, fierce advocate, and problem solver for every client I work with. Whether you're buying, selling, or investing, I bring a resilient, relationship-first mindset to every transaction—along with a touch of humor and a serious eye for strategy.

I work with Whissel Realty Group, one of the top-performing teams in San Diego, where we combine data-driven marketing, local expertise, and heart-led service to get incredible results for our clients. My favorite part of the job? Helping people make confident decisions that change their lives. Whether it’s a buyer finding the home, a seller getting top dollar for a place full of memories, or an investor spotting the right opportunity—I’m here to make it happen.

If you’re thinking about buying, my advice is: don’t stress. You don’t have to know everything—that’s what I’m here for. We’ll take it one step at a time, starting with getting you pre-approved and dialed in so we can shop smart. And if you’re selling, know this: first impressions and pricing matter, and I’ll help you prep and position your home to stand out from day one.

San Diego has so much to offer, but North County has a special place in my heart. From the surf and sunsets of Encinitas to the community feel of Vista and Carlsbad, I love helping people discover what makes these neighborhoods unique. When I’m not working, you’ll probably find me hiking Los Peñasquitos Canyon, biking the Coastal Rail Trail, or chasing sea lions on a kayak in La Jolla. And if you ever hear someone whistling “Keep Going” by The Revivalists—yep, that’s probably me.

I’m a people person, a relentless problem-solver, and (according to my high school yearbook) a “boujee clown”—so yes, I believe in keeping things both professional and fun. Let’s connect, talk about your goals, and make your next move the right one.