Bree Gillespie

Sales Associate

Bree Gillespie's love for homes began long before she ever entered real estate. Growing up in California, she spent much of her childhood alongside her father on construction sites and in his workshop as a general contractor. Watching homes come to life from the ground up sparked a lifelong appreciation for craftsmanship, design, and the thoughtful details that make a house truly feel like home.

After spending seven years in Lake Havasu City, Arizona, Bree moved to Big Sky, Montana in 2022. It didn't take long for her to fall in love with the beauty, community, and lifestyle of Southwest Montana. Today she proudly calls Gallatin Gateway home, where she purchased her first home and helped relocate her mom to Belgrade as well. Having personally navigated the process of moving across states and establishing roots in a new place, Bree understands firsthand both the excitement and the challenges that come with relocation.

Before transitioning into real estate, Bree built her career in hospitality as a Concierge Manager in Big Sky. In this role, she spent months at a time working closely with guests to design personalized Montana experiences, carefully coordinating itineraries and communicating with local guides, outfitters, and adventure companies to ensure every detail of their stay was seamless. Through this work she developed lasting relationships with many of the region's most respected outdoor businesses and built a deep knowledge of the best ways to experience Montana in every season. Whether it's a quiet fly-fishing trip on the river, a winter sleigh ride through the snow, or a full Yellowstone adventure, Bree loves helping people discover the moments that make this place so special.

Her drive to support people through major life transitions led her into Human Resources, where she recruited employees from across the country and around the world to live and work in Big Sky. In this role she guided new team members through the relocation process, helped them secure housing, and supported them as they adjusted to life in Montana. From coordinating logistics to helping newcomers build community, Bree gained a deep understanding of what it takes to help someone truly settle into a new place.

Now as a real estate professional, Bree brings that same level of care, attention to detail, and dedication to every client she works with. Her background allows her to support buyers and sellers not only through the transaction itself, but through the entire process of building a life in Montana. Whether you're arriving from another state or simply ready for a new chapter in a different corner of the valley, Bree brings the same deep local knowledge and personalized approach to every move. Helping make the transition feel smooth, informed, and exciting.

Combined with her personal journey as a new homeowner, Bree approaches every transaction with empathy, transparency, and thoughtful communication. She understands that purchasing a home is one of life's most important decisions and believes every client deserves personalized support and advocacy every step of the way.