Bailey Chalfont

Bailey Chalfont is a dedicated real estate professional with a background in Aspen’s luxury real estate and hospitality industries. Originally from Winter Park, Florida, he attended Auburn University, where he earned a degree in Supply Chain Management. After graduating, Bailey moved to Colorado where began his career in real estate, developing a strong understanding of lifestyle-driven communities. He now brings his thoughtful, client-focused approach to Miami Beach and its surrounding neighborhoods.

A passionate skier since childhood, Bailey consistently placed in the top 10 at the Junior U.S. Extreme Freeskiing Championships in Crested Butte, Colorado, and continues to seek out the mountains whenever he can. His love for the outdoors extends beyond skiing to the golf course—a setting that naturally aligns with the lifestyle many of his clients appreciate. Whether discussing Florida’s top courses or exploring new communities, this passion gives him a deeper understanding of properties and neighborhoods that embrace an active, leisure-focused way of living.

Time spent with family at The Yellowstone Club and Shell Bay, along with a decade of living and skiing in Aspen prior to moving to Miami, has given him firsthand insight into what discerning clients value most. This perspective shapes his belief that a home should be more than an investment — it should reflect how each client truly wants to live. He pairs this understanding with strategic market expertise and a commitment to discretion in every transaction.

Bailey combines market analysis with strategic marketing to deliver results aligned with each client’s goals. By studying neighborhood trends and buyer behavior, he provides clear, data-backed insights that help clients make confident, informed decisions. His attentive listening and thoughtful guidance ensure every recommendation reflects real market conditions and each client’s unique vision.

Every property is showcased through polished branding, professional staging, and compelling visual storytelling. From targeted digital campaigns to personalized outreach, Bailey maximizes exposure and positions each listing to stand out in Miami’s competitive market.

With a calm, professional approach, he guides each step of the buying or selling process with care and intention. Backed by the reach of Compass and the strength of The Nancy Batchelor Team — Miami Beach’s top-ranked large team three years in a row — he brings market expertise and attentive service to every client relationship, with a clear commitment to delivering results.

As a Florida native, Bailey takes pride in helping clients find their perfect property in the state he’s always called home.