Bailey Chalfont

For Bailey Chalfont, the most compelling homes do more than meet a list of requirements. He considers the life a property offers and the market in which it sits. Both shape the advice he gives buyers and the way he brings a home to market for sellers.

Born in Winter Park, Florida, Bailey graduated from Auburn University with a degree in Supply Chain Management, studying how decisions in one part of a market affect another. He spent a decade in Aspen, working in hospitality and retail, including as a concierge at The St. Regis Aspen Resort. He earned his Colorado real estate license in 2018. Those years taught him the value of discretion, attentive service, and knowing a community beyond what appears in the listing data.

Based in Miami Beach and licensed in both Florida and Colorado, Bailey represents buyers and sellers throughout Miami-Dade. Since joining The Nancy Batchelor Team in 2025, he has negotiated more than $22 million in real estate transactions. His work spans single family homes, luxury condominiums, waterfront residences, and pre-construction developments. He considers each property in the context of its neighborhood and the broader market, giving clients a clear understanding of its value.

For sellers, Bailey considers a home through the eyes of its next owner: what will draw them in, what sets it apart, and how it should be introduced to the market. From there, he shapes its pricing and presentation and brings it directly to buyers and brokers who may see its value. He is just as considered with buyers, studying a property’s history, condition, and comparable sales before offering a candid assessment.

Outside of work, Bailey’s interests keep him connected to both the mountains and Miami. He grew up skiing competitively and spends time at the Yellowstone Club with his family. In South Florida, he enjoys golf and time at Shell Bay, while his membership in New World Angels and Jackson Health Foundation’s Young Impact Collective connects him with Miami’s business and philanthropic communities. The time he spends in these places informs his understanding of what clients value beyond the home itself.

Through Compass and The Nancy Batchelor Team, the #1 Large Team in Miami for 2023, 2024, and 2025, Bailey offers the reach and relationships of one of South Florida’s leading luxury real estate teams while remaining personally involved at every stage. Whether you are considering a tropical escape or mountain retreat, contact Bailey Chalfont directly for his expert insight and a clear path for your next move.