Jesse Fifield

Jesse Fifield is an experienced real estate professional currently serving as an Associate Broker at Portside Real Estate Group since August 2025, specializing in residential sales, new construction, investments, and property management. Prior to this role, Jesse worked at RE/MAX By The Bay from July 2023 to January 2025 as both an Associate Broker and New Construction Coordinator, and previously held an Associate Broker position at Portside Real Estate Group from October 2020 to September 2023. Jesse began a career in real estate at Jacob Realty from April 2015 to September 2023, focusing on selling and leasing properties in the Boston area. Additionally, Jesse has served as a Customer Support Specialist at L.L.Bean since September 2025 and gained retail management experience as an Associate Store Manager at Club Monaco from June 2013 to April 2014. Jesse holds a Bachelor of Arts degree in Journalism from Hobart and William Smith Colleges, earned between 2004 and 2008.