Courtney Cregan

A second-generation Realtor and proud Chicagoan, Courtney joins the Olive Well team at Compass in Chicago after working with the #1 small real estate team in Palm Beach, FL. There, she leveraged advanced product marketing techniques for their listings and facilitated transactions for buyers that propelled them into the brokerage’s national top 10, achieving in excess of $200 million in transactions.

Now part of the Olive Well team, where treating clients like family is the norm, Courtney combines her marketing acumen with her passion for connecting clients with homes they truly love. She excels at showcasing properties to their fullest potential through strategic marketing and personalized service, and is dedicated to finding the right fit for her clients, expertly negotiating deals that exceed their expectations.

Prior to getting into real estate, Courtney enjoyed a successful 11-year career in marketing that took her from her hometown in Lake Forest to San Francisco. During that time, she directed successful multichannel campaigns and go-to-market strategies for organizations ranging from Fortune 500 companies to startups. Most recently, she spearheaded the launch of a global financial technology company’s new innovation lab and ran marketing for a startup that was later acquired by LinkedIn. Courtney regularly obtained coverage for clients in The Wall Street Journal and The New York Times, and at one point, even spearheaded her own marketing agency.

An advocate for childhood social and emotional development, Courtney was previously a public school social worker in Denver where she was trained in psychology at the University of Denver. She has volunteered with organizations like the Junior League, where she mentored teenagers who have aged out of the foster system, and Edgewood Center for Children and Families. Passionate about restorative justice, Courtney is also a regular volunteer in correctional facilities, providing programs to support incarcerated and recently released individuals.

Growing up surrounded by beautiful architecture and rich heritage in both the midwest and on the east coast, Courtney found her love for history as her family pingponged between Chicago, Fairfield County, Lake Forest, and Manhattan. She supports several historical societies and preservation foundations, and you can often spot her on history tours across the Chicagoland area. Courtney maintains strong ties with her alma maters: Lake Forest Country Day School, Lake Forest Academy, The Hotchkiss School, and Trinity College.

An avid traveler, Courtney has run her own luxury travel consultancy and temporarily ex-pated to Southeast Asia where she fell for the coffee in Vietnam. (Ask her about her run in with the monkeys.) An outdoor enthusiast, she enjoys camping, hiking, skiing, and snowboarding and is always eager to embrace new adventures.

At home in Wicker Park, you can find Courtney curled up with a good book alongside her better half and their beloved pet family—an English Bulldog, a mini Golden Retriever, and two rescue cats.

Visit OliveWell.com for more information.