Success, Luxury, and Life (and Career) Pivots with Broker Cadey O’Leary episode artwork

EPISODE · May 4, 2026 · 23 MIN

Success, Luxury, and Life (and Career) Pivots with Broker Cadey O’Leary

from Just Call Claudia

Cadey O’Leary is a successful, award-winning Chicago broker who has seen firsthand how helpful CMFTO can be in a move. As a client and collaborator with CMFTO, she describes her personal experience moving from a single-family home to a condo during a time of transition in her life, and details how CMFTO has been an exceptional asset for her clients and development projects. In addition, Cadey is a friend, and I’m so excited for her next venture: Boutique by Design, a consultancy that works closely with developers of boutique condo buildings and single-family homes—and their investors—to create impactful, intentional products that embody true luxury and have lasting impact in the market. Listen for more on this new venture, and Cadey’s insights into the Chicago real estate market!Learn more about CMFTO on our website, Instagram, Facebook or LinkedIn.Cadey O’Leary is founder and CEO of Cadey O’Leary Collection, a boutique residential real estate brokerage committed to delivering an exemplary real estate experience. She possesses strong expertise in luxury new construction, the city’s upper condo market and Lincoln Park. Cadey and her team have collaborated with several developers in helping design, market and sell new condominium projects and Single-Family Homes across the city’s north side, many of which have achieved new pricing thresholds.She led the intensive ground-up developer collaboration and successful sellout of The Orchard Private Residences, Lincoln Park’s premier address and the standard for luxury on the city’s north side. Over the past five years, she and her team have brokered one-third of Lincoln Park’s upper-market condo sales of $2 million or more. Cadey’s latest initiative—Boutique by Design™--reflects her business’s intentional scale, strategic approach to growth and uncompromising commitment to exemplary service. She has established a new business under this moniker to consult developers and their investment partners in designing, marketing and selling refined residential offerings.Cadey is dedicated to nurturing long-term relationships with her clients, colleagues and partners across the city and beyond. She has curated a network of brokers and service providers that reflect her standards of service.She is a long-term resident of Lincoln Park.

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Success, Luxury, and Life (and Career) Pivots with Broker Cadey O’Leary

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This episode is 23 minutes long.

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This episode was published on May 4, 2026.

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Cadey O’Leary is a successful, award-winning Chicago broker who has seen firsthand how helpful CMFTO can be in a move. As a client and collaborator with CMFTO, she describes her personal experience moving from a single-family home to a condo during...

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