Cadey O'Leary

Cadey O’Leary has honed her knowledge and passion for quality new construction and design into a successful residential real estate business where she serves a range of clients from real estate developers to buyers and sellers of fine homes and condos on the city’s north side. She is devoted to her clients, values long-term relationships and is appreciated for her candor, responsiveness, marketing and sales skill and personability. 

With over ten years of upmarket real estate experience, an extensive background as a successful entrepreneur and marketing expert and a staunch commitment to excellence, Cadey has emerged as one of Chicago’s award-winning and top-producing agents. Cadey’s unwavering dedication to go above and beyond for each and every client and her proficiency in communication and negotiation have earned her recognition as one of Chicago Agent Magazine’s “Who’s Who of Real Estate,” a Top Producer by the Chicago Association of Realtors and Platinum Producer at Jameson Sotheby’s International Realty in Chicago.  
Cadey is an active member of the Lincoln Park Chamber and University Club of Chicago and is a long-time parishioner of St. Vincent de Paul Catholic Church; she has co-founded several networking groups and works closely with local Aldermen and small business owners in contributing to the future vitality of her Lincoln Park neighborhood.

Lincoln park expert

Cadey has spent a decade cultivating relationships and a keen market understanding for Lincoln Park’s upper market.  She truly has an expertise for the area and her clients find her knowledge to be invaluable.  

She shares her thought leadership and Lincoln Park expertise in her modest blog and monthly market updates. 


As a seasoned luxury Real Estate professional, Cadey curates monthly newsletters, as well as, useful resources for both buyers and sellers.  

Cadey’s goal is to empower her clients to buy and sell real estate with clarity, confidence and ease.


2331 Montana blends classic design with coastal influences and modern lines to deliver urban refined living that is inviting, casual and timeless. The contemporary urban architecture integrates a brick façade, large, black-framed windows and light-filled interiors with clean lines in light, neutral tones to produce an elegant, design-forward home with a hint of edge.

Cadey joins a talented team of architects, designers, builders and marketers to bring 2331 Montana to life.


An Uncommon Standard of Living

The hallmark of Cadey’s career has been the intensive ground-up developer collaboration of The Orchard Private Residences in Lincoln Park. For years, Cadey worked alongside the development, architectural and interior design teams from the building’s conceptualization to refinement of the unparalleled features and finishes of the 32 residences. The result is a masterfully detailed, highly curated, boutique residential building that has established a new standard for high-design and elegance in Lincoln Park. As sales lead, she is especially delighted by the market’s thunderous response.  The Orchard Private Residences has become the most sought-after address on the city’s north side.

Born from a meaningful collaboration of the foremost design and development talent, on one of the most coveted blocks in Chicago, comes an address so rare and well imagined, it’s available only once in a generation.