Meet Diana Soldo Massaro

When Diana Soldo Massaro steps in, the roar of the Chicago real estate market quiets. As a seasoned Realtor, Diana has made it her life’s work to fiercely protect her clients from the volatility of the market she knows intimately, pouring over data and trends to empower them to make thoughtful, wildy happy decisions.

Diana is known for her ability to connect deeply with clients, offering honest insights into their current needs while helping them envision what lies ahead. She guides them in imagining the life they want to build—and finding a space that truly fits. For Diana, the process goes far beyond simply finding a house; she helps her clients discover homes that feel grounding, life-giving, and aligned with their values and aspirations. Whether it’s a painting studio, room for a soon-to-arrive puppy, or a chef’s kitchen for a passionate home cook, Diana understands that the magic of a dream home is born in the details. For clients selling their homes, Diana brings a strategic, market-savvy perspective—advising on everything from pricing and timing to the nuances of a successful sale. Diana also offers specialized expertise in multi-unit properties and estate sales, providing tailored guidance in these often-complex transactions.

Her work is shaped by her history. As the proud daughter of self-made Croatian immigrants, Diana is guided by the values her parents embodied: hard, honest work and abundant gratitude. She remembers cleaning every banister in every building her parents managed—an early lesson in diligence that still defines how she shows up for her clients every day. A former photographer and television producer, Diana honed her creative problem-solving skills in fast-paced, high-pressure environments. Today, she couples that same agility and resourcefulness to real estate, pairing it with deep market knowledge to transform challenges into opportunities.

When she’s not helping her clients establish gorgeous nests or make smooth transitions, she’s likely on the tennis court, cheering on her sons at a Lakefront soccer game, or dining at one of the many amazing restaurants in Andersonville, where she and her family live. Avid travelers, they make it a priority to discover new destinations around the globe together.

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