Dream Town Realty Top Producer, 2021
Dream Town Realty 5th Highest Individual Sales Volume Company Wide, 2021
Dream Town Realty 4th Highest Number of Units Sold Company Wide, 2021
Chicago Association of Realtor's Top Producer, 2021
Chicago Agent Magazine Who's Who, 2021
Certified Pricing Strategy Advisor

Heart-centered, data-driven guidance through a tricky, ever-changing market

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, wildly happy decisions.

Diana is known for her ability to connect deeply with clients, making an honest assessment of their current needs, imagining those yet on the horizon, and helping them dream about the life they can build in a space that fits them. Far beyond the simple search for a house, Diana finds her clients grounding and life-giving homes that reflect what’s most important to them and their exciting hopes about who they might become. A painting studio? Space for the puppy who’s about to become part of the family? A chef’s kitchen for the amateur but passionate home cook? Diana inherently knows that the delight of finding a dream home is born in the details. For clients selling their homes, Diana uses her big-picture understanding of the market to help them make wise decisions about strategic pricing, opportune listing time, and navigating the overall process.

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. During childhood, she recalls cleaning every single banister at every single property her parents managed; she shows up for her clients each day with that same tireless resolve. As a former photographer and television producer, creative problem solving around high-stakes issues became second nature to Diana. Today, she couples that same quick thinking with a deep knowledge of real estate to turn obstacles into opportunities.

In an intimidating urban market, Diana is a confident, reassuring presence. Even as she continues to rank among the Top Producers across Dream Town and most recently, 5th Individual Top Producer company-wide, she remains unwaveringly obsessed with the hunt for each client’s have-it-all home or strategic sale. She is the calm voice on the other end of the phone, the knowing nod across the table that lets her clients know she’s there to defend their interests and their dreams wholeheartedly. When she’s not helping her clients establish gorgeous nests or make smooth transitions, she can be found enjoying a match on the tennis court, singing her heart out in a music festival crowd, or snuggled up in Andersonville with her husband, two sons, and dog.

Meet The Rest Of The Team