

Diana Soldo Massaro
About Diana
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, wildy 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. 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.
“Sold by Soldo” is SO MUCH MORE than a Real Estate transaction. Diana is a consummate professional, advising us through an endeavor that is life changing. We are grateful for her expertise and heartfelt friendship, and cannot recommend her enough!
Diana Massaro Group’s Past Sales
See what people are saying about Diana
-
Darrin & MelissaAndersonville Diana has extensive knowledge and tools that help you understand the local market and pricing. She has a no pressure approach and made sure we were comfortable with the whole process, offering assistance when we needed. She proved great communication skills when negotiating with sellers, and offered valuable guidance on pricing and credits during contracting phase. Because we had access to her network of experts (lawyers, inspectors, contractors, etc), we could quickly put a $$ and time value on potential issues. This allowed us to move through the process quickly and smoothly. We’ve bought properties before, but this was easily the least stressful experience overall. Diana listened carefully to our wants and needs, and found the perfect home for our family.
-
Emily C What do you do when you want to find an affordable home in Chicago ... in this market ... with low inventory .. in good-school neighborhood ... all while living in DC? You enlist Diana Massaro. Here's what Diana will do for you: She will first pull up what has been bought and sold in your price range based on the type of home you're interested in buying. She's set realistic expectations but also inspire you to think outside the box. She'll get a sense of what you want even though you might not be articulating it so perfectly because the process stresses you out and you forget how to use words. Diana will then get to work. She will send you homes: private listings, 'inside-scoop' properties she has worked hard to cultivate based on previous client experience, as well as homes as they hit the market. She will stop by properties you're sort of/kind of interested in (not even fully) in the snowy rain (rainy snow?) ... with her kids ... and take video for you to get a sense if it's worth scheduling a tour. One of the properties we were curious about had the Chicago El tracks behind it and Diana legit stood there waiting for the train so we could see how close and loud it might be (too close BTW). When you get nervous and randomly ask you to look up rentals because this market is so scary and maybe you won't ever get a house, she will send you a list of rentals but also gently nudge you to stay positive and continue the search. Diana will Facetime you for every home tour she conducts. If you can't be present for FT or if you get motion sickness from FT (like me) she will send several videos as an alternate. She will talk to neighbors and walk around the block. She will set the phone down on the floor and raise her hands up high-high in the basement so you can see how tall the ceilings are. Diana will put in as many offers as you'd like, often working late into the night after a son's birthday party or during a harrowing week when she had to say goodbye to her beloved pup. She will explain what she is doing and why; she will also listen to your input and make sure the offer reflects where you stand. When you buy your house from a distance, Diana will do a walk through with all of the family members who live in the area, including fathers and mothers and brothers and in-laws and nephews and friends of the family who are also contractors. She will befriend them all, but also make sure you are the most important person in the room, even though you are on a tiny screen. She will recommend a lender (thank you Luke and Jennifer!), a solid inspector (we love you Steve!) and befriend the seller's agent (shout out to Rhonda!). On your closing day, Diana will walk to your house as a symbolic gesture of support even though the closing is happening in an office somewhere else with powers of attorney doing the signing. She will drop off a beautiful bottle of champagne in a tiny retro-refrigerator box because she knows you want to embrace the vibe of a Chicago bungalow. She will take a picture with the seller's agent in solidarity and celebration. She will also follow up to see how things are going and get just excited as you do that the linoleum floors have beautiful original wood underneath! Enlisting Diana is the right choice for your remote home-buying journey ... and my two sisters can attest that she also is the perfect realtor for searches in your own Chicago backyard. We are so grateful for you, Diana, best of luck with future buyers!
-
Jeff and Sharon Diana is phenomenal. We couldn’t ask for a better realtor. She always has “our back”. ALWAYS. She is knowledgeable, helpful, responsive, caring. She consistently goes above and beyond making us feel “special”. We bought a house from 700 miles away with only two visits, using modern technology to keep us informed and connected. She quickly assessed exactly what we were looking for, consistently reassured us that we would find it, knowing that our requirements severely limited the number of properties. She kept close contact, carefully monitoring the scene, always providing thoughtful analysis and counsel