2017 & 2020 Top Producer, Awarded by the Chicago Association of Realtors
Certified Pricing Strategy Advisor, PSA
A full time Real Estate Broker, Diana was born and raised in Chicago to hard working immigrant parents. Diana’s passion for real estate is instantly noticeable. Her father told her long ago that she would be “great at this business not only because she knows how to sell, but because she has a good heart,” and that resonates with her every day. Clients say Diana is a very honest and trustworthy individual, and she genuinely loves helping people. Diana’s unparalleled work ethic and understanding for real estate is deeply rooted in her family history of property management and investment. At an early age, she learned first hand every aspect of the business from maintenance to marketing.
Diana’s extensive experience with sales, management and knowledge of the local real estate market make her a valued expert in the field. Diana is both a homeowner and investor which gives her the ability to relate to her clients on a variety of levels. Whether buying or selling, she helps clients accomplish their goals by listening to their wants and needs. Diana offers advice and pertinent information so that her clients can make smart, informed decisions.
Diana is pleased to announce another record year of sales. In addition to achieving a 98.3% list-to-sale ratio in 2019, she outperformed the Illinois market average by selling homes 34 days faster! Diana is a member of the Chicago Association of Realtors and has been recognized many years as a Top Producer in Chicago, most recently in 2017. She is also a Certified Pricing Strategy Advisor (PSA). Negotiating strategies, continually analyzing market trends and building solid relationships for the benefit of her clients are Diana’s top priorities.
Whether you are looking to buy or sell your home, obtain guidance on acquiring an investment property, need contacts to reputable contractors and professional partners, or general information on what’s happening in ‘all-things Chicago’, contact Diana. She is delighted to share her knowledge and is your go-to resource.
At the end of the day, the most important piece of the transaction is you, the client. And Diana works tirelessly to make sure all of her clients are 100% satisfied with their results. When you’re working with Diana you will feel as if you’re her only client because she offers you 100% of her energy and attention... because you deserve it.
Diana currently lives in Andersonville with her husband Paul, two sons, and dog Buddy. She is fluent in both Croatian and German, and loves to travel. In her free time she loves going to concerts and music festivals with friends, playing at the dog beach, and taking her kids on mini adventures in the city.
Diana was my first realtor in over 10 years. I had no idea how much the industry had changed and she guided me through it expertly. She utilizes docusign and can get a bid together in record time! Thanks Diana!
Diana is beyond amazing! So personable, knowledgeable, and resourceful. She found us the perfect off-market home by honing in our preferences and our taste, walking us through the process with patience and care, and helping us craft a personal letter that, ultimately, helped us win the hearts of the sellers. She made herself available to us at all hours and worked tirelessly to ensure we got our dream house for the best price. We couldn’t be happier!!!
I used her to buy my first home and now to sell my first and upgrade to an investment property. She was an invaluable resource as we decided to make this change, having done it many times herself. She helped us narrow our neighborhood window and find and get into competitive properties before anyone else. With her help, we closed quickly on a dream investment property and closed on our first home with difficult buyers at the same time. Whew! Can wait to do it again but when we are ready, we won't use anyone else.
Selling a condo sounds horrible but by using Diana and her team it was a "dream". 4 offers in 72 hours and over asking price. She handled everything and it couldn't have been easier. Really wish i had used Diana when I bought. Very experienced and knowledgeable
Diana made everything so easy and as stress-free as possible. I loved working with her and her team. Very professional approach and I highly recommend her to anyone I hear that needs an outstanding Realtor!
Diana was an exceptional resource when we were selling our condo and buying a house at the same time. We were very nervous going into the process, as it seemed like so much to take on, but Diana's experience and instincts made the process about as painless as it could be. From advising us on how to price and handle offers on our condo, to answering our questions about home amenities, and every step of the home buying process in between, Diana helped us get a house we love at a price well within our budget. Diana knows the city really well, is tremendously market savvy, and is a wonderful person to boot. Our family is so happy to be here in West Ridge and to be able to call Diana not just a trusted advisor but a friend.
I don't know if there is enough room to truly express how great Diana is as a realtor and person. When we were ready to look for a house, we had multiple people refer us to talk to Diana. We are so happy we did. She is prompt, understanding, and kind. There were many times that my fiance and I would like a house and would tell her on short notice, and she would need to schedule to see it the very next day. She would do it without hesitation and with such kindness. It was especially difficult because we were looking at houses in the suburbs and she mainly worked in the city. Not once did she ever say anything about making numerous long trips to see us. She did this for months! Overall, Diana is amazing. She is an expert and knows what she is doing! If you don't believe me, the other reviews are spot on as well. Susan and Steve
Diana was amazing! She was always available to answer any and all questions we had and made the process very easy!
As a first time homebuyer, I needed an extra patient agent to help me through the home purchasing process. Through all my questions (and there were a lot) Diana stuck by my side to find an amazing place! Diana offered patience, trusted advice and around the clock communications. It's very reassuring when your agent is available for late night calls and responds to early morning texts. It was very pleasant working with Diana. I have already recommended her to friends and relatives! Angie B., Wicker Park
Diana was amazing. Her patience and knowledge of the market and neighborhoods was incredibly valuable as we looked for our first home in the City. She offered wisdom and guidance at exactly the right times. We ultimately decided on new construction, and this is where her stamina and positive attitude really shined. Our closing was delayed, and delayed, and delayed again. Through it all, Diana was our sounding board, therapist, and trusted professional. Her responsiveness and attention to detail saved us from mistakes on more than one occasion. Moreover, she was our friend. We could not be happier with our choice to work with Diana, and we are happy that we are now part of the Sold by Soldo family!
We are so glad that we chose Diana Soldo Massaro as our agent for the sale of our building. Diana devoted all her energies to this project, which led to a fast (a contract was signed in less than a week!) and most successful sale. Her ideas about staging the property were very insightful, and she recommended workers who were speedy and cost effective and who performed very high quality work. She suggested excellent strategies for showing the building to potential buyers (both online and in person), and she guided us through the pricing decision and the eventual sale negotiations. We have worked with other brokers in the past, and Diana was light -years ahead. She answered our emails, texts and questions within minutes, and we were totally in the loop at every point in time. On top of all that, she was a joy to work with; she kept us laughing throughout the process. We are certain that, without her hard work and guidance, we would not have achieved the fabulous result that we did. We cannot thank her enough for all her efforts. She was not only worth her fee to us; she was worth her weight in gold! Candace and Tom, Loyola Park
Diana helped make selling my condo a very quick and painless process! Throughout the real estate transaction, Diana had my best interest at heart! Svetlana Dordevic
Diana was incredibly enthusiastic and knowledgeable. She knows the market and was able to sell my condo in less than two weeks! She was great with feedback and with working around tenants' schedules. Overall great experience! Rebecca F., Lincoln Park
We would like to thank you and Diana for a great experience in selling our condo in Bucktown. From the moment we reached out to Diana until the closing, she provided exceptional guidance. Her depth of knowledge in the Chicago housing market was quite impressive. She expertly evaluated the area and real estate landscape, and in the end, helped us close at an incredible price. In addition, Diana went above and beyond to accommodate our demanding schedules, as we were in the midst of planning our wedding for May 31. She made everything seamless and was an absolute joy. Again, we are incredibly grateful to the service provided to us during the sale of our condo. We hope to work with Diana and Dreamtown once again! Regards, Goran and Svetlana Kovac
In dealing with Diana I found her to be very well organized, timely and professional in all interactions. She understands the real estate market in Lincoln Park and demonstrated her knowledge and concern through out the process. She anticipated and reacted positively to a potentially deal-break situation when the buyers did not meet the required date for their loan approval. Also, the Dream Town brochure of the condo was quite impressive. Exceptionally well done, including but not limited to the layout, design and photography. Thanks for everything! Sharon
As a first time homebuyer, I was a bit nervous to start the process of looking for a condo. Diana was always there to answer questions and book showings at times that were convenient for my schedule. Diana guided me every step of the way, and she helped me find just the right home in just the right neighborhood! Ana Bolotin
From the very beginning of our home search, Diana was there to make sure we found the perfect place for us. Always patient with our changing needs, Diana helped us through the process as first-time home buyers with helpful information and explanations each step of the way. She was extremely prompt in responding to our questions and in getting last minute showings arranged around our busy schedule and when we finally found the right place, her knowledge and expertise helped us with the final-walk through, closing and beyond. She felt more like a friend than a realtor, and we would highly recommend her to anyone who asked!
After months of searching, it is surreal that we are holding the keys to our brand new home! Today we are blessed to be living that dream and it is all because of the most dedicated, professional and caring realtor: Diana Soldo Massaro. The search for a home can be stressful and seemingly impossible at times. She was always optimistic, tenacious, trustworthy and extremely reliable. She answered all of our endless questions and helped guide us throughout this entire process. Thank you Diana. You are a true friend and an amazing realtor. From the bottom of our hearts, we are extremely grateful! Slav and Diana Medved
Diana came recommended as a real estate agent for my sister a few years ago and since then not only has she become our family's go to agent but we consider her a dear friend! She has always been available for showings even with little notice! We have had a lot of questions throughout this home buying process and she has been extremely helpful! Always quick to respond to our messages! She even kept me from giving up on searching and I'm so thankful for that as we just purchased a beautiful home for our family...which at one point I thought we'd never find! Thanks so much! Dan and Mira
When we were ready to make the leap to a single family home, Diana Massaro was there for us - for over a year! Diana became our go to person, our confidant, our fountain of 'patience' during a very long and narrowly focused search. Diana has an excellent eye for architectural detail, offers in-depth knowledge of Chicago neighborhoods and provided us with the perfect guidance throughout the entire search. Diana also understands the investment process - during our search she guided us toward homes that would have the best opportunity for appreciation over a 15 year horizon. I loved that she looked at our whole 'family' and took into consideration all of our needs. She's smart, diligent and kept us on track. What happens when you're dealing with difficult sellers? Diana was brilliant in dealing with the complexities of the transaction and managing all of the personalities involved. This path to our dream home had so many twists and turns - it was epic! Diana remained calm and was a persistent negotiator and got us our first choice in the end. Diana continues to be a source of support now that we are remodeling and has connected us to skilled contractors, craftspeople, painting firms and the like. We highly recommend Diana and her firm, Dream Town Realty, to anyone whether a first time buyer or experienced buyer. We felt like Diana cared about us during the process and this wasn't just a 'deal' to get done. Her professionalism, attention to detail and ability to connect with her clients make her an asset to her industry and her peers. We are forever grateful to her for making our dream come true - owning a mid-century modern home in a wonderful Chicago neighborhood! Tony and Christine
When my husband and I finally became serious about looking for our first home together, we performed a cold search through various search engines and contacted various realtors. After many conversations, nothing felt quite right. It was then that we asked a good friend who she and her partner worked with to find their first home, and she enthusiastically replied, "Diana Soldo Massaro!" I trust my friend, and if she trusted Diana, we decided that Diana was the way to go. From the moment we met her, we felt informed and part of the decision making process. Feeling that we knew less than the average person about home buying, Diana quickly put us at ease and made sure to explain every process and term along the way. It was apparent how successful and in demand Diana is, though one would never know it by the way she was ever-present and always hearing our thoughts and feelings. Diana is tough and assertive, but kind and respectful in her communication. Diana held our hand throughout the entire process, and continued to even after we found our beautiful home. She served as our advocate (and sometimes therapist!) to ensure that we were happy and would continue to be down the line. Even after we closed, Diana was available when we had questions about our new home. Though we can't imagine ever leaving our home, we will be working with Diana in the future should we ever decide to make a change, and we will be recommending her to anyone in search of a new home. Thank you, Diana! Meg and Jon
As a first-time homeowner, I could not have asked for a more knowledgeable, patient, and hard-working realtor. From the start, Diana took a genuine interest in working together to find my ideal place and understanding exactly what I was looking for. She was there every step of the way-explaining how the process worked, patiently answering my questions, and always acting as my advocate. The showings she arranged proved that she had listened-the price range, neighborhood, and specifications were exactly what I was looking for. No time was wasted. When I found the place I loved, Diana truly delivered. We learned that an offer had already been made, but she hand-delivered a contract the day of the showing to seal the deal and beat the competing offer. At a time when properties are snapped up in under a week and sellers are dealing with multiple offers, Diana recommended that I move quickly when I found a place I liked. Her recommendations were honest and on-target, and together we found the perfect home for me. I also appreciated Diana's strong relationships with others in the industry. She put me in touch with a lawyer, mortgage broker, and inspector-all of whom performed wonderful work. Working with Diana was a wonderful experience, from start to finish. She is professional, genuine, and very hard-working-there's nothing more I could ask for. Cory L.
I went to Dream Town after working with another Broker and having a real estate deal go bad and losing over a $1000. I used Dream Town's instant messaging on their website and Diana called me within minutes of my request for a realtor. Diana was on her 'A' game at all times. She bent over backwards to find me the right condo and make the process run smoothly. We ended up finding one and closing within 2 months. It was a great experience working with Diana and Dream Town. Mary Doyle, Rogers Park
The best! 10 Gold Stars, excellent customer service, & she's always available! Samantha Price
As my Realtor, Diana provided an exceptional level of customer service and was able to find the perfect match for our home. She truly met the gold standard. Throughout our property search, Diana remained enthusiastic, professional and found unique properties that exceeded the expectations of our search criteria. Through working with Diana, the "hunt" for the perfect home was a pleasure throughout the entire experience. She is a very sociable and knowledgeable individual in her field and was always provided a prompt response to any question that we encountered. In the end, Diana found us a property that went beyond our dreams, while remaining within our budget. I remain grateful to Diana for finding us the perfect home and would recommend her as a real estate agent to any of my family and friends in search of "The Perfect 10" in terms of quality, customer service and, most importantly, the perfect property to call your own. Thank you again! Jennifer
Love this realtor! Diana was a perfect fit for us as first-time homebuyers. She arranged an initial consultation to find out what our wants and needs were, and really took the time to figure us out. She walked us through the whole process step-by-step, taught us about what to look for in a home and was readily available when we needed her. Once we found a place, she quickly negotiated an incredible deal. We're thrilled with our home! Diana is not the kind of agent who pushes for a fast deal to collect her commission; instead she's like a friend who is looking out for you and genuinely cares about connecting you with a home you'll love. Martina & Rob, Old Irving Park
Oh dear. Where do I start. I didn't do any due diligence in trying to find a realtor - HIGHLY unusual for me. It was a pleasant turn of fortune that I ended up with Diana. This was a long process. We didn't go under contract until April, and didn't close until June. And over that 8-month process, Diana became my confidante, advisor, go-to expert and friend. Now, I said 8-month process. Never once did she lose her patience, even though I was always a bit indecisive and there were probably moments when she thought I was never going to pick a place. She was an incredibly helpful resource and sounding board - always answering my questions, prodding for how I was feeling and what I was looking for, but NEVER pushing me towards anything I didn't want to do. She was available at incredible hours. She probably worked longer weeks than I did - and that's saying something. And she always bent her schedule to an extent that I felt my showings, conversations, emails were always a priority. She is very very cheerful. I'm a very energetic person myself, so it was great that we bounced off each other's enthusiasm that way (we could have powered the nearest cell tower between the two of us). She genuinely loves her job, which makes her that much better at it. There were some things that I still had to handle myself - I felt more comfortable deciding on the numbers behind the offer and the negotiation myself; I picked my own broker because I did the research to find the best rate; I did a second due diligence behind the property (consider it the equivalent of a second opinion with a medical diagnosis). She made herself available throughout all this and never took it the wrong way that I chose to handle these myself. I could keep writing about this. I could tell you that I've recommended her to two different co-workers, who have both been very happy (and for whom Diana has given me referral gifts :) - because she's just that thoughtful) I could tell you that when I had my housewarming on a night when she was busy - she made sure to come over with her husband at some point to give me a housewarming gift. I could tell her that I genuinely don't think I could have found the place where I'm very very happy without her. I could tell you that when I buy another place in the future, there's only one agent I'd consider. Or... you could just go talk to Diana and see for yourself. Hariharan V.
Words cannot express the gratitude that we feel towards Diana for her extensive care & consideration with our family & selling our home. She is truly a beautiful woman who lives life with sensitivity to those around her. Thank you so much for everything you have done! The Houlis Family, Elmhurst
I came across Diana and Dream Town by chance, and I could not have been luckier. I entered the process with a vague idea of what I wanted, but minimal understanding of how the process worked - from searching to closing. After our initial contact, Diana worked hard to help me narrow down my scope and discover what I was really looking for in a property. She never pressed me with anything and was always extremely accommodating with my schedule and decisions. She went above and beyond my expectations every step of the way, and was instrumental in putting all of the people and pieces together when it was finally time to choose my new home. She was a great girl to work with - fun, optimistic, and hard working. I couldn't imagine working with anybody else! Dan Roos, The Loop
From the minute I met Diana Soldo Massaro, I knew she was the perfect choice to help me find a condo worthy of investing in. She has patience in spades, and she knows the city like the back of her hand. This knowledge was invaluable in giving me a sense of neighborhoods to consider, places to avoid, and areas where I could find my trifecta of price, quality and proximity to great restaurants. What I appreciated most about her is that she never pressured me into a purchase. She understood I was nervous about this big decision, and she only offered guidance and support as I worked to figure out what I wanted. Once my decision was made, she made herself consistently available to answer questions, while ensuring the process from offer to closing went as smoothly as possible. I couldn't be happier with my purchase, or the process to get here! Cassie Ringsdorf, Bucktown
I just completed my second cross country move in the past 12 years and can't believe my good fortune in finding Diana Massaro of Dreamtown on-line and in having her lead me through the search process. She KNOWS Chicago, she works with a great team of lawyers and mortgage brokers to assure that nothing falls through the cracks in the often frustrating closing process. What a pro, and the most punctual and pleasant person to work with that anyone could find. I feel honored to now call her my friend! Ken Swanson,Lincoln Park
We first met Diana "virtually," while searching for Chicago properties online from Switzerland. After seeing some properties with her during a short visit to Chicago, we resumed the search after we arrived here. Within a few weeks we had found our home. There were many qualities about Diana that we liked and admired tremendously — her efficiency and thoroughness to detail, and going out of her way to make sure that the entire process was smooth and stress-free, but most of all her patience and good nature, without ever compromising her professionalism. Having closed on our condo just a couple of weeks ago, there is no question in our mind that Diana will be our realtor if we ever need one again. Dhilanthi and Shatna, Hyde Park
We were randomly connected with Diana via the Dream Town website while searching for a listing. Meeting her in person you quickly feel her warmth and excitement for what she does, truly a lovely young lady. Beyond just being nice she is trustworthy, always accessible, so knowledgeable, tenacious, and patient. We were difficult clients. After spending a great amount of time searching we decided to put our home search on hold. Starting again a few months later it took us no time at all to find something......when that fell through we were crushed......but decided after that to just put the whole search in Diana's hands. Success! Now we are living in a place we could have never imagined. If Diana didn't REALLY listen this wouldn't have happened. The whole experience is a little bittersweet. Diana has played an important role in a milestone in our lives. As much as I feel we had circumstances that connected us more than the average realtor/client relationship I can't help but feel that all of Diana's clients have the same experience. We wouldn't hesitate for one moment to refer her to anyone we know or don't know for that matter. Lisa Wilson & Brian Schoenbeck, Edgewater
Diana was the best! I began the process uncertain of what exactly I was looking for in a new condo. Diana took the time to get to know me on a personal level, and by doing so she was able to help me find the perfect fit. I am so thankful I worked with her and I would whole-heartedly recommend Diana to anyone looking for a new home. Melissa H., Gold Coast
Diana is knowledgeable, responsive, friendly and fun. She made the whole process as pain-free as possible, from setting the initial search parameters (resulting in finding my condo in just one afternoon) through the closing. I feel lucky to have found her and my condo! Laura P., Gold Coast
We met Diana through our son, and can't say enough wonderful things about her. We had very specific parameters — location, price, age, etc. — and a short window of time to find the right property (2 days!). I should also mention we were doing this from out of state. Everything fell together perfectly, and the transaction closed in less than a month. Her recommendations for an attorney and lender were also terrific professionals from start to finish. Having been in Real Estate myself for 17 years, I truly appreciate Diana's outstanding expertise and work ethic from both a professional and personal point of view!
We first connected with Diana randomly through the Dream Town web chat, and it was quite a fortunate find for us! She was the most responsive, courteous, and knowledgeable realtor we had met, which is why we very easily decided to go from web chat to looking at properties she had helped us find. We always felt very comfortable with Diana, had great confidence in her knowledge of the real estate market and Chicago, and knew she had our best interests in mind. I never felt pressured and she made our first home purchase very fun and rewarding. I highly recommend her to anyone interested in any kind of property in and around Chicago.
As first time home buyers, we weren't too sure what we were getting ourselves into. From our first conversation with Diana, we knew we were in good hands. She was always available and attentive to every one of our needs (at all hours of the day/night). She assured us what we were doing was the right thing and guided us along the way, while putting our best interest above all. In what could have been an extremely stressful process, Diana made our first home buying experience such an enjoyable one. Needless to say, Diana gave us 100% of her attention and helped our dreams come true! We absolutely LOVE our place and couldn't imagine living anywhere else! Thanks again for EVERYTHING! Allison and Brian, Near North
I cannot say enough good things about my experience with Diana. I was a first time home-buyer with really no idea about what I was doing. I was taking this on completely by myself, and was not sure where to go or who to use. I found Diana from a link online, and I was a bit skeptical about using someone I had no connection to other than a few emails and a call. Well, I decided to trust my gut, and exclusively work with her. Honestly, I feel like I won the real-estate agent lotto! She was always available, responded to emails and calls instantly, and truly fought for my best interest throughout the entire process. I decided I would follow her blindly early, and she never lead me astray. When we finally found the place I wanted, and entered the bidding process, she set a price she would not let me go over. If we did not get to the price, she advised me to walk. Honestly, I would have paid more, and she knew it, but she was not in it for the extra commission. Diana truly had my best interest in mind, and we got the place at our price point! At the end of the process, I feel lucky to have had her as my agent, and more importantly a new buddy! I truly would recommend her services to all.Andrew Ripani, West Loop
Diana is a wonderful and charming person, and a great Realtor. For first time buyers she was easy to work with, always available (day, night, weekends) and very helpful. She had our best interest always in mind, and made a personal relationship with us, this understanding our needs and desires. Not only did we buy a great first home, we also gained a good friend.The Diaz Family, Craigin
Diana was extraordinarily helpful in our house hunt. She identified our dream house the day it came on the market. She then helped us negotiate in an extremely competitive situation. I'm convinced we would not have won our home without her creative tactics. We're so grateful for your hard work Diana!Julie and Joe, North Center
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