Diana Soldo Massaro

Broker Associate
Real Estate Agent Diana Soldo Massaro View Listings
Lincoln Square
4553 North Lincoln Ave
Chicago, IL, 60625

Diana Soldo Massaro

Broker Associate

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 was ranked among the Top Producers across Dream Town and  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.  

Read More
Read Less

Testimonials

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

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

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 m...

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 cou...

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...

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 ...

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...

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

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

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 d...

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 goin...

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 pr...

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 pr...

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

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-m...

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...

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 t...

The best! 10 Gold Stars, excellent customer service, & she's always available! Samantha Price

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 ...

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. T...

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...

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 through...

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...

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 a...

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...

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

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...

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 Dr...

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 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

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

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 w...

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 amazing! She was always available to answer any and all questions we had and made the process very easy!

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 ...

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...

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!

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

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 f...

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...

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!

*Highly* recommended. Can't say enough great things about our experience with Diana. The most important thing is that she found us our dream house in our dream neighborhood pretty close to our target price -- even though the market was absolutely bonkers during the pandemic. Also, she was a delight to work with the entire time. My wife and I had many specific things we wanted...

“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 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 exact...

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 e...

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 ...

My Listings

$45,000
  • 2 Beds
  • 1 Full Baths
  • 945 sqft
511 E 8th Street, Rock Falls, IL 61071
MLS Logo
$315,000
New
  • 1 Beds
  • 1 Full Baths
1954 N Cleveland Avenue, Chicago, IL 60614
MLS Logo
$550,000
  • 4 Beds
  • 2 Full Baths
  • 2,200 sqft
4885 N Austin Avenue, Chicago, IL 60630
MLS Logo
$185,000
  • 3 Beds
  • 2 Full Baths
8018 S Bennett Avenue, Chicago, IL 60617
MLS Logo
$35,000
3823 W Gladys Avenue, Chicago, IL 60624
MLS Logo
$70,000
3855 W Gladys Avenue, Chicago, IL 60624
MLS Logo
$35,000
4008 W Monroe Street, Chicago, IL 60624
MLS Logo
$75,000
3854 W Van Buren Street, Chicago, IL 60624
MLS Logo
$35,000
4252 W Wilcox Street, Chicago, IL 60624
MLS Logo
$25.00
  • 1,200 sqft
5459 N Broadway Street, Chicago, IL 60640
MLS Logo
$2,232,000
  • 10,000 sqft
  • 0.27 Acreage
1618-22 N Throop Street, Chicago, IL 60642
MLS Logo
$39,000
405 N Wabash Avenue, Chicago, IL 60611
MLS Logo
$1,550,000
  • 8,700 sqft
  • 0.10 Acreage
3121 N Lincoln Avenue, Chicago, IL 60657
MLS Logo
$2,000,000
  • 5 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 4,100 sqft
2127 W Huron Street, Chicago, IL 60612
MLS Logo
$2,300,000
  • 6 Beds
  • 5 Full Baths
  • 1 Partial Baths
4132 N Claremont Avenue, Chicago, IL 60618
MLS Logo
$3,200,000
  • 6 Beds
  • 5 Full Baths
  • 1 Partial Baths
  • 6,272 sqft
4425 N Winchester Avenue, Chicago, IL 60640
MLS Logo
$675,000
  • 7 Beds
  • 5 Full Baths
8940 Lamon Avenue, Skokie, IL 60077
MLS Logo
$750,000
  • 5 Beds
  • 4 Full Baths
  • 4,000 sqft
4621 N Anthon Avenue, Chicago, IL 60656
MLS Logo
$2,595,000
  • 0.07 Acreage
1950 N Sedgwick Street, Chicago, IL 60614
MLS Logo
$300,000
  • 3 Beds
  • 1 Full Baths
  • 1,122 sqft
  • 0.25 Acreage
2039 Scott Street, Melrose Park, IL 60164
MLS Logo
$569,900
  • 6 Beds
  • 3 Full Baths
  • 1 Partial Baths
  • 3,990 sqft
  • 0.29 Acreage
13734 Meadow Lane, Plainfield, IL 60544
MLS Logo
$650,000
  • 3 Beds
  • 3 Full Baths
1011 N Mozart Street, Chicago, IL 60622
MLS Logo
$595,000
  • 6 Beds
  • 3 Full Baths
4813 W 22nd Place, Cicero, IL 60804
MLS Logo
$750,000
  • 5 Beds
  • 2 Full Baths
1242 W Elmdale Avenue, Chicago, IL 60660
MLS Logo

My Past Sales

3307 N Nottingham Avenue , Chicago, IL 60634
$495,000
Sold
  • 3 Beds
  • 3 Full Baths
  • 0.09 Acreage
3307 N Nottingham Avenue, Chicago, IL 60634
MLS Logo
4848 N SHERIDAN Road , Unit 203, Chicago, IL 60640
$290,000
Sold
  • 1 Beds
  • 1 Full Baths
  • 1 Partial Baths
  • 1,021 sqft
4848 N Sheridan Road, Chicago, IL 60640
MLS Logo
653 N KINGSBURY Street, Unit 802, Chicago, IL 60654
$370,000
Sold
  • 1 Beds
  • 1 Full Baths
  • 1 Partial Baths
  • 850 sqft
653 N Kingsbury Street, Chicago, IL 60654
IDX - MRED MLS
1116 W Hubbard Street , Unit 1E, Chicago, IL 60642
$905,000
Sold
  • 3 Beds
  • 3 Full Baths
  • 2,700 sqft
1116 W Hubbard Street, Chicago, IL 60642
IDX - MRED MLS
3300 N Lake Shore Drive , Unit 10D, Chicago, IL 60657
$290,000
Sold
  • 2 Beds
  • 1 Full Baths
3300 N Lake Shore Drive, Chicago, IL 60657
MLS Logo
175 E DELAWARE Place , Unit 5618, Chicago, IL 60611
$2,700
Sold
  • 1 Beds
  • 1 Full Baths
175 E Delaware Place, Chicago, IL 60611
MLS Logo
7537 W 61st Street , Summit, IL 60501
$145,000
Sold
  • 2 Beds
  • 1 Full Baths
7537 W 61st Street, Summit, IL 60501
MLS Logo
7746 S Kolmar Avenue , Chicago, IL 60652
$215,000
Sold
  • 3 Beds
  • 1 Full Baths
7746 S Kolmar Avenue, Chicago, IL 60652
MLS Logo
301 RIVER Drive , DeKalb, IL 60115
$160,000
Sold
  • 3 Beds
  • 1 Full Baths
  • 0.18 Acreage
301 River Drive, DeKalb, IL 60115
MLS Logo
628 W Grace Street , Unit 2W, Chicago, IL 60613
$740,000
Sold
  • 3 Beds
  • 2 Full Baths
628 W Grace Street, Chicago, IL 60613
MLS Logo
535 Weidner Road , Buffalo Grove, IL 60089
$393,000
Sold
  • 3 Beds
  • 1 Full Baths
  • 1 Partial Baths
535 Weidner Road, Buffalo Grove, IL 60089
MLS Logo
5414 May Avenue , Richmond, IL 60071
$225,000
Sold
  • 3 Beds
  • 1 Full Baths
  • 1 Partial Baths
5414 May Avenue, Richmond, IL 60071
MLS Logo
1413 Scully Drive , McHenry, IL 60050
$300,000
Sold
  • 3 Beds
  • 2 Full Baths
1413 Scully Drive, McHenry, IL 60050
MLS Logo
3207 N Clifton Avenue , Unit 402, Chicago, IL 60657
$665,402
Sold
  • 2 Beds
  • 2 Full Baths
3207 N Clifton Avenue, Chicago, IL 60657
MLS Logo
24625 Woodstock Drive , Plainfield, IL 60585
$625,000
Sold
  • 6 Beds
  • 4 Full Baths
  • 1 Partial Baths
24625 Woodstock Drive, Plainfield, IL 60585
MLS Logo
7028 S HONORE Street , Chicago, IL 60636
$135,000
Sold
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Baths
7028 S Honore Street, Chicago, IL 60636
MLS Logo
1239 W Jarvis Avenue , Unit 3, Chicago, IL 60626
$425,000
Sold
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Baths
1239 W Jarvis Avenue, Chicago, IL 60626
MLS Logo
3116 N Oakley Avenue , Chicago, IL 60618
$435,625
Sold
  • 1 Beds
  • 1 Full Baths
3116 N Oakley Avenue, Chicago, IL 60618
MLS Logo
2217 W FOSTER Avenue , Unit 1, Chicago, IL 60625
$274,900
Sold
  • 2 Beds
  • 1 Full Baths
2217 W Foster Avenue, Chicago, IL 60625
IDX - MRED MLS
901 W 37TH Street , Chicago, IL 60609
$875,000
Sold
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Baths
  • 3,500 sqft
901 W 37th Street, Chicago, IL 60609
IDX - MRED MLS
6625 N Fairfield Avenue , Chicago, IL 60645
$602,000
Sold
  • 4 Beds
  • 2 Full Baths
  • 2,513 sqft
  • 0.09 Acreage
6625 N Fairfield Avenue, Chicago, IL 60645
IDX - MRED MLS
1836 W Farwell Avenue , Chicago, IL 60626
$520,000
Sold
  • 3 Beds
  • 1 Full Baths
  • 1 Partial Baths
  • 2,000 sqft
1836 W Farwell Avenue, Chicago, IL 60626
IDX - MRED MLS
9816 S Forest Avenue , Chicago, IL 60628
$158,500
Sold
  • 3 Beds
  • 1 Full Baths
  • 1 Partial Baths
9816 S Forest Avenue, Chicago, IL 60628
IDX - MRED MLS
1449 N Artesian Avenue , Chicago, IL 60622
$799,000
Sold
  • 7 Beds
1449 N Artesian Avenue, Chicago, IL 60622
IDX - MRED MLS

Login to my Baird & Warner account

Pixel