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Jason Webb

Chicago Real Estate Expert

Mobile - 312.505.9322

About Jason

Jason has extensive experience as a licensed real estate broker, and credits his ability to educate and fully explain all aspects of the process to his clients as one of his greatest strengths. Although he has worked all over the city, he specializes in the West Loop, South Loop, Pilsen, and UIC area including University Village and University Commons, where he lives. While he represents a variety of clients, he especially enjoys working with first-time buyers and sellers.

When not spending time with his clients, Jason is very involved in the 6-building University Commons complex he has resided in for the past 14 years. He served on his building’s Condo Board for those 14 years and regularly sat on the Master Board, as well. He has participated in a number of community volunteer efforts, including the clean-up of local viaducts. He also helps manage the complex’s social media page and participates in just about every social event, including the monthly book club. He takes all of his experience with him to every transaction, but still admits to learning at least one new thing at every closing!

Jason is also an investor, with his business partners, in multi-family buildings on Chicago's near west side.

What Jason's Clients Say

It was an absolute pleasure to work with Jason! He made the process of selling our old home, and finding and buying our new home enjoyable! He has a wealth of knowledge, has your best interests at heart, and makes himself available for any questions at any time. He is professional, organized, a pleasure to work with, and goes above and beyond for his clients. I would recommend Jason to anyone looking to buy or sell! Thank you for everything, Jason!

Over the years I have recommended Jason Webb to many friends and acquaintances to help them buy, rent or sell their homes. When it was my turn, my experience with Jason Webb was absolutely outstanding. From the moment we talked about putting my place on the market through day of closing – it was amazing. Between the beautiful pictures of my home, the video taken, and the couple clients - because that is all it took- brought in to tour, Jason was professional, informative, and confident in the ability to sell. He gave me overall reassurance and kept me in the know. Jason was superb - an excellent agent who is more than in the know on real estate, neighborhoods and the community. Thanks Jason, was an awesome experience.

As a first time homebuyer, I couldn't have gone with a better guy to guide me through the process. From the start, Jason was highly personable. He came over to my current place and walked through the initial steps and honed in on what I was looking for in a home. He was very quick to line up a list of properties for me to review. During my browsing, he was always quick to respond to my questions and comments. Showings were a breeze. He made sure to ask the important questions I hadn't thought of throughout the process. When things seemed overwhelming, Jason as able to break it down easily. I felt like he really had my back through the whole experience. When it came time to close, again he seemed to always be available and had reputable references for for all my needs. Even after I closed, he continued to make sure everything was smooth with the moving process. He really takes the time to connect with his clients, and it shows. I couldn't have made it through without him.

Both Jason and his partner Ashley assisted us with our University Village condo purchase and we were very pleased with their level of detail, especially when it came to negotiating, the inspection items, and their response times. Their knowledge of the business, and this complex in particular, were of great benefit to us...and they have been very helpful after the sale!

Jason is a fantastic caring person, not just a realtor and we're very grateful to have found him! His advice was great and he also taught us a lot about buying a place in the city. We also asked for help with lining up a lawyer, inspector, and loan company. They shared knowledge that we wouldn't have thought to ask about - that's a big part of this buying thing. His recommendations were better than the ones we were looking at on our own. It felt like a team was helping us along the process. We hope Jason will help us sell when the time is right in a few years. Thanks Jason - we wish you all the BEST!

What can I say, Jason knows his business. He helped me find my apartment 4 years ago and now helped me find my dream home. He was so patient with me throughout this process and offered valuable advise throughout. Not only was he able to negotiate an offer $35K below asking price, the home automatically appraised for $14K over what I paid for. Jason knows Chicago and is an expert in the home buying and selling world. His advise didn't stop once we found my home. He walked me through each step of the process until close. We might have talked multiple times a day to make sure I was feeling good and that we were on schedule. I would recommend Jason to anyone looking to find a home in Chicago. He is one of a kind. He is a true partner who anyone would be lucky to work with.

We are so pleased that we had Ashley and Jason sell our University Commons condo! The fact they both live there--Jason is right up on the fourth floor and Ashley lives in a first floor unit just like ours, in an adjacent building--was the key factor. Ashley did a great job selling the virtues of first floor living, while Jason was helpful analyzing the comparable units before listing and then negotiating our offer. They also recommended a fabulous attorney to handle the closing. This unit became an investment property for us over the last several years, so we are thrilled to have it off our hands, thanks to Ashley and Jason!

University Village

Jason was an absolute pleasure to work with. He knows the condo development we sold from better than anyone else which ultimately helped get us a great offer. And he was extremely responsive to all our needs.

When my wife and I decided to buy a foreclosure, we were very concerned, even apprehensive, about going through the process with a bank. Fortunately, we had Jason with us the whole way. He eased our concerns by letting us know how the process works and what to expect each step of the way. He also set us up with an experienced attorney who worked very efficiently with the bank to get us closed smoothly. We are LOVING our new condo and can't wait to have Jason over for the house-warming party!

What an easy and wonderful experience! Jason exudes confidence and knowledge in his job and the entire process. We would highly recommend him.

Jason was exceptional to work with. He was thoughtful, timely, listened to my preferences in terms of what I was looking for, and helped with all the interim steps to the close. As a first time home buyer in Illinois, this was invaluable.

Jason worked with us for over a year trying to locate the right property. At no time in the process did we feel pressured or discouraged. Jason came to every open house, tracked down every seller, and was available by phone day or night. We will definitely have Jason find our next property.

Jason showed a tremendous amount of care and effort towards the sale of our condo, he was always looking out for our best interest and working hard for us. We appreciated Jason getting our condo sold.

We've been so thankful to have Jason as our Broker over of the past 5 years! Not only did he help us find our dream condo in Andersonville in 2013, but last month he sold it for us, twice. When the first set of buyers got cold feet and backed out, Jason kept us in check emotionally - and then was able to sell the condo again just a few weeks later for full price, CASH. He is extremely responsive and was such a great help throughout the whole process. The best part of having him as our realtor is the confidence and insight he brings when helping us make such big choices for our family. We were thrilled and would recommend Jason to anyone looking to buy or sell a home in Chicago.

Great customer service and had a viable offer within a week of listing my unit. I'd highly recommend Jason.

We had a wonderful experience selling our home with Jason. He went above and beyond at every step of the way, and helped us sell in record time. We would HIGHLY recommend Jason to our family and friends.

When looking to put my condo at University Commons back on the market after a disappointing experience with another agent I really did my homework to make sure I hired an EXPERT! Every real estate transaction is nuanced and for the best results I've learned that you really can't take anything for granted and need someone who not only is a seasoned real estate professional but also someone who has intimate knowledge of the market factors in your neighborhood. After reviewing several potential agents, I chose Jason, and that was the best decision I could have made! Less than four weeks on the market and we were under contract! Jason's recommendations prior to listing, and his guidance from contract negotiations to close all paid off in getting the deal done so quickly. I couldn't be more pleased with having decided to work with Jason, he was the difference for me!

I highly recommend Jason. He is thorough, attentive to every detail, responsive and professional. There is no other realtor who is as knowledgable about the West Loop and University Commons condominiums where I recently sold my unit. Even during the dead of winter, he was able to get a recent all-time high sales price for my unit. Until Jason, I had not experienced this level of service from a realtor. He is the absolute BEST!

University Village

I have known Jason for many years and not only is he truly a kind and considerate person, and he is exceptionally helpful and generous with his knowledge and expertise. Several years ago, he went out of his way to help a friend of mine navigate her way through the Chicago rental market just because he could. He is the consummate professional who provides outstanding service. I highly recommend him for any real estate service needs you may have.

East Coast

If you're even thinking of selling your condo this year, you need to call Jason Webb. I had moved to Massachusetts and rented my condo in Chicago out sporadically. Over time, it became costly and a lot to manage, so I decided to sell. I was concerned about trying to do this from a long distance - but I came across Jason Webb, and my experience with him as been amazing by far. Not only did he get it sold, but he helped me with all the things I was never going to be able to do from far away: he let various vendors in to clean and repair items and, most importantly, he met with several folks who were buying all of my furniture: meeting them in the lobby, letting them in, he even carried a couch down a flight of stairs. He has made this experience so easy for me, and I am so thankful for his help. Jason is not just my realtor now, but I would consider him a friend.

University Village

Having just closed on my first condo, I'm pleased to write this recommendation for Jason Webb. Jason's name was actually given to me a few years ago and he had helped me find the perfect rental in Lincoln Park. Based on that experience, I knew that I'd be relying on his service and expertise when it came time to make a purchase. I involved Jason early on in the discussions about buying and he explained the entire process to me in great detail. I knew that I could count on him to walk me through the entire process of finding a place that met both my needs and my desires. Jason is the best in the business, in my opinion. His level of customer service goes above and beyond and he also had great recommendations for the other the key players in the transaction, including a lender, inspector and an attorney. My new condo in the West Loop is more than I could have imagined for a first home and I would recommend Jason to anyone looking to buy real estate!

West Loop

Now that I live out of state, I needed someone to handle my investment property in Chicago. I knew that Jason was a long time condo board member and very active in the community. From showings to screening tenants to finding me the perfect tenant, Jason handled the entire transaction from soup to nuts. Jason was responsive and detailed, which was exactly what I needed. If you have any real estate needs in Chicago, I highly recommend that you contact Jason Webb.

University Village

In 2014, I had been renting a penthouse condo at University Commons and loved the floorplan and the neighborhood so much that I knew I wanted to buy one. A co-worker who lives in the complex with her husband had used Jason to purchase their duplex unit and suggested that I speak with him. Jason and I met and we made a plan to keep our eyes on the market until the right opportunity came up. When the perfect penthouse (it even had city views!) came on the market, Jason helped me negotiate a great price for it, helped me find a lender, inspector, lawyer and movers. I couldn't be happier living there. Jason was excellent!

University Village

My husband I used Jason Webb when we bought our duplex condo at University Commons. He was incredibly helpful throughout the process, as this was our very first home purchase. We highly recommend Jason.

University Village

Thank you for taking Erik and us on this journey and new chapter and into home ownership. You were fantastic. Hope you stay in touch after the sale.

University Village

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Jason's Past Sales

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Reviews For Jason

See what people are saying about Dream Town's Jason Webb

It was an absolute pleasure to work with Jason! He made the process of selling our old home, and finding and buying our new home enjoyable! He has a wealth of knowledge, has your best interests at heart, and makes himself available for any questions at any time. He is professional, organized, a pleasure to work with, and goes above and beyond for his clients. I would recommend Jason to anyone looking to buy or sell! Thank you for everything, Jason!

Karl Elvin

Over the years I have recommended Jason Webb to many friends and acquaintances to help them buy, rent or sell their homes. When it was my turn, my experience with Jason Webb was absolutely outstanding. From the moment we talked about putting my place on the market through day of closing – it was amazing. Between the beautiful pictures of my home, the video taken, and the couple clients - because that is all it took- brought in to tour, Jason was professional, informative, and confident in the ability to sell. He gave me overall reassurance and kept me in the know. Jason was superb - an excellent agent who is more than in the know on real estate, neighborhoods and the community. Thanks Jason, was an awesome experience.

Joanne Shaw

As a first time homebuyer, I couldn't have gone with a better guy to guide me through the process. From the start, Jason was highly personable. He came over to my current place and walked through the initial steps and honed in on what I was looking for in a home. He was very quick to line up a list of properties for me to review. During my browsing, he was always quick to respond to my questions and comments. Showings were a breeze. He made sure to ask the important questions I hadn't thought of throughout the process. When things seemed overwhelming, Jason as able to break it down easily. I felt like he really had my back through the whole experience. When it came time to close, again he seemed to always be available and had reputable references for for all my needs. Even after I closed, he continued to make sure everything was smooth with the moving process. He really takes the time to connect with his clients, and it shows. I couldn't have made it through without him.

Brandon Bell

Both Jason and his partner Ashley assisted us with our University Village condo purchase and we were very pleased with their level of detail, especially when it came to negotiating, the inspection items, and their response times. Their knowledge of the business, and this complex in particular, were of great benefit to us...and they have been very helpful after the sale!

Todd Reks

Jason is a fantastic caring person, not just a realtor and we're very grateful to have found him! His advice was great and he also taught us a lot about buying a place in the city. We also asked for help with lining up a lawyer, inspector, and loan company. They shared knowledge that we wouldn't have thought to ask about - that's a big part of this buying thing. His recommendations were better than the ones we were looking at on our own. It felt like a team was helping us along the process. We hope Jason will help us sell when the time is right in a few years. Thanks Jason - we wish you all the BEST!

Tony Konold

What can I say, Jason knows his business. He helped me find my apartment 4 years ago and now helped me find my dream home. He was so patient with me throughout this process and offered valuable advise throughout. Not only was he able to negotiate an offer $35K below asking price, the home automatically appraised for $14K over what I paid for. Jason knows Chicago and is an expert in the home buying and selling world. His advise didn't stop once we found my home. He walked me through each step of the process until close. We might have talked multiple times a day to make sure I was feeling good and that we were on schedule. I would recommend Jason to anyone looking to find a home in Chicago. He is one of a kind. He is a true partner who anyone would be lucky to work with.

George Trakas

We are so pleased that we had Ashley and Jason sell our University Commons condo! The fact they both live there--Jason is right up on the fourth floor and Ashley lives in a first floor unit just like ours, in an adjacent building--was the key factor. Ashley did a great job selling the virtues of first floor living, while Jason was helpful analyzing the comparable units before listing and then negotiating our offer. They also recommended a fabulous attorney to handle the closing. This unit became an investment property for us over the last several years, so we are thrilled to have it off our hands, thanks to Ashley and Jason!

Tom S
University Village

Jason was an absolute pleasure to work with. He knows the condo development we sold from better than anyone else which ultimately helped get us a great offer. And he was extremely responsive to all our needs.

Scott Benbrook

When my wife and I decided to buy a foreclosure, we were very concerned, even apprehensive, about going through the process with a bank. Fortunately, we had Jason with us the whole way. He eased our concerns by letting us know how the process works and what to expect each step of the way. He also set us up with an experienced attorney who worked very efficiently with the bank to get us closed smoothly. We are LOVING our new condo and can't wait to have Jason over for the house-warming party!

Paul Jenkins

What an easy and wonderful experience! Jason exudes confidence and knowledge in his job and the entire process. We would highly recommend him.

Kelly kachmarik

Jason was exceptional to work with. He was thoughtful, timely, listened to my preferences in terms of what I was looking for, and helped with all the interim steps to the close. As a first time home buyer in Illinois, this was invaluable.

Theresa Gorenc

Jason worked with us for over a year trying to locate the right property. At no time in the process did we feel pressured or discouraged. Jason came to every open house, tracked down every seller, and was available by phone day or night. We will definitely have Jason find our next property.

Craig Collins

Jason showed a tremendous amount of care and effort towards the sale of our condo, he was always looking out for our best interest and working hard for us. We appreciated Jason getting our condo sold.

Perry Meyers

We've been so thankful to have Jason as our Broker over of the past 5 years! Not only did he help us find our dream condo in Andersonville in 2013, but last month he sold it for us, twice. When the first set of buyers got cold feet and backed out, Jason kept us in check emotionally - and then was able to sell the condo again just a few weeks later for full price, CASH. He is extremely responsive and was such a great help throughout the whole process. The best part of having him as our realtor is the confidence and insight he brings when helping us make such big choices for our family. We were thrilled and would recommend Jason to anyone looking to buy or sell a home in Chicago.

Ken Kerr

Great customer service and had a viable offer within a week of listing my unit. I'd highly recommend Jason.

Michael Magee Jr

We had a wonderful experience selling our home with Jason. He went above and beyond at every step of the way, and helped us sell in record time. We would HIGHLY recommend Jason to our family and friends.

Jose Melendez

When looking to put my condo at University Commons back on the market after a disappointing experience with another agent I really did my homework to make sure I hired an EXPERT! Every real estate transaction is nuanced and for the best results I've learned that you really can't take anything for granted and need someone who not only is a seasoned real estate professional but also someone who has intimate knowledge of the market factors in your neighborhood. After reviewing several potential agents, I chose Jason, and that was the best decision I could have made! Less than four weeks on the market and we were under contract! Jason's recommendations prior to listing, and his guidance from contract negotiations to close all paid off in getting the deal done so quickly. I couldn't be more pleased with having decided to work with Jason, he was the difference for me!

Ibrahim Shillo

I highly recommend Jason. He is thorough, attentive to every detail, responsive and professional. There is no other realtor who is as knowledgable about the West Loop and University Commons condominiums where I recently sold my unit. Even during the dead of winter, he was able to get a recent all-time high sales price for my unit. Until Jason, I had not experienced this level of service from a realtor. He is the absolute BEST!

Carole
University Village

I have known Jason for many years and not only is he truly a kind and considerate person, and he is exceptionally helpful and generous with his knowledge and expertise. Several years ago, he went out of his way to help a friend of mine navigate her way through the Chicago rental market just because he could. He is the consummate professional who provides outstanding service. I highly recommend him for any real estate service needs you may have.

Amanda
East Coast

If you're even thinking of selling your condo this year, you need to call Jason Webb. I had moved to Massachusetts and rented my condo in Chicago out sporadically. Over time, it became costly and a lot to manage, so I decided to sell. I was concerned about trying to do this from a long distance - but I came across Jason Webb, and my experience with him as been amazing by far. Not only did he get it sold, but he helped me with all the things I was never going to be able to do from far away: he let various vendors in to clean and repair items and, most importantly, he met with several folks who were buying all of my furniture: meeting them in the lobby, letting them in, he even carried a couch down a flight of stairs. He has made this experience so easy for me, and I am so thankful for his help. Jason is not just my realtor now, but I would consider him a friend.

Erika
University Village

Having just closed on my first condo, I'm pleased to write this recommendation for Jason Webb. Jason's name was actually given to me a few years ago and he had helped me find the perfect rental in Lincoln Park. Based on that experience, I knew that I'd be relying on his service and expertise when it came time to make a purchase. I involved Jason early on in the discussions about buying and he explained the entire process to me in great detail. I knew that I could count on him to walk me through the entire process of finding a place that met both my needs and my desires. Jason is the best in the business, in my opinion. His level of customer service goes above and beyond and he also had great recommendations for the other the key players in the transaction, including a lender, inspector and an attorney. My new condo in the West Loop is more than I could have imagined for a first home and I would recommend Jason to anyone looking to buy real estate!

Tom
West Loop

Now that I live out of state, I needed someone to handle my investment property in Chicago. I knew that Jason was a long time condo board member and very active in the community. From showings to screening tenants to finding me the perfect tenant, Jason handled the entire transaction from soup to nuts. Jason was responsive and detailed, which was exactly what I needed. If you have any real estate needs in Chicago, I highly recommend that you contact Jason Webb.

Denise
University Village

In 2014, I had been renting a penthouse condo at University Commons and loved the floorplan and the neighborhood so much that I knew I wanted to buy one. A co-worker who lives in the complex with her husband had used Jason to purchase their duplex unit and suggested that I speak with him. Jason and I met and we made a plan to keep our eyes on the market until the right opportunity came up. When the perfect penthouse (it even had city views!) came on the market, Jason helped me negotiate a great price for it, helped me find a lender, inspector, lawyer and movers. I couldn't be happier living there. Jason was excellent!

Kathy
University Village

My husband I used Jason Webb when we bought our duplex condo at University Commons. He was incredibly helpful throughout the process, as this was our very first home purchase. We highly recommend Jason.

Caitlyn
University Village

Thank you for taking Erik and us on this journey and new chapter and into home ownership. You were fantastic. Hope you stay in touch after the sale.

Mary, Stan & Erik
University Village

Contact Jason Webb

Mobile - 312.505.9322

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