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Ann Connolly

Chicago Real Estate Expert

Mobile - 312.476.0224

About Ann

Consistently a Top Producer, Awarded by the Chicago Association of Realtors

Ann has over 20 years experience in the real estate industry. After buying her first condo, she realized she wanted a career in real estate. She subsequently obtained her real estate license while working full time and her brokers license when she was nine months pregnant with her first child. With her children in school full time, Ann now has the opportunity work full time in real estate.

As a lifelong Chicagoan, Ann brings a deep knowledge of the Chicago marketplace to her clients. She believes every client should be treated with the same respect and care that she would like to receive. Her sense of humor and attention to detail make the home buying and selling process as safe, fun and hassle-free as possible.

Ann was born and raised on Chicago's far southwest side, the 4th of 7 children of a Chicago fire chief and a full time mom. She was a standout athlete and played volleyball for the first Mother McAuley high school state volleyball champions. She was named 'best server in the state' after that tournament. She attended the University of the Pacific on an academic/athletic scholarship, graduating summa cum laude and playing in the NCAA Division I volleyball championship. Ann has an MBA from Trinity College, Dublin.

She is married to Liam O'Connor and has 2 boys, Rory (13) and Cathal (12), pronounced "Ca' hal" ... Irish for Charles. In her free time, Ann enjoys reading and working out, but likes nothing more than watching her kids run cross country, play basketball, soccer and Irish football.

What Ann's Clients Say

We've worked with Ann on 4 transactions since 2009. She sold a condo downtown, bought and sold a condo in Wrigleyville, and most recently we purchased a single family home in the Chicago suburbs (April, 2020). Ann's professionalism shines through every imaginable bump in these kinds of transactions and we were so happy we had Ann on our side guiding us through.

Park Ridge

During our quest to find a nice and spacious apartment for our family on a tight budget, we were lucky enough to have been recommended to Ann Connolly. She understood our needs and combined with her in depth knowledge of the market was able to ensure viewings the minute any relevant properties appeared on the market. She went out of her way to help us and we will definitely be contacting her whenever we decide to move again. Thank you Ann for going above and beyond the call of duty!

North Center

I give score of 5 Ann is an excellent agent and goes out of her way to give client satisfaction I highly recomment Ann anytime

Ann is down to earth and extremely competent. Her manner is calm and intentional. My experience with Ann was nothing but positive. She is a true professional. I highly recommend her.

Ann Connolly went above and beyond my expectations. I had very difficult asks as i was selling my condo remotely and she was absolutely amazing. She essentially walked me through all i needed to do to sell my first condo and she helped me find everything from cleaning people to selling some of the furniture left over in the unit. I really appreciated her responsiveness and her willingness to stop at nothing to help her client. Do yourself a favor and have Ann on your side when buying or selling real estate! Tanks Ann!

University Village

I highly recommend my friend and realtor Ann Connolly through Dream Town Real Estate. Not only is she a great friend and someone I've been staging homes for and working with for over 10 years, but she has truly done an amazing job selling my home for top dollar and helped me to find my future home, helped negotiate both deals, and provided a lot of professional and personal guidance. Ann has done so much hand holding, listening, and has been extremely responsive throughout the process. I know I could not have done this without her. It's one thing to work with someone and another to be a client. Trust me....this lady knows what she's doing! She knows how much I truly love my home and helped me through a very difficult decision and process. Thank you Ann!

Evanston

We worked with Ann Connolly to provide a CMA (competitive market analysis) of our home. We were in a bit of a rush since we had put an offer in on another home. We wanted to interview several agents before settling on one to list ours. Ann was quick, thoughtful and professional. While we did not ultimately list our home, we would have welcomed working further with Ann.

Chicago

Ann did an outstanding job locating the perfect condominium for our needs. She was very accessible throughout the entire process. We highly recommend Ann!

Ann was a fantastic guide through my first-time home buying experience. She took all of my needs in to account and found me properties that fit them. She truly got what I was looking for and there was never ANY pressure to settle for something that was not a good fit or to look beyond my means. She was lightning-fast with responses and gave me invaluable advice throughout the process. Her demeanor and approach was a perfect fit for me: it was like having a knowledgeable friend guiding me through the experience. I can't recommend Ann highly enough or to enough people! She was fabulous! Thank you, Ann!

Ann's prospective and vision was truly amazing. I trusted her and was able to sell my home in 3 weeks.

Ann was wonderful to work with...she kept us fully informed every step of the way until the sale was finally made....in addition she helped us find resources to prepare our condo for sale. She also asssisted us in finding a moving company...We give her an A++

Ann was referred to us by my sister and her husband. She was very accommodating with our schedule and flexible to go take us on open houses even on Sundays. She answered all of our questions and helped us through the buying process up until our closing.

I enjoyed working with Ann and was generally happy with the process.

Ann was there at every turn to guide us through the process. Her expertise in the negotiation was very valuable.

I rate my experience with Ann Connolly a 5. She was always accessible and responsive and had my back throughout the entire process. She was quick yet thorough and went above and beyond throughout the process of renting my condo and subsequently selling it. I had a high comfort level that I was in good hands and that she had my best interests at heart.

Edgewater

My husband and I had the pleasure of meeting Ann three years ago (yes-we are officially the worst clients in the world) and after a long search we closed last week on a beautiful home in Lakeview. She was so incredibly patient and kind to us throughout the process. Ann recommended an excellent inspector and a wonderful attorney as well and with her guidance the entire process went smoothly from start to finish. We can't say enough about Ann and would recommend her to anyone!

Ann helped customize our experience by taking our individual needs into account. She did additional research that helped us to get an incredibly good deal. She helped us every step of the way, accommodating our lively toddler and even offering to babysit for our closing! She was at our unit in -20 degree weather, making sure our future furnace worked the night before our final sale. We could not have asked for a more dedicated, thorough, thoughtful or kind person to work with.

We loved working with Anne. She was super friendly, highly professional and made us feel very confident about our sale and purchase. What we valued most about Ann was that she was extremely responsive to our calls/emails. We would recommended Ann to any of our friends in need of a realtor.

Ann did a great job for us, especially when it came to developing our offer to the seller. We were in a hyper competitive market with many potential buyers and with Ann's help we were able to close the deal at less than asking price. Great job Ann!

Chicago

Ann was a pleasure to work with and very thorough in analyzing and showing prospective properties for purchase. She has an excellent understanding of Chicago's numerous neighborhoods and will save you tons of time as buyer by vetting properties for you.

Bucktown

Our agent was Ann Connolly and she was fantastic. I met with her two years ago to put my condo on the market and we decided it wasnt the right time. When my fiance and I decided to look for a house I contacted her again. She was patient, knowledgeable and realistic about the market and our options. Ann went above and beyond for us and we plan to use her to sell our condos once the market turns for the better. I would highly recommend Ann to any of my friends and family. Anita and Matt

Ann was a fantastic buyer's agent for my family. We were interested in a condo with nice vintage features and lots of character. Our favoured locations were in and around Andersonville and we had the usual financial constraints that seem to be an issue for many people at the moment. Ann's personality matched ours perfectly, she had amazing patience, and her insight into our desires was exactly spot-on. We recently closed on a two-bed condo in Andersonville and have found that we are even more excited after closing as we were leading up to making an offer. We have been extremely happy with having worked with Ann and would highly recommend her without reservation. David Shay and Amelie

Ann was great, on the sell and buy side. Didn't push, and was very patient. Great advice on how to maximize my sales price by staging my condo.

I have worked with Ann twice - once when I bought my first house in Chicago and again when I sold it 10 years later - and can highly recommend her! We put our house on the market in 2009 when we relocated to NJ, in one of the lowest points of the housing market. I don't think any of us realized just how difficult the market was, but we soon found out. Ann did a great job - holding countless open houses, advising us on pricing changes and even making sure the sidewalk was shoveled during the long Chicago winter. She went above and beyond to sell our house and was great at keep us up-to-date with feedback from potential buyers. It's not easy to sell your house from long distance, but it helps to have someone you can trust completely. And that's Ann. Thanks again, Ann! Jeanne, Ludwig, Mia and Lily, Roscoe Village

Roscoe Village

I would like to thank you for your support and extra help in getting my son Daniel into a condo on Elk Grove in Wicker Park. He is in, settled down and continuing to do well in school. Your prediction, during the inspection, that this condo will appraise at least at 250K when the building is fully occupied is right on. Daniel called and said the young lady on the first floor is getting a mortgage and the banks appraisal was 200K with the building only half occupied. I want you to know what an important part you played in getting Daniel started on the right foot in a big city.Ernest Hawkins, Wicker Park

Wicker Park

Ann did a great job helping to sell my place in the difficult 2009 market. Her first piece of good advice was that we work with a stager to make sure the place would show as well as possible. She even brought some of her own belongings to help the condo look its best. When I got an offer, she helped me figure out how to negotiate the right price. After that, she helped with everything else in the process through the closing. When the inspection report came back, she and her husband (a builder) personally helped to fix things for me. Also, I really give her credit for always maintaining a very positive relationship with the buyer and the other agent. She is not even remotely pushy or high strung like some agents can be, and this helped immensely. She let a number of people in to the condo when I was at work for all sorts of things (appraisal, repairs). During the 45 day waiting period from offer to close, I can't even count how many emails and phone calls we exchanged. There are dozens of steps of the sale process, and she always got back to me right away (sometimes within minutes) which I appreciated a lot. This was the first place I ever sold, so I didn't really have the experience to know how to deal with all the little things that come up during the process, and she was always there to help.Aaron, Lakeview

Lakeview

I cannot recommend Ann Connolly highly enough. From the moment we exchanged our first emails, she demonstrated the highest level of attentiveness and professionalism. She has a deep understanding of the market and the city; she listened to my wants and needs, and gave me honest, thoughtful opinions on the homes we viewed. Because of her, I ended up with a place I absolutely love. The entire home-buying process is stressful, but she did everything possible to help and support me throughout, way above and beyond what a realtor is expected to handle. After closing, she even offered to wait at my loft for my internet & satellite setups so I wouldn't have to take any more time off work. Ann's kindness, integrity and true concern for her clients are just a few of the qualities that make her a wonderful realtor (and an even better person); I consider her a friend. You will not be disappointed in working with her. Ronnie Hunt, Bucktown

Bucktown

Ann was very professional and even more patient with us as new home buyers. She is very knowledgeable about the industry. Barb, Pilsen

Pilsen

Ann is great! She takes the time to answer any questions a buyer may have. I plan to use Ann if I ever sell my condo. Kay Frederick, Pilsen

Pilsen

Ann was a pleasure to work with. She worked around our schedule, picked us up at the airport several times and did not hesitate to give us the time we needed. Being from out of town, her knowledge of Chicago helped us find the ideal location for our needs. We couldn't have been more pleased with the service. Jay and Debbie, Bridgeport

Bridgeport

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Reviews For Ann

See what people are saying about Dream Town's Ann Connolly

We've worked with Ann on 4 transactions since 2009. She sold a condo downtown, bought and sold a condo in Wrigleyville, and most recently we purchased a single family home in the Chicago suburbs (April, 2020). Ann's professionalism shines through every imaginable bump in these kinds of transactions and we were so happy we had Ann on our side guiding us through.

Dan and Lisa K
Park Ridge

During our quest to find a nice and spacious apartment for our family on a tight budget, we were lucky enough to have been recommended to Ann Connolly. She understood our needs and combined with her in depth knowledge of the market was able to ensure viewings the minute any relevant properties appeared on the market. She went out of her way to help us and we will definitely be contacting her whenever we decide to move again. Thank you Ann for going above and beyond the call of duty!

Katy
North Center

I give score of 5 Ann is an excellent agent and goes out of her way to give client satisfaction I highly recomment Ann anytime

Judy Agnos

Ann is down to earth and extremely competent. Her manner is calm and intentional. My experience with Ann was nothing but positive. She is a true professional. I highly recommend her.

Anna Johnson

Ann Connolly went above and beyond my expectations. I had very difficult asks as i was selling my condo remotely and she was absolutely amazing. She essentially walked me through all i needed to do to sell my first condo and she helped me find everything from cleaning people to selling some of the furniture left over in the unit. I really appreciated her responsiveness and her willingness to stop at nothing to help her client. Do yourself a favor and have Ann on your side when buying or selling real estate! Tanks Ann!

Yohannes Teckie
University Village

I highly recommend my friend and realtor Ann Connolly through Dream Town Real Estate. Not only is she a great friend and someone I've been staging homes for and working with for over 10 years, but she has truly done an amazing job selling my home for top dollar and helped me to find my future home, helped negotiate both deals, and provided a lot of professional and personal guidance. Ann has done so much hand holding, listening, and has been extremely responsive throughout the process. I know I could not have done this without her. It's one thing to work with someone and another to be a client. Trust me....this lady knows what she's doing! She knows how much I truly love my home and helped me through a very difficult decision and process. Thank you Ann!

Amy Scott
Evanston

We worked with Ann Connolly to provide a CMA (competitive market analysis) of our home. We were in a bit of a rush since we had put an offer in on another home. We wanted to interview several agents before settling on one to list ours. Ann was quick, thoughtful and professional. While we did not ultimately list our home, we would have welcomed working further with Ann.

NPV
Chicago

Ann did an outstanding job locating the perfect condominium for our needs. She was very accessible throughout the entire process. We highly recommend Ann!

Ann McCartin

Ann was a fantastic guide through my first-time home buying experience. She took all of my needs in to account and found me properties that fit them. She truly got what I was looking for and there was never ANY pressure to settle for something that was not a good fit or to look beyond my means. She was lightning-fast with responses and gave me invaluable advice throughout the process. Her demeanor and approach was a perfect fit for me: it was like having a knowledgeable friend guiding me through the experience. I can't recommend Ann highly enough or to enough people! She was fabulous! Thank you, Ann!

Jessica Voigts

Ann's prospective and vision was truly amazing. I trusted her and was able to sell my home in 3 weeks.

Darlene Menser

Ann was wonderful to work with...she kept us fully informed every step of the way until the sale was finally made....in addition she helped us find resources to prepare our condo for sale. She also asssisted us in finding a moving company...We give her an A++

Carl Defaria

Ann was referred to us by my sister and her husband. She was very accommodating with our schedule and flexible to go take us on open houses even on Sundays. She answered all of our questions and helped us through the buying process up until our closing.

Caryn Hess

I enjoyed working with Ann and was generally happy with the process.

Rob Chalupnik

Ann was there at every turn to guide us through the process. Her expertise in the negotiation was very valuable.

Jarret Blum

I rate my experience with Ann Connolly a 5. She was always accessible and responsive and had my back throughout the entire process. She was quick yet thorough and went above and beyond throughout the process of renting my condo and subsequently selling it. I had a high comfort level that I was in good hands and that she had my best interests at heart.

Mary Neil Crosby
Edgewater

My husband and I had the pleasure of meeting Ann three years ago (yes-we are officially the worst clients in the world) and after a long search we closed last week on a beautiful home in Lakeview. She was so incredibly patient and kind to us throughout the process. Ann recommended an excellent inspector and a wonderful attorney as well and with her guidance the entire process went smoothly from start to finish. We can't say enough about Ann and would recommend her to anyone!

Melissa Mabley

Ann helped customize our experience by taking our individual needs into account. She did additional research that helped us to get an incredibly good deal. She helped us every step of the way, accommodating our lively toddler and even offering to babysit for our closing! She was at our unit in -20 degree weather, making sure our future furnace worked the night before our final sale. We could not have asked for a more dedicated, thorough, thoughtful or kind person to work with.

Ashley Alexander Furrow

We loved working with Anne. She was super friendly, highly professional and made us feel very confident about our sale and purchase. What we valued most about Ann was that she was extremely responsive to our calls/emails. We would recommended Ann to any of our friends in need of a realtor.

Jessica Richardson

Ann did a great job for us, especially when it came to developing our offer to the seller. We were in a hyper competitive market with many potential buyers and with Ann's help we were able to close the deal at less than asking price. Great job Ann!

Will Vogelsang
Chicago

Ann was a pleasure to work with and very thorough in analyzing and showing prospective properties for purchase. She has an excellent understanding of Chicago's numerous neighborhoods and will save you tons of time as buyer by vetting properties for you.

Dan Hawkins
Bucktown

Our agent was Ann Connolly and she was fantastic. I met with her two years ago to put my condo on the market and we decided it wasnt the right time. When my fiance and I decided to look for a house I contacted her again. She was patient, knowledgeable and realistic about the market and our options. Ann went above and beyond for us and we plan to use her to sell our condos once the market turns for the better. I would highly recommend Ann to any of my friends and family. Anita and Matt

Anita and Matt

Ann was a fantastic buyer's agent for my family. We were interested in a condo with nice vintage features and lots of character. Our favoured locations were in and around Andersonville and we had the usual financial constraints that seem to be an issue for many people at the moment. Ann's personality matched ours perfectly, she had amazing patience, and her insight into our desires was exactly spot-on. We recently closed on a two-bed condo in Andersonville and have found that we are even more excited after closing as we were leading up to making an offer. We have been extremely happy with having worked with Ann and would highly recommend her without reservation. David Shay and Amelie

David Shay and Amelie

Ann was great, on the sell and buy side. Didn't push, and was very patient. Great advice on how to maximize my sales price by staging my condo.

Noreen Connolly

I have worked with Ann twice - once when I bought my first house in Chicago and again when I sold it 10 years later - and can highly recommend her! We put our house on the market in 2009 when we relocated to NJ, in one of the lowest points of the housing market. I don't think any of us realized just how difficult the market was, but we soon found out. Ann did a great job - holding countless open houses, advising us on pricing changes and even making sure the sidewalk was shoveled during the long Chicago winter. She went above and beyond to sell our house and was great at keep us up-to-date with feedback from potential buyers. It's not easy to sell your house from long distance, but it helps to have someone you can trust completely. And that's Ann. Thanks again, Ann! Jeanne, Ludwig, Mia and Lily, Roscoe Village

Zebrauskas Family
Roscoe Village

I would like to thank you for your support and extra help in getting my son Daniel into a condo on Elk Grove in Wicker Park. He is in, settled down and continuing to do well in school. Your prediction, during the inspection, that this condo will appraise at least at 250K when the building is fully occupied is right on. Daniel called and said the young lady on the first floor is getting a mortgage and the banks appraisal was 200K with the building only half occupied. I want you to know what an important part you played in getting Daniel started on the right foot in a big city.Ernest Hawkins, Wicker Park

Ernest Hawkins
Wicker Park

Ann did a great job helping to sell my place in the difficult 2009 market. Her first piece of good advice was that we work with a stager to make sure the place would show as well as possible. She even brought some of her own belongings to help the condo look its best. When I got an offer, she helped me figure out how to negotiate the right price. After that, she helped with everything else in the process through the closing. When the inspection report came back, she and her husband (a builder) personally helped to fix things for me. Also, I really give her credit for always maintaining a very positive relationship with the buyer and the other agent. She is not even remotely pushy or high strung like some agents can be, and this helped immensely. She let a number of people in to the condo when I was at work for all sorts of things (appraisal, repairs). During the 45 day waiting period from offer to close, I can't even count how many emails and phone calls we exchanged. There are dozens of steps of the sale process, and she always got back to me right away (sometimes within minutes) which I appreciated a lot. This was the first place I ever sold, so I didn't really have the experience to know how to deal with all the little things that come up during the process, and she was always there to help.Aaron, Lakeview

Aaron
Lakeview

I cannot recommend Ann Connolly highly enough. From the moment we exchanged our first emails, she demonstrated the highest level of attentiveness and professionalism. She has a deep understanding of the market and the city; she listened to my wants and needs, and gave me honest, thoughtful opinions on the homes we viewed. Because of her, I ended up with a place I absolutely love. The entire home-buying process is stressful, but she did everything possible to help and support me throughout, way above and beyond what a realtor is expected to handle. After closing, she even offered to wait at my loft for my internet & satellite setups so I wouldn't have to take any more time off work. Ann's kindness, integrity and true concern for her clients are just a few of the qualities that make her a wonderful realtor (and an even better person); I consider her a friend. You will not be disappointed in working with her. Ronnie Hunt, Bucktown

Ronnie Hunt
Bucktown

Ann was very professional and even more patient with us as new home buyers. She is very knowledgeable about the industry. Barb, Pilsen

Barb Hemmerling
Pilsen

Ann is great! She takes the time to answer any questions a buyer may have. I plan to use Ann if I ever sell my condo. Kay Frederick, Pilsen

Kay Frederick
Pilsen

Ann was a pleasure to work with. She worked around our schedule, picked us up at the airport several times and did not hesitate to give us the time we needed. Being from out of town, her knowledge of Chicago helped us find the ideal location for our needs. We couldn't have been more pleased with the service. Jay and Debbie, Bridgeport

Jay and Debbie Seaver
Bridgeport

Contact Ann Connolly

Mobile - 312.476.0224

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