Bill Flemming

LICENSE: 471.000179

(847) 495-5000
(847) 495-5000 (Office)


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Dependable, Thorough, Honest – “Give BILL a BUZZ!”

What a pleasure it is to serve home buyers and sellers in and around my hometown, Chicago! A 30+ year veteran REALTOR®, I love heading to work each day as I am passionate about real estate and giving every client personalized service. Outgoing, a great listener, and fair-minded, I take time to understand your needs, and act accordingly.

As a managing broker for more than 25 years - There’s very few situations in a Real Estate Transaction that I have not seen. Rest-assured, if there is a bump in the road, I have most-likely been there and maneuvered through it successfully in the past. An excellent communicator, my team and I I keep you well-informed… from our initial contact, to the closing table, and beyond.

As a listing specialist, I offer a comprehensive marketing strategy that makes your home stand-out among potential buyers. My seasoned know-how extends to lease homes, condos, land development, new construction and historic homes.

My team of experienced agents, under my direct watch, handle the buying process. We are enthusiastic about life and real estate. We enjoy career sales of more than 2.5 Billion and these days our team will commonly sell 70-100 homes per year. 

I am the Principal Owner and Managing Broker of HomeSmart Connect, and represent clients in commercial and residential real estate markets.

Being an Inverness Soccer Commissioner, and former Indian Princess Chief, I strive to be an ally of my community and with my kids and others. A sports fan that enjoys boating & volleyball, I spend time with my amazing wife and three amazing daughters every chance I get.

I am committed and pro-active about putting your needs first; let’s talk soon if you are contemplating a home sale or purchase in Chicago or Chicago’s Northwest Suburbs.

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Professional Experience

2013 - Today

Principal/Managing Broker

HOMESMART Connect Real Estate


2011 - Today


Referral Connections LTD


1999 - 2011


RE/MAX Unlimited Northwest

1990 - 1999

Managing Broker

RE/MAX Suburban

1988 - 1990

Broker Associate

Starck Realtors

1986 - 1988

Sales Associate

Merrill Lynch Realty

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Reviews on Zillow Real Estate on Zillow

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Listed and sold a home

Bill Flemming and his team have been great to work with. My wife and I bought our house and sold the same house using Bill, and we couldn't be happier! They were helpful at every stage of the process, and were able to answer all of our questions with detailed but easy to understand answers. Their communication during the entire process limited the stresses of buying and selling our first home. We would absolutely recommend Bill Flemming and his team to anyone who wants their home buying or selling process to be handled with enthusiasm and expertise!

Helped me buy home

Bill has a charismatic personality and puts his heart and soul into helping his client's. He has many years of experience in the real estate business from all aspects. I enjoyed my personal experience buying a home. Bill found my husband and I the perfect house and he negotiated at a stellar price and we are still enjoying it seventeen years later. I would highly recommend him if you need any real estate services.

Listed and sold a home

Bill Flemming is a top notch agent who works extremely hard for his clients! From the background research to hitting the pavement, I am amazed at his commitment to satisfying the customer at every level. Bill also offers great negotiation skills which will surpass most expectations!

Helped me buy home

I have worked with Bill over the years in the purchase of 2 homes and the sale of one and he is very knowledgable, professional and helpful. He really listened to what we were looking for and was sure to take us only to properties that fit our wants and needs and kept us updated in a timely manner on every step of the process. Purchasing a home especially the first time was so overwheliming but Bill helped make it much easier! I will definately use Bill for any future real estate needs and refer him

Helped me buy and sell homes

Since the mid-90's, Bill has helped me three times, to sell and buy each home I've ever owned. I highly recommend Bill Flemming to anyone seeking to buy or sell a home, based on his experience, knowledge, skills, and most importantly; his true and honest desire to facilitate his clients reaching their real estate goals.

Helped me buy home

Bill is a highly responsible, highly knowledgeable agent. I am glad to have known him and have been very impressed with his work. I believe that he has always had his customers needs at the heart of his work and would call him whenever I or any of my friends and family have need of his services.

Listed and sold a home

Bill has sold 3 homes for us and helped buy all our homes as well. Bill has always been honest and helpful and has great marketing ideas!! Bill always is very accurate with his pricing and very good at negotiating as well.

Showed me homes

I have worked with Bill on a number of real estate related matters and always find him to be extremely knowledgeable, honest and diligent. I highly recommend Bill to anyone interested in obtaining high quality and professional service.

Showed me homes

I've personally know Bill for over 12 years. He's an honest and hard working person. A devout family man who cares about his clients. Bill will use all resources and methods at his disposal to help his clients achieve their goals and desires. I highly recommend Bill to anyone who needs help buying and/or selling homes and properties.

Helped me buy and sell homes

I've Known Bill for decades and he's always been professional, responsive and understanding of what we are looking for in a property. He knows the area well and works hard to make sure you're able to find a great home at a fair price.