Elegant Retreat

About Bob Winding

If you would like to work with someone who knows and appreciates Madison, Bob Winding would love to help you. He grew up in Madison and graduated from East High School and the University of Wisconsin-Madison.  After college, Bob made moves to and from Milwaukee, New York City and Minneapolis, so he understands the moving process, along with the challenges and stress that can be a part of it.  Clients who have worked with Bob appreciate his strong communication skills, consultative approach and his genuine interest in helping them achieve their desired outcomes.

In addition to his passion for real estate, Bob enjoys being involved in the community, spending time with his wife, three great kids and the family golden retriever, Darla. Bob also loves playing platform tennis.


Community Service & Affiliations

  • Has served on the Board of Directors for:
    • Middleton Outreach Ministry (MOM)

    • Downtown Madison Inc (DMI)

    • High Point Estates Homeowners Association

    • Wisconsin Health Charities of Wisconsin

    • Children’s Cancer Research Fund

  • Co-Chair of Capital Campaign Committee for MOM

  • Downtown Madison Rotary

  • DMI

  • Middleton Chamber of Commerce

  • Realtors Association South Central Wisconsin (RASCW)

  • Wisconsin Realtors Association (WRA)

  • National Association of Realtors (NAR)

  • South Central Wisconsin MLS

  • President of Madison Platform Tennis Association


**Client References/Testimonials**


Bob Winding made the effort of finding our dream home an enjoyable experience. He is the nicest and hardest working realtor we had the fortune to work with. He was tireless, courteous, professional, very knowledgeable, and always there for us when we needed him, any day of the week. He was very patient with our long “wish list” of requisites and worked hard to find the home that would fulfill all our needs, which we certainly did. And once we found the home, he made every effort to guarantee our offer’s success, by being proactive and very flexible, working with the sellers to resolve any issue they raised. This was the third time we buy a home, and, by far, the best search and buying experience we ever had, thanks to Bob. We are definitely recommending him to all our friends looking for a new home in the area.

-Pedro and Angelica


Bob was truly amazing with assisting us to purchase our home. He is an outstanding communicator, open, honest, first class professional, personable and friendly human being. He provided us with a streamlined continuum of care and highest level of customer satisfaction. He builds strong relationships and is a strong networker. His strong work ethic is commendable. We loved our relationship with him and recommend him unconditionally.

-Roma and Dusty


I write to offer to anyone interested an account of our house marketing experience at the hands of Bob Winding. We had spent a lot of time and money getting our property ready to sell. It would have to sell as a vacant house which we realized might present additional marketing challenges. With gentle persistence Bob convinced us that along with the strength and capabilities of First Weber, he was the right person to take our house to the market. His polite and intuitive nature drew us in. We signed a listing contract and Bob went to work. I'm quite certain that he did the same things that all good realtors do to bring property to the attention of potential buyers, but he did it all with class, perfect timing and great communication. Bob answered all of our questions and was never afraid to say "Let me check on that". He wanted to get all of the details right. Getting it right is more important to him than giving a quick answer. I really liked that. We didn't have a lot of house selling experience, most people don't. That is one more reason we were so pleased to have Bob on our team. We could ask for his opinion and get a professional response. If we had an idea that he knew would require a little modification, he could suggest a modifier in such a way as to make us think that we had a great idea. If a professional, polite, very competent realtor (who also happens to be a real nice guy) is what you seek, hire Bob Winding, I'm certain you will be glad you did.

-Jim and Tom


We recently had the pleasure of working with Bob Winding during our relocation from North Carolina to Madison.  Bob worked with us for eight months before we found our perfect home. During this time, he showed us a number of houses and was very patient as we ruled them out for one reason or another.  He also went above and beyond his realtor duties by recommending things to do, restaurants, and by giving us a wonderful overview of our new hometown. His knowledge of the area is remarkable.  When we finally found the perfect house, we were one of four bids submitted. He helped us navigate a very emotional and stressful process and offered us excellent guidance on suggestions to improve our chances of being the winning bid.  In the end, our bid was selected. We would recommend Bob to anyone in need of a responsive, professional, well-informed and super- nice real estate agent.

-Tracy and Scott


Thanks so much to Bob for making our first-time buying a home less intimidating! We enjoyed working with him so much and are so happy with the end result. Thank you, thank you, THANK YOU!!!

-Brittany and Adam


It is our immense pleasure to recommend Bob Winding as a real estate agent for any individual or family searching for the ideal home for their unique situation. We have been searching for homes since we moved to Madison from San Diego in July of 2013 and we met Bob at an Open House he was holding.  He was the only agent that introduced himself to us out of the several open houses that we attended, even after we indicated that we did not have an agent. He has been very prompt and incredibly personable. He made our buying experience enjoyable and memorable. He went above and beyond by recommending other services such as contractors, home inspectors, and other sub-contractors.  He has stayed in contact with us even post-sale and we appreciate his kindness. We are pleased to recommend Bob Winding to anyone looking to buy or sell a home. He is an astute professional, and an overall great human being and if we ever need to buy more residential property, he will be our first choice.

-Chris and Curtis

Working with Bob Winding has been an absolute joy. He is both incredibly business savvy, and also a genuinely kind person. Over the course of our time together, Bob really got to know my family. He put forth effort to cultivate and maintain what ultimately became a true sense of camaraderie. His perpetually positive attitude was very much appreciated as it took us quite a while to find just the right house. I will highly recommend Bob to anyone looking for a trustworthy agent with a solid work ethic. He is a gem!

-Kathryn and Chris

What a great process and a great new home for our family. Thank you!

-Zach and Lora


Bob went above and beyond the call of duty to move my mother's home quickly.  His effort was exemplary. I would be glad to refer Bob to other sellers and buyers.



We were initially worried about trying to buy a house in Wisconsin while we still lived in California, but Bob made everything easy and fun! He has been remarkably helpful and we could not have done it without him.



From the day I met Bob (he toured me around Madison when my husband interviewed for his job), he was helpful, friendly, enthusiastic, and professional. House hunting was not an easy process for us, both because we were first time buyers, and also because we were relocating for Portland, Oregon. Bob went above and beyond being our eyes and ears when he checked out countless homes for us, and he also did an excellent job keeping our family's specific needs and wants in mind. Bob led us to find a more beautiful home than I thought we could find - and in a great location! He was always available to answer questions, FaceTime us through properties, and even after closing, Bob helped us with some immediate needs for our new home, as we were still in Oregon. My husband and I cannot praise Bob enough for a job well done. We would absolutely use Bob again in the future, as well as recommend him to friends and family.

-Lauren and Adam


Bob was amazing to work with! He went above and beyond to make our experience effortless. Bob was there to answer questions and help us in any way possible. Bob is so resourceful and was always there for us!

-Jeana and Eric


Bob is a real professional and supported the sale and purchase in a great manner. I will recommend him to any friend or family member with the highest level of confidence. He made this a great experience and has continued to offer support and advice throughout it all.



We faced the challenge of selling our parents' house in Madison from half a continent away. It was clear to us at the outset that Bob would be likely to handle the difficulties of this task. And we were impressed on our first meeting Bob that he is highly professional and has extremely well honed communication skills. All of these were tested during the process of selling the house. There were unexpected torrential rainstorms - Bob checked on the house after these, and discovered basement leakage, for example. He then coordinated, with our approval, workmen to remedy the issue. The home inspection process discovered additional electrical issues - which again, with our approval, Bob coordinated correctional action for. At every step, his communication was prompt, his responses to our questions were nearly immediate, and he was a joy to work with throughout. Bob knows the real estate business extraordinarily well, and provided us with local knowledge and expertise. We highly recommend Bob Winding as a real estate agent - he will provide superb service to every one of his clients.



Bob was an absolute pleasure to work with and you can be sure we will recommend him highly to anyone who is looking to purchase or sell a home! We can't thank him enough for all he did for us during this transition. He took all the worry off our shoulders and then some. He truly went above and beyond.

-Joleen and Bruce


My husband and I could not be happier with our experience working with Bob. He was organized, dependable and knowledgeable. His warm and kind demeaner was second to none. He put our needs and interests first. We will recommend Bob to friends and family without hesitation! He is a class act.

-Brooke and John


Bob did an outstanding job for us. He was thoroughly professional, focused on our goals, and creative in his approach. He gave us thoughtful and insightful advice throughout the process. Bob is an excellent listener and regularly solicits feedback. When we decided to make improvements to enhance salability Bob willingly volunteered his contacts and helped supervise getting the work done. We thoroughly enjoyed working with him; we have and will continue to recommend him to others. If you want an agent who will do everything he can to sell your home, Bob is the one for you.

-Linda and Dave


Bob is the best real estate agent we have ever used. He is a true professional and really takes care of his clients. He made our sale process smooth and easy.

-Dave and Ellie


Bob was an outstanding advocate for us as Buyers. Quick to respond to requests and great communicator. Could not have asked for a better agent.

-Kevin and Julia


Bob went out of his way to be helpful during every phase of the process. Pleasant, engaging, informative and willing to go with the flow when I changed my mind. Top marks all around.



We were first-time home buyers and Bob did a great job of walking us through the process and helping us along the way. He was always extremely communicative and great to work with. I would recommend Bob to anyone.

-Jason and Emily


“Bob exceeded our expectations. He patiently helped us through our first home-buying experience. House visits were always scheduled more timely than we expected. Bob addressed every question we had and provided answers to questions we hadn't thought to ask. Bob is a very knowledgeable and experienced realtor. Communication was always timely and professional. We used several of Bob's recommendations for service providers (plumber, locksmith, painter etc.) and were glad we did as we received quality work. We will recommend Bob to others and come back to him if/when we need a realtor in the future. Thank you very much!

-Marsha and Nicholas


Bob was extremely helpful, always available, considerate, extremely knowledgeable, and handled our unique situation with integrity and professionalism. We also appreciated how prompt and quickly he responded to any issues that came up that needed attending to. We had an excellent experience and appreciate how well we were taken care of. We would use him again and would highly recommend his services and your company.

-Deb and Jen


Bob was wonderful to work with. Right after we started on my home search I had a death in my immediate family and Bob was so understanding and patient with me as I worked through my grief and got back on the wagon to look for my future home. We eventually found the perfect place; Bob helped me weed through what I was looking for and how each place ranked through my priorities. We shared a lot of laughs and, as a first time home buyer, I never felt stupid asking a question. Bob was honest and prompt with feedback/info/responses and I appreciate the work he did for me very much.



“I've enjoyed working with Bob Winding thru sale of my home and then purchase of a new home. I've learned to respect his high work ethics, his punctuality and his can-do attitude. Bob's positive outlook and resourcefulness (for instance his network of reliable and affordable pool of repairs people; " I know a guy":)) carried us thru a comprehensive list of contingency removals. I am not sure I could have done the transactions with anyone else; were it not for his commitment to see thru the process I might have decided to give up and not be able to elevate the quality of my wife and my own life to a higher level. With the sales out of the way, I am honored to have him as a friend whom I would highly recommend to other friends. He is a true gentleman!”



Bob not only helped us find a house when we moved to Madison from Canada, he helped us find and worked with a mortgage lender and tradespeople to ensure that we could close quickly. He has continued to be a resource even after closing, helping me deal with last week’s flash flooding.

-Heidi and Stephen


Bob is a first-class individual who has gone above and beyond to serve our needs in three separate transactions!

-Scott and Tracy

First Weber Inc

Bob Winding

Bob Winding



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429 Gammon Place
Madison - WI 53719

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Office: 1-608-692-9400

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