Social Media
Specialties
First Time Home Buying
Residential Listing
Condominium Listing
Builder Services
Land & Housing Development
Luxury Real Estate
Relocation Services
Property Concierge
Housing Trends
Marketing & Advertising
Certified Residential Specialist (CRS)
Graduate, REALTOR® Institute (GRI®)
Accredited Buyer's Representative® (ABR®)
About Sherry
Lessing Real Estate Website
"We had a great experience with Sherry Lessing when we bought our current property and sold our then current house.”
★★★★★
"Amy & Sherry are a great team! Extremely responsive and knowledgeable. If you want to buy or sell real estate, do not look anywhere else. Amy helped me buy my home and she helped me sell my mother's home. Both sales were done quickly without any anxiety. The process was easy and an absolute pleasure! Would certainly work with them again. “
★★★★★
"Amy and Sherry were professional and easy to work with selling our parents' house. Amy's communication with us was wonderful and she was prompt in responding. They were realistic in helping us price the house as they know the market extremely well. As a side note, they love dogs, too.”
★★★★★
"Amy and Sherry Lessing are phenomenal real estate agents and wonderful people. We give them our highest recommendation! We worked with them to purchase an amazing house in an amazing neighborhood (8 years ago) and again to sell the house this year. In 2016, they helped us to purchase our first home as out of town buyers, which of course is a daunting process, and their expertise was so helpful to make the process not only go very smoothly but also to help educate us on aspects of the process that are quite unfamiliar to first time home buyers (loan process, inspections, etc.). Over our 8 years living in the home, they were available for any questions or recommendations for repairs that we needed. This year, we sold the house because we were moving out of state, and there was no question that we would go with Amy and Sherry again. They worked with us on pricing, maintenance, staging, negotiation, and closing (all from out of state as well). They are so trustworthy and communicative - We had no concerns at all that we would not be in Wisconsin as we were selling our home. They are so supportive with any questions and requests we have had over the past decade, and always offer excellent advice that fit our needs as the client. We give them our highest recommendation!”
★★★★★
"Amy and Sherry are amazing realtors! Whether buying or selling they will be by your side the entire time, they have your best interests at heart and will see things through to the end. I whole heartedly recommend them without any reservations!”
★★★★★
"Amy and Sherry Lessing are the premiere real estate agents in Madison. We worked with them thru both the home buying and selling process and they proved to be wonderful brokers and people, who we consider much more than our agents. On the buying side, they got us into a wonderful home for a great price where we lived for almost 8 years in a neighborhood we loved. They provided a number of recommendations for our house throughout the years, that were super helpful. On the selling end, Amy went above and beyond with accurate pricing, staging, negotiation, and closing, to get us a great offer. We give them our highest recommendation.”
★★★★★
"We have bought and sold two homes with Lessing Real Estate. Amy and Sherry know the near west side and all its treasures. We have been happy with the Lessing team at every stage of the process and are so confident about this team! They are the best!”
★★★★★
"Amy and Sherry are the best in the area. We were referred to them by multiple friends and coworkers and they did not disappoint. They helped us find our first and hopefully "forever" home and we could not be happier with it. What was a nerve-wracking and daunting process being first time buyers was made simple with Amy and Sherry and they totally made us feel confident in the process.
I love working with strong, confident women and these two were the perfect team for us. Love keeping in touch with them and would definitely recommend to anyone buying or selling.
★★★★★
"By far the best realtors that we have every worked with. Super-organized, super-professional, and super-focused on serving our needs as the seller. Fantastic communicators and educators (of the selling process and their strategy). If we needed something done (e.g., housecleaning) and were too occupied to make it happen, they brought in other professionals to get it done for us. They also got us the high-end price we were seeking. If we have a need for realty services in the future, these are the first and only folks we'll be calling. Highly recommended!!!
★★★★★
"Amy & Sherry helped us find our dream home! In this market you need to act fast. We were always able to get showings the first day a home went on the market. They were very responsive and knowledgeable throughout the whole process. So glad we went with the Lessing team!”
★★★★★
"Amy and Sherry are the best. I hope to never move again (or at least not for a long time) but if I do, I'll be calling them up again!”
★★★★★
"I couldn't have been luckier than to have worked with both Sherry and Amy. They worked tirelessly to help me find the perfect home. They left no stone unturned; What a terrific team! I was so very grateful to have had them by my side every step of the way. They are hands down The Best in the industry! Thank you so much!!”
★★★★★
"I totally enjoyed working with Sherry and Amy Lessing. Highly recommended for anyone buying or selling real estate. They are professional, effective and accessible.”
★★★★★
"Sherry & Amy are the best realtors! We’ve worked with them several times in the Madison, WI area when both buying and selling real estate and they have always provided us with top notch service & guidance throughout the process.”
★★★★★
"Amy and Sherry Lessing are 2 of the most dedicated, knowledgeable and caring real estate agents I've ever had the pleasure of working with. The Madison, WI real estate market is lucky to have them!”
★★★★★
"Sherry Lessing and her daughter Amy are real pros! We were so impressed! They were always on top of everything.”
★★★★★
"Amy and Sherry were wonderful! They are very knowledgeable in their field and never pushed me into anything. They always suggested ideas and let me think about it. It was lovely to work with them. I highly recommend them.”
★★★★★
"We highly recommend Lessing Real Estate based on our experiences as both a seller and a year later as a buyer. They are extremely knowledgeable and provide prompt communication, confidence inspiring attention to detail, and honest feedback and advice.”
★★★★★
"5 stars! Total professionals. We felt very taken care of throughout the lot purchase, and the level of care and expertise shown through the builder selection, design and selection process was incredible.
★★★★★
"Complete understanding of the market conditions and what is required to achieve best pricing — professionalism that stands out in the crowd of realtors!”
★★★★★
"Simply the best! Got us our dream home in an impossible market!”
Over the past 35+ years, Sherry Lessing has built her real estate business from the bottom up. She started at First Realty (now First Weber, Inc.) in 1989 with no sales experience, yet a drive toward success. She has been an unstoppable force in the real estate industry earning the title of 'Top Sales Agent' continuously since 1994! If you’ve had the opportunity to work with Sherry, you know that she’s not just a realtor, she’s a powerhouse. Her reputation precedes her. Sherry’s level of professionalism, expertise, experience & ability to seamlessly handle it all with grace are the cornerstones that have allowed her to grow her real estate business.
In 1998, Michael, Sherry's husband, joined her in real estate & the pair continued to build the business, working with buyers & sellers, tirelessly striving to give their clients the best buying and/or selling experience. As a team, the duo continued to excel in the real estate market. The combination of Sherry's extraordinary sales & negotiation skills and experience with Mike's problem-solving capabilities & affability allowed these two to stay atop of the Madison real estate market. We lost Mike in 2018 to cancer. He was not only a wonderful husband, father, mentor, friend, realtor but also such an important member of the Lessing Team & the First Weber family. He is loved and missed by all who had the good fortune to know him.
Amy, Sherry & Mike's daughter, joined the team in 2013 with a background in sales, instructional design & human resources. Growing up in a real estate family gave Amy a unique perspective having watched the industry evolve over the years. She was trained by the best negotiator in the business, her mom & the best back-end systems implementor & tracker, her dad. Her lifetime of real estate training has made Amy able to provide her clients with excellent client service, thorough market knowledge & local expertise.
In October 2024, the team joined Compass, a national real estate brokerage with exceptional technology & marketing. As one of the first few teams to join Compass in the Madison market, they look forward to helping grow the brokerage in the coming years.
We love the opportunity to work with new clients, referrals & of course, our recurring clients. Our goal is to treat each person, not as a transaction, but as a person, trusting us with their most important possession, their home. We give each person our respect, our time & provide them with the top tier of service. We look forward to working with you!
In 1998, Michael, Sherry's husband, joined her in real estate & the pair continued to build the business, working with buyers & sellers, tirelessly striving to give their clients the best buying and/or selling experience. As a team, the duo continued to excel in the real estate market. The combination of Sherry's extraordinary sales & negotiation skills and experience with Mike's problem-solving capabilities & affability allowed these two to stay atop of the Madison real estate market. We lost Mike in 2018 to cancer. He was not only a wonderful husband, father, mentor, friend, realtor but also such an important member of the Lessing Team & the First Weber family. He is loved and missed by all who had the good fortune to know him.
Amy, Sherry & Mike's daughter, joined the team in 2013 with a background in sales, instructional design & human resources. Growing up in a real estate family gave Amy a unique perspective having watched the industry evolve over the years. She was trained by the best negotiator in the business, her mom & the best back-end systems implementor & tracker, her dad. Her lifetime of real estate training has made Amy able to provide her clients with excellent client service, thorough market knowledge & local expertise.
In October 2024, the team joined Compass, a national real estate brokerage with exceptional technology & marketing. As one of the first few teams to join Compass in the Madison market, they look forward to helping grow the brokerage in the coming years.
We love the opportunity to work with new clients, referrals & of course, our recurring clients. Our goal is to treat each person, not as a transaction, but as a person, trusting us with their most important possession, their home. We give each person our respect, our time & provide them with the top tier of service. We look forward to working with you!
Client Testimonials
Scroll down for more
★★★★★"We had a great experience with Sherry Lessing when we bought our current property and sold our then current house.”
★★★★★
"Amy & Sherry are a great team! Extremely responsive and knowledgeable. If you want to buy or sell real estate, do not look anywhere else. Amy helped me buy my home and she helped me sell my mother's home. Both sales were done quickly without any anxiety. The process was easy and an absolute pleasure! Would certainly work with them again. “
★★★★★
"Amy and Sherry were professional and easy to work with selling our parents' house. Amy's communication with us was wonderful and she was prompt in responding. They were realistic in helping us price the house as they know the market extremely well. As a side note, they love dogs, too.”
★★★★★
"Amy and Sherry Lessing are phenomenal real estate agents and wonderful people. We give them our highest recommendation! We worked with them to purchase an amazing house in an amazing neighborhood (8 years ago) and again to sell the house this year. In 2016, they helped us to purchase our first home as out of town buyers, which of course is a daunting process, and their expertise was so helpful to make the process not only go very smoothly but also to help educate us on aspects of the process that are quite unfamiliar to first time home buyers (loan process, inspections, etc.). Over our 8 years living in the home, they were available for any questions or recommendations for repairs that we needed. This year, we sold the house because we were moving out of state, and there was no question that we would go with Amy and Sherry again. They worked with us on pricing, maintenance, staging, negotiation, and closing (all from out of state as well). They are so trustworthy and communicative - We had no concerns at all that we would not be in Wisconsin as we were selling our home. They are so supportive with any questions and requests we have had over the past decade, and always offer excellent advice that fit our needs as the client. We give them our highest recommendation!”
★★★★★
"Amy and Sherry are amazing realtors! Whether buying or selling they will be by your side the entire time, they have your best interests at heart and will see things through to the end. I whole heartedly recommend them without any reservations!”
★★★★★
"Amy and Sherry Lessing are the premiere real estate agents in Madison. We worked with them thru both the home buying and selling process and they proved to be wonderful brokers and people, who we consider much more than our agents. On the buying side, they got us into a wonderful home for a great price where we lived for almost 8 years in a neighborhood we loved. They provided a number of recommendations for our house throughout the years, that were super helpful. On the selling end, Amy went above and beyond with accurate pricing, staging, negotiation, and closing, to get us a great offer. We give them our highest recommendation.”
★★★★★
"We have bought and sold two homes with Lessing Real Estate. Amy and Sherry know the near west side and all its treasures. We have been happy with the Lessing team at every stage of the process and are so confident about this team! They are the best!”
★★★★★
"Amy and Sherry are the best in the area. We were referred to them by multiple friends and coworkers and they did not disappoint. They helped us find our first and hopefully "forever" home and we could not be happier with it. What was a nerve-wracking and daunting process being first time buyers was made simple with Amy and Sherry and they totally made us feel confident in the process.
I love working with strong, confident women and these two were the perfect team for us. Love keeping in touch with them and would definitely recommend to anyone buying or selling.
★★★★★
"By far the best realtors that we have every worked with. Super-organized, super-professional, and super-focused on serving our needs as the seller. Fantastic communicators and educators (of the selling process and their strategy). If we needed something done (e.g., housecleaning) and were too occupied to make it happen, they brought in other professionals to get it done for us. They also got us the high-end price we were seeking. If we have a need for realty services in the future, these are the first and only folks we'll be calling. Highly recommended!!!
★★★★★
"Amy & Sherry helped us find our dream home! In this market you need to act fast. We were always able to get showings the first day a home went on the market. They were very responsive and knowledgeable throughout the whole process. So glad we went with the Lessing team!”
★★★★★
"Amy and Sherry are the best. I hope to never move again (or at least not for a long time) but if I do, I'll be calling them up again!”
★★★★★
"I couldn't have been luckier than to have worked with both Sherry and Amy. They worked tirelessly to help me find the perfect home. They left no stone unturned; What a terrific team! I was so very grateful to have had them by my side every step of the way. They are hands down The Best in the industry! Thank you so much!!”
★★★★★
"I totally enjoyed working with Sherry and Amy Lessing. Highly recommended for anyone buying or selling real estate. They are professional, effective and accessible.”
★★★★★
"Sherry & Amy are the best realtors! We’ve worked with them several times in the Madison, WI area when both buying and selling real estate and they have always provided us with top notch service & guidance throughout the process.”
★★★★★
"Amy and Sherry Lessing are 2 of the most dedicated, knowledgeable and caring real estate agents I've ever had the pleasure of working with. The Madison, WI real estate market is lucky to have them!”
★★★★★
"Sherry Lessing and her daughter Amy are real pros! We were so impressed! They were always on top of everything.”
★★★★★
"Amy and Sherry were wonderful! They are very knowledgeable in their field and never pushed me into anything. They always suggested ideas and let me think about it. It was lovely to work with them. I highly recommend them.”
★★★★★
"We highly recommend Lessing Real Estate based on our experiences as both a seller and a year later as a buyer. They are extremely knowledgeable and provide prompt communication, confidence inspiring attention to detail, and honest feedback and advice.”
★★★★★
"5 stars! Total professionals. We felt very taken care of throughout the lot purchase, and the level of care and expertise shown through the builder selection, design and selection process was incredible.
★★★★★
"Complete understanding of the market conditions and what is required to achieve best pricing — professionalism that stands out in the crowd of realtors!”
★★★★★
"Simply the best! Got us our dream home in an impossible market!”
Sherry Lessing’s Listings
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