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Lessing Real Estate

Providing clients with ultimate bespoke representation, customized marketing strategy, and white-glove service. Excelling in exceeding expectations for buyers, sellers, investors, developers, and beyond.

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The Team That Makes It Happen

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 real estate agent, 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 the Madison real estate market. We lost Mike in 2018 to cancer. He was not only a wonderful husband, father, mentor, friend, and real estate agent but also 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.

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Trusted Real Estate Partners

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 implementer & tracker, and 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, and our time & provide them with the top tier of service. We look forward to working with you!

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