Lessing Real Estate

Lessing Real Estate Whether you're moving into, out of, or just around town, let us help you with your real estate needs Her reputation precedes her. We lost Mike in 2018 to cancer.

Over the past 35+ years, Sherry Lessing has built her real estate business from the bottom up. She started 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 powerh

ouse. 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. He was not only a wonderful husband, father, mentor, friend, realtor but also such an important member of real estate community. 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. 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!

💥 Congrats to my Sellers + Buyers! Another lot is under contract in Westwind! If you've thought about building, we have ...
05/30/2026

💥 Congrats to my Sellers + Buyers! Another lot is under contract in Westwind! If you've thought about building, we have 3 lots left in this phase and are working on Phase 2!
🍎 Middleton Schools
🔨 Bring your own builder & build on your timeline!
📐 .23 -.58 acres
💰 Prices start at $200,000
💻 Looking for more information ➡️ https://buff.ly/CnYtyPl
📲 [email protected]

🎉 ACCEPTED OFFER 🎉Congratulations to my buyers who are officially under contract on a beautiful home in Edgerton! 🏡Findi...
05/28/2026

🎉 ACCEPTED OFFER 🎉

Congratulations to my buyers who are officially under contract on a beautiful home in Edgerton! 🏡

Finding the right home is always exciting, but getting your offer accepted makes it feel real. After exploring options and navigating the process together, I'm thrilled to help these clients take the next step toward their move to Wisconsin.

💪 The market is competitive but so are we - reach out to find out how we can help you secure your dream home!
Curious to learn more? Reach out today for a consultation. ⤵️
💻 Learn more - https://buff.ly/3SnDSzb
📲 [email protected]

🏡 Another one SOLD in Kilkenny Farms! 🏡There’s no greater compliment than when clients come back again for one of life’s...
05/28/2026

🏡 Another one SOLD in Kilkenny Farms! 🏡

There’s no greater compliment than when clients come back again for one of life’s biggest decisions. Being trusted to help not just once, but through multiple moves and milestones, is something I never take for granted and for these clients, this is 3 transactions is 9 months (possibly a record for me!)

And a big thank you , .madison for always making it so easy for my clients on the lending side!

🏡 JUST SOLD in Kilkenny Farms! 🏡This gorgeous home sold within HOURS of hitting the market! ⚡️↪️ Swipe to take one last ...
05/27/2026

🏡 JUST SOLD in Kilkenny Farms! 🏡

This gorgeous home sold within HOURS of hitting the market! ⚡️
↪️ Swipe to take one last look at this stunner.

A huge congratulations to my wonderful repeat clients on the successful sale of their home. There’s no greater compliment than having clients come back to us time and time again for their real estate needs.

Congratulations to my sellers and the new homeowners and a big thanks to Liz Quinn Homes Compass Wisconsin & Megan Davis, Park Bank for being the absolute dream team! 🎉

Thinking about selling? The right preparation and marketing plan truly make all the difference.
💻 Learn more about us - https://buff.ly/3SnDSzb
📲 [email protected]

Today, we honor and remember the brave men and women who made the ultimate sacrifice for our country. ❤️🤍💙 We remember. ...
05/25/2026

Today, we honor and remember the brave men and women who made the ultimate sacrifice for our country. ❤️🤍💙 We remember. We honor. We thank you.

💥 Congrats to my Sellers! Another lot is under contract in Westwind! If you've thought about building, we only have a fe...
05/23/2026

💥 Congrats to my Sellers! Another lot is under contract in Westwind! If you've thought about building, we only have a few lots left in this phase and are working on Phase 2!
🍎 Middleton Schools
🔨 Bring your own builder & build on your timeline!
📐 .23 -.58 acres
💰 Prices start at $200,000
💻 Looking for more information ➡️ https://buff.ly/CnYtyPl
📲 [email protected]

✨ JUST SOLD at Rockery Pointe Condos! ✨We first helped these clients purchase this condo — and now we had the privilege ...
05/22/2026

✨ JUST SOLD at Rockery Pointe Condos! ✨

We first helped these clients purchase this condo — and now we had the privilege of helping them sell it FAST! 🏙️

From purchase to resale, it’s always an honor to be part of our clients’ next chapter. Strategic pricing, preparation, and marketing made all the difference, and this one moved quickly!

Big congratulations to our sellers and thank you again for trusting us through another move.

Thinking about selling? Let’s talk about how to position your home for maximum impact.
💻 Learn more about us - https://buff.ly/3SnDSzb
📲 [email protected]

✨ JUST SOLD in Wexford Village! ✨This one was extra special — not only was this our 3rd time listing this home over the ...
05/21/2026

✨ JUST SOLD in Wexford Village! ✨

This one was extra special — not only was this our 3rd time listing this home over the years, but we also helped this wonderful client purchase it in the first place. 🏡

There’s something incredibly rewarding about being part of our clients’ journeys through multiple chapters of life, and we’re so grateful for the continued trust year after year. Thank you for allowing us to help guide another successful move!

Congratulations to our seller and the new homeowners and a big thanks to Stephanie Knutson, Insiders Realty I Madison, WI for always being so lovely to work with! 🎉

Thinking about selling? The right preparation and marketing plan truly make all the difference.
💻 Learn more about us - https://buff.ly/3SnDSzb
📲 [email protected]

🎉 Congrats to our Sellers + Builder! Lot 61 in Westwind is officially sold & what's being built by Willow Ridge Design B...
05/14/2026

🎉 Congrats to our Sellers + Builder! Lot 61 in Westwind is officially sold & what's being built by Willow Ridge Design Build is going to be a stunner! Thinking about building your dream home? Reach out and let’s talk about this gorgeous floor plan and how we can customize it to fit your style and needs. ✨🏡
〰️〰️〰️〰️
If you've thought about building, we have beautiful lots still available!
🍎 Middleton Schools
🔨 Bring your own builder & build on your timeline!
📐 .23 -.58 acres
💰 Prices start at $200,000
💻 Looking for more information ➡️ https://buff.ly/CnYtyPl
📲 Contact me with any questions or to schedule a tour - [email protected]

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Middleton, WI
53562

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