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! Another lot is under contract in Westwind! If you've thought about building, we have 2 lots le...
08/21/2026

💥 Congrats to my Sellers! Another lot is under contract in Westwind! If you've thought about building, we have 2 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]

🏡 **OPEN HOUSE | 2233 LUANN LN  #5** 🏡**NOW OFFERED AT $245,000!**Come take a look at this move-in ready Madison condo a...
08/18/2026

🏡 **OPEN HOUSE | 2233 LUANN LN #5** 🏡

**NOW OFFERED AT $245,000!**

Come take a look at this move-in ready Madison condo and see everything it has to offer! ✨

🏠 **HOME HIGHLIGHTS:**
• Fresh interior paint
• Updated HVAC
• Newer dishwasher + disposal
• **2 assigned underground parking spaces**
• Private storage unit
• Convenient Madison location

📍 **2233 Luann Ln #5 | Madison, WI**
💰 **$245,000**
🗓 **OPEN HOUSE: 8/23 | 11-1pm**

Can’t make the open house? Reach out to schedule your private showing ➡️ [email protected]

💻 Learn more: lessingrealestate.com/properties/2233-luann-lane-5-madison-wi-us-53713-2026746

Co-listed with

**Madison WI condos for sale • Madison WI real estate • condos under $250K • Madison condos • Wisconsin real estate • Madison WI Realtor • condos with underground parking • move-in ready condos**

✨ **NEW PRICE | $874,900** ✨Luxury living in **Hawk’s Landing** just became an even better opportunity.Beautifully updat...
08/18/2026

✨ **NEW PRICE | $874,900** ✨

Luxury living in **Hawk’s Landing** just became an even better opportunity.

Beautifully updated, spacious, and truly move-in ready, **1802 Autumn Hill Drive** offers **4,001 sq. ft.** of living space on an impressive **0.52-acre lot** in one of Madison’s most desirable neighborhoods.

From the dramatic two-story foyer and cherry hardwood floors to the bright, open layout, this home offers the space, updates, and amenities today’s buyers are looking for.

🏡 **PROPERTY HIGHLIGHTS**
• 4 bedrooms + private home office with wet bar
• 3.5 bathrooms
• Refreshed kitchen with granite countertops + custom built-in buffet
• Great room with gas fireplace
• Finished lower level with home theater + fitness/dance studio
• 3-car garage with Tesla charger + incredible storage
• Deck + new 20' stamped concrete patio
• Spacious 0.52-acre lot with invisible fence

✨ **MAJOR UPDATES**
Roof (2025) • Gutters (2026) • Carpet (2026) • A/C (2021) • Water heater (2021) • Refreshed kitchen (2019) + more

Move-in ready, beautifully maintained, and ready for its next owner. Schedule your private showing today!

📍 1802 Autumn Hill Drive | Hawk’s Landing
📩 [[email protected]](mailto:[email protected])
💻 lessingrealestate.com/properties/1802-autumn-hill-drive-verona-wi-us-53593-2026512
**Madison WI real estate • Hawk’s Landing homes for sale • Madison WI luxury homes • West Madison homes • Dane County real estate • luxury homes for sale in Madison WI • Madison Wisconsin Realtor • move-in ready homes • homes with finished basements • homes with 3-car garages**

✨ **LUXURY LIVING IN HAWK’S LANDING** ✨Beautifully updated, spacious, and truly move-in ready — **1802 Autumn Hill Drive...
08/12/2026

✨ **LUXURY LIVING IN HAWK’S LANDING** ✨

Beautifully updated, spacious, and truly move-in ready — **1802 Autumn Hill Drive** offers **4,001 sq. ft.** of living space on an impressive **½-acre lot** in one of Madison’s most desirable neighborhoods.

Step inside to a dramatic two-story foyer, cherry hardwood floors, abundant natural light, and a bright, open layout designed for both everyday living and entertaining.

🏡 **Property Highlights:**
• 4 bedrooms + private home office with wet bar
• 3.5 bathrooms
• Refreshed kitchen with granite counters & custom built-in buffet
• Great room with gas fireplace
• Finished lower level with home theater + fitness/dance studio
• 3-car garage with Tesla charger & incredible storage
• Deck + new 20' stamped concrete patio
• Spacious 0.52-acre lot with invisible fence

✨ **Major updates include:** Roof (2025), gutters (2026), carpet (2026), A/C (2021), water heater (2021), refreshed kitchen (2019) & more.

**Move-in ready and waiting for its next owner.**

📍 1802 Autumn Hill Drive | Hawk’s Landing
📩 [email protected]
💻 https://lessingrealestate.com/properties/1802-autumn-hill-drive-verona-wi-us-53593-2026512

**Madison WI real estate • Hawk’s Landing homes for sale • Madison WI luxury homes • West Madison homes • Dane County real estate • luxury homes for sale in Madison WI • Madison Wisconsin Realtor • move-in ready homes • homes with finished basements • homes with 3-car garages**

🏡 **ACCEPTED OFFER | 311 CLEAR POND WAY in WESTWIND**Another beautiful new construction home is officially underway in *...
08/11/2026

🏡 **ACCEPTED OFFER | 311 CLEAR POND WAY in WESTWIND**

Another beautiful new construction home is officially underway in **Westwind!** ✨

We are excited to represent Willow Ridge Design Build on this beautiful new home and see another thoughtfully designed & beautifully executed residence coming to life in the neighborhood.

Westwind continues to grow, with more custom and new construction homes taking shape — and this one is officially spoken for!

Interested in building in Westwind? Let’s talk - [email protected]

Colisted with Brittany Trent - Compass Real Estate

🏡 **Just Listed + Open Houses in Hawks Landing!** ✨Say hello to 1802 Autumn Hill Drive! 🏠✨✨ Highlights you’ll love:☀️ Br...
08/06/2026

🏡 **Just Listed + Open Houses in Hawks Landing!** ✨

Say hello to 1802 Autumn Hill Drive! 🏠✨

✨ Highlights you’ll love:
☀️ Bright, open-concept living spaces
🍳 Modern & updated kitchen perfect for hosting with adjacent dinette & formal dining room
🛌 Spacious primary suite
🌳 Recently stained deck & new paver patio on .52 acres
🚗 3-car garage

Can't make the open house? Reach out to schedule your private showing ➡️ [email protected]
💻 Learn more - https://buff.ly/sHCbGfZ

🎉 Congrats to our Sellers! Lot 63 in Westwind is officially sold!Also a big thanks & congrats to Josh Brost, CORE Collec...
07/30/2026

🎉 Congrats to our Sellers! Lot 63 in Westwind is officially sold!

Also a big thanks & congrats to Josh Brost, CORE Collective Realty Group - Compass bringing his builder to Westwind! Looking forward to seeing another beautiful home in our neighborhood!
〰️〰️〰️〰️
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
📲 Contact me with any questions or to schedule a tour - [email protected]
Compass Wisconsin

🏡 **JUST LISTED | 62 Settler Hill Circle in Settler Hill Condo Association**Sophisticated design meets effortless living...
07/30/2026

🏡 **JUST LISTED | 62 Settler Hill Circle in Settler Hill Condo Association**

Sophisticated design meets effortless living situated within the Blackhawk neighborhood!

This stunning stand-alone condo offers soaring ceilings, a dramatic floor-to-ceiling stone fireplace, a beautifully updated chef's kitchen, and an ideal layout featuring 2 spacious primary suites, a private office with floor-to-ceiling built-ins, sunroom, loft, and an unfinished lower level ready for your vision.

✨ Highlights include:
• Stand-alone condo in Settler Hill
• 2 primary suites with en suite baths
• Private office with custom built-ins
• Chef's kitchen with granite & quartz countertops, stainless appliances & abundant storage
• Sunroom filled with natural light
• Loft plus additional bedroom & full bath
• Unfinished lower level with exposure
• 2-car attached garage

📩 Message me for pricing, a private tour, or more details before it's gone - [email protected]
💻 Learn more - https://buff.ly/V3VHK17

🏡 **JUST SOLD in Cherokee Park!** ✨Some client relationships become family traditions. ❤️This sale was especially meanin...
07/29/2026

🏡 **JUST SOLD in Cherokee Park!** ✨

Some client relationships become family traditions. ❤️

This sale was especially meaningful because my mom first had the privilege of helping these wonderful clients back in **1992**. More than 30 years later (and several condos & homes later), I was honored to help them sell their home and continue a relationship built on trust, loyalty, and a generation of service.

Even more exciting? We secured a **site-unseen offer**—a testament to strategic pricing, thoughtful preparation, and strong marketing that connected with the right buyer before they ever stepped through the front door.

To our incredible clients, thank you for trusting our family for more than three decades. It has truly been an honor to be part of your real estate journey, and we're so grateful to have helped you begin this next chapter.

Congratulations, and thank you for letting us be part of your story! 🥂

🏡 **JUST SOLD in Eagle Trace!** ✨Congratulations to my wonderful clients on their brand-new Veridian Homes! There's some...
07/28/2026

🏡 **JUST SOLD in Eagle Trace!** ✨

Congratulations to my wonderful clients on their brand-new Veridian Homes! There's something special about starting with a blank canvas and creating a home that's perfectly tailored to your lifestyle.

Building new construction is an exciting journey—from selecting the perfect homesite and floor plan to choosing finishes and watching it all come to life. I'm so grateful I had the opportunity to help guide them through the process and make their vision a reality.

Thank you for trusting me once again with one of life's biggest milestones. Wishing you many years of happiness in your beautiful new home! 🥂

Thinking about building? I'd love to help you navigate the process from start to finish.
💻 Learn more about us - https://buff.ly/3SnDSzb
📲 [email protected]

Address

Middleton, WI
53562

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