Lessing Real Estate

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Middleton, WI
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 powerhouse. 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!

11/05/2026

🏡✨ **JUST SOLD | 2233 Luann Lane #5 | Christopher Terrace Condos** 🥂

Another condo SOLD, and another exciting chapter begins for my sellers! 🎉

Condo sales come with their own unique considerations, and having the right experience and strategy matters! From understanding the condo market and positioning the property competitively to professional marketing, negotiations, and navigating the details through closing, my goal is always to make the process as seamless and successful as possible.

With **over 20% of my business dedicated to condominium sales**, I know how important it is to understand the nuances of condo ownership and what today's buyers are looking for.

A huge congratulations to my sellers! Thank you for trusting me with the sale of your condo. I'm so grateful to have been part of your journey! ❤️

**Thinking about selling your condo?** Whether you're ready to make a move or just curious about its value, I'd love to put my condo experience to work for you!

📍 **Lessing Real Estate | Compass Wisconsin**
🌐 www.lessingrealestate.com
📧 [email protected]

11/03/2026

🎉 **ACCEPTED OFFER in Sauk Creek!** 🏡✨

Another exciting purchase for a wonderful client who continues to put their trust in me for all of their real estate needs!

One of the most rewarding parts of my business is building long-term relationships with clients who turn to me time and time again. Whether it's buying, selling, or investing, I'm so grateful to be their trusted real estate agent year after year!

Thinking about buying, selling, or investing? I'd love to help you with your next move!

📍 **Lessing Real Estate | Compass Wisconsin**
🌐 www.lessingrealestate.com
📩 [email protected] or DM me to connect!

11/02/2026

🏡✨ **JUST SOLD | 10 Apple Hill!** 🥂

**Under contract within just days of hitting the market!** 🎉

A great result for my sellers and another reminder that the right strategy makes all the difference!

From thoughtful preparation and professional photography to strategic pricing and marketing, we worked to make sure this beautiful home made a strong first impression. And it paid off with an accepted offer just days after going live!

Selling a home isn't just about getting it on the market. It's about positioning it to stand out, attract the right buyers, and achieve a successful outcome.

A huge congratulations to my sellers! I'm so grateful you trusted me to guide you through the process and help you move on to your next chapter. ❤️

**Thinking about selling?** Let's talk about how we can position your home for success!

📍 **Lessing Real Estate | Compass Wisconsin**
🌐 www.lessingrealestate.com
📧 [email protected]

11/01/2026

🏡 **ANOTHER ACCEPTED OFFER IN WESTWIND!** 🎉

Another lot is officially under contract in Westwind! We're excited to see another beautiful build come to fruition! We're over 1/3rd sold through within phase 2 so reach out if you're considering building before your favorite lot is gone!

✨ Bring your own builder
✨ Build on your timeline
✨ City water & sewer
✨ Convenient location near shopping, dining, parks & more!

💻️ westwindmadison.com
📲 [email protected]

10/23/2026

🎉 Congrats to our Sellers + Buyers! Lot 12 in Westwind is officially sold and we can't wait to see wait this beautiful home!
〰️〰️〰️〰️
If you've thought about building, we have 2 lots left in this phase and just opened 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]

10/21/2026

🏡 **ACCEPTED OFFER | 62 Settler Hill Circle!** 🥂

Another beautiful condo is officially under contract!

Getting to an accepted offer isn't always about waiting for the right buyer. It's about having the right strategy.

From positioning and pricing to marketing and adjusting to buyer feedback, every decision matters. We worked closely with our sellers to navigate the market, make strategic adjustments, and ultimately get this beautiful property under contract!

A huge congratulations to our sellers! 🎉

**In today's market, strategy matters more than ever.** If you're thinking about selling, let's talk about how we can position your home for success.

📲 www.lessingrealestate.com

10/20/2026

🏡 **ANOTHER ACCEPTED OFFER IN WESTWIND!** 🎉

Another lot is officially under contract in Westwind! We're excited to see another buyer take the next step toward building their dream home in this beautiful west Madison community!

✨ Bring your own builder
✨ Build on your timeline
✨ City water & sewer
✨ Convenient location near shopping, dining, parks & more!

Phase 2 lots are available now—reach out before your favorite is gone!

💻️ westwindmadison.com
📲 [email protected]

10/12/2026

🎉 **ACCEPTED OFFER | 2233 Luann Lane #5!** 🏡

Another one officially under contract! Congratulations to my sellers on their accepted offer at 2233 Luann Lane #5! 🥂

Strategic pricing, professional marketing, and a little patience helped us get this one across the finish line. So excited for my sellers as we move one step closer to closing!

Thinking about selling? Let's talk about how to position your home for success in today's market.

📲 [email protected]
💻 www.LessingRealEstate.com

10/10/2026

OPEN HOUSE - 1802 Autumn Hill Drive, Verona, WI
📅 Saturday, 10/10 from 12:30 - 2pm

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.

Now priced at $850,000!

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://buff.ly/gmKbAKQ

10/09/2026

🏡 **NEW PRICE + OPEN HOUSE | 62 SETTLER HILL!**

Sophisticated design meets effortless living in Madison's sought-after Blackhawk neighborhood!

This stunning stand-alone condo offers soaring ceilings, a dramatic floor-to-ceiling stone fireplace, a beautifully updated chef's kitchen, and a thoughtfully designed floor plan with the space and flexibility you've been looking for.

✨ **PROPERTY HIGHLIGHTS:**
• Stand-alone condo in Settler Hill
• 2 spacious primary suites with en suite baths
• Private office with floor-to-ceiling custom built-ins
• Chef's kitchen with granite & quartz countertops, stainless steel appliances & abundant storage
• Sunroom filled with natural light
• Loft plus additional bedroom & full bath
• Unfinished exposed lower level ready for your vision
• 2-car attached garage

🚪 **OPEN HOUSE — COME SEE IT FOR YOURSELF!**

📅 Saturday, October 10
⏰ 12:30–2:00 PM
📍 62 Settler Hill | Madison, WI

💰 **NEW PRICE: $799,000**

All the space and sophistication of a single-family home with the convenience of condo living. And now at a NEW PRICE!

Can't make the open house? Contact us for a private showing!
💻 www.lessingrealestate.com
📲 [email protected]

Address

Middleton, WI
53562

Website

http://www.lessingrealestate.com/

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