Lessing Real Estate
Nearby law practices
Greenway Boulevard
Greenway Boulevard
Terrace Avenue
Excelsior Drive, Madison
Excelsior Drive, Madison
Madison 53562
N Oakland Avenue, Milwaukee
Nearby finance companies
Odana Road, Madison
N High Point Road
Greenway Boulevard
Greenway Boulevard
Greenway Boulevard
PO Box 5191, Madison
Nearby accountants
Greenway Boulevard
John Q Hammons Drive
Greenway Boulevard
Greenway Boulevard
John Q Hammons Drive, Madison
John Q Hammons Drive, Madison
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!
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]
10/09/2026
🏡 **UNDER CONTRACT | 10 APPLE HILL CIRCLE!** 🎉
Another beautiful home in Wexford Village is officially under contract! I'm thrilled for my sellers as they move one step closer to closing day! From professional photography and strategic marketing to getting the right buyers through the door, every detail matters.
Thinking about selling? Let's talk about how we can position your home to stand out in today's market.
💻 www.lessingrealestate.com
📲 [email protected]
10/05/2026
🎉 **JUST SOLD | 8860 Iroquois Circle, Baraboo**
Big congratulations to my buyers on closing on their beautiful new home in Baraboo! 🏡🔑
This one was extra special because these buyers came to me as a referral from a past client. There’s truly no better compliment than having past clients trust me enough to send their friends and family my way. ❤️
A big thank you to Julie Klemm & Kristine Bunbury Terry, Bunbury Realtors, for the great communication and being so easy to work with throughout the transaction — and for letting me use their photo!
And a huge shout-out to Patrick Averill at Thompson Kane & Company, Madison - NMLS 898428 for the incredibly fast turnaround on the lending side and helping us get this one to the closing table!
Thinking about buying? I’d love to help you make your next move. ⤵️
💻 Learn more — https://buff.ly/3SnDSzb
📲 [email protected]
09/17/2026
🎉 JUST SOLD in Bentley Green! 🎉
Another one closed—and this one is extra special because we represented both the buyers + sellers!
We’ve now sold 106 condos in this development… yes, you read that right—there are only 96 total units. That means we’ve not only helped sell out the project, but we’ve also successfully handled multiple resales along the way.
That level of experience matters. From initial releases to resales, we know every floor plan, every finish, and how to position each unit to get the best results.
Curious what your condo could sell for? Let’s connect ⤵️
📩 [email protected]
💻 https://buff.ly/3SnDSzb
09/15/2026
✨ JUST LISTED + OPEN HOUSE | 10 Apple Hill Circle, Madison ✨
🏡 Beautifully maintained raised ranch home tucked on a quiet cul-de-sac backing to Wexford Village HOA green space & steps from Wexford Park! The inviting living room features a vaulted ceiling, cozy wood-burning fireplace. The kitchen offers a breakfast bar, stainless steel appliances beautiful birch hardwood flooring, white cabinetry & adjacent dinette. The family room features a gas stove and french door that leads to the maintenance free deck. Primary suite includes a walk-in closet w/org. & en-suite bath. Walk-out & finished lower level w/new carpet offers a rec room w/wet bar & wood burning fireplace, den & full bath, with plenty of unfinished space. Roof - 2026, A/C - 2025, water heater - 2026, Microwave - 2023, LL carpet - 2026. 2-car attached garage.
Ready to see it for yourself? Reach out to schedule a private showing - [email protected]
Learn more - https://buff.ly/z0ATDFP
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Middleton, WI
53562
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