Leave a Message

By providing your contact information to Husky Homes, your personal information will be processed in accordance with Husky Homes's Privacy Policy. By checking the box(es) below, you consent to receive communications regarding your real estate inquiries and related marketing and promotional updates in the manner selected by you. For SMS text messages, message frequency varies. Message and data rates may apply. You may opt out of receiving further communications from Husky Homes at any time. To opt out of receiving SMS text messages, reply STOP to unsubscribe.

Thank you for your message. We will be in touch with you shortly.

Explore Our Properties

About Jonathan Gaspero

Jonathan

Agent Details

Meet Jonathan

Jonathan is a Dane County native with deep roots in the community he serves. After graduating from Sun Prairie High School, he attended Madison College, where he was 4.0 student and annually a in the Phi Theta Kappa Honors Society. He studied healthcare administration and management. He spent nearly a decade working at Meriter UnityPoint Hospital before discovering his true passion: real estate.

That healthcare background shaped how Jonathan approaches his clients today — with patience, clear communication, and genuine care. He found that real estate gave him something special: the chance to help people build wealth and find joy through homeownership. He specializes in guiding first-time homebuyers, sellers, and Veterans through the process, making sure it’s never confusing and always personal.

Jonathan’s dedication to his craft and community hasn’t gone unnoticed. Ranked in the top 1% of agents nationwide, he has closed over 150 transactions throughout his career. He’s also a recipient of the RASCW 40 Under 40 Award (Class of 2026), an ambassador for the Own It Program, President of the BNREP, and a recipient of the 2022 Emerging Agent of the Year Award.

Outside of work, Jonathan’s world revolves around his family. He owns a home in Sun Prairie with his wife, Denise. They share five children — Austin, Ella, Evan, Jayda, and Jimera. When he’s not cheering them on at hockey or volleyball games, you can find him cooking up a gourmet meal, reading a good book, or enjoying a nice glass of bourbon.

Words From Happy Clients

See why our clients love working with us.
Curtesia R from Madison, WI

Curtesia R from Madison, WI

I worked with Jonathan and he was there every step of the way providing great communication, timely updates and expert knowledge. As a first time homebuyer, I truly enjoyed working with Jonathan and the team and would recommend...
Read More
Shannon L from Edgerton

Shannon L from Edgerton

We will continue to use Husky Homes and Jonathan.
Read More
Greg B. from Madison, WI

Greg B. from Madison, WI

Jonathan Gaspero is an absolute rockstar. He was able to help my family find an amazing house. Jonathan had excellent communication, supported and understood our changing needs, and made us feel comfortable through the entire p...
Read More
Brendt G.

Brendt G.

Jonathan Gaspero did an exceptional job during our first time home buying process. His positive attitude, personable communication skills, and knowledge of Madison's competitive market gave my family the edge we needed to put u...
Read More
Sheri W.

Sheri W.

I had the opportunity to work with Jonathan Gaspero on a recent transaction where his client purchased my listing. It was a particularly challenging deal that nearly fell apart, but thanks to Jonathan’s professionalism, persist...
Read More
Virginia W.

Virginia W.

We worked with Jonathan, and he was outstanding! He was always available to us, he would get back to us quickly with answers to questions, was quick to set up showings, and was helpful with information on the houses we walked t...
Read More
Kevin L.

Kevin L.

I recently had the pleasure of partnering with Jonathan Gaspero on a couple of transactions, and it quickly became clear that his genuine and caring nature is a true asset to his clients. His strong communication skills and unw...
Read More
Aji B

Aji B

Jonathan is a great realtor, who has helped me throughout this journey in purchasing a home. He has gone above and beyond in helping me work with the family selling their home. I appreciate all he’s done for my family and I in ...
Read More
Megan P from WI

Megan P from WI

Jonathan and Kerri were great to work with! Were able to answer our questions each step of the process.
Read More

Featured Listings

For Sale
For Lease

Find Your Next Dream Home

Browse Homes

Let’s Find Your Perfect Home Together

We pride ourselves in providing personalized solutions that bring our clients closer to their dream properties and enhance their long-term wealth. Contact us today to discuss all your real estate needs!

Follow Us on Instagram