Social Media
Education
Madison Area Technical College
About 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 ā 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 itās never confusing and always personal.
Jonathanās dedication to his craft and community hasnāt gone unnoticed. Ranked in the top 1% of agents nationwide, he has closed over 150 transactions throughout his career. Heās 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, Jonathanās world revolves around his family. He owns a home in Sun Prairie with his wife, Denise. They share five children ā Austin, Ella, Evan, Jayda, and Jimera. When heās 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.
"Jonathan was the best! He is kind, professional, knowledgeable, and very responsive. He paid attention to key home details that I would have missed and helped me find the perfect home. Iāve bought homes before, but never had this level of high quality service.ā - Tiffany Mitchell
ā ā ā ā ā
"I am not sure what more you could ask for. They helped get amazing photos of our house for the listing, provided additional staging, and provided a deep clean before it hit the market so it was 100% show ready. They helped us sell our house fast and with an offer over asking price. One of the best experiences I have had selling a home up to this point and would absolutely recommend them to anyone.ā - Nick & Sam B from Deforest, WI
ā ā ā ā ā
"Being a single guy trying to find a place to live and be comfortable financially was not easy. Jonathan Gaspero stuck with me for months finding places, looking at places constantly staying in contact with me until I finally found the right home, let me just say this guy goes way above and beyond being a real estate agent, always taking the calls and questions!
A 5 star rating doesn't cut it with me, he is beyond that!ā - John Grugu
ā ā ā ā ā
"The Husky Homes team helped my wife and I purchase a new home in the Sun Prairie area. I absolutely LOVED every step of the process working with them. They are very tech-savvy and represent a real estate team that is dedicated to helping you purchase or sell a home in the 21st century. They were there answering questions every step of the way and always went above and beyond for us. Our closing gift was beyond thoughtful and such a perfect art piece for our new walls. Thank you Husky Homes for providing such an excellent purchasing experience for the wife and I!ā - Thomas D
ā ā ā ā ā
"We have bought and sold a couple houses in the past but NEVER had such amazing care and follow up as we did with Husky Homes all the way through! We had constant follow up the whole way! If you are looking to buy or sell your home, Husky, hands down is the best Reality Company to go with!! Jonathan was wonderful and a great person! Our home sold in 2 days!ā - Julie & Jeff G. from Belleville
ā ā ā ā ā
"Jonathan, our real estate agent, was amazing throughout our entire process! He truly made our home buying experience easy and was able to get us our dream home! The communication on all ends of their staff kept us up to date at all points of the home buying process. We could not have asked for a better team. Thank you so so much for all you did for us. We couldnāt have gotten this home without you! <3ā - Destiny G. from Janesville, WI
ā ā ā ā ā
"Had the opportunity to work with Jonathan as the lender for a VA client. Jonathan went out of his way to make difficult situations very easy to deal with. Jonathan listens to the challenge, evaluates the challenge, then acts on a solution QUICKLY...Not many better than Jonathan, excellent service provided.ā - Tony B. from Madison
ā ā ā ā ā
"Very professional team & overall great experience! When we sat down with Husky Homes to discuss selling our home, we were walked through the process from start to finish. Everything went exactly as they explained, and we were kept informed every step of the way. Showings were scheduled in a manner that was convenient for us and limited our disruption. Any time we had a question, it was answered promptly, no matter what day or time it was. We appreciate the extra effort they put into their work and highly recommend them!ā - Leah and Don D from Verona
ā ā ā ā ā
"Best team out there! Diligent, superior service and keen market insights ensures success for buyers and sellers. Wouldnāt work with anyone else!ā - Cat B. from Fitchburg
ā ā ā ā ā
"We had the pleasure of working with Jonathan! He was awesome and easy to work with! We went through many houses with him and always reassured us that we will find your perfect house, we FINALLY did.ā - Jeanne Fisherf
ā ā ā ā ā
"We worked with Jonathan and could not have been more impressed. He answered all of our MANY questions as first-time homebuyers and was always available when we needed him. We would highly recommend him for anyone without a doubt. 5 stars for work ethic, knowledge of the process, and thoughtfulness. He went above and beyond!ā - Amanda L.
ā ā ā ā ā
"First time buying a house . I didnāt know much about the process but Jonathan made it super easy for me to understand. Super friendly and Professional !!!! He isnāt one of these pushy salesman that wants you to just buy the first home u see. He was patient with us. We looked at homes for over a year. Ended up looking at 3! 3rd one was are dream house with everything we could ever ask for and more . Highly Highly Highly recommend Husky Homes !!! Staff is amazing!!! At closing one of the staff members there painted us a water painting of the front of our house very thoughtful and awesome. Thank you to Jonathan and the Staff!!!!ā - Nick W & Harmony S from Brodhead, Wisconsin
ā ā ā ā ā
"First home purchase. Great team. Jonathan was my realtor. Always had time for me. Always eager to help and answer questions, and I had a lot. Made the biggest financial decision of my life completely stress free and found me the perfect house that met my needs and budget. Would highly recommend.ā - Mark F
ā ā ā ā ā
"Thanks to Our Realtor, Mr. Gaspero, from Husky Homes I was able to close on my first ever house! He was a tremendous help, answered all of Our questions and kept Us in the loop the whole time. We could not have asked for better!ā - Corey J from Beloit, Wisconsin
ā ā ā ā ā
"Jonathan Gaspero was not only a gentleman, but very professional that went above and beyond to make sure I was taken care of during my journey to search for a place to live. He answered all my questions and would dig deeper into the root of the issue at hand. Highly recommend going to him if you want to get settled in quick with many options available to live in your area! ā - Jose R
ā ā ā ā ā
"Worked with Husky Homes to purchase my first place. They have professional realtors working for them. Overall, smooth experience with a lot of help to make sure important milestones were hit. They also found a great place for me!ā - Matt W. from Verona
ā ā ā ā ā
"I had a great experience with Jonathan. He helped me a lot to get the house that I like and always wanted. He responds fast at anytime day or night, very thorough and thoughtful. He always give me a solid advice. Any questions I ask during the tour, He makes the calls and get you the answers immediately.
I told him my criteria for a house and within a short period of time I found the options that exactly matched my criteria. He goes far and beyond to help you through the process. When I moved to the new house I had some concerns about the cleaning, Immediately, He acted on it and the issue was solved to the expectation.
I really liked my experience with Jonathan and Husky group and definitely he will be the one I will recommend to family and friends. Thank you Jonathan.ā - Ahmed H from Fitchburg, WI
ā ā ā ā ā
"I was very happy with everyone who helped make our family dream come true. Our realtor is indeed the best of all. He works side by side with us, he was always on time, respectful, kind, professional, awesome etc. I really enjoyed working with him. He even gave us a gift to put in our new home Jonathan, you are the best!!!ā - Elizabeth from Beloit
ā ā ā ā ā
"Buying our first home was such a unique experience, I can't imagine trying to do it with anyone else! Husky Homes was the perfect choice!ā - Chris H. from Madison, WI
ā ā ā ā ā
"We weāre treated as though we where buying a mansion but only buying a common Condominium. We highly recommend this realtor. Oh did I mention the amazing gift they sent us afterwards. Incredible.ā - Dave & Lori D from Deerfield, WI
ā ā ā ā ā
"I am very pleased with my experience and am a repeat customer.ā - Kathryn R and Jason C from Middleton, WI
ā ā ā ā ā
"I want to say once again how much I appreciate all of you for the great work you did for us. Our situation is unique, and all of you went above and beyond to meet all of our needs and exceeded all of our expectations! A huge THANK YOU!!!!ā - Susan B. - Madison
ā ā ā ā ā
"INSERT TESTIMONIAL IN BETWEEN CODING HERE
ā ā ā ā ā
"Husky Homes Madison, Keller Williams Real Estate Team went above beyond for us. They not only helped us sell our home in a timely manner but also found us a beautiful home. We recommend this team for your next home buying/selling experience.ā - Dawn T from Lodi, WI
That healthcare background shaped how Jonathan approaches his clients today ā 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 itās never confusing and always personal.
Jonathanās dedication to his craft and community hasnāt gone unnoticed. Ranked in the top 1% of agents nationwide, he has closed over 150 transactions throughout his career. Heās 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, Jonathanās world revolves around his family. He owns a home in Sun Prairie with his wife, Denise. They share five children ā Austin, Ella, Evan, Jayda, and Jimera. When heās 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.
Client Testimonials
Scroll down for more
ā ā ā ā ā"Jonathan was the best! He is kind, professional, knowledgeable, and very responsive. He paid attention to key home details that I would have missed and helped me find the perfect home. Iāve bought homes before, but never had this level of high quality service.ā - Tiffany Mitchell
ā ā ā ā ā
"I am not sure what more you could ask for. They helped get amazing photos of our house for the listing, provided additional staging, and provided a deep clean before it hit the market so it was 100% show ready. They helped us sell our house fast and with an offer over asking price. One of the best experiences I have had selling a home up to this point and would absolutely recommend them to anyone.ā - Nick & Sam B from Deforest, WI
ā ā ā ā ā
"Being a single guy trying to find a place to live and be comfortable financially was not easy. Jonathan Gaspero stuck with me for months finding places, looking at places constantly staying in contact with me until I finally found the right home, let me just say this guy goes way above and beyond being a real estate agent, always taking the calls and questions!
A 5 star rating doesn't cut it with me, he is beyond that!ā - John Grugu
ā ā ā ā ā
"The Husky Homes team helped my wife and I purchase a new home in the Sun Prairie area. I absolutely LOVED every step of the process working with them. They are very tech-savvy and represent a real estate team that is dedicated to helping you purchase or sell a home in the 21st century. They were there answering questions every step of the way and always went above and beyond for us. Our closing gift was beyond thoughtful and such a perfect art piece for our new walls. Thank you Husky Homes for providing such an excellent purchasing experience for the wife and I!ā - Thomas D
ā ā ā ā ā
"We have bought and sold a couple houses in the past but NEVER had such amazing care and follow up as we did with Husky Homes all the way through! We had constant follow up the whole way! If you are looking to buy or sell your home, Husky, hands down is the best Reality Company to go with!! Jonathan was wonderful and a great person! Our home sold in 2 days!ā - Julie & Jeff G. from Belleville
ā ā ā ā ā
"Jonathan, our real estate agent, was amazing throughout our entire process! He truly made our home buying experience easy and was able to get us our dream home! The communication on all ends of their staff kept us up to date at all points of the home buying process. We could not have asked for a better team. Thank you so so much for all you did for us. We couldnāt have gotten this home without you! <3ā - Destiny G. from Janesville, WI
ā ā ā ā ā
"Had the opportunity to work with Jonathan as the lender for a VA client. Jonathan went out of his way to make difficult situations very easy to deal with. Jonathan listens to the challenge, evaluates the challenge, then acts on a solution QUICKLY...Not many better than Jonathan, excellent service provided.ā - Tony B. from Madison
ā ā ā ā ā
"Very professional team & overall great experience! When we sat down with Husky Homes to discuss selling our home, we were walked through the process from start to finish. Everything went exactly as they explained, and we were kept informed every step of the way. Showings were scheduled in a manner that was convenient for us and limited our disruption. Any time we had a question, it was answered promptly, no matter what day or time it was. We appreciate the extra effort they put into their work and highly recommend them!ā - Leah and Don D from Verona
ā ā ā ā ā
"Best team out there! Diligent, superior service and keen market insights ensures success for buyers and sellers. Wouldnāt work with anyone else!ā - Cat B. from Fitchburg
ā ā ā ā ā
"We had the pleasure of working with Jonathan! He was awesome and easy to work with! We went through many houses with him and always reassured us that we will find your perfect house, we FINALLY did.ā - Jeanne Fisherf
ā ā ā ā ā
"We worked with Jonathan and could not have been more impressed. He answered all of our MANY questions as first-time homebuyers and was always available when we needed him. We would highly recommend him for anyone without a doubt. 5 stars for work ethic, knowledge of the process, and thoughtfulness. He went above and beyond!ā - Amanda L.
ā ā ā ā ā
"First time buying a house . I didnāt know much about the process but Jonathan made it super easy for me to understand. Super friendly and Professional !!!! He isnāt one of these pushy salesman that wants you to just buy the first home u see. He was patient with us. We looked at homes for over a year. Ended up looking at 3! 3rd one was are dream house with everything we could ever ask for and more . Highly Highly Highly recommend Husky Homes !!! Staff is amazing!!! At closing one of the staff members there painted us a water painting of the front of our house very thoughtful and awesome. Thank you to Jonathan and the Staff!!!!ā - Nick W & Harmony S from Brodhead, Wisconsin
ā ā ā ā ā
"First home purchase. Great team. Jonathan was my realtor. Always had time for me. Always eager to help and answer questions, and I had a lot. Made the biggest financial decision of my life completely stress free and found me the perfect house that met my needs and budget. Would highly recommend.ā - Mark F
ā ā ā ā ā
"Thanks to Our Realtor, Mr. Gaspero, from Husky Homes I was able to close on my first ever house! He was a tremendous help, answered all of Our questions and kept Us in the loop the whole time. We could not have asked for better!ā - Corey J from Beloit, Wisconsin
ā ā ā ā ā
"Jonathan Gaspero was not only a gentleman, but very professional that went above and beyond to make sure I was taken care of during my journey to search for a place to live. He answered all my questions and would dig deeper into the root of the issue at hand. Highly recommend going to him if you want to get settled in quick with many options available to live in your area! ā - Jose R
ā ā ā ā ā
"Worked with Husky Homes to purchase my first place. They have professional realtors working for them. Overall, smooth experience with a lot of help to make sure important milestones were hit. They also found a great place for me!ā - Matt W. from Verona
ā ā ā ā ā
"I had a great experience with Jonathan. He helped me a lot to get the house that I like and always wanted. He responds fast at anytime day or night, very thorough and thoughtful. He always give me a solid advice. Any questions I ask during the tour, He makes the calls and get you the answers immediately.
I told him my criteria for a house and within a short period of time I found the options that exactly matched my criteria. He goes far and beyond to help you through the process. When I moved to the new house I had some concerns about the cleaning, Immediately, He acted on it and the issue was solved to the expectation.
I really liked my experience with Jonathan and Husky group and definitely he will be the one I will recommend to family and friends. Thank you Jonathan.ā - Ahmed H from Fitchburg, WI
ā ā ā ā ā
"I was very happy with everyone who helped make our family dream come true. Our realtor is indeed the best of all. He works side by side with us, he was always on time, respectful, kind, professional, awesome etc. I really enjoyed working with him. He even gave us a gift to put in our new home Jonathan, you are the best!!!ā - Elizabeth from Beloit
ā ā ā ā ā
"Buying our first home was such a unique experience, I can't imagine trying to do it with anyone else! Husky Homes was the perfect choice!ā - Chris H. from Madison, WI
ā ā ā ā ā
"We weāre treated as though we where buying a mansion but only buying a common Condominium. We highly recommend this realtor. Oh did I mention the amazing gift they sent us afterwards. Incredible.ā - Dave & Lori D from Deerfield, WI
ā ā ā ā ā
"I am very pleased with my experience and am a repeat customer.ā - Kathryn R and Jason C from Middleton, WI
ā ā ā ā ā
"I want to say once again how much I appreciate all of you for the great work you did for us. Our situation is unique, and all of you went above and beyond to meet all of our needs and exceeded all of our expectations! A huge THANK YOU!!!!ā - Susan B. - Madison
ā ā ā ā ā
"INSERT TESTIMONIAL IN BETWEEN CODING HERE
ā ā ā ā ā
"Husky Homes Madison, Keller Williams Real Estate Team went above beyond for us. They not only helped us sell our home in a timely manner but also found us a beautiful home. We recommend this team for your next home buying/selling experience.ā - Dawn T from Lodi, WI
Jonathan Gasperoās Listings
1/52
1/43
1/30
1/11
$55,000
- Unavailable
- Bedrooms
- Unavailable
- Bathrooms
- Unavailable
- Square Feet
- 0.78
- Acres
Jonathan Gasperoās Transactions
Past Sales
