Section Image

Jonathan Gaspero

Compass Real Estate Wisconsin
148 Closed Sales
$46.2M Total Value
$183K - $850K Price Range
$312.3K Average Price
Prior 5 years

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 — 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.
Home Types: House, Multifamily, Condo, Mobile Homes, Townhouse, Lot/Land
Years of Experience: 5
Education: Madison College

Transaction History

Seller Deals

Total Deals 12
Total Value $4,877,000
Average Sale Price $406,417
Price Range $176K - $518K

Buyer Deals

Total Deals 32
Total Value $12,062,750
Average Sale Price $376,961
Price Range $125K - $850K

Production Over Time

1 Year View by Quarter

Seller Deals

Total Deals 22
Total Value $7,796,500
Average Sale Price $354,386
Price Range $176K - $518K

Buyer Deals

Total Deals 61
Total Value $21,582,050
Average Sale Price $353,804
Price Range $125K - $850K

Production Over Time

2 Year View by Quarter

Seller Deals

Total Deals 35
Total Value $10,958,262
Average Sale Price $313,093
Price Range $11K - $518K

Buyer Deals

Total Deals 113
Total Value $35,264,160
Average Sale Price $312,072
Price Range $70K - $850K

Production Over Time

5 Year View

Jonathan's Listings and Deals

Other Experience

First Time Homebuyers, Investments, Military Families, Veteran's Programs, Senior Communities, Short Sales, Luxury Homes, New Construction, Distressed Properties
Agent License: Wisconsin #9312794
Agent Photo

Jonathan Gaspero