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Jonathan Gaspero

Compass Real Estate Wisconsin
145 Closed Sales
$45.2M Total Value
$183K - $850K Price Range
$311.7K 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, Townhouse, Manufactured, Condo, 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 29
Total Value $11,035,680
Average Sale Price $380,541
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 58
Total Value $20,554,980
Average Sale Price $354,396
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 110
Total Value $34,237,090
Average Sale Price $311,246
Price Range $70K - $850K

Production Over Time

5 Year View

Jonathan's Listings and Deals

Other Experience

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

Jonathan Gaspero