Jonathan Gaspero

Madison WI

Compass Real Estate Wisconsin

142 Closed Sales

$44M Total Value

$179.9K - $850K Price Range

$309.5K Average Price

Prior 5 years

About Jonathan

Jonathan is a Madison area native. After graduating from Sun Prairie High School, he studied at Madison Area Technical College and was on the Phi Theta Kappa Honors Society. He studied healthcare administration and management while working at Meriter Unity Point Hospital for almost a decade.
He found a passion for real estate quickly and found joy in assisting others to build wealth with the joy of home ownership.

Jonathan loves making the real estate process easy to understand while specializing in assisting first-time homebuyers, sellers, and Veterans. He is a receipient of the RASCW 40 under 40 Award Class of 2026, an ambassador for the Own It Program, President of the BNREP, and received the 2022 Emerging Agent of the Year Award.

He owns a home in Sun Prairie with his wife, Denise. They share 5 amazing children. Austin, Ella, Evan, Jayda, and Jimera. When he is not attending his children's hockey or volleyball games, he enjoys cooking gourmet meals and reading, while drinking a nice glass of bourbon.

Home Types: House, MultiFamily, Townhouse, Manufactured, Condo, Lot/Land

Years of Experience: 5

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	12
Total Value	$4,619,000
Average Sale Price	$384,917
Price Range	$176K - $502K

Buyer Deals
Total Deals	39
Total Value	$14,314,180
Average Sale Price	$367,030
Price Range	$125K - $850K

1 Year View by Quarter

Seller Deals
Total Deals	22
Total Value	$7,443,500
Average Sale Price	$338,341
Price Range	$165K - $502K

Buyer Deals
Total Deals	63
Total Value	$21,870,780
Average Sale Price	$347,155
Price Range	$105K - $850K

2 Year View by Quarter

Seller Deals
Total Deals	34
Total Value	$10,440,262
Average Sale Price	$307,067
Price Range	$11K - $502K

Buyer Deals
Total Deals	108
Total Value	$33,510,090
Average Sale Price	$310,279
Price Range	$70K - $850K

5 Year View

Neighborhoods Jonathan is Experienced In

Jonathan's Active Listings

$445,000
- 3 Beds
- 2.5 Baths
- 1,566 Sq Ft
705 Reflection Dr

Verona, WI
Welcome to 705 Reflection Drive, where updated comfort meets convenience in lovely Verona! Inside, stylish new laminate flooring (2024) flows through the living room, while updated ceiling fans (2021) in every room keep things breezy year-round. The primary bedroom features an upgraded closet light, adding brightness to your mornings. The almost-finished basement offers endless

Jonathan Gaspero Compass Real Estate Wisconsin

$380,000
- 2 Beds
- 2.5 Baths
- 2,233 Sq Ft
631 Cardinal Way

Sun Prairie, WI
Step into this quality-built end unit ranch condo blending modern updates with timeless charm. Featuring 2 bedrooms, 2 and a half baths, and a sun-drenched 4-season sunroom, this home is designed for comfort. The great room impresses with cathedral ceilings, solar tubes that brighten the living space and kitchen, and a cozy fireplace, while the private primary suite offers a peaceful retreat.

Jonathan Gaspero Compass Real Estate Wisconsin

$60,000
- Land
- 0.78 Acre
- $76,923 per Acre
100 Honeycrisp Dr

Beaver Dam, WI
Build your dream home in the last available lot in the Apple Valley subdivision! Wait until you see the incredible view that you simply must experience. Enjoy the convenience of city water and sewer while savoring the rural feel, giving you the best of both worlds. With utilities already in place, you can bring your future plans and building designs. With this being the last available lot in the

Jonathan Gaspero Compass Real Estate Wisconsin

$550,000
- 3 Beds
- 3 Baths
- 3,312 Sq Ft
9021 County Road Kp

Cross Plains, WI
Welcome to your dream home, where modern upgrades meet everyday comfort! Nestled on a spacious .66-acre lot, there’s room to relax, entertain, and let kids or pets roam. Outdoors, craft your ideal backyard oasis. Inside, enjoy conveniences like a central vacuum and invisible fence. The kitchen, updated in 2019, boasts soft-close cabinets and 2018 appliances. Bathrooms have been stylishly

Jonathan Gaspero Compass Real Estate Wisconsin

Recently Sold

$495,000

Sold May 1, 2026
- 3 Beds
- 2 Baths
- 2,551 Sq Ft
1609 Oakridge Way

Stoughton, WI
- $194/SF
- 20 Days On Market
- Current Est. Value $496K
Jonathan Gaspero Compass Real Estate Wisconsin

$176,000

Sold Mar 30, 2026
- 2 Beds
- 1 Bath
- 665 Sq Ft
5325 Garden View Ct

Unit 101

Madison, WI
- 1% Above List
- $265/SF
- 5 Days On Market
- Current Est. Value $171K
Jonathan Gaspero Compass Real Estate Wisconsin

$360,000

Sold Mar 24, 2026
- 4 Beds
- 1.5 Baths
- 1,928 Sq Ft
W2069 Elk Ct

Montello, WI
- 20% Below List
- $187/SF
- 151 Days On Market
- Current Est. Value $366K
Jonathan Gaspero Compass Real Estate Wisconsin

$465,000

Sold Feb 13, 2026
- 4 Beds
- 4 Baths
- 2,971 Sq Ft
1162 Crossing Ridge Trail

Sun Prairie, WI
- 1% Above List
- $157/SF
- 40 Days On Market
- Current Est. Value $469K
Jonathan Gaspero Compass Real Estate Wisconsin

$415,000

Sold Jan 20, 2026
- 3 Beds
- 3.5 Baths
- 2,065 Sq Ft
502 Traveler Ln

Madison, WI
- 8% Below List
- $201/SF
- 95 Days On Market
- Current Est. Value $428K
Jonathan Gaspero Compass Real Estate Wisconsin

$489,000

Sold Dec 12, 2025
- 4 Beds
- 2 Baths
- 2,144 Sq Ft
N53W35963 W Lake Dr

Oconomowoc, WI
- 1% Below List
- $228/SF
- 28 Days On Market
- Current Est. Value $514K
Jonathan Gaspero Compass Real Estate Wisconsin

$405,000

Sold Nov 14, 2025
- 3 Beds
- 2 Baths
- 1,190 Sq Ft
4310 Hegg Ave

Madison, WI
- 8% Above List
- $340/SF
- 6 Days On Market
- Current Est. Value $406K
Jonathan Gaspero Compass Real Estate Wisconsin

$212,000

Sold Oct 15, 2025
- 4 Beds
- 1 Bath
- 1,689 Sq Ft
318 Park St

Theresa, WI
- 1% Above List
- $126/SF
- 15 Days On Market
- Current Est. Value $229K
Jonathan Gaspero Compass Real Estate Wisconsin

$420,000

Sold Aug 21, 2025
- 3 Beds
- 2 Baths
- 1,789 Sq Ft
656 Wileman Dr

Edgerton, WI
- 1% Below List
- $235/SF
- 10 Days On Market
Jonathan Gaspero Compass Real Estate Wisconsin

Other Experience

First Time Home Buyers, Investments, Luxury Homes, Military Families, New Construction, Veteran Programs

Agent License: Wisconsin #9312794

Jonathan Gaspero

(608) 640-3845

Homes for Sale by City

Jonathan Gaspero

About Jonathan

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Jonathan is Experienced In

Jonathan's Listings and Deals

Jonathan's Active Listings

Recently Sold

Other Experience