Trusted by Businesses Across Wisconsin
Counties Served Statewide
Residential, Multifamily, Short-Term Rental & Commercial Expertise
Chris Olson brings a data-driven, client-focused approach to residential, multifamily, short-term rental, and commercial real estate throughout Southern Wisconsin. With a strong foundation in accounting and investment analysis, Chris helps clients understand the full financial picture of each opportunity – from operational performance to long-term asset value. He specializes in acquisitions, management strategy, and value-add potential across multiple asset types, supporting both new and experienced investors.
Analytical Insight, Real World Experience
With a Bachelor’s degree in Accounting and an MBA from Edgewood College, Chris combines academic rigor with hands-on industry experience. Before joining brokerage, he oversaw administrative operations for more than 2,700 residential units across Southern Wisconsin, gaining deep insight into property performance, tenant relations, and operational efficiencies. His clients value his ability to translate complex financial data into clear, actionable guidance that supports confident decision-making.
Local Roots, Personal Passions
Born and raised in Madison, Chris has an intimate understanding of Dane County and the surrounding markets. He is passionate about helping clients build stable, long-term real estate portfolios that support community growth and neighborhood vitality. Outside of work, Chris enjoys gaming, traveling, and spending time with his dog, Lily.
Licensed & Connected
A recognized real estate professional with statewide reach
Your Licensed Real Estate Professional in Wisconsin
Chris Olson is a licensed Wisconsin Commercial Real Estate Sales Advisor, bringing certified expertise and local knowledge to every transaction. Based in Dane County, Derek is deeply connected to the communities he serves and is actively engaged across Southern Wisconsin.
Wisconsin Real Estate Broker
License # 114572 – 94
Licensed Across the State
Licensed to serve clients in Dane County and throughout Wisconsin.
Available Properties
Lovejoy Manor & Event Center
10,000 SF Retail Building • 220 Saint Lawrence Ave, Janesville, WI 53545
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Price: $1,800,000
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Size: 10,000 SF
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Price per SF: $180
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Lot Size: O2 – Mixed use
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Stories: 3
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Year Built / Renovated: 1880 / 2020
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Main Building: 7,000 SF
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Event Center: 3,000 SF
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Historic Status: National Register of Historic Places
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Lot Size: National Register of Historic Places
A.D. German Warehouse
Historic Frank Lloyd Wright Building • 300 S Church St, Richland Center, WI 53581
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Space: Min. 500 SF, Max. 3,500 SF
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Size Available: 10,000 SF
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Gross Leasable Area: 16,000 SF
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Rental Rate: $15.00 /SF/YR
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Year Built / Renovated: 1917 / 2024
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Term: Negotiable
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Stories: 4
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Total Suites: 20
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Parking: 12 spaces
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Rent Type: Triple Net (NNN)
Experience in Numbers
MBA Edgewood University
Wisconsin Real Estate License Granted
Proudly Serving All Counties Across Wisconsin
Connect with Chris
Contact Chris Olson Today