Wisconsin House Hack

Whitewater, WI · Member since 2025 · 6 posts · 18 votes

I am looking to buy a 2-4 unit property in Wisconsin. I have been doing broad market research in the Milwaukee and Madison area. I am looking to start off with a house hack, then eventually move more into BRRRR. I have been looking at median home prices and median rent prices for Racine, Sun Prairie, and Watertown, and none of them seem like they will have positive cash flow. Is there something I'm missing here?

If you have recommendations for other cities near the Milwaukee and Madison area that would cash flow, I would greatly appreciate the help.

Thanks, Evan Rekowski

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Peter Falk

Real Estate Broker · Madison, WI · Member since 2015 · 118 posts · 60 votes

9mo

I agree with using sold price data and think you will see the sold terms are generally a little better than the asking terms and get a feel for what the general range is for the market. However, in Madison, WI, I will see prices paid that won't cash flow after paying some assumed mortgage payment to acquire the property and even using the listing agent's predictions for higher market rents, so understand you wondering what am I missing or what are these buyers thinking, knowing sellers want the best terms they can get.

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Doug Anderson
Real Estate Broker · Member since 2020 · 12 posts · 6 votes
9mo
@Evan Rekowski have you looked in kenosha or Janesville? We have found a few this year that cash flowed in kenosha.
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Wale LawalBusiness Member
Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
9mo
@Evan Rekowski
I think you should check out some of the smaller areas a bit further away, like Janesville, Beloit, Sheboygan, Fond du Lac or Oshkosh. Also I think rents there are usually steadier and prices have not risen. If you look at similar places and compare rents to prices in those spots, you will often find properties that make money even after you account for everyday costs and property management.
Good luck!
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Charles ClarkBusiness Member
Real Estate Broker · Milwaukee, WI · Member since 2020 · 306 posts · 209 votes
9mo
@Evan Rekowski
Great question—this is a common issue when looking at median prices and rents. Medians often hide deal-level opportunities, especially for small multifamily and house hacks. Cash flow can still work with the right purchase price, value-add strategy, or owner-occupied financing.

I'd recommend looking beyond medians and focusing on specific submarkets, older duplex/triplex inventory, and off-market or distressed deals. Areas slightly outside the core metros can also perform better with BRRRR strategies.

Happy to share a few nearby markets and what typically makes deals pencil there if helpful.
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Drew SygitBusiness Member
Property Manager · Royal Oak, MI · Member since 2012 · 12k+ posts · 9k+ votes
9mo
Quote from @Evan Rekowski:

I am looking to buy a 2-4 unit property in Wisconsin. I have been doing broad market research in the Milwaukee and Madison area. I am looking to start off with a house hack, then eventually move more into BRRRR. I have been looking at median home prices and median rent prices for Racine, Sun Prairie, and Watertown, and none of them seem like they will have positive cash flow. Is there something I'm missing here?
If you have recommendations for other cities near the Milwaukee and Madison area that would cash flow, I would greatly appreciate the help.

Thanks, Evan Rekowski

Common newbie mistake!
Why do you think you have to offer asking price?
Work the numbers backwards to determine offer price and make those offer amounts:)
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Daniel L.
Rental Property Investor · Toronto, ON · Member since 2026 · 6 posts · 0 votes
9mo
Agree with @Drew Sygit Asking price is the ask. How long has it been on the market? Have a look at the comps in the area and formulate a price that works for you. The seller could be motivated to sell. Do you have your financing in order? Will a quick close help entice the seller to take a lower price? All questions you could ask. Good luck!
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Peter Falk
Real Estate Broker · Madison, WI · Member since 2015 · 118 posts · 60 votes
9mo
I agree with using sold price data and think you will see the sold terms are generally a little better than the asking terms and get a feel for what the general range is for the market. However, in Madison, WI, I will see prices paid that won't cash flow after paying some assumed mortgage payment to acquire the property and even using the listing agent's predictions for higher market rents, so understand you wondering what am I missing or what are these buyers thinking, knowing sellers want the best terms they can get.
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