I’m new to the BiggerPockets community and excited to be here.
I currently live in Massachusetts but own a single family rental property in Madison, Wisconsin. My wife and I previously lived in the home and decided to keep it as a rental rather than sell it, largely because of our low mortgage rate. That experience has motivated us to start building a larger real estate portfolio.
I’d love to hear from investors who have experience in the Madison or Milwaukee markets. Do you view southern Wisconsin as a strong market for building a long term portfolio? How do you feel about the area’s housing prices, rental demand, job growth, population trends, and overall investment outlook over the next 5 to 10 years?
I’d also appreciate any advice you’d offer someone who is just beginning to scale beyond their first rental property.
Thanks in advance for your insights. I’m looking forward to learning from this community and contributing wherever I can.
Rental Property Investor · Member since 2026 · 56 posts · 29 votes
3mo
Hey @Gavin Nieto, happy to help pull data on trends via Tenantry. Median home values in Milwaukee are rising a bit faster at 5.2% YoY, vs 2.7% for Madison. Wisconsin (and really the Midwest as a whole) is looking strong with a median home value of approximately $340k and a rental market that's seen a YoY increase of 7.2%, an attractive option for both investors and renters.
I’m new to the BiggerPockets community and excited to be here.
I currently live in Massachusetts but own a single family rental property in Madison, Wisconsin. My wife and I previously lived in the home and decided to keep it as a rental rather than sell it, largely because of our low mortgage rate. That experience has motivated us to start building a larger real estate portfolio.
I’d love to hear from investors who have experience in the Madison or Milwaukee markets. Do you view southern Wisconsin as a strong market for building a long term portfolio? How do you feel about the area’s housing prices, rental demand, job growth, population trends, and overall investment outlook over the next 5 to 10 years?
I’d also appreciate any advice you’d offer someone who is just beginning to scale beyond their first rental property.
Thanks in advance for your insights. I’m looking forward to learning from this community and contributing wherever I can.
– Gavin Nieto
Keeping your first rental because of a great mortgage rate was a smart move. Madison has solid long-term fundamentals, but if you're looking to scale, I'd compare it with other Midwest markets too. A lot of investors look at the Midwest markets because the lower entry prices and stronger cash flow make it easier to grow a portfolio without tying up as much capital. No matter which market you choose, the biggest advantage comes from buying solid deals and having a reliable local team that can help you scale confidently.
Rental Property Investor · Member since 2026 · 56 posts · 29 votes
3mo
Hey @Gavin Nieto, happy to help pull data on trends via Tenantry. Median home values in Milwaukee are rising a bit faster at 5.2% YoY, vs 2.7% for Madison. Wisconsin (and really the Midwest as a whole) is looking strong with a median home value of approximately $340k and a rental market that's seen a YoY increase of 7.2%, an attractive option for both investors and renters.
Property Manager · Milwaukee, WI · Member since 2024 · 162 posts · 97 votes
3mo
We manage about 500 units in Southeastern, WI (mainly the Milwaukee area). Milwaukee is consistently a top rental market in the nation, and we see demanding rents as well as steady appreciation. Feel free to message me if you'd like to chat more about the market or run through any properties!
Real Estate Broker · Madison, WI · Member since 2015 · 118 posts · 60 votes
3mo
Glad to hear your house is working out well as a rental. I'm sure your low interest rate helps with that and you have seen there aren't that many single family homes for rent in Madison given the higher home prices (and taxes based off those values). With higher interest rates (both in the market and now from getting an investment loan as it won't be owner occupied) would suggest looking at multi-family property to help cover expenses and provide some cash flow. Being remote, you can invest anywhere, but if you decide you like the familiarity of Madison, I would be happy to offer more details on what the current market is looking like to compare with other areas. I am a broker and long time landlord in Madison.
Hey Gavin, happy to add some data via Area AI: Madison's median is $440K, up 1.4% YoY, homes selling in ~41 days. Milwaukee's cheaper and appreciating faster — median $236K, up 3.0% YoY, ~40 days on market (Redfin, 3-month avg ending May 2026). Worth comparing both if cash flow matters more to you than pure appreciation — Milwaukee's lower entry point plus faster growth is a notably different profile than Madison's.
Rental Property Investor · Oconomowoc, WI · Member since 2016 · 996 posts · 431 votes
2mo
Madison and Milwaukee are both solid investments but they each have their own tradeoffs.
Mke has diverse pockets for investing, which is great but also a hazard if you aren't familiar with the neighborhoods. There's a neighborhood or location for every class of property you are seeking. However, it comes with the trade-off of higher crime in some of those neighborhoods.
Madison is a market where it gets a fair chunk of tenants from students and government-type workers. Its need for housing is definetly consistent and reliable, in the sense that there are numerous reasons to live in or around Madison. However, for long-term rentals, they are known for having the strongest pro-tenant regulations in the state at both the county and city level. These shouldn't deter you from investing there, but be aware of them on all levels so you can plan how they affect the way you operate your rentals.
That being said Mke has its own regualtions at County and city level however in general they have been considered less overtly restrictive on rental property owners.