The problems started before Virginia Jackson ever moved into her most recent North Side rental. 

She had applied for a place on Palmer Street. The landlord, embattled California-based Highgrove Holdings, accepted her application. Then they wouldn’t let her in. There was work to be done, she was told. Days passed. Then weeks. By the end of the month, Jackson needed to leave her old home or risk losing her security deposit. 

The landlord offered her another property in Old North Milwaukee. Jackson had little choice. She had nowhere else to go and worried about ending up on the street with her adult son, who has a disability from a traumatic brain injury. 

The home quickly revealed itself as a lemon. “It’s supposed to be a three-bedroom, but it’s only two because the windows didn’t open in one,” Jackson said. “My son lives in that room now, and we need to run two fans in the summer. Then, on the second day, the basement flooded. I lost a lot of stuff. The landlord and no one ever came out. I had to replace my deep freezer and the washer out of my pocket.” 

Over the past two years, Jackson has documented myriad problems. She has shoveled the snow and maintained the yard because the landlord wouldn’t. She repaired a fallen fence. When she realized the stairs had no handrails, she installed them herself so her son could safely get up and down. 

The rent: $1,395 a month. 

With utilities and other bills, Jackson says her monthly housing costs approach $2,000. After retiring as a personal care worker, the 67-year-old went back to work to help pay for it. Jackson’s property was one of dozens stripped of Highgrove by court order this year, so she has a new landlord, but she’s had enough.

“I’m in the process of looking for a place,” Jackson says. “All I want is a decent place to live. I can’t be on the streets with my son. He’s 47. He’s disabled. I’m paying [nearly] $1,500 a month to have all these problems. Not a pool, tennis court, nothing. I don’t want those things. I just want a place without problems. If he didn’t work, we’d be on the street. It’s hard on the people that live here on the North Side.” 

For years, Milwaukee was known as a relatively cheap place to rent. That distinction is getting harder to recognize. 

The average Milwaukee rent has climbed from $1,236 in 2023 to $1,458 in 2026, according to Zillow – a $222 monthly increase. Nationally, the median increase over the same period was $120. 

“It’s brutal if you’re a poor person in Milwaukee; the share of people who are spending half their income on rent is so high,” says John Johnson, a research fellow at the Lubar Center for Public Policy Research and Civic Education. (The rule of thumb is to spend 30% or less of income on housing.) “That makes you less likely to leave a place where you are, even if you wanted to. It’s a very difficult environment for renters, and the research shows, the poorest neighborhoods of the poorest cities are where profits from rent are the highest.” 

How We Got Here 

Milwaukee’s rental crisis did not begin with today’s rising rents. Teig Whaley-Smith, chief alliance executive for the Community Development Alliance, traces it back decades, to a time when many of the city’s duplexes and single-family homes were built as opportunities for homeownership rather than investments.  

In the 1950s and ’60s, as suburbs expanded and federally subsidized highways and infrastructure helped draw families out of the city, he says many white homeowners left Milwaukee’s neighborhoods without selling their homes to the Black families moving in. Instead, the properties increasingly became rentals – either kept by their former owners or sold to landlords.

What followed was a slow deterioration of the city’s housing stock, Whaley-Smith says. Properties changed hands from one landlord to another, with some successive owners having a greater tolerance for deferred maintenance – extracting rent without putting enough money back into the homes.

“We’re basically at the seventh circle of landlords right now,” Whaley-Smith says, referring to investors who run properties dry until they deteriorate beyond repair and become a public problem. “Over time, these properties just decrease in value and code compliance until they get demolished.” 

That cycle accelerated after the Great Recession. With property values so depressed in some low-income neighborhoods, traditional banks would often refuse to lend to prospective homeowners there, and investors with cash stepped in instead. The neighborhoods hit hardest included Amani, Harambee, Lindsay Heights and Washington Park, Whaley-Smith says. Each lost hundreds of housing units between 2010 and 2020, contributing to the city’s roughly 3,000 vacant lots. 

At the same time, Milwaukee has not built enough new entry-level housing to replace what has been lost. The city’s population remains around 600,000, Whaley-Smith notes, but average household sizes have shrunk dramatically. That means the same population now requires far more housing units because fewer people reside together. The result is a market in which fewer homes are for sale while more people compete for them. 

That pressure keeps would-be homeowners in the rental market, where rents have risen dramatically in recent years. When rent rises across the board, tenants like Jackson can find themselves paying high prices for aging homes with serious problems. 

Whaley-Smith says residents his organization works with report homes with major water damage, holes in exterior walls and dangerous electrical problems. They fear that complaining could jeopardize their housing and get them evicted instead of having these dangerous issues resolved. 

The result, he argues, is bigger than rent.

“This is a home ownership crisis, disguised as a rental crisis.” – Teig Whaley-Smith

“Tenants get stuck in this rental situation where they’re paying so much in rent, they can’t save up and pay for a down payment for a home,” he added. “We’re seeing landlords not selling properties because they are cash cows with very little regulation on them. It’s going to take a lot of political willpower to restore those homes and help the next generation of homeowners.”

The Reality

Jackson’s situation is all too familiar to tenant advocates, especially when an out-of-state landlord is involved. 

Roye Logan, a Milwaukee tenant organizer and board member with the member nonprofit Tenants United, experienced this firsthand. She first organized with residents of the Mitchell Court Apartments against the problem-plagued Housing Authority of the City of Milwaukee, complaining of mistreatment, lockouts, retaliation and ignored maintenance requests.  

Since working with tenants across the area, she has seen rents climb even as the condition of some properties remains poor due to neglect. She describes a one-bedroom apartment renting for as high as $1,800, a cost that can force multiple people to share a home simply to cover rent and utilities. In other cases, she says, tenants are paying upwards of $1,500 per month for homes plagued by rodents, roaches and other serious problems like outdated fuse boxes, holes in the roof, and water leaking through electrical outlets. 

“People are paying $1,500 a month to babysit your rats, your roaches,” she says. “Yet, rent prices have gone up profoundly. A two-bedroom should be like $1,500. That’s a one-bedroom now. If they’re working a McDonald’s job, that’s their paycheck. Then you can’t afford to leave because everything else is just as expensive if not higher. Then what? You’re trapped.”

For many renters, leaving a bad situation is not as simple as finding another place. Staying near family and other social connections matters. A past eviction (warranted or not), criminal history or poor credit can limit options, too, leaving some to choose between substandard housing and the risk of having nowhere to go.

Even when problems with a property are brought up with the city, Logan says it takes four to eight weeks for an inspector to come out. If issues are found, the landlord has a month to correct it. If they don’t, the fine is $200 for the first offense and then $400 the second time. Many landlords, she says, just eat the fines and don’t remedy the issues. 

Kevin Solomon, an organizer for the nonprofit Common Ground, says this dynamic can effectively trap tenants in deteriorating properties. Application fees, higher rents elsewhere and the prospect of rejection by other landlords make the costs of leaving nearly as high as the cost of staying. “The difference between being stuck and being trapped is, if you’re trapped, other people are holding you in that situation,” he says. “A lot of tenants are trapped. They aren’t stuck circumstantially; they’re trapped with few or no options.” 

The Future

Fixing Milwaukee’s housing problems will require more than building apartments. At the state and city levels, housing advocates say the goal should be to keep people in their homes, give renters more leverage and create more opportunities for ownership. 

At the state level, Whaley-Smith says, that starts with reducing the tax burden on low-income seniors, many of whom play an important role in keeping neighborhoods stable. He also supports Wisconsin adopting a law to give renters the first chance to buy single-family homes and duplexes if their landlords decide to sell. And, more broadly, he says “every level of government” should shift more of its housing investment toward homeowners rather than investors. There are signs that some of those investments can work.  

At the city level, advocates like Tenants United want faster, more proactive code enforcement when landlords allow properties to deteriorate, and basic protections such as requiring tenants to have leases so they have clearer rights. 

“Fundamentally, at the local level, we want to see enforcement have real teeth, not baby teeth,” Solomon says. “We want to see real, proactive enforcement.” 

The hope is for more affordable, and habitable, housing options. 

“I’m working. I’m paying my rent,” Jackson says. “The only reason I’m struggling is because of these conditions. I just want doors that reach the ground so I don’t have to keep cold air out in the winter by stuffing blankets at the bottom. It’s not that much to ask, is it?” 

For decades, Black homeownership in metro Milwaukee moved in the wrong direction. From 2010-19, the city lost roughly 1,000 homeowners of color each year, pushing the share of Black households who owned their homes down 5 percentage points to about 27%. (The rate of non-Hispanic white homeownership is 68.5%.) Then, the community changed course. In 2021, the Community Development Alliance brought neighborhood groups, nonprofits, funders and government together around a collective housing plan. Since then, that Black homeownership rate has started rising for the first time in 15 years. The work has included more homebuyer counseling and down-payment assistance, a $10 million fund with Acts Housing to acquire properties from landlords and return them to owner-occupants, and a dramatic increase in entry-level home construction – from about 20 homes a year to 80, with a goal of reaching 100 in 2027. “At every level of government, we need to spend more money on homeowners than we do investors,” the CDA’s Teig Whaley-Smith says. “If we do that, we can get ourselves out of this homeownership crisis.”