Upper East Side
{Going Big}
Median Single-Family Price: $412,100
The Upper East Side has long been blue-chip territory, filled with homes you won’t find anywhere else. Name a famous Wisconsin architect – such as Frank Lloyd Wright or Russell Barr Williamson – and chances are he’s designed a home around here. “It’s hard to find houses with that architecture,” says Julie Bulgrin, a broker with Gallagher Kies & Company. “The historic, extravagant homes are still there and on the bluffs of Lake Michigan.” Be prepared to invest in maintenance; the housing stock is well-preserved, but old. Framed by Oakland Avenue and the lake, North and Edgewood avenues, its tree-lined streets boast some of the city’s largest lawns. UWM profs and Columbia St. Mary’s docs like the short commute. If you’re seeking small, you might look elsewhere. “It’s not really where people go for condos,” says Bulgrin.
Thirty homes sold in the Upper East Side in 2017 for a combined $13 million and an average price of $154 per square foot.
Read the full story
Where to Live Now: Your Guide to the Top Places to Live in Milwaukee
[/alert]West Milwaukee
{Starting Out}
Median Single-Family Price: $139,000
Reports of the West Allis-West Milwaukee School District’s cash-strapped status might deter families, but this is a great locale for first-time buyers who aren’t raising kids yet. This village, which borders West Allis and Milwaukee, consists mostly of colonials and bungalows. A three-bedroom pad here starts around $150,000, and will put you within a bicycle ride of West Allis’ evolving downtown, which includes a wine bar and farmers market.
Bay View
{Downsizing}
Median Single-Family Price: $175,700
Fleeing the suburbs and starting anew in the city has become a mini-trend among those looking to downsize. Kathy Castillo, a Realtor with Keller Williams, and her husband, Willie, did just that, trading their 3,700-square-foot Whitefish Bay home for a 1,500-squarefoot Bay View bungalow in 2016. “My husband was spending a lot of time in this area building a wooden sailboat, and I started coming down here, too. We liked the water and the bike paths,” she says. “We walk everywhere – to restaurants, the Avalon (Theater), shopping. The neighborhood is great … It’s a very friendly vibe.” Bungalows reign here, but there are other styles, too, including Victorians. There are many choices in the $225,000-$275,000 range, but be ready to act fast, as some houses can attract multiple offers within a day or two of hitting the market.
Enderis Park
{Trading Up}
Median Single-Family Price: $168,800
A longtime fave for city employees, Enderis Park is great for those who crave the community feel of the suburbs but still want to be in close proximity to Downtown. This enclave is loaded with affordable four-bedroom Tudors and bungalows, so close to Tosa it’s across the street. Geographic boundaries lie between Center and Burleigh streets and Lisbon Avenue. There’s an active neighborhood association that runs a Christmas-decorating contest and other events, including “summer concerts that bring out hundreds of neighbors who bring picnic suppers to the park to enjoy the music and have a wonderful evening,” says Jean Henning of RE/MAX Realty 100’s Greenfield office. Families with kids, listen up: “There’s a great variety of schools – public, Lutheran and Catholic – all within walking distance,” says Henning.

Luxe Condos: Urbanity at its Finest
Where are the most stylish designer condos in Milwaukee? A current four-bedroom listing at University Club Tower (built in 2007) – the state’s tallest residential building, with some 52 units spanning 36 stories – is asking $4.75 million. “When you think of Miami- and London-style condos,” says David Price, a broker who specializes in condos with Milwaukee Realty Inc., the University Club Tower is a great example. This unit has two terraces and walls of windows – many curved – overlooking Lake Michigan. Another eye-catching listing is at 601 Lofts on East Ogden Avenue. With a home theater, suspended catwalk, 5,000-square-foot terrace and an 11-foot custom waterfall, the two-story penthouse clocking in at 6,500 square feet is poised to attract the uber-wealthy. It’s listing for $2.6 million. Shopping in the Third Ward? Trulia lists the cost per square foot there at $258, compared with the city’s average of $120. “It is the most expensive price per square foot in the city,” says Price. A departure from typical condo design are the Harbor Front and Hansen’s Landing developments on Erie Street, both at the hands of Renner Architects, with timber-beamed ceilings and chef-grade kitchens (granite countertops and stainless-steel appliances). Most units overlook the Milwaukee River, through wall-to-wall windows on one side. Listing prices for both buildings start at $224,000 and go up to $975,000.

Hot Hipster ‘Hood: Walker’s Point
It’s not just the tapas and farm-to-fork restaurants on South Second Street that make Walker’s Point so desirable. Homes there, too, are a hot ticket – and once they’re on the market, they go fast. Historic in nature, and rich in design, some of the properties need TLC, but the price is often right to budget for those repairs. A move-in-ready 1870 Cream City brick Italianate with a chef-grade kitchen and three bedrooms listed for $265,000 last Labor Day weekend. An offer of $270,000 was accepted within days.
Last fall, Portrait Society Gallery owner Debra Brehmer snapped up a brick duplex at Fourth and Washington streets. The second day it went on the market, Brehmer’s was among five bids. After a second round, it was hers, for the asking price. “It was the art neighborhood, where artists had their studios,” Brehmer recalls about living in Walker’s Point (at Ninth Street and National Avenue) during the 1990s, before moving to Shorewood when her youngest child was 4. “There’s life on the street, neighbors who are always out. There’s a different kind of life there that I respond to,” says Brehmer. Spearheading Walker’s Point’s development and cultural renaissance is Juli Kaufmann of Fix Development, which cleaned up contaminated sites to develop Clock Shadow Creamery and Purple Door Ice Cream in eco-friendly buildings. “Walker’s Point [is] a diverse, quirky, authentic and affordable neighborhood, offering all the great benefits of urban living in an ideal location accessible to everything,” she says. “My hope is that we won’t let this drive to make a profit undermine what has always been great about Walker’s Point.”

