Greendale is not like most Milwaukee suburbs, and the reason is history. It is one of only three federal Greenbelt Towns built anywhere in the United States (the other two are in Maryland and Ohio), and it was designed in the 1930s as an experiment in New Deal-era planned communities. Streets curve, utilities are buried, the village center is walkable by design, and the whole town center is a National Historic Landmark.
That planning shows. The village center feels closer to a small town from a movie set than a Milwaukee suburb. Colonial Revival civic buildings, tens of thousands of flowers planted every year, and a real stretch of shops and restaurants on foot.
The most distinctive housing here is the Originals. These are the 366 homes built by the federal government in 1938, concrete-block with clay tile roofs, and most of them have distinctive artistic chimney designs. There is nothing else like them in the metro. Around that original core, standard suburban expansion has filled in.
Schools have a strong reputation. Greendale High has been ranked among the country's better public high schools, and the marching band has been a state champion 18 years running. Southridge Mall and the S 76th retail corridor cover most of the daily errand shopping.
Greendale is a planned village from the 1930s, one of only three Depression-era planned "greenbelt towns" the federal government built, and you can still see the intent everywhere. Curved streets, connected greenspace, a distinctive village core along Broad Street with covered sidewalks and the original town hall. It looks and feels like nowhere else in the metro.
The Greendale clients I see tend to be families drawn to the schools and the town center, or long-time Milwaukee locals who grew up visiting and always wanted to live there. Households here often go back generations, and the neighbor-to-neighbor familiarity shows.
Buyers new to Greendale should know: the original village homes have real historic personality (and real historic quirks). The newer subdivisions on the edges are a different product entirely. Both are Greendale on the map, but they are two different searches.
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What Greendale costs right now
Movoto puts the June 2026 median sale price at about $387,900, and Homes.com shows a similar figure near $392,500, up about 9 percent year over year. Greendale's inventory is unusually distinctive (the Originals are unlike anything else in the Milwaukee suburbs), which affects how a specific home prices.
Who tends to like Greendale
Not who "should" live here. Just what kind of daily life this place fits.
The honest tradeoffs
The original village homes are protected by a review board that limits certain exterior changes. That preserves the neighborhood's character but means less flexibility if you want to remodel outside the historic aesthetic. Know what you are signing up for before you write the offer.
Greendale sits further from the city than the north-shore suburbs, so the daily commute for anyone working in Milwaukee or the East Side is longer. Retail along Highway 100 is decent but not within walking distance of most of the village. It functions as a suburb even though it looks like a village, and buyers looking for city energy will not find it here.
