The Most Expensive Houses in Wisconsin

March 9, 2023

most expensive houses in Wisconsin

Wisconsin is not typically thought of as the most opulent state in America, but it is home to some of the most expensive houses in the country.

The Driehaus Estate is one of the most expensive homes in the entire state, and it is currently on sale for $36 million.

1. The Driehaus Estate

In an idyllic summer retreat town, there's a storybook-style mansion tucked on a peninsula that turns heads. With 13 fireplaces, a boathouse and a guest wing, this grand estate on Geneva Lake is currently one of the most expensive houses in Wisconsin.

The property is owned by trusts named for investment manager Richard Driehaus and his two daughters, Tereza and Caroline. They sold the house for $1.5 million.

Driehaus was known for his passion for philanthropy and historic preservation, and he held spectacular summer birthday parties at his baronial estate. He passed away last March at age 78.

2. The Hillcroft

The Hillcroft, built in 1888, is one of Lake Geneva's most prestigious estates. It boasts 415 feet of shoreline, the most for any property in the area.

Previously owned by the Wrigley family, this lakefront home was razed and redesigned by Roger O'Neill in the 1980s. It's a classic English cottage-inspired estate that features a gatehouse, guest quarters, carriage house and greenhouses.

In addition to the extensive shoreline, the estate also includes a boathouse designed to accommodate four yachts. It's a fun relic of Lake Geneva's past and well worth the visit today.

3. The Lakeshore Drive

The Lakeshore Drive (pronounced "Lake Shore Drive") is a multilevel expressway that runs alongside the shoreline of Lake Michigan, adjacent to parkland and beaches in Chicago.

Real estate along the Drive is coveted by many people for its stunning views, beach access and seemingly endless lakefront park space. And the area isn't just limited to residential property; dozens of upscale condominium and apartment buildings line the drive.

It's also been featured in the opening credits of TV shows such as Married with Children and ER. And it is the backdrop for an EA NASCAR video game called Chase for the Cup.

4. The Black Point Drive

The Black Point Drive is a 7-mile one-way loop through one of the best wildlife viewing areas on Merritt Island National Wildlife Refuge. The drive is a must for any birder or nature lover in the area and offers stunning views of a variety of landscapes and animals.

The drive is best viewed at sunrise or sunset, as the light levels are most dramatic in the latter. Be sure to check out the visitor center for an array of interesting exhibits, a video on the refuge and a 1/4 mile boardwalk.

5. The Cambridge Road

The Cambridge Road is a historic residential street in Maple Bluff. This street is home to one of the Governor's Residences, which was the official residence of all 18 Wisconsin governors.

It also features a variety of architecture including Prairie, Shingle, Mediterranean Revival and French Norman Revival styles. Discover the lives of those who called this place home, and learn about the prominent architects who designed these homes.

Whether you’re looking for a new luxury house or an old-school estate, you’ll find plenty of options here. You can filter results by price, square footage, number of bedrooms and bathrooms, and more. Plus, you can receive notifications when new high-end listings match your preferences.

6. The Pabst Road

Pabst Road is a short drive from Milwaukee and has the distinction of being one of the most expensive houses in Wisconsin. The house is a stunner with a slew of features including a paneled library, swimming pool and party-sized screening room.

The mansion was built in the 1890s, and has since been preserved by the nonprofit organization Pabst Mansion Inc. The organization preserves, shares and interprets the home with immersive tours, educational programs and events.

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