The popular resort town of Lake Geneva has long had connections to Chicagoland going back to the 19th century. Once known as the “Newport of the West,” wealthy Chicagoans like William Wrigley, Jr. and Charles H. Wacker built palatial second homes along the shoreline. Nestled in between were religious camps and social clubs — usually established by middle-class families — that consisted of wooden cottages and a shared kitchen in a central clubhouse. Located less than two hours from downtown Chicago, it’s no surprise that the area is still a summer getaway and tourist attraction for many people looking to escape Illinois. While many of the historic mansions are long gone, you can still see a handful that survive during one of the many boat tours on the lake. Last year, the former 40-acre lakefront estate of the late Richard Driehaus broke records when it sold for $36 million, becoming Wisconsin’s most expensive home. Whether you’d like to live in town or along the lake, there are a variety of options available right now on the real estate market. 

N1619 East Lakeside Ln, Lake Geneva, $7,995,000

When one thinks of an impressive lakefront property, this high-end six-bedroom, ten-bathroom mansion is probably what comes to mind. Though not as expensive as some other estates (Edward Swift’s Villa Hortensia was most recently listed at $20 million), it fits the post-COVID trends around Geneva Lake. Prices have soared as homeowners hold onto their lakeside residences and inventory is at an all-time low. Not only does this particular home come fully furnished but it has all the bells and whistles, including a cook’s kitchen, game room, elevator, wine room, and twelve-seat media room. It’s part of the private, 40-residence community of South Shore Club located along a 1,000-foot stretch of the lake. 

720 High St, Lake Geneva, $1,125,000

On the market for the first time in almost twenty years, this listing comes with two separate homes occupying the same one-acre piece of land. The main house is an 1870s Victorian full of updates that makes the interior space feel bright and airy. It has four bedrooms plus two full and two half bathrooms. The second structure is open-concept on the ground level with a combo kitchen/family room. The upstairs has a bedroom, bathroom, and laundry room. It’s perfect to use a guest house. The best part is this tree-lined property feels like an escape but is still close to town.

101 Broad St UNIT 802, Lake Geneva, $899,000

Maybe you’d like to live in the center of everything, specifically Lake Geneva’s vibrant downtown where you can walk to various restaurants and shops. This two-bedroom, two-bathroom condo is located in Geneva Towers, which infamously replaced Frank Lloyd Wright’s Lake Geneva Hotel when it was demolished in 1970. Owners have access to a heated indoor pool and one attached garage space, which is definitely something you’d want during the hustle and bustle of the summer season. Plus living on the eighth floor means you can take in sunset views from your own private balcony. 

421 Elmwood Ave, Lake Geneva, $425,000

This cute 1920 bungalow has seen quite a price jump since it last sold seven years ago, going from $140,000 to $425,000. But as we’ve already discussed, living in Lake Geneva can cost you a pretty penny. So this property is an affordable option for anyone interested in being close to all the action in town. The updated two-bedroom, two-bathroom home comes with a finished basement as well as a spacious and fenced backyard. There is potential in turning the attic/upper level of the garage into a great entertainment space for the family.

N1702 Durand Ln, Lake Geneva, $949,000

The grand Loramoor estate owned by multi-millionaire capitalist James H. Moore originally consisted of thirty-two buildings. Unfortunately the majority of them, including the Tudor-Revival mansion, were torn down by a developer in 1984. But this sprawling structure covering 4.5 acres was spared. Such great details here include the breezeway, stone-faced fireplace, and the beautifully detailed wooden bar from Chicago’s Gas Light Club. While the four-bedroom, four-bathroom residence does not come with water views, you do have an in-ground pool and are walking distance from the south shore of Geneva Lake and its 21-mile shore path. What an ideal property for anyone looking to bring a piece of history back to life.