5 Lakeside and Riverfront Estates Across Wisconsin and Illinois

Along the shores of Sheboygan Bay, this 1.9-acre lakeside retreat is designed for summers that stretch long into the evening. One of the best sandy beaches sets the scene, complemented by a private pier and decks positioned for sunset views. Fully remodeled in 2012, the home balances polish with practicality: a stylish kitchen with a butler’s pantry and wine fridge anchors spacious living areas made for game nights and unhurried time together. A den that can serve as a fifth bedroom adds flexibility for guests, work, or quiet escape. Two oversized garages provide generous storage for lake toys and race day cars. Convenient to Road America and the village’s dining, shops, and entertainment, it’s a setting that invites return traditions year after year.

On a serene, country-like stretch of Winnetka’s North Shore, this stately two-story brick residence sits in the coveted Indian Hill neighborhood, just steps from the Indian Hill Golf Club. Completed in 2012 and held by a single owner, the home opens to a gracious two-story marble foyer, with the main level finished in hardwood oak and cherry, while the family room features plank flooring. The first floor is thoughtfully arranged with a spacious living room, dining room, family room, eat-in kitchen, den, and mudroom—spaces designed for both daily ease and easy entertaining. Upstairs, the enormous primary bedroom reads as a quiet retreat, paired with a spa-like bath offering a jacuzzi, walk-in shower, and travertine tile. A large finished basement adds a full bathroom, generous storage, and plumbing in place for a future kitchen.

Set on 5.3 picturesque acres in Libertyville, 25291 North St. Mary’s Road presents a French Country estate that pairs timeless elegance with modern luxury. Thoughtfully updated in recent years, the interiors feature a beautifully redesigned chef’s kitchen, all-new spa-inspired baths, and rich hardwood flooring throughout. A highly sought-after first-floor primary suite creates a quiet retreat, complemented by a sunroom just off the suite and an enclosed sunroom off the kitchen that invites slower mornings and easy entertaining. Downstairs, a finished basement adds exceptional additional living space for gathering and relaxing. Beyond the grounds, daily life feels effortless with convenient expressway access for commutes and quick trips to O’Hare, close proximity to Vernon Hills shopping, and the boutiques, restaurants, and nightlife of downtown Libertyville, plus nearby train stations in Libertyville and Lake Forest.

Along the Rock River just outside Rock Falls, this stone residence unfolds across 4.4 acres with a setting designed for unhurried days on the water. Since 2008, the interior has been totally rebuilt and remodeled into an updated floor plan that keeps the river in constant view. A large living room centers on a stone fireplace, while the formal dining room and one of two primary suites on the main level take in breath-taking river vistas. The kitchen and breakfast area anchor daily routines, and a main-floor office looks out to the front yard. Upstairs, two bedrooms share a full bath, joined by a family room overlooking the river. Downstairs, additional entertaining spaces include a bar and another stone fireplace, with a boathouse and two outbuildings—one a man-cave with built-in pizza oven and full bath—for everything that comes with river life.

Along the Illinois River, this expansive parcel offers a rare chance to shape a riverfront lifestyle—whether as a private riverside retreat or a thoughtfully planned riverfront community. The land sits just outside the town of Marseilles in LaSalle County, an area noted in the listing for active development into recreational, residential, and resort living. Practicality is built into the vision: city water and sewer can be extended to the property, supporting a wide range of future uses. Days here naturally revolve around the water, with the listing highlighting excellent boating and fishing, along with hunting for those drawn to the outdoors. Beyond the shoreline, the wider setting adds everyday ease and weekend energy, with dining, shopping, a marina, and busy state parks all mentioned as part of the local draw.

Size: 36.00 acres