Illinois’ Most Valuable Lakefront Estate Returns to the Market for $29.9 Million

Set on two private acres along Lake Michigan, the Winnetka compound combines a private sandy beach, a hidden wellness wing, and amenities that current lakefront regulations would no longer allow to be built.

A rare opportunity has returned to Chicago’s ultra-luxury housing market.

Listed for $29.9 million, the estate at 319 Sheridan Road in Winnetka represents one of the most significant lakefront residences currently available in Illinois. Occupying approximately two acres with 141 feet of private Lake Michigan frontage, the property offers a combination of scale, location, and grandfathered features that would be virtually impossible to recreate under today’s shoreline development regulations.

Completed in 2007, the residence spans approximately 20,000 square feet with eight bedrooms and thirteen bathrooms, while its resort-style amenities transform the estate into a fully self-contained private retreat just 30 minutes from downtown Chicago.

A Lakefront Estate That Could Never Be Rebuilt Today

In luxury real estate, scarcity often determines long-term value.

For 319 Sheridan Road, that scarcity extends beyond its coveted location. According to the listing, many of the estate’s lakefront improvements—including its proximity to the shoreline and several outdoor amenities—would not qualify for approval under today’s more restrictive building ordinances governing Lake Michigan waterfront construction.

That distinction immediately separates the residence from newly built competitors.

“This is one of those properties where replacement cost tells only part of the story,” said Jena Radnay of @properties Christie’s International Real Estate. “The real value lies in owning features and a lakefront setting that simply cannot be recreated today.”

Positioned within one of the most desirable stretches of Sheridan Road, the property also benefits from a location where multiple homes exceeding $30 million have recently changed hands, reinforcing the neighborhood’s standing among the Midwest’s premier luxury enclaves.

Architecture Designed Around Lake Michigan

The home embraces Lake Michigan as its defining architectural feature.

Floor-to-ceiling windows throughout the principal living areas frame uninterrupted water views, while formal entertaining rooms, family gathering spaces, and private terraces are oriented toward the lake.

Guests arrive beneath soaring 15-foot ceilings before encountering the dramatic bridal staircase—instantly recognizable to television audiences as a filming location featured in the hit series Empire.

Throughout the residence, traditional craftsmanship is paired with contemporary functionality. A richly paneled mahogany office opens directly onto the pool terrace, while the expansive great room creates a seamless transition between interior entertaining spaces and the lakefront landscape beyond.

Natural light floods nearly every room, reinforcing the home’s connection to its extraordinary setting.

A Chef’s Kitchen Built for Everyday Living and Grand Entertaining

At the center of the home is a kitchen designed to perform at a professional level without sacrificing warmth.

Dual islands provide generous preparation and gathering space, complemented by extensive custom cabinetry, premium appliances, expansive countertops, and specialized culinary features—including a built-in rice cooker rarely found in residential kitchens.

Nearby, the glass-enclosed solarium breakfast room offers panoramic garden views throughout every season, while an adjoining sunroom opens onto terraced outdoor seating areas overlooking the estate’s resort grounds.

“The home was designed so every major gathering space naturally flows outdoors,” Radnay said. “Whether it’s a casual family breakfast or a large celebration, the lake is always part of the experience.”

A Wellness Wing Connected by a Hidden Passage

One of the estate’s most remarkable features remains hidden from view.

Beneath the main residence, a private tunnel connects the lower level directly to a dedicated wellness complex overlooking the lake.

The facility includes an indoor swimming pool, state-of-the-art fitness center, and sauna, creating a private health club that sits only steps from the estate’s own sandy beach.

Combined with the home’s commercial-quality boathouse and direct access to Lake Michigan, the wellness wing delivers a lifestyle more commonly associated with exclusive waterfront resorts than private residences.

Resort Amenities Extend Across the Entire Property

Beyond the residence itself, the estate continues to unfold through a remarkable collection of outdoor amenities.

A 20-by-40-foot swimming pool and spa anchor the main entertainment terrace, accompanied by a fully equipped cabana, outdoor kitchen, fire pit lounge, and multiple landscaped gathering spaces.

A full-size grass tennis court offers additional recreational opportunities, while terraces built directly into the bluff create elevated viewing areas overlooking Lake Michigan.

At the shoreline, a private commercial-grade boathouse provides immediate lake access, allowing owners to launch directly into open water within minutes.

“This property delivers virtually every lifestyle amenity buyers seek today, yet combines them with a setting that simply doesn’t exist elsewhere on Chicago’s North Shore,” Radnay said.

A Third-Floor Private Residence Above It All

Privacy remains a recurring theme throughout the estate.

The entire third floor functions almost as a separate residence, offering an in-law or guest suite complete with a private bar, studio, terrace, and panoramic lake views.

On the second floor, five additional bedroom suites surround an extraordinary primary retreat featuring dual dressing rooms, marble bathrooms, fireplace, and a private terrace overlooking Lake Michigan.

The result is a floor plan capable of comfortably accommodating multiple generations while preserving privacy for every resident.

Why Winnetka Continues to Define Illinois Luxury

Winnetka has long represented the pinnacle of Chicago’s residential market.

Its combination of lakefront estates, nationally recognized schools, walkable downtown, and convenient commuter rail access has consistently attracted executives, entrepreneurs, professional athletes, and business leaders seeking both privacy and accessibility.

From 319 Sheridan Road, residents can reach downtown Winnetka within minutes, while Chicago’s Loop remains approximately a 30-minute train ride away.

For buyers evaluating the broader market, our Illinois Luxury Real Estate Market Guide explores the state’s highest-value residential communities. Readers may also enjoy Largest Homes in Illinois and Architecture Styles of Luxury Homes in Illinois, which provide additional context on the region’s most significant estates.

Additional photography, floor plans, pricing history, and current availability can be viewed on Zillow.

Property Overview

• Address: 319 Sheridan Road, Winnetka, Illinois 60093
• Price: $29,900,000
• Bedrooms: 8
• Bathrooms: 13
• Living Area: Approximately 20,000 square feet
• Lot Size: Approximately 2 acres
• Lake Frontage: 141 feet of private Lake Michigan shoreline
• Year Built: 2007

---

Listing Representation

The property is represented by Jena Radnay of @properties Christie’s International Real Estate.

For additional information or to arrange a private showing, interested buyers may contact the listing agent at (312) 925-9899.