On Sunday, August 18, the world’s most beautiful and valuable collector cars will roll onto the 18th fairway at lovely Pebble Beach Golf Links, California, for the world’s most prestigious automotive exhibition: the Pebble Beach Concours d’Elegance.  

In honor of the 73rd edition of the event, Luxury Defined offers its own concours of deluxe homes with sleek, high-tech amenities for those with the four-wheeler fever of auto enthusiast Jay Leno, a frequent attendee at Pebble Beach. At last, best count, there were more than 181 cars (and 160 motorcycles) in Jay Leno’s Garage. (That count fluctuates, because the comedian is continually buying and selling vehicles to keep his collection fresh.) 

And Jay Leno’s “Big Dog Garage”? It’s actually a complex of enormous hangars at Hollywood Burbank Airport. 

He doesn’t live there, among his precious wheels. In our collection of dazzling homes for serious car collectors, he could—with a showcase for his daily drive Lamborghini. For in these homes, it’s all about the garage.  

1. McKinley Park Contemporary in Chicago, Illinois 

In Chicago’s historic McKinley Park neighborhood, this contemporary home’s vast, dramatic interior spaces were created by its bowstring-truss structural framing, a technology patented in 1841. 

What was an industrial warehouse became a modernist work of art, with three huge en suite bedrooms, two partial baths, two artist’s ateliers, two private office spaces, and a grand, open floor plan for luxurious living and entertaining.  

With custom steel cabinetry and door frames throughout, the interiors’ gallery lighting and Venetian plastered walls create the high drama of its black-on-white color scheme, warmed by natural wood accents and furnishings in cream and chocolate brown.  

The great room, a living/dining lounge space served by a contemporary kitchen, features a 40-foot NanaWall moveable glass door system. It opens to the landscaped garden and patio with custom built-in seating and dining, and a fire pit. 

Beside the great room is the great gallery, a 17-by-45-foot hall entered by a huge, glass-paneled, electric-rollup garage door. It is suitable for the display of any automotive artworks on hand—with drive-through access to the great room! Two workshops/studios adjoin. 

The home is fully sprinklered and fitted with a security system, with electric gate access and private parking for the daily drivers. 

2. Dream Villa on the Golden Mile, Marbella, Spain 

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This dazzling resort villa has an exclusive location in Marbella’s Golden Mile, just 300 meters from the beach and within walking distance to the upscale boutiques and restaurants, and superyacht marina of Puerto Banús.  

The interiors are elegantly appointed and epically scaled with an array of luxury lifestyle features. There’s an elevator from the roof terrace to the subterranean garage with LED lighting and space for eight supercars. Glass doors open to a lounge, bar, and cinema. 

Light imbues the atrium-style lobby, landscaped with an olive tree rising to the mezzanine level. The space invites grand-scale entertaining with a lounge and fully integrated chef’s kitchen and another terrace for alfresco soirees.  

Five en suite bedrooms include the supersized primary suite, with its boutique-worthy dressing room, freestanding soaking tub, enormous marble bathroom, and private terrace with coastal views. 

Luxury abides outdoors, too, with tropically inspired gardens, sweeping sea-view terraces, and two resort-worthy swimming pools to bask in the Costa del Sol’s 325 days of sunshine. 

Related: Discover Homes with Gardens and Groves

3. Designer Ski Chalet in Kitzbühel, Austria 

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This luxurious turnkey chalet in Reith, near the jet-set Austrian ski resort of Kitzbühel, provides an incomparable living experience in the Tyrolean Alps, but there’s much more on offer here than snow. 

Behind that beautiful timber façade are three levels of sleek living space, elegantly appointed with exquisite wood paneling, and bespoke furnishings, fixtures, and finishes. 

Among the standout features is a vast underground garage with murals of vintage cars. This level also provides a wellness suite with an indoor pool and sauna, as well as a cinema and wine bar for apres-ski relaxation. 

An elevator rises to the upper-level fireside lounge and its grand terrasse with unobstructed vistas of the Kitzbüheler Horn and the Kaiser Mountains.  

The four bedrooms each have a luxury en suite bathroom—and breathtaking views of the Alps beyond the fairways of Golf Course Kitzbühel-Schwarzsee-Reith. 

It’s also a smart home built with all the very latest green technologies for comfort, energy efficiency, and sustainability: geothermal underfloor heating, sensor-controlled intelligent lighting, heating, and security; and a PV (photovoltaic power) solar-powered system on the roof. 

4.  Grand Villa in Quinta Patino, Cascais, Portugal  

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Quinta Patino, a hillside enclave above the resort town of Cascais, is the setting for this classically inspired limestone villa.  

The entrance hall has gallery-scale walls for the display of grand paintings. Its black-and-white checkered tile floors extend to the dining hall and the kitchen, with a butler’s pantry and floor-to-ceiling pastel green cabinets. Nearby are a powder room, a media lounge, and a drawing room with a fireplace. All principal rooms open to the swimming pool and the lush private gardens. 

The lower level is dedicated to the garage (with six parking bays), a cinema, and wine cellar, laundry, and a tech systems room. Two of the six bedrooms are also on this floor, including a guest apartment with a living room, kitchenette, and shower room.  

The remaining bedrooms include four upper-floor suites with access to a wraparound balcony overlooking the gardens. 

Seek a car collector’s luxury home? Start your engines here.