It’s been 70 years since Cortina d’Ampezzo, “Pearl of the Dolomites,” was host to the Winter Games. Back in 1956, there were just 24 medal events. Three of them went to the dashing Austrian skier Anton “Toni” Sailer—the “Blitz from Kitz”—who swept all three alpine competitions: the downhill; slalom; and the twisty, high-speed giant slalom, winning that by a margin of 6.2 seconds.
These were the first winter games in which the Soviet Union participated and the first to be televised live to a European audience, sealing the international prestige of winter sports—and permanently establishing Cortina as a jet-set destination.
The 2026 Winter Games are an altogether different story: This year, Cortina and its grand backdrop, the Dolomites, share the spotlight with Italy’s high-fashion capital, Milan. Their games will be the most gender-balanced ever, with 47 percent female participation and 50 contested women’s events. Then there’s also the historic debut of a new event, ski mountaineering, or “skimo,” with three medal events.
Also historic is the sustainable use of 13 venues this year, the most widespread in history, covering some 22,000 square kilometers, or 8,500 square miles across Northern Italy’s Lombardy and Veneto regions. In this Luxury Defined property spotlight, we showcase four of them.
1. Palatial Villa on Via San Primo, Milan
In the historic heart of Milan, this stately villa has an exclusive setting on Via San Primo, a quiet street that runs alongside the historic Senate Palace, between Via Marina and Corso Venezia, at the edge of the famous Quadrilatero della Moda fashion district.
Classical statuary and frescoed walls grace the grand hall, which leads out to a serene garden courtyard with statuary, flowerbeds, and a fountain shaded by a towering palm tree. Of particular note is the rear facade, adorned with bas-reliefs of Michelangelo, Leonardo da Vinci, and other luminaries of the Renaissance.
Other grand architectural details include solid wood doors, ornate wood paneling, decorative marble floors, and a cellar with a magnificent, vaulted ceiling. Contemporary style notes include a lovely, landscaped terrace with lounge seating.
Each floor is self-contained and served by an elevator, ideal for use as private apartments. The location offers peace and privacy away, yet a stone’s throw from chic boutiques and restaurants, the Villa Reale Gallery of Modern Art, and the Indro Montanelli Public Gardens.
2. Traditional Chalet in Madonna di Campiglio, Trentino
This alpine chalet has a picturesque location in northern Italy’s Brenta Dolomites, within minutes of the historic village and ski resort of Madonna di Campiglio.
The chalet was completely rebuilt in 2011 to the highest standards of bio-architecture. The result is a home that blends traditional Tyrolean architecture with 21st-century engineering, design—and style.
The central living space harks to the old with its 200-year-old wooden floor, beautiful stone and wood fireplace, and a balcony with a showstopping, panoramic view of the mountain peaks.
Six en suite bedrooms, all elegantly furnished with reclaimed wood and Swiss pine, create a healthy and natural indoor climate for residents and guests.
The primary suite, tucked away in the spacious attic, offers a bird’s-eye view of the forest that surrounds the home.
The ski and equipment rooms are tailored for winter sports enthusiasts, with a wellness suite and a Finnish sauna facing the Cima Tosa, the highest peak of the Brenta Dolomites.
Another delight is the lawned garden, in all about 1,500 square meters (0.37 acres) of land—all just minutes from the chair lifts and the glamorous après-ski diversion of Madonna di Campiglio.
3. Liberty-Style Villa on Lake Maggiore, Lombardy
Italian Art Nouveau, or Liberty-style architecture, takes center stage in this serene villa overlooking Lake Maggiore from a shady parkland of 6,600 square meters, or 1.6 acres, with centuries-old trees, ornamental flowers, a belvedere, and panoramic terraces.
The villa, set in the quiet lakeside village of Germignaga, extends across four levels with interior space of more than 800 square meters, or 8,611 square feet. Conservative restoration would enhance its original architectural features: majestic lake-view windows, carved wood ceilings, decorated tiles, wrought-iron details, and a stone staircase under a large Liberty-style stained-glass window.
On the ground floor there is a spacious living room facing the lake, utility rooms, and cellars. The upper floors host additional lounges with fireplaces, 10 bedrooms, three bathrooms, and a kitchen. Two splendid balconies on the upper floors complete the main façade.
Within the park lies the secluded, fully renovated guesthouse and its two independent apartments with separate entrances. A large terrace provides the perfect space for relaxation or outdoor entertaining.
4. Locanda on Lake Misurina, Belluno
Set beneath the three iconic peaks of Tre Cime di Lavaredo, this distinctive Alpine inn faces a scenic mountain lake in the heart of Italy’s Dolomites, offering spectacular views, deluxe accommodation, a spacious restaurant/pizzeria, and great development potential.
Built in the 1990s, the inn’s restaurant seats up to 250 guests across 360 square meters (3,875 square feet), extending outside to an inviting, wood-framed deck above beautiful Lake Misurina—its frozen waters were the stage for the speed skating events at the 1956 Winter Games.
The lake frames the views from the upstairs bedrooms: six spacious, comfortable guest suites, all with balconies to contemplate the alpenglow. Staff accommodations and service and operational areas share the floor. Four separate apartments, on this level and in the attic space, offer an additional living space of 450 square meters, or 4,843 square feet. An outbuilding and ample parking round out the offering.
“Pearl of the Dolomites,” host city Cortina d’Ampezzo, is only 13 km (8 miles) away.
Luxury living in northern Italy? See here!
Writer’s bio: Lucy Carsen is a regular contributor to the Luxury Defined blog and has written for luxury lifestyle publications including Worth, Christie’s and Christie’s International Real Estate magazines.
Source: https://www.christiesrealestate.com/blog/
