THE history of Nanjing Road W. is bound up in the city’s past.

It was built on the north of the city’s third racecourse in 1862 when horse racing was a huge fad among expatriates, especially for carriages to go through.

As the west end stretched to the Jing’an Si, or Jing’an Temple, it was called Jing’ansi Road, while in English it was Bubbling Well Road, called so because of a disappearing bubbling well in front of the temple.

Over 40 years, it has maintained some kind of rustic charm. And the countryside path took a fascinating turn after 1900, thanks to the increasing investments from foreigners.

Western bankers and rich tycoons built their glamorous residences on the road, which soon formed Shanghai’s earliest high-end villa zone. It became a busy hub in 1920s and 30s when large-scale shikumen communities, modern apartments and high-end retail and recreation venues sprung up.

The area around Wujiang Road was the first to have garden villas. The most noticeable three are mansions of legendary Qing Dynasty (1644-1911) minister Sheng Xuanhuai, minister Li Hongzhang’s brother Li Fengzhang and Shanghai’s top leader Shao Youlian.

The mansions didn’t survive the social changes. While maybe one of their rendezvous, Zhangyuan Garden, not far, was retained.

Foreigner rendezvous

It was built in 1872 by a British merchant, but it later fell into the hands of Chinese entrepreneur Zhang Shuhe, who made it a public gathering spot and Arcadia Hall, the tallest building in Shanghai at that time.

In the late 1800s and early 1900s, Chinese operas, magic shows, gambling and dining were on offer here. It shrank from importance as competition from newer indoor entertainment complexes like cinemas sprang up. In 1919, it was turned into a private residence.

But today renovation has given it a new lease on life. It’s now a popular hangout for expats at nights. A bierstube, cocktail bar and tapas restaurant are found in the courtyard.

Similar shikumen-style Jing’an Villa, which has been restored to its original environment, is another must-see spot for expats.

In the heart of downtown Shanghai, the neighborhood harks back to the environment of Old Shanghai. Skilled craftsmen mingle among older residents in long alleyways.

The area was one used by the English to breed horses. In 1932, 183 Anglo-American style red brick buildings were erected to house wealthy Westerns, entrepreneurs, celebrities and intellectuals.

Writer Eileen Chang used to hang out at cafés in the area. The movie version of her book “Lust, Caution,” starring Tony Leung, was filmed here.

During the 1970s, many of the prominent families moved away, and their houses were partitioned into smaller flats occupied by multiple families.

European-style garden villas

Westerners and tycoons preferred to be settled a little bit westward.

The most renowned architecture used to be the fancy 26-acre Aili Garden, completed by Jewish tycoon Silas Aaron Hardoon. But just like many others, it has been wiped out from the map.

The site now features the Shanghai Exhibition Center. It’s one of the very few reminders of the influence the Soviet Union once had in Shanghai. Built in 1955, it was initially called the Sino-Soviet Friendship Building.

The building represents a strong Stalinist architectural style, modeled on St Petersburg’s Admiralty Building. And some Chinese elements in the building embody the political symbols of that era.

Hardoon’s neighbor, a senior manager of HSBC who lived just across the road on the north, also failed to keep his property. The site was taken over by the Shanghai Center. But former residences of Guo’s brothers, just minutes’ walk to the west, has been luckily retained, and now are used as government offices.

They are two beautiful white villas surrounded by trees, also known as the “Brethren Buildings” because they are symmetrical and identical.

Built in 1926 in the French Renaissance style, the two three-story villas were originally the homes of business tycoons Guo Le and his younger brother Guo Shun, who founded Wing On Department Store on the Nanjing Road E. The garden features a pavilion, bridge and artificial hill.

The former residence of Rong Zongjing, scion of a renowned tycoon family, is another outstanding relic.

Also called Rong Villa, it is a grand garden villa hidden around the street corner of Nanjing Road W. and Shaanxi Road N.

Built in 1918, the complex features architecture in the French Renaissance and Eclectic style, while its interior design is more traditional Chinese.

After Rong fled to Hong Kong in 1938 as he refused to work for the Japanese occupation forces, the building was rented by the China Economic Research Institute.

In 2002, media tycoon Rupert Murdoch rented the villa as the office for his News Corp business. Luxury brand Prada became the next tenant. Prada said it has plans to open part of the building to the public, but no date has been set.

Unlike other garden villas, Moller Villa, about a 10-minute walk from Shanghai Exhibition Center, is more like a marvelous castle.

It was a gift from British businessman Eric Moller to his daughter, who was smitten with castles she read about in Hans Christian Andersen fairy tales.

The Scandinavian-style villa was completed in 1936, featuring brown and multicolored tiled Gothic and Tudor steeples, gables and spires.

In the spacious garden, there’s a bronze statue of a horse, erected above the burial ground of Moller’s favorite racehorse. The garden also features stone lions, dogs and drums.

Modern apartments

While many garden villas have disappeared, most of upper-class apartments, concrete constructions featuring modern Western styles like Art Deco and equipped with modern facilities like elevator, still exist.

They include Yates Apartments, Denis Apartments and Majestic Apartments, mostly designed by foreigners. But the former Cosmopolitan Apartments complex was an exception. It is one of few modern apartments in Old Shanghai that were designed by Chinese architecture, Li Jinpei.

Built in 1934 in a Spanish architecture style, it has an eight-story main building and two four-story wings, which are linked by corridors. Red tiles were used as roofing, and the outdoor facade is an inlay of glass blocks.

Playwright Li Jianwu, and renowned actresses Zhang Ruifang and Wang Danfeng once lived here.

Jewish footprints

In the 1930s and 40s, about 25,000 Jews took refuge in Shanghai to escape the Nazis back home. The Ohel Rachel Synagogue is a legacy of that era. It’s considered to be the best-preserved one of the seven synagogues in Shanghai and also the biggest remaining in the Far East.

The ivy-covered, Greek revival-style synagogue, built by tycoon Jacob Sassoon in 1920 to commemorate his dead wife, was used until 1952, with the exception of two years during World War II. It was listed on the World Monuments Watch list of endangered buildings in 2002. Shanghai’s Jewish community still uses the building.

Not far sits former Jewish residence. This four-story red-brick villa was once home to a wealthy Jew engaged in gold trading. In the early 1950s, the family moved to Israel, and the house was gradually partitioned into smaller flats.

Now the building has a painting in its façade of the fourth floor, showing a Jewish woman leaning on the window, with a flower pot near her and pigeons flying around.