Beauty Parades

There are more than 100 beaches in and around Sydney, Australia’s second most populous city. A few are rated among the best in the world. You won’t find any of them in the eastern suburb of Paddington, but this has not stopped it from becoming one of the most desirable areas in town.

On a Sunday afternoon, the cafes and restaurants at the Five Ways roundabout heave with al fresco diners. Schooners of beer are sipped. Bouquets of flowers frame the open entryway of a neighborhood grocery store. This is the heart of “Paddo,” as the locals call it. It is a 10-minute drive from the central business district and runs alongside the lively main thoroughfare, Oxford Street. Aside from eateries, boutiques, and art galleries, Paddington is best known for its pretty terraced housing. Its roughly 3,800 homes mostly built between 1860–90 make it a rare, largely intact enclave of early Victorian residential architecture. The community’s historical Paddington Society, run by volunteers, has been successfully working to preserve it since 1964.

Australian terraces date from its time as a British colony and match designs found in Britain. With their compact footprint, they fulfilled fast-growing demand for housing during urban expansion in the 19th century. The decorative wrought-iron-clad balconies that give Paddington much of its charm were often added later as a concession to the much warmer climate.

The properties line winding, narrow streets and today many doors and entire houses are painted in bright colors. Sidewalks are framed with towering jacaranda trees, whose trumpet-like flowers bloom every spring. “It’s a feast of purple,” says Australian designer Lee Mathews, who lives in the area and opened a Paddington outpost for her eponymous brand on Glenmore Road in 2015.

Mathews is one of Australia’s best-known womenswear designers, creating feminine clothing made from high-quality fabrics, like silk, wool, and cashmere, as well as accessories and homeware. She says that Paddington is “the charming, Knightsbridge equivalent in Sydney,” referring to the affluent west London neighborhood.

“We’re not a city brand. The customer who resonates with us lives and shops in their own area. And Paddington was always a very strong customer base for us, apart from the fact that it’s a lovely suburb with a strong retail footprint.”

At The Intersection, a 10-minute walk from Five Ways, Lee Mathews is among a cluster of boutiques that emphasize great Australian design, such as men’s and women’s leisurewear label Venroy, and Rachel Gilbert and Scanlan Theodore, both known for well-crafted, elegant womenswear. Nearby Lucy Folk is a contemporary lifestyle gem designed by the antique dealer and designer Tamsin Johnson. The store helps to demonstrate the area’s pull to sought-after names in interiors and architecture.

With the rise in wealthier residents has come a raft of sensitive residential upgrades to Victorian properties—often including added lightwells and windows, but also harnessing the beauty of homes’ original features. Paddo Pool Terrace is a recent conversion of a property from the late 1800s into a modern home “with a feminine sensibility,” says Jane McNeill, associate director at Luigi Rosselli Architects. This was partly achieved with interiors by Tania Handelsmann (another Paddington terrace resident, and one half of award-winning firm Handelsmann + Khaw). Norwegian rose marble, Popham tiles in petal, and hand-painted silk wallpaper complement the “Himalayan salt” color chosen for the external render. A double-height, glass-roofed atrium was used to infill a courtyard, while original features such as the fireplaces and cornices were retained and restored. “We sought to create a reclusive and calm oasis that turns away from busy Paddington and looks to the harbor beyond,” says McNeill.

For those not looking to buy, the boutique hotel Oxford House is a recent addition to Paddington and entirely in line with its laidback creative energy. Its mid-century building on Oxford Street, between an art deco Mexican cocktail bar and a bookshop, has been renovated in cool Californian style with work by contemporary local artists on the walls. The central terrace has a heated pool, bar, and all-day dining; the cutlery is by Marc Newson and bathrobes are by Double Rainbouu, a local designer from across the road.

Fred’s is known for its friendly atmosphere and farm-to-table cooking

It might now be one of Sydney’s most desirable neighborhoods, but Paddington has been through some changes. Fine jeweler Sarah Gardner founded her eponymous store here in 2011 and has built up a following for her distinctive hand-made pieces using opals and other rare stones. She says when she was growing up in the late 1980s and early 1990s, the area was “bohemian.”

“I first started working here in 1993 when it was super eclectic,” she says. “It was a constant stream of people. Every shop was packed. There were so many restaurants and amazing cafes. Interesting people, lots of musicians.”

She remembers the height of Paddington Markets, held outside Paddington Uniting Church since 1973. Australian homeware brand Dinosaur Designs, known for its resin homeware including bowls and vases, and women’s fashion label Zimmermann, which has shown at New York and Paris Fashion Weeks, both started there. It is still a platform for local artists, craftspeople, bakers, and chefs who still sell their goods in the more than 150 stalls.

The opening of a nearby mall in the early 2000s—Westfield Bondi Junction—meant footfall and fortunes in Paddington declined. The area was in a recession phase when brothers Gio and Enrico Paradiso opened their now-legendary bar and restaurant, 10 William St, in 2010. It brings seasonal cooking to the fore, and was one of the first bars in the world, let alone Australia, to serve natural wine. “I just love the challenge of opening in places where there doesn’t seem to be anything going for it at [that] moment,” Gio Paradiso says. “It was pretty uncool to open in Paddington… We brought energy to that street.”

His restaurant takes its cues from the bars he loves in Europe. It is housed in a modest, two-story converted terrace, with a chic white-and-timber interior and chalkboard displaying a constantly changing selection of wines and pasta specials. Past chefs have included Dan Pepperell, formerly at one of Sydney’s best-known French venues Restaurant Hubert; Trisha Greentree, formerly at award-winning restaurant Brae in Victoria; and Luke Burgess, chef and owner of renowned Garagistes in Hobart, Tasmania.

Art and design gallery Saint Cloche

Major Sydney hospitality company Merivale has a strong presence in Paddington. The popular Fred’s—a restaurant with a “friend’s country home” feel—launched 2016 and, in its basement, the cocktail bar Charlie Parker’s. A few doors down is the stylish Saint Peter. The 22-seater fish restaurant bills itself as “fin to scale” dining, with sustainable seafood prepared by chefs in front of you at a marble-top bar. The smart Jackies Cafe, right off Oxford Street and with a covered patio and wall of greenery, is another local highlight.

Around the same time as 10 William St, the art and design gallery Saint Cloche opened. Its founder and curator, Kitty Clark, moved to Paddington with her family when she was in her teens and says many residents have lived here for decades and through many generations. Now, she’s seeing more young families moving in, bringing a different feel. She says: “It’s such a beautiful area. People want to be in nature and Paddington is so green. The council has done really well in upkeeping that.”

Clark’s favorite Paddington spot is the area where her gallery is, on MacDonald Street, next to a small park to which the neighborhood flocks at 4pm daily. “It’s one of those corners where everybody in the area crosses paths. You walk past each other, walking your dog, getting a coffee. We have a lot to offer, in terms of community.”

When the jacaranda trees bloom in spring, it’s a “feast of purple.”

McIntyre Apparel has been drawn to join in. The store, which opened on Oxford Street in June this year, sells 100% merino wool knitwear and basics. It is the second from the brand after its flagship location in Melbourne. Co-founder Ned Scholfield says a Paddington presence made sense because, “we wanted to align ourselves with boutique Australian fashion brands.” Scholfield recommends visiting The Hood, a diminutive cafe with an exciting Japanese fusion menu, which opened in a William Street terrace in 2022. Or try the small but welcoming Cafe Köket, tucked in the backyard of fashion and home store Funkis, two doors down from McIntyre. You might also wander down beyond Paddington to Rushcutters Bay, a small residential suburb with a great park and a harbor full of sailboats.

Sarah Gardner, the jeweler, suggests a route around Paddington that naturally includes a stop at her own store. (You’ll find a great vibe inside, particularly on a Saturday, she says.) She advises grabbing a coffee at the Paddington Alimentari, an authentic, Italian-owned deli on Hopetoun Street, or Bonython Café on Underwood Street, which, if you can find the entrance, hides a lush courtyard within.

And if you’re in Paddington outside of the jacaranda flowering season, no worries. “I know a lot of people in the area have a green thumb, and I think there’s guerrilla planting happening, but in a beautiful way,” says Kitty Clark. “If you walk around, you’ll see the most unusual species of flora and fauna—ones that you’ve never seen before.” So, while major efforts are preserving Paddington’s architectural history, its natural environment—its shopping, cafe and restaurant scene—is evolving nicely.

Sydney | Price upon request
sothebysrealty.com/id/GJH38N
Michael Pallier | Sydney Sotheby’s International Realty

On the waterfront

This contemporary interpretation of a wrap-around veranda house stakes a claim for one of the best views of Sydney harbor in the city. Over two floors, it is one of only six north-facing homes at the end of  the exclusive Darling Point peninsula, and was overseen by architects  Polly Harbison Design, known  for sculptural and sophisticated residential work. Grounds are  by Will Danger, one of Australia’s preeminent landscape designers, and there is an infinity pool, two rooftop gardens, a private beach, and direct access to the water for boats.

Photos: Trent van der Jagt for Local Paddo/Visit Paddington; Anne Peters; Tommy Devy; Hugh Stewart; Prue Ruscoe, courtesy of Luigi Rosselli Architects; Rhiannon Taylor; courtesy of Fred’s; Rory Gardiner; Jacqui Turk; Anastasia Nielsen; Nikki To; Rennie Ellis; Bianca Spender.