Windsor has long been overshadowed by its more flamboyant neighbours, Prahran and South Yarra. As recently as 2005, the bottom end of Chapel Street was mostly tired two-dollar shops and didn’t have much going for it.

You wouldn’t know it now – the suburb has developed one of the most dynamic restaurant scenes in Melbourne. And thanks to Jungle Boy and classics such as Lucky Coq and The Windsor Castle, it’s also a great place for a drink.

Wander away from Chapel Street and things get real quiet. The narrow streets mix ‘70s-era apartments, older terraces and a few newer developments, with few shops or other businesses. It’s a good place to live if you like to be close to the action, but not right in the thick of it.


  • Henrietta is not a “grab your chook and go” situation. If the $2.5 million fit-out doesn’t draw you in, the garlicky aroma of toum, fresh bread and fire-grilled chicken surely will.

  • Pop into this warm, retro-feel restaurant for weeknight dinners of 72-hour-fermented focaccia, handmade pasta and woodfired meats. On weekends, party in the basement with amaro cocktails and DJs spinning Italo disco.

  • A sleek wine bar and restaurant serving up Middle Eastern-inspired dishes, some borrowed from its elder sibling Maha. Tuck into share plates of Armenian beef dumplings, lamb cutlets and taramasalata fried buns. There’s also a 120-strong wine list.

  • Short for “small eco-footprint”, this pizzeria is mostly vego – but when there is meat, it’s locally sourced. It’s also completely glass-free (all drinks are poured from a tap), and staff can deliver your pizza to nearby Victoria Gardens.

  • A late-night sub shop with a tropical-themed cocktail bar hidden behind a coolroom door.

  • A buzzing food and beer hall inspired by Singaporean and Malaysian hawker halls. Work your way through a hit-list of hawker market dishes. Expect various dishes of noodles, rice, roti and curry (from the trusted team behind Chin Chin, Society and Baby Pizza). Plus, order lots of easy-drinking beers.

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  • At this frozen desserts store by pastry chef Christy Tania, bestselling ice-creams include the pavlova and cookies and cream flavours. But don’t miss out on the range of ice-cream cakes, babkas and macarons either.

  • Scandinavian open sandwiches and clean, modernist design. And cocktails, too.

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  • A beautifully-designed cafe backed by Dukes Coffee Roasters.

  • A cosy cafe with the usuals, and the not-so-usuals.


  • This quirky lime castle is an improbable oasis away from bustling Chapel Street, and it has a huge courtyard. During the warmer months it’s thronged with locals, all drinking iced beverages and frosty beers.

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  • A gleaming 100-litre still sits at the centre of this red-accented bar and restaurant. It’s where distiller (and chef) Carlo Tran makes the gin you’ll find in your Asian-inspired cocktails – most of which are on tap. Pair them with pan-Asian dishes such as chargrilled prawns, beef rendang, deconstructed bao and karaage chicken.

  • Everyone (and their dog) is welcome at this bar, inspired by a short-lived Italian micronation from the ’60s. BYO food, enjoy Victorian brewers on tap, have a glass of natural wine and hang out with the locals.

  • This two-storey joint is warmly lit and moody, with long timber tables and cosy booths. Order Mediterranean-style share plates, choose a bottle (or three) from the wall, and tuck in with your favourite people. Neptune seats up to 105 people.

  • Hit this airy warehouse for natural wine and limoncello slushies on tap, pop-up kitchen takeovers, late-night DJ sessions and rotating artist residencies – all courtesy of Nic Coulter, co-owner of the adjacent Neptune Food & Wine.

  • An old-world Polish vodka bar and restaurant.

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  • This bold and glitzy vintage store is one of Melbourne's most iconic. It showcases retro pieces from many eras, be it an ’80s leather jacket, a ’60s day dress or a contemporary rhinestone-encrusted number. Plus, plenty of bright shoes, bags and accessories to complete your look.

  • With sandstone, dark timber and reclaimed terracotta, the first shopfront for trans-seasonal womenswear label Elka feels almost like a luxury villa in Spain or Italy.

  • The playful-luxe label has an outpost in Windsor selling its signature jewellery, sunnies and hand-loomed apparel, plus pieces from other designers.

  • Bespoke suits and shirts from extremely well dressed tailors.

  • Casual daywear and accessories from Elwood Apparel Co.

  • More kinds of wine and beer than you can imagine – and you're welcome to drink in-house.