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.

Restaurants

Freddy’s Pizza

Restaurant

A traditional Italian restaurant in the heart of Chapel Street.

Hanoi Hannah Windsor

Restaurant

A taste of Victoria Street on the south side.

The Railway Hotel

Restaurant

A local boozer and dining spot with an eye on paddock-to-plate eating. And a 24-hour bottle shop.

Hawker Hall

Restaurant

A vibing Asian beer hall from the group behind Chin Chin, Kong and Baby.

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Small Print Pizza

Restaurant

Sourdough pizzas with a small environmental footprint.

Cafes

Öppen

Cafe

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

Glacé

Cafe

A frozen desserts store from pastry chef Christy Tania.

Journeyman

Cafe

A beautifully-designed cafe backed by Dukes Coffee Roasters.

The School of 7 Bells

Cafe

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

Mr Mister

Cafe

You’ll feel refreshed as soon as you enter this bright, airy cafe.

Bars

Borsch, Vodka & Tears

Bar

An old-world Polish vodka bar and restaurant.

High Bar

Bar

Channel your inner flapper to live jazz, cabaret and drag performances, with a Charlie Chaplin cocktail in hand at this art-deco lounge.

Chacho’s

Bar

Pizza and tequila meet head-on at this local haunt serving up late-night eats and tequila that’s meant for sipping, not slamming.

Galah

Bar

Natural wine, craft beer and cocktails with an Australian focus.

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Lover

Bar

A late-night dining spot with a playful but serious cocktail program.

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Windsor Castle Hotel

Bar

This quirky lime castle with a huge courtyard is a getaway from bustling Chapel Street.

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Shops

Elka Collective

Shop

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 Lucy Folk Salon

Shop

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

P.Johnson Tailors

Shop

Bespoke suits and shirts from extremely well dressed tailors.

Shag

Shop

Like stepping into Grandma’s closet on the way to Narnia, Shag is a vintage treasure-trove showcasing retro pieces from many eras.

The Windsor Annex

Shop

Casual daywear and accessories from Elwood Apparel Co.

Chapel Street Cellars

Shop

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