Woodfired Pizza, Bajan-Style Sangas and an “Ice-Cream Listening Room”: The Windsor Spots Locals Love

You can’t talk about Melbourne’s inner south-east without including Windsor in the conversation. The suburb is best known for its nightlife, vintage shopping and hospitality, and while it may not be the city’s most obvious dining destination, it has plenty of gems – if you know where to look.

While visiting it on a weekend can be nice, it’s hard to get a full grasp of Windsor’s charms and everyday pleasures if you don’t live there. And with so much packed into a small pocket of the city, it’s easy to see why so many people choose to call the suburb home.

The Raleigh by The Keys is all about the lifestyle that Windsor gives you, bringing a design-led build-to-rent offering to the suburb and giving people even more reason to move in. With shared spaces, considered resident amenities, pet-friendly apartments and flexible leasing options, it’s designed around how people actually live – with service, comfort and connection to community built into everyday life.

From cosy cafes to standout restaurants and bars, here are a few spots within the small but mighty suburb to check out, as a visitor or as a local.

Eat

Caribbean cuisine is hard to come by in Melbourne, but Barbados Slim brings a taste of the region to the heart of Chapel Street. The sandwich menu includes a Bajan-style macaroni pie and barbeque chicken melt alongside a plantain, black bean and avo sandwich.

Melbourne’s first Ukrainian restaurant, Otakoi, has built a loyal following thanks to its warm service and comforting food. The pierogi are essential, while the blintzes, herring salad and borscht are equally worth exploring. Even better, it’s BYO.

Freddy’s is a local favourite for pizza and its drinks label Tommy’s, which produces a range of Italian-inspired liqueurs. The community focus comes through via warm service and consistently good food, whether you’re dining in or grabbing takeaway.

For a buzzy dinner without the formality, Studio Amaro strikes a great balance. The moody, design-led space serves an Italian-leaning menu and strong cocktail offering. On Fridays and Saturdays, it trades until midnight – ideal for dinners that turn into drinks.

Japanese flavours like black sesame, matcha and hojicha form the backbone of Kori, an ice-cream shop that balances novelty flavours with good execution. The team calls it an “ice-cream listening room”, with tunes always playing over vinyl and flavours displayed the way you would a record sleeve. In summer there are daytime raves and DJ sets on weekends, and in winter? A yuzu hot chocolate that’s perfect to sip on your way home.

Drink

Rose Island is a cosy neighbourhood bar and bottle shop tucked slightly off the main strip. It looks like a dive at first glance, but the beer and wine list is considered and mostly local. Owner Lachlan Gravier is often around, adding to the community feel.

Vinyl is the focus at Rumbler, a listening bar built around the owner’s love of high-end audio. To keep the night going, head next door to sibling venue Coil, which leans more heavily into late-night techno.

Part restaurant, part bar, part live music venue, Young Hearts fills a lot of roles at once. There are affordable weeknight specials, jazz sessions, DJs and enough going on throughout the week to make it an easy default for starting or ending the night.

Shop

Windsor balances contemporary retail with old-school Chapel Street character. Vintage stores like Stupid Vintage and Shag are go-tos for retro clothing, antiques and homewares. For something more contemporary, head to Bye Bambi – the Melbourne label is known for colourful tracksuits, elevated basics and playful accessories.

This article is produced by Broadsheet in partnership with The Keys Living.