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Hip Neighborhoods on Oʻahu: Your Guide to What Hawaiʻi’s Shopping, Nightlife and Dining Looks Like

Businesses in burgeoning Kakaʻako, Ward Village and Kailua are defining the island’s evolving retail and restaurant scenes.

There’s a certain mix of classy cafés, happening bars and exciting new developments that make a neighborhood “hip.” And while there’s no wrong choice when it comes to picking a district to call home, some sections of Oʻahu seem to have more of an undercurrent of electrifying growth. And while they may not be deemed hip forever, they certainly are now. Below are three neighborhoods and towns on Oʻahu that we, and a few agents from List Sotheby’s International Realty, recommend if you’re looking for a community at the forefront of cool.

1. Kakaʻako

Located in the heart of Honolulu, you won’t find a row of blocks and buildings flourishing more than Kaka’ako. “There’s a lot going on in Kakaʻako, and from 2016 on we’ve seen a lot of new buildings and developments, like The Collection and Halekauwila Place,” says List Sotheby’s International Realty agent Jenny Chen. But it’s not all affordable housing and luxury condos. The neighborhood has numerous restaurants and gastropubs, including Moku Kitchen and Honolulu Beerworks, so you’ll have somewhere to go every night. And the many beachy boutiques and clothing stores in the vibrant Salt at Our Kakaʻako shopping complex will supply you with the outfits, apparel and accessories to mix with the in-crowd.

“Another huge draw to the neighborhood is its love for art,” says Tiffany Chen, a Realtor with List Sotheby’s International Realty. “Artists are invited to Hawaiʻi each year for Pow! Wow! Hawai‘i to showcase their art, host workshops and most notably, paint huge murals throughout the neighborhood, adding to its colorful and hip vibe.”

2. Kailua

Living in Kailua offers the best of both worlds: It’s a quick drive from Hawaiʻi’s only major city, Honolulu, and even closer to world-class beaches like Lanikai Beach and Kailua Beach. There’s an air of youthful energy on the beachside town’s sandy streets. This invigorating spirit can also be seen in the town’s many small businesses, like Lanikai Brewing Co.—a Hawaiʻi-based craft beer company that has done so well since launching in 2015 that it’s opened its own tasting room, Tap & Barrel—and ChadLou’s Coffee Roasters, which offers farm-to-cup specialty coffee and features a very Instagrammable interior.

3. Ward Village

Yes, technically Ward Village is within Kakaʻako; however, the 60-acre master plan community has made a name for itself with its close proximity to world-class eateries such as Merriman’s Honolulu, Piggy Smalls and Nobu Honolulu. Conveniently located by Ala Moana Regional Park and about 2 miles away from the bustling streets of Waikīkī, the Ward Village area has also seen a recent boom in luxurious condominium complexes that feature complex and thoughtful design, such as Waiea, Anaha and Aeʻo, the latter of which is anchored by a two-story Whole Foods Market. “I actually reside in this community and it’s exactly what you’d expect,” says List Sotheby’s International Realty agent Yukiko Yang. “The area offers equal opportunity to live, work and play.”

And while Ward Village could eventually lose its “hip” moniker, Nancy Maeda, vice president of List Sotheby’s International Realty, makes a case that more than just being currently fashionable, Ward Village’s appeal will endure. “Communities like Ward Village are sustainable,’” says Maeda. “I call it a ‘fingertip community,’ because everything is at your fingertips. For example, you have a plethora of choices for cuisine, there’s a clinic, it’s near hospitals, it’s close to beach parks and there’s condos, towers and villas to choose from.”

If you’re looking to purchase a piece of paradise, visit the List Sotheby’s International Realty website for a list of real estate agents and properties.

Nancy Maeda, Realtor, HI License RS-27914, (808)216-2166, nmaeda@listsir.com. Visit her agent profile here

Yukiko Yang, Realtor, HI License RB-22654, (808)439-8523, yyang@listsir.com. Visit her agent profile here

Jenny Chen, Realtor, HI License RS-76176, (808)783-8881, jchen@listsir.com. Visit her agent profile here