Kawailoa Kailua Real Estate

Welcome to Kawailoa Kailua, a hidden gem nestled on the stunning windward coast of Oahu, Hawaii. This idyllic neighborhood is renowned for its breathtaking natural beauty, vibrant community spirit, and laid-back island lifestyle, making it a perfect haven for families, retirees, and anyone seeking a slice of paradise.

Kawailoa is characterized by its pristine beaches, with the famous Kailua Beach and Lanikai Beach just a stone's throw away. These picturesque stretches of white sand and crystal-clear waters are perfect for sunbathing, swimming, kayaking, and paddleboarding. The lush, tropical landscape is complemented by the majestic backdrop of the Ko'olau Mountains, providing a stunning setting for outdoor enthusiasts and nature lovers alike.

The neighborhood exudes a charming, small-town vibe, with friendly locals and a close-knit community. Here, you’ll find a delightful mix of local shops, cafes, and eateries that serve up delicious Hawaiian cuisine and fresh local produce. Don’t miss out on the chance to explore the nearby Kailua Town, where you can enjoy boutique shopping, art galleries, and lively farmers' markets.

Families will appreciate the highly-rated schools in the area, as well as the abundance of parks and recreational facilities. With its safe streets and welcoming atmosphere, Kawailoa Kailua is an ideal place to raise children or enjoy a peaceful retirement.

Whether you’re looking for a vacation home, a permanent residence, or simply a place to unwind, Kawailoa Kailua offers an unparalleled lifestyle that captures the essence of island living. Experience the magic of this enchanting neighborhood, where every day feels like a vacation!

Newest Listings in Kawailoa Kailua

$1,495,000

2 Beds ⋅ 2 Baths ⋅ 202519242 MLS ⋅ FS - Fee Simple Tenure ⋅ 325 DOM

Your gateway to turquoise waters, soft white sand, and the quintessential island lifestyle! Waking up to ocean breezes and a stroll across the street to world-famous Kailua Beach, this charming 2-bedroom, 2-bath cottage makes every day feel like vacation. A cozy size set on a low-maintenance parcel, it lives comfortably larger—providing all the benefits of a single-family home without the maintenance fees of a condo. Enjoy park and partial ocean views from multiple rooms, and dining al fresco on your private lanai. Wander a few minutes to Kailua or Lanikai Beach for paddleboarding, kite boarding, kayaking, snorkeling, or open-water swims. With bike paths out your front door, a restaurant a stroll away, a public charter school just up the road, and a private country club nearby, this cottage places you in the heart of Kailua’s active, outdoor lifestyle.

29 Alala Road, Kailua

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.