Kawailoa Kailua Real Estate

Welcome to Kawailoa Kailua, a hidden gem nestled on the picturesque windward coast of Oahu, Hawaii. This enchanting neighborhood is a perfect blend of serene beauty and vibrant community spirit, making it an ideal place to call home.

Kawailoa Kailua is renowned for its breathtaking beaches, including the pristine shores of Kailua Beach and Lanikai Beach, both just a stone's throw away. Here, residents enjoy sun-soaked days filled with swimming, paddleboarding, and beach volleyball, all set against a backdrop of turquoise waters and swaying palm trees. The gentle trade winds provide a refreshing breeze, making outdoor activities a year-round delight.

Nature lovers will appreciate the nearby hiking trails, including the iconic Lanikai Pillbox hike, which offers panoramic views of the ocean and surrounding landscapes. The lush greenery and vibrant flora create an idyllic setting for those who cherish the great outdoors.

Kawailoa Kailua is not just about natural beauty; it boasts a warm, welcoming community. Local shops, cafes, and restaurants reflect the island's unique culture and flavors, offering everything from fresh seafood to delicious shave ice. The nearby Kailua Town is alive with boutique shopping and local events, fostering a true sense of belonging.

Families will find excellent schools and parks, making it a safe and nurturing environment for children to grow and thrive. With its laid-back lifestyle, friendly neighbors, and stunning scenery, Kawailoa Kailua is more than just a neighborhood—it's a lifestyle that invites you to savor the beauty of island living every day. Discover your slice of paradise in Kawailoa Kailua today!

Newest Listings in Kawailoa Kailua

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 106 DOM ⋅ Windsurfer BLDG.

Experience the quintessential Kailua LIFESTYLE at The WINDSURFER, a boutique 10-unit townhome community situated directly across from Kailua Beach. LOCATION. This part of Kailua Beach has Oahu's BEST KITESURFING; it's heaven! The Windsurfers Unit #4 Is the Special Unit that sits right on the lily pond, a happy and serene spot to reflect the days activities. This RARELY AVAILABLE residence features a freshly painted interior, loft, new washer and dryer, and updated kitchen and bathrooms from a 2018 renovation. The versatile layout can accommodate either three bedrooms, or two bedrooms with a flex space and a half bath. The large tiled private patio offers many opportunities, entertaining, dining, outdoor living room and is has a lighted walk in storage closet for bikes, tools, and equipment. 2 reserved and excellent parking spaces right outside your door and guest parking is available for your friends. Most importantly ... Yes, PET FRIENDLY! Located just steps from world-class windsurfing, Kalapawai Market, and BUZZ'S Steakhouse, this serene retreat offers a welcome escape from the bustle of Honolulu. CALL today to learn all about the outstanding lifestyle at the Windsurfer!

445 Kawailoa Road Unit 4, 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.