Kawailoa Kailua Real Estate

Welcome to Kawailoa, Kailua – a hidden gem nestled on the beautiful island of Oahu, Hawaii. This enchanting neighborhood is renowned for its stunning natural beauty, laid-back atmosphere, and vibrant community spirit. With its pristine beaches, lush landscapes, and a friendly, welcoming vibe, Kawailoa offers a unique blend of tranquility and adventure that captivates both residents and visitors alike.

One of the standout features of Kawailoa is its proximity to the breathtaking Kailua Beach, often hailed as one of the best beaches in the world. Here, you can enjoy sunbathing on soft, golden sands, swimming in crystal-clear waters, or partaking in thrilling water sports like kayaking and paddleboarding. The nearby Lanikai Beach, with its picturesque views of the Mokulua Islands, is just a short drive away, making it a perfect spot for a day of relaxation or exploration.

Kawailoa is also a haven for outdoor enthusiasts. The lush hiking trails of the nearby Maunawili Valley and the scenic views from the Lanikai Pillbox Hike offer unforgettable experiences for nature lovers. The neighborhood is dotted with charming local shops, delightful eateries, and community parks, fostering a sense of connection and belonging among residents.

Families will appreciate the excellent schools and safe environment, while those seeking a tight-knit community will find plenty of opportunities to engage with neighbors through local events and activities. Whether you’re looking for a serene retreat or an active lifestyle, Kawailoa, Kailua is a place where you can truly feel at home in paradise. Come and discover the magic of this picturesque neighborhood!

Newest Listings in Kawailoa Kailua

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 82 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.