Kawailoa Kailua Real Estate

Welcome to the enchanting neighborhood of Kawailoa Kailua, a hidden gem nestled on the stunning windward coast of Oahu, Hawaii. Known for its breathtaking natural beauty and laid-back atmosphere, Kawailoa offers a unique blend of island charm and modern conveniences, making it a perfect place to call home.

Kawailoa is renowned for its pristine beaches, including the famous Kailua Beach and Lanikai Beach, both just a stone's throw away. These picturesque shorelines boast soft, white sands and crystal-clear turquoise waters, ideal for swimming, paddleboarding, or simply soaking up the sun. The area is also surrounded by lush greenery, with the majestic Ko'olau Mountains providing a stunning backdrop for outdoor enthusiasts. Hiking trails, such as the popular Lanikai Pillbox hike, offer panoramic views that will take your breath away.

Community spirit thrives in Kawailoa, where friendly neighbors and local businesses create a warm, welcoming atmosphere. The nearby Kailua Town features a delightful array of shops, cafes, and restaurants, showcasing the diverse flavors of island cuisine. From fresh poke bowls to artisanal coffee shops, you'll find plenty of options to satisfy your cravings.

Families will appreciate the excellent schools and recreational facilities, including parks and playgrounds, ensuring a safe and nurturing environment for children to grow and thrive. With its idyllic surroundings, vibrant community, and close-knit feel, Kawailoa Kailua is not just a place to live; it’s a lifestyle that embraces the beauty and spirit of Hawaii. Explore this captivating neighborhood and discover your dream home in paradise!

Newest Listings in Kawailoa Kailua

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 71 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.