Kawailoa Kailua Homes with Sunset View

Welcome to Kawailoa Kailua, a hidden gem nestled on the beautiful windward coast of Oahu, Hawaii. This enchanting neighborhood is renowned for its breathtaking scenery, stunning beaches, and a laid-back lifestyle that makes it a paradise for those seeking tranquility and natural beauty. With the majestic Ko'olau Mountains as a backdrop and the sparkling Pacific Ocean just steps away, Kawailoa Kailua offers a unique blend of outdoor adventure and serene living.

One of the standout features of this neighborhood is its captivating sunset views. Imagine unwinding each evening on your lanai, sipping a tropical drink as the sun dips below the horizon, painting the sky in hues of orange, pink, and purple. Homes in Kawailoa Kailua are designed to maximize these picturesque vistas, with many properties boasting expansive windows and spacious decks that invite the outdoors in. Whether you're looking for a cozy cottage or a luxurious beachfront estate, you’ll find options that cater to your lifestyle and taste.

Kawailoa Kailua is not just about stunning views; it’s also a community that thrives on outdoor activities. From paddleboarding and kayaking in the calm waters of Kailua Beach to hiking the nearby trails, residents enjoy an active lifestyle surrounded by nature. The neighborhood is also home to charming local shops, delightful eateries, and a friendly atmosphere that welcomes newcomers with open arms.

If you’re dreaming of a home where sunsets are a daily spectacle and the spirit of aloha is alive, Kawailoa Kailua is the perfect place to call home. Experience the magic of island living in this idyllic neighborhood, where every day feels like a vacation.

Newest Kawailoa Kailua Homes with Sunset View

$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

Start Your Search

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.