Kawailoa Kailua Homes with Other Frontage

Welcome to Kawailoa Kailua, a hidden gem nestled on the picturesque windward coast of Oahu, Hawaii. This charming neighborhood is renowned for its stunning natural beauty, laid-back atmosphere, and vibrant community spirit. With its pristine beaches, lush landscapes, and breathtaking mountain views, Kawailoa offers residents a slice of paradise that feels both tranquil and invigorating.

Kawailoa Kailua is an ideal location for those seeking a lifestyle that embraces outdoor living. The neighborhood is just a stone's throw away from the world-famous Kailua Beach and Lanikai Beach, where you can indulge in sunbathing, swimming, and water sports. The surrounding area is dotted with scenic hiking trails, including the popular Lanikai Pillbox hike, offering panoramic views of the coastline and the Mokulua Islands.

The homes in Kawailoa Kailua boast unique architectural styles, many of which feature other types of frontage, enhancing the character and charm of the community. From cozy beach cottages to modern family homes, there’s something for everyone in this diverse neighborhood. The close-knit community fosters a welcoming environment, making it easy for newcomers to feel at home.

Beyond the natural beauty, Kawailoa is conveniently located near local shops, restaurants, and markets, providing residents with easy access to everything they need. With its perfect blend of relaxation and recreation, Kawailoa Kailua is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover the magic of this enchanting neighborhood and find your dream home in paradise!

Newest Kawailoa Kailua Homes with Other Frontage

$1,450,000

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

Listing courtesy of Compass.

$1,495,000

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

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

Listing courtesy of Carvill Sotheby's Intl. Realty.

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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.