Kawailoa Kailua Real Estate

Welcome to Kawailoa, a hidden gem nestled within the charming town of Kailua on the beautiful island of Oahu, Hawaii. Known for its stunning natural beauty and laid-back island vibe, Kawailoa offers a perfect blend of tranquility and convenience for those seeking a serene lifestyle.

Surrounded by lush greenery and breathtaking ocean views, Kawailoa is an idyllic neighborhood that boasts some of the most pristine beaches in Hawaii. Just a stone's throw away, you’ll find the famous Kailua Beach and Lanikai Beach, both renowned for their powdery white sands and crystal-clear waters. Whether you're a fan of swimming, kayaking, or simply soaking up the sun, these beaches provide a picturesque backdrop for your outdoor adventures.

Kawailoa is also characterized by its friendly community atmosphere. With a mix of families, retirees, and young professionals, the neighborhood fosters a strong sense of belonging. Residents enjoy local parks, walking trails, and a variety of recreational activities that promote an active lifestyle. The nearby Kailua Town offers a delightful array of boutique shops, cafes, and restaurants, perfect for leisurely strolls or grabbing a bite to eat.

For those who appreciate nature, the nearby Maunawili Trail and the lush Ko'olau Mountains provide endless opportunities for hiking and exploration. With a mild climate year-round, outdoor enthusiasts will find themselves in paradise.

In Kawailoa, you’re not just buying a home; you’re investing in a lifestyle that embraces the beauty of island living. Experience the magic of Oahu in this enchanting neighborhood where every day feels like a vacation. Welcome home to Kawailoa!

Newest Listings in Kawailoa Kailua

$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.

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.