Kawailoa Kailua Homes with Fee Simple Land tenure

Welcome to Kawailoa, a hidden gem nestled in the picturesque town of Kailua on the beautiful island of Oahu, Hawaii. This charming neighborhood is a harmonious blend of serene coastal living and vibrant community spirit, making it an ideal place for families, retirees, and anyone seeking a slice of paradise.

Kawailoa is renowned for its stunning beaches, including the famed Kailua Beach and Lanikai Beach, both just a short stroll away. The soft sands and crystal-clear waters invite residents to indulge in sunbathing, swimming, and a variety of water sports. With the majestic Ko'olau Mountains as a backdrop, the area offers breathtaking views and endless opportunities for outdoor activities such as hiking, biking, and kayaking.

The neighborhood is characterized by its friendly atmosphere and a close-knit community. Local shops, cafes, and restaurants provide a taste of the island's unique culture, while farmers' markets and community events foster a sense of belonging. Families will appreciate the highly-rated schools and parks, making Kawailoa an excellent choice for those with children.

One of the standout features of homes in Kawailoa is the fee simple land tenure, offering homeowners true ownership of their property. This means you can enjoy the ultimate peace of mind, knowing that your investment is secure and that you have the freedom to create your dream home in this idyllic setting.

Whether you're looking for a quaint cottage, a modern beach house, or a luxurious estate, Kawailoa has something to suit every taste. Discover the magic of this enchanting neighborhood and experience the true essence of island living in Kailua, Hawaii. Your dream home awaits!

Newest Kawailoa Kailua Homes with Fee Simple Land tenure

$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.