Kawailoa Kailua Homes with Fee Simple Land tenure

Welcome to Kawailoa Kailua, a hidden gem nestled on the beautiful windward coast of Oahu, Hawaii. This enchanting neighborhood is known for its stunning beaches, vibrant community, and a lifestyle that embodies the true spirit of island living. With its lush landscapes and serene atmosphere, Kawailoa Kailua offers a perfect retreat from the hustle and bustle of urban life.

One of the most appealing aspects of Kawailoa Kailua is its proximity to some of the island's most breathtaking beaches, including the famous Kailua Beach and Lanikai Beach. Here, residents can indulge in a plethora of outdoor activities such as kayaking, paddleboarding, and swimming in crystal-clear waters. The neighborhood also boasts scenic hiking trails, providing stunning panoramic views of the coastline and the majestic Ko?olau Mountains.

The homes in Kawailoa Kailua are a blend of charming bungalows and modern residences, many of which come with fee simple land tenure. This means homeowners have full ownership of both the home and the land it sits on, offering a sense of security and investment potential that is highly sought after. With spacious yards and tropical landscaping, these properties provide an ideal setting for families and individuals alike.

In addition to its natural beauty, Kawailoa Kailua is home to a warm and welcoming community. Residents enjoy local shops, farmer’s markets, and dining options that highlight the rich flavors of Hawaiian cuisine. Whether you’re looking for a peaceful retreat or an active lifestyle, Kawailoa Kailua is a place where you can truly feel at home. Come and discover the magic of this extraordinary neighborhood!

Newest Kawailoa Kailua Homes with Fee Simple Land tenure

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 63 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

$1,495,000

2 Beds ⋅ 2 Baths ⋅ 202519242 MLS ⋅ FS - Fee Simple Tenure ⋅ 328 DOM

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

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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.