Kawailoa Kailua Homes with Garden View

Welcome to the enchanting neighborhood of Kawailoa in Kailua, Hawaii, where island charm meets a vibrant community spirit. Nestled on the beautiful windward coast of Oahu, this picturesque locale is renowned for its stunning beaches, lush landscapes, and a laid-back lifestyle that invites you to unwind and embrace the beauty of island living.

Kawailoa is characterized by its stunning homes, many of which boast breathtaking garden views. Imagine waking up to the gentle sounds of nature, with your own private oasis just outside your door. The homes here are thoughtfully designed, often featuring spacious yards adorned with tropical flora, vibrant flowers, and swaying palm trees. These gardens not only enhance the aesthetic appeal of your property but also provide a serene escape, perfect for morning coffee or evening gatherings with friends and family.

The neighborhood is a haven for outdoor enthusiasts, with easy access to Kailua Beach, one of the most beautiful beaches in the world. Whether you enjoy kayaking, paddleboarding, or simply soaking up the sun, Kawailoa offers a wealth of recreational opportunities. The community is also known for its friendly atmosphere, where neighbors become friends, and local events foster a strong sense of belonging.

With its ideal blend of natural beauty, community spirit, and proximity to Kailua’s vibrant town center, Kawailoa is not just a place to live; it’s a lifestyle. Discover your dream home in this idyllic neighborhood, where every day feels like a vacation in paradise. Embrace the charm of Kawailoa and make it your own!

Newest Kawailoa Kailua Homes with Garden View

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 202607704 MLS ⋅ FS - Fee Simple Tenure ⋅ 64 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 ⋅ 329 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.