Kawailoa Kailua Homes with Garden View

Welcome to Kawailoa, a hidden gem nestled in the heart of Kailua, Oahu. This picturesque neighborhood is renowned for its stunning natural beauty, where the lush greenery meets the serene coastline, offering residents a tranquil island lifestyle. With its close-knit community feel and breathtaking surroundings, Kawailoa is the perfect place to call home.

As you stroll through the charming streets, you’ll be captivated by the vibrant gardens and palm-lined paths that define this enchanting area. Homes in Kawailoa often boast beautiful garden views, allowing you to bask in the splendor of Hawaii’s tropical landscape right from your own backyard. Imagine sipping your morning coffee while surrounded by fragrant flowers and the soothing sounds of nature – it’s a daily retreat that many only dream of.

Kawailoa is not just about stunning homes and gardens; it’s also a community that values outdoor living. Residents enjoy easy access to some of the most pristine beaches in Hawaii, where you can surf, paddleboard, or simply soak up the sun. The nearby Lanikai Beach and Kailua Beach Park are perfect for weekend adventures, family picnics, or peaceful sunset strolls.

With a rich blend of local shops, cozy cafes, and vibrant cultural experiences, Kawailoa offers the perfect balance of relaxation and recreation. Whether you’re looking for a serene family haven or a vibrant community to thrive in, Kawailoa Kailua is a place where your dreams of island living can come true. Come discover the magic of this enchanting neighborhood and find your perfect home among the gardens!

Newest Kawailoa Kailua Homes with Garden View

$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.