Kalaheo Hillside Homes with Waterfront Frontage

Welcome to Kalaheo Hillside, a hidden gem nestled in the picturesque town of Kailua on the stunning island of Oahu, Hawaii. This enchanting neighborhood is renowned for its breathtaking views, lush landscapes, and a serene atmosphere that perfectly captures the essence of island living. Imagine waking up each morning to the gentle sound of waves and the vibrant colors of a Hawaiian sunrise, all from the comfort of your own home.

Kalaheo Hillside is characterized by its charming, upscale residences that boast waterfront frontage, providing homeowners with direct access to the pristine waters of Kailua Bay. Whether you’re an avid water sports enthusiast or simply enjoy the tranquility of ocean views, living in this idyllic community offers a unique lifestyle that is hard to resist. Picture yourself kayaking on calm waters, taking leisurely strolls along the shoreline, or hosting sunset barbecues with friends and family, all while surrounded by the natural beauty that surrounds you.

The neighborhood is also conveniently located near Kailua’s vibrant town center, where you can explore an array of local boutiques, cafes, and restaurants. Enjoy the laid-back Hawaiian vibe while indulging in fresh, locally-sourced cuisine or discovering unique artisanal crafts. Families will appreciate the proximity to top-rated schools and lush parks, making Kalaheo Hillside an ideal place to raise children.

In Kalaheo Hillside, you’re not just buying a home; you’re embracing a lifestyle rich in natural beauty, community spirit, and endless opportunities for adventure. Come discover the magic of this enchanting neighborhood and make it your own slice of paradise in Hawaii!

Newest Kalaheo Hillside Homes with Waterfront Frontage

$3,880,000

3 Beds ⋅ 3 Baths ⋅ 202605289 MLS ⋅ FS - Fee Simple Tenure ⋅ 153 DOM

Your dream waterfront Kailua residence. This hidden jewel fronting Kawainui Canal with access to the ocean offers an exceptional blend of contemporary design and Kama‘aina elegance. Architecturally designed and tastefully refreshed, this 3 bdrm, 2.5 ba residence with 3,291 sq ft of living space offers vaulted ceilings (which elevate the sense of space and natural light), fresh interior/exterior paint, vinyl plank flooring, new carpet, and an open chef’s kitchen featuring custom cabinetry, quartz countertops, and a spacious 10’ island. An expansive primary suite overlooks the pool deck with canal and majestic Ko’olau Mountain views. Designed for effortless indoor/outdoor living, there are multiple lanais along with a swimming pool—ideal for entertaining and everyday relaxation. Lush landscaping on the 14,866 sq ft lot enhances the already tranquil setting. The cul-de-sac location maximizes the already private location. An owned photovoltaic system with a net metering agreement adds energy efficiency. Just minutes from Kailua’s beaches, shopping, and dining, this home offers elevated island living in one of Oahu’s most desirable neighborhoods.

1110 Ilikala Place, 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.