Kalaheo Hillside Homes with Waterfront Frontage

Welcome to Kalaheo Hillside, a picturesque neighborhood nestled in the heart of Kailua on the stunning island of Oahu, Hawaii. This charming community is renowned for its breathtaking views, lush landscapes, and a laid-back lifestyle that perfectly embodies the spirit of island living. With its elevated position, residents of Kalaheo Hillside enjoy panoramic vistas of the sparkling Pacific Ocean, the majestic Ko’olau Mountains, and the vibrant greenery that surrounds them.

One of the standout features of this neighborhood is its proximity to the pristine beaches that Kailua is famous for. Just a short drive away, you’ll find the soft sands and turquoise waters of Kailua Beach and Lanikai Beach, perfect for sunbathing, swimming, and water sports. For those who appreciate the serenity of nature, the nearby hiking trails offer a chance to explore the island’s stunning landscapes while taking in the fresh, salty air.

Homes in Kalaheo Hillside often boast waterfront frontage, providing direct access to the serene waters and creating a tranquil atmosphere for residents. Imagine waking up each day to the sound of gentle waves lapping at the shore, with the ocean just steps away from your doorstep. These properties are not just homes; they are a lifestyle, offering a unique blend of comfort, luxury, and the natural beauty of Hawaii.

With a strong sense of community and a variety of amenities nearby, including shops, restaurants, and parks, Kalaheo Hillside is the perfect place to call home. Whether you’re looking for a family-friendly neighborhood or a serene retreat, this enchanting area has something for everyone. Experience the magic of island living in Kalaheo Hillside—where every day feels like a vacation.

Newest Kalaheo Hillside Homes with Waterfront Frontage

$3,880,000

3 Beds ⋅ 3 Baths ⋅ 202605289 MLS ⋅ FS - Fee Simple Tenure ⋅ 142 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.