Kalaheo Hillside Homes with Other Frontage

Welcome to Kalaheo Hillside, a hidden gem nestled in the picturesque town of Kailua on the beautiful island of Oahu, Hawaii. This enchanting neighborhood boasts stunning views of the Ko'olau Mountains and the azure waters of the Pacific Ocean, making it a paradise for nature lovers and outdoor enthusiasts alike.

Kalaheo Hillside is known for its tranquil atmosphere, where lush greenery and tropical landscapes create a serene backdrop for your dream home. With a mix of charming single-family residences and modern architectural designs, the homes in this area cater to a variety of tastes and lifestyles. Many properties feature unique frontages, allowing for creative landscaping and inviting curb appeal that reflects the spirit of island living.

The community is characterized by its friendly neighbors and a strong sense of camaraderie. Residents enjoy easy access to Kailua's vibrant town center, where you can find an array of local shops, delightful cafes, and mouthwatering dining options. The nearby beaches, such as Lanikai and Kailua Beach, are perfect for sunbathing, swimming, and water sports, offering endless opportunities for relaxation and adventure.

Families will appreciate the highly-rated schools in the area, as well as the numerous parks and recreational facilities that promote an active lifestyle. Whether you're looking to hike the nearby trails, paddleboard in the calm waters, or simply enjoy a sunset stroll along the beach, Kalaheo Hillside offers the perfect blend of tranquility and excitement.

Discover your slice of paradise in Kalaheo Hillside, where every day feels like a vacation in this idyllic Oahu neighborhood.

Newest Kalaheo Hillside Homes with Other Frontage

$2,185,000

4 Beds ⋅ 3 Baths ⋅ 202614657 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 DOM

This is the one you have been waiting for! This home, in the desirable Kalaheo Hillside neighborhood, is strategically positioned on a large 10,000 sq. ft. lot to allow the cool ocean breezes to flow through. Large front windows overlook a welcoming tropical garden. There’s something for everyone! A large gourmet kitchen, open floor plan, sparkling tiled pool, indoor laundry, attached garage with workshop area, 4 bedrooms and three full bathrooms. Included in the 4 bedrooms is a studio with private entrance, kitchen, washer/dryer and ensuite bathroom totally separate from the rest of the house! Room for all and great for multi-generational living or long-term rental income. Ideally located with close proximity to Aikahi elementary school, Kalaheo High School, Aikahi Shopping Center, Kaneohe Marine Corp Base, H-3, Kailua Beach and mere minutes from Kailua town. Outside, a shower is conveniently located for washing off the beach sand and toys. The grounds surrounding the house are filled with beautiful Hawaiian flora, green grass lawn and mango, avacado and starfruit trees. On a quiet night you can even hear the sound of the breaking waves!

361 Iliaina Street, 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.