Kalaheo Hillside Homes with Other Frontage

Welcome to Kalaheo Hillside, a hidden gem nestled in the enchanting town of Kailua on the beautiful island of Oahu, Hawaii. This picturesque neighborhood offers a unique blend of tranquility and vibrant island life, making it an ideal place for families, retirees, and anyone seeking a slice of paradise.

Kalaheo Hillside is characterized by its lush landscapes, sweeping ocean views, and a friendly community atmosphere. The neighborhood is known for its diverse range of homes, many of which feature other types of frontage, providing a unique opportunity for homeowners to enjoy a variety of scenic vistas. Whether you prefer a home that overlooks the verdant hills or one that captures the stunning coastline, Kalaheo Hillside has something for everyone.

Residents here enjoy easy access to Kailua's pristine beaches, renowned for their soft white sands and crystal-clear waters. Spend your days basking in the sun, swimming, or partaking in thrilling water sports. The nearby Lanikai Beach, often voted as one of the best beaches in the world, is just a short drive away, inviting you to explore its breathtaking beauty.

Kalaheo Hillside is also conveniently located near local shops, restaurants, and parks, making it easy to indulge in the vibrant lifestyle that Kailua has to offer. With a strong sense of community, friendly neighbors, and a wealth of outdoor recreational activities, Kalaheo Hillside is not just a place to live—it's a place to thrive. Come discover your dream home in this idyllic neighborhood, where the spirit of aloha truly comes alive!

Newest Kalaheo Hillside Homes with Other Frontage

$2,185,000

4 Beds ⋅ 3 Baths ⋅ 202614657 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 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

$2,300,000

4 Beds ⋅ 3 Baths ⋅ 202611972 MLS ⋅ FS - Fee Simple Tenure ⋅ 45 DOM

Tucked onto one of Kalaheo Hillside's most sought-after streets, 445 Iliwahi Loop is a fully reimagined 4-bed, 3-bath retreat blending timeless island architecture with a clean, considered renovation — vaulted ceilings, an open great room flowing to covered lanais, and walls of glass framing the pool, gardens and fountains. This generous lot sits against the conservation hillside adding to the peace and quiet of this location. The chef's kitchen pairs a Viking range and Sub-Zero refrigeration w/a generous island open to the dining & living areas. Two primary suites suit multigenerational living or a guest wing, the spa-inspired primary bath w/a soaking tub and oversized shower. Two additional bedrooms w/shared bath PLUS 2 office/flex rooms Outside is your own resort: a sparkling pool (plus spa hookup), mature landscaping, a garden gazebo and covered lanai seating for golden-hour gatherings. NEM metering, 2 Tesla Powerwalls, + a new GACO roof! Freshly painted inside & out, new flooring, lighting & fans throughout. Minutes to Kailua Beach, a short hop to Marine Corps Base Hawaii, and moments from H-3, Pali and Likelike — with Aikahi Shopping Center and dining close at hand.

445 Iliwahi Loop, 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.