Kalaheo Hillside Homes with Garden View

Welcome to Kalaheo Hillside, a hidden gem nestled in the heart of Kailua, Oahu. This charming neighborhood is a paradise for those seeking a serene lifestyle, surrounded by breathtaking natural beauty. With its lush landscapes and stunning views, Kalaheo Hillside offers a unique blend of tranquility and convenience, making it the perfect place to call home.

As you explore this picturesque community, you’ll be captivated by the vibrant gardens that adorn many of the homes, creating a delightful ambiance that invites relaxation and outdoor enjoyment. Imagine waking up every morning to the gentle rustle of leaves and the sweet scent of blooming flowers right outside your window. Homes with garden views in Kalaheo Hillside are not just residences; they are sanctuaries that foster a deep connection with nature.

The neighborhood is renowned for its friendly atmosphere, where neighbors become friends and community events bring everyone together. Families will appreciate the proximity to top-rated schools and parks, while outdoor enthusiasts will revel in the nearby hiking trails and stunning beaches just a short drive away.

Kalaheo Hillside is more than just a place to live; it’s a lifestyle choice that embraces the beauty of island living. Whether you’re sipping coffee on your lanai while soaking in the garden views or enjoying a sunset stroll through the neighborhood, you’ll find that life here is simply enchanting. Discover the magic of Kalaheo Hillside, where every day feels like a vacation in paradise.

Newest Kalaheo Hillside Homes with Garden View

$2,185,000

4 Beds ⋅ 3 Baths ⋅ 202614657 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 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 ⋅ 49 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

Start Your Search

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.