Kalaheo Hillside Homes with Garage Parking Features

Welcome to Kalaheo Hillside, a hidden gem nestled in the picturesque town of Kailua, Oahu. This charming neighborhood is known for its stunning views, lush landscapes, and a welcoming community that embodies the spirit of island living. With the majestic Ko'olau Mountains as a backdrop and the sparkling Pacific Ocean just a stone's throw away, Kalaheo Hillside offers residents a tranquil escape while still being close to the vibrant amenities of Kailua.

One of the standout features of this neighborhood is the array of beautiful homes, many of which come equipped with convenient garage parking. This thoughtful inclusion not only provides protection for your vehicle from the elements but also adds an extra layer of security and ease for busy families and professionals alike. Imagine coming home after a long day and pulling into your private garage, ready to unwind in your serene oasis.

Kalaheo Hillside is perfect for those who appreciate outdoor living, with nearby hiking trails, beaches, and parks that invite you to explore the natural beauty of Oahu. The community also boasts a selection of local shops, cafes, and restaurants, allowing residents to indulge in the island's culinary delights without venturing far from home.

Whether you’re a first-time homebuyer or looking to invest in a slice of paradise, Kalaheo Hillside offers a unique blend of comfort, convenience, and breathtaking scenery. Discover your dream home in this enchanting neighborhood, where the spirit of aloha awaits!

Newest Kalaheo Hillside Homes with Garage Parking Features

$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

$1,590,000

3 Beds ⋅ 2 Baths ⋅ 202614057 MLS ⋅ FS - Fee Simple Tenure ⋅ 21 DOM

Welcome home to this spacious three-bedroom, two-bathroom residence in the highly sought-after Kalaheo Hillside. Freshly painted along with other upgrades throughout, this Kailua home offers a seamless blend of modern comfort and island charm. The open-concept interior is designed for indoor-outdoor living, leading you towards the large, flat fully-enclosed backyard oasis framed by lush tropical landscaping—a perfect backdrop for weekend gatherings or quiet afternoons in the sun. Situated just a short walk Castles Beach and the convenience of Aikahi Shopping Center, this location puts everything Kailua has to offer at your fingertips. Located within the Aikahi school district and just minutes to the vibrant dining and boutique shopping of Kailua town, this property captures the relaxed, active lifestyle you’ve been looking for.

923 Mokapu Boulevard, Kailua

$1,875,000

3 Beds ⋅ 3 Baths ⋅ 202609716 MLS ⋅ FS - Fee Simple Tenure ⋅ 74 DOM

Nestled within one of Kailua’s favorite neighborhoods, Kalaheo Hillside, 315 Iliaina Street is filled with potential and island charm. The property includes two separate structures --- a cute, detached cottage studio with a full bath and kitchenette, plus a classic home offering 3 bedrooms, 2 full baths, a great open floor plan, and a separate dining area with large windows looking out to the backyard. Much of the home remains in its original condition, including beautiful koa kitchen cabinet doors that could shine again with restoration. The spacious yard features a large in-ground pool and plenty of room to reimagine the outdoor spaces! Just minutes from Aikahi Shopping Center, Aikahi Elementary School, Kailua’s beaches, shopping, dining opportunities, markets, and so much more! Also close to MCBH Kaneohe, H-3, and Likelike Highway access, this property combines location, flexibility, and opportunity in one of Kailua’s most convenient neighborhoods. Split ACs in each room. PV panels on net metering.

315 Iliaina Street, Kailua

$3,880,000

3 Beds ⋅ 3 Baths ⋅ 202605289 MLS ⋅ FS - Fee Simple Tenure ⋅ 146 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.