Kalaheo Hillside Homes with Three or more Spaces Parking Features

Welcome to Kalaheo Hillside, a hidden gem nestled in the heart of Kailua, Oahu. This picturesque neighborhood is renowned for its stunning views, lush landscapes, and a sense of community that makes it truly special. With its close proximity to the pristine beaches of Kailua and Lanikai, residents enjoy easy access to some of the best sun, sand, and surf that Hawaii has to offer.

Kalaheo Hillside is characterized by its charming homes, many of which boast three or more parking spaces—an invaluable feature in this popular area. Whether you're a family with multiple vehicles or an outdoor enthusiast needing space for your gear, these homes provide the convenience and flexibility you desire.

As you stroll through the neighborhood, you’ll find beautifully landscaped yards, friendly neighbors, and a welcoming atmosphere that encourages outdoor living. The area is perfect for families, retirees, and anyone looking to embrace the laid-back Hawaiian lifestyle. Local parks and hiking trails are just a stone's throw away, offering endless opportunities for recreation and relaxation.

Kalaheo Hillside is also conveniently located near top-rated schools, shopping centers, and dining options, making it an ideal place for those seeking both tranquility and convenience. With its unique blend of community spirit, natural beauty, and practical amenities, Kalaheo Hillside is not just a place to live—it’s a place to thrive. Discover your dream home in this enchanting neighborhood and experience the best of Kailua living!

Newest Kalaheo Hillside Homes with Three or more Spaces 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

$1,690,000

4 Beds ⋅ 3 Baths ⋅ 202614340 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 DOM

Experience elevated island living in this fully remodeled, single-level home in the heart of Kailua. Renovated from top to bottom, this property feels virtually new and offers the perfect blend of modern design and everyday comfort. The home features a 3-bedroom, 2-bath main residence plus a connected 1-bedroom, 1-bath suite with a kitchenette, providing exceptional flexibility for extended family, guests, a home office, or potential rental income. Inside, a bright open-concept floor plan seamlessly connects the kitchen, living, and dining areas, creating an inviting space for both entertaining and daily living. The bedrooms feature premium DuChâteau hardwood flooring, adding warmth and an elegant finish throughout. A thoughtfully designed hidden laundry room enhances functionality while maintaining clean lines and a spacious feel. Outside, enjoy a fully fenced, oversized backyard—perfect for entertaining, pets, or relaxing in your own private retreat—along with a generous front yard that enhances the home's curb appeal. Turnkey and move-in ready, this exceptional property offers modern island living in one of Oahu's most desirable beach communities.

1225 Mokapu Boulevard, 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

$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

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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.