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361 Iliaina Street, Kailua
$2,190,000
4 Beds ⋅ 3 Baths ⋅ 202614657 MLS ⋅ FS - Fee Simple Tenure ⋅ 45 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
923 Mokapu Boulevard, Kailua
$1,600,000
3 Beds ⋅ 2 Baths ⋅ 202614057 MLS ⋅ FS - Fee Simple Tenure ⋅ 35 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
445 Iliwahi Loop, Kailua
$2,310,000
4 Beds ⋅ 3 Baths ⋅ 202611972 MLS ⋅ FS - Fee Simple Tenure ⋅ 52 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
304 Ilimano Street, Kailua
$2,415,000
8 Beds ⋅ 5 Baths ⋅ 202603590 MLS ⋅ FS - Fee Simple Tenure ⋅ 130 DOM
Enjoy best of Kailua living, sunshine & breezes, in coveted Kalaheo Hillside. This multigenerational home offers a perfect harmony of connection and independence, designed for a lifestyle where everyone has a place to call their own. Unique side-by-side wings (6/3 and 2/2) provide separate private retreats for extended family or guests, with versatility. Rich wood floors in the living room and expansive primary suite create an atmosphere of warmth and modern elegance, with luxury vinyl plank and tile floors throughout the rest of the home. Enjoy a backyard oasis created for making memories, featuring a sparkling tiled pool and multiple covered and open lanais for golden hour gatherings or quiet tropical nights. Perched on a prominent corner lot, on a peaceful, friendly street, it’s just blocks from the soft sands of Kailua’s world-class beaches. With the convenience of Aikahi Shopping Center dining, shopping, coffee & banking, nearby MCBH facilities, desirable schools and parks, this is more than a house- it’s a lifestyle decision. You’ll appreciate options for seamless access to H-3, Kam, Likelike, and Pali highways for best commute possible. Bedroom count doesn’t match TMK.

304 Ilimano Street, Kailua
1142 Mokapu Boulevard, Kailua
$2,229,100
4 Beds ⋅ 4 Baths ⋅ 202606138 MLS ⋅ FS - Fee Simple Tenure ⋅ 52 DOM
Island luxury abounds in this newer-built single-family residence in Kailua. Very privately situated, and tucked behind a gated driveway, the CPR home welcomes you with expansive parking and 2+ car garage. Soaring ceilings and open entry foyer set the tone for a light-filled, spacious interior. The open-concept living area features built-in entertainment center and flows seamlessly to a covered lanai, where tranquil canal views and sunrise hues create a serene daily backdrop over the lush landscaping. A chef’s kitchen is appointed with quartz, high end appliances, gas, and a decked out indoor butler pantry/laundry area, perfect for entertaining and everyday living. Upstairs, the primary suite is a peaceful retreat with huge walk-in closet and a glass-enclosed shower, dual vanities. Two additional bedrooms, and hallway bath with tub. A separate downstairs bedroom suite with exterior access, full bath, and walk-in closet provides flexibility for guests, multigenerational living, or a private workspace. LVP flooring, quality craftsmanship and thoughtful design complete this exceptional opportunity to enjoy modern Kailua living indoor and out, your personal paradise.

1142 Mokapu Boulevard, Kailua

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.