Kailua Homes with Penthouse Style

Welcome to Kailua, Hawaii, a picturesque paradise nestled on the eastern coast of Oahu. Known for its stunning beaches, vibrant community, and lush landscapes, Kailua offers a unique blend of relaxation and adventure. With the majestic Koolau Mountains as a backdrop and the sparkling waters of Kailua Bay at your doorstep, this charming town is a haven for outdoor enthusiasts and those seeking a tranquil lifestyle.

Kailua is not just about breathtaking views; it boasts a rich cultural scene, with local boutiques, farmers' markets, and delightful eateries that celebrate the flavors of Hawaii. The warm, welcoming community is perfect for families, retirees, and anyone looking to embrace the Aloha spirit. With its ideal climate, residents enjoy year-round outdoor activities, from paddleboarding and kayaking to hiking and biking along scenic trails.

For those seeking a touch of luxury, Kailua features exquisite homes with penthouse-style living. Imagine waking up to panoramic ocean views, enjoying sunsets from your private terrace, and indulging in spacious, elegantly designed interiors. These homes often come equipped with modern amenities, high-end finishes, and expansive living spaces that cater to both relaxation and entertaining. Whether you’re sipping coffee while gazing at the turquoise waters or hosting a sunset gathering with friends, a penthouse-style home in Kailua elevates everyday living to a new level of sophistication.

Discover the magic of Kailua, where the beauty of nature meets the comforts of home, and let your dreams of coastal living come true in this enchanting Hawaiian paradise.

Newest Kailua Homes with Penthouse Style

$645,000

1 Beds ⋅ 1 Baths ⋅ 202614387 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 DOM ⋅ Windward Passage BLDG.

Rarely available prestigious penthouse unit at the top of Windward Passage! Floor to ceiling windows open to a panoramic view out over Enchanted Lake & down the majestic Koolau Mountain range. You can even enjoy the colors of the sunset as the sun sinks below the mountains in the evenings. The whole apartment opens to the view, and all that window space gives you a bright airy open feel that makes the unit seem even larger than it is. The kitchen & bathroom have been upgraded. The bathroom renovation included replacing the tub with a full-size shower & brand-new vinyl plank flooring was just installed throughout. Everything is ready for you to move in & enjoy! Add to this the resort style amenities that Windward Passage has to offer including tennis courts, pickleball, a racquetball court, swimming pool, whirlpool, BBQ areas, dog park, fitness center with saunas, storage areas for surfboards & bicycles & additional storage for each unit. Plus, a can't beat location right in Kailua Town with easy access to shopping, restaurants, the open markets and so much more with Kailua Beach just moments away. What more could you ask for? This is just what you've been waiting for!

322 Aoloa Street Unit PH8, Kailua

$925,000

3 Beds ⋅ 2 Baths ⋅ 202608120 MLS ⋅ FS - Fee Simple Tenure ⋅ 72 DOM ⋅ Windward Harbour BLDG.

Wake up to breathtaking mountain views and end your day on your own private rooftop lanai. This rare, 3-bedroom 2-bathroom gem at Windward Harbor blends modern Kailua elegance with resort-style amenities. This is island living at its finest. From the floor-to-ceiling windows that bathe the open-concept of indoor and outdoor living space with a screened in lanai to enjoy the tropical water features and landscapes. The Primary Suite is located downstairs with a large walk in closet and shower and two bedrooms plus full bathroom upstairs. Enjoy two covered side by side parking right at the walk way for easy entry. Conveniently located in the heart of Kailua Beach Town, Whether you're strolling to Kailua Town for your morning coffee or hitting the sands of world-famous Kailua Beach, this isn't just a condo—it’s your personal sanctuary. Gated Community with amenities including an on-site manager, pool, jacuzzi, sauna, BBQ, car wash, Pickleball and Tennis courts. This is a pet-friendly building!

1030 Aoloa Place Unit 2/302B, 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.