Hillcrest Homes for Sale

Welcome to Hillcrest, a hidden gem nestled in the heart of Kailua, Oahu! This charming neighborhood is renowned for its lush landscapes, friendly community, and stunning views of the Ko'olau Mountains. With its serene atmosphere and close-knit feel, Hillcrest offers a perfect blend of tranquility and convenience, making it an ideal place to call home.

As you stroll through Hillcrest, you’ll be greeted by beautifully maintained streets lined with an array of homes that reflect the unique architectural styles of Hawaii. From cozy single-family residences to spacious modern homes, there’s something for everyone in this delightful community. Each property boasts easy access to Kailua's pristine beaches, vibrant shops, and delectable dining options, ensuring that all your needs are just a stone's throw away.

For those considering a move, there are a variety of homes for sale in Hillcrest, catering to different lifestyles and budgets. Whether you’re a first-time homebuyer or looking to upgrade, the real estate options here are as diverse as the residents themselves. Many homes feature open floor plans, expansive backyards, and eco-friendly amenities, perfect for enjoying the island’s beautiful weather year-round.

Living in Hillcrest means embracing the spirit of aloha, with friendly neighbors and a strong sense of community. Experience the joy of island living in a neighborhood that feels like home. Explore the homes for sale in Hillcrest today, and discover the perfect place to start your next chapter in paradise!

Newest Hillcrest Homes for Sale

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 202614621 MLS ⋅ FS - Fee Simple Tenure ⋅ 42 DOM

2.75% assumable loan, open to anyone. Veteran or not. That rate doesn’t exist today. Completely remodeled — 3x5 granite kitchen island, luxury vinyl plank throughout, split AC, double wall construction, leased PV on tile roof. 2 car garage. Minutes to Kailua Beach. From this house in Hillcrest, the views arrive at your windows. 180 degrees of Kailua, windward O'ahu, Enchanted Lake unobstructed from nearly every room. Sunrise over water, sunsets behind the Ko'olaus. Enjoy fruit trees and puakenikeni. Open the interior stairwell and it’s one home — 1,950 sq ft, 3 bed, 2.5 bath, primary on the main level overlooks the front garden, oversized closet, dedicated laundry. Leave it closed and the lower level stays a private one bed, one bath rental with its own entrance and lanai. The floor plan can change. The expansive views never will.

1312 Aupapaohe Street, Kailua

$2,450,000

4 Beds ⋅ 3 Baths ⋅ 202612934 MLS ⋅ FS - Fee Simple Tenure ⋅ 70 DOM

Live at the top of Keolu Summit in Hillcrest with 180 degree views of the Koolau mountains, Olomana peaks, Enchanted Lake, and Kailua Bay. A stunning viewscape captured from your wrap around lanais and large picture windows framed by high vaulted ceilings. The open layout of the home embraces the essence of Hawaiian living with modern finishings and covered ipe wood lanais offering you a variety of settings for entertaining and indoor/outdoor living. The main house provides a large primary bedroom with an en suite bath, a spacious second bedroom, and a third bedroom or office. The separate cottage with full bath and kitchenette has equally captivating views with a large lanai. The resort-like blue tiled pool with spa and water feature is surrounded by lush tropical landscaping providing beauty and privacy. Features an owned PV system, 2-car enclosed garage, and adjacent workshop/storage. There are 2 dedicated parking stalls along the private road for guests. This cul-de-sac location places you at the high point of the Summit bordered by conservation land. Minutes to the white sandy beaches of Kailua and Waimanalo and the trendy shops and restaurants of Kailua Town.

1461 Aunauna 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.