Hillcrest Homes for Sale

Welcome to Hillcrest, an enchanting neighborhood nestled in the heart of Kailua, Oahu, where the beauty of island living meets a vibrant community spirit. Known for its stunning landscapes and friendly atmosphere, Hillcrest offers residents a perfect blend of tranquility and convenience. This charming enclave is surrounded by lush greenery and breathtaking mountain views, making it an ideal retreat for those seeking a serene lifestyle without sacrificing access to modern amenities.

In Hillcrest, you’ll find a diverse selection of homes for sale that cater to various tastes and budgets. From cozy single-family residences to spacious modern designs, each property reflects the unique character of the neighborhood. Many homes boast expansive yards, perfect for outdoor gatherings or simply soaking in the sun, while others feature contemporary upgrades that blend comfort with style. With a strong sense of community, neighbors often come together for local events and activities, fostering connections that make Hillcrest feel like home.

Living in Hillcrest means enjoying the best of Kailua's offerings—from pristine beaches just a short drive away to a variety of shopping and dining options that cater to every palate. Families will appreciate the proximity to highly-rated schools and parks, while outdoor enthusiasts can explore nearby hiking trails and water sports.

If you're looking for a place that combines the charm of island life with a welcoming community, Hillcrest is the perfect destination. Discover your dream home in this idyllic neighborhood today!

Newest Hillcrest Homes for Sale

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 202614621 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 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 ⋅ 45 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.