Hillcrest Real Estate

Welcome to Hillcrest, a hidden gem nestled in the picturesque town of Kailua on the beautiful island of Oahu, Hawaii. Known for its serene ambiance and lush surroundings, Hillcrest offers a unique blend of tranquility and community spirit that makes it an ideal place to call home.

The neighborhood is characterized by its charming streets lined with swaying palm trees and vibrant tropical foliage. Residents enjoy a laid-back lifestyle, with easy access to some of the best beaches in the world, including the renowned Kailua Beach and Lanikai Beach. These pristine shores are perfect for sunbathing, swimming, and water sports, making every day feel like a vacation.

Hillcrest is also rich in outdoor activities, with numerous hiking trails and parks just a stone's throw away. The nearby Maunawili Trail offers breathtaking views of the Ko'olau Mountains and the lush landscape that defines this stunning area. Families appreciate the excellent local schools and community parks, which foster a friendly and welcoming environment for children to play and grow.

In addition to its natural beauty, Hillcrest boasts a vibrant local culture with charming shops and delectable dining options just a short drive away in downtown Kailua. From farm-to-table restaurants to cozy cafes, there's something to satisfy every palate.

Whether you're looking for a peaceful retreat or an active lifestyle, Hillcrest offers the perfect blend of both. Experience the warmth of this inviting community and discover why so many have chosen to make Hillcrest their home. Come and explore the beauty and charm of Hillcrest, where paradise meets community!

Newest Listings in Hillcrest

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 202614621 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 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 ⋅ 34 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.