Hillcrest Real Estate

Welcome to Hillcrest, a charming neighborhood nestled in the picturesque town of Kailua on the stunning island of Oahu, Hawaii. Known for its serene atmosphere and breathtaking natural beauty, Hillcrest offers residents a unique blend of suburban tranquility and vibrant island life.

As you stroll through the tree-lined streets of Hillcrest, you'll be captivated by the lush greenery and well-maintained homes that reflect the community's pride. The neighborhood is characterized by its friendly residents and a strong sense of community, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

One of Hillcrest's standout features is its proximity to some of Kailua's most beautiful beaches, including the renowned Kailua Beach Park and Lanikai Beach. These pristine stretches of sand are perfect for sunbathing, swimming, and water sports, providing endless opportunities for outdoor enjoyment. Additionally, the neighborhood is just a short drive from the scenic hiking trails of the Ko'olau Mountains, offering breathtaking views and adventures for nature enthusiasts.

Hillcrest is also conveniently located near a variety of local shops, restaurants, and cafes, where you can savor delicious Hawaiian cuisine and experience the island's vibrant culture. The Kailua town center, with its charming boutiques and farmer's market, is just a stone's throw away, making it easy to enjoy the best that the area has to offer.

Whether you're looking for a place to call home or a serene getaway, Hillcrest in Kailua is a hidden gem that promises a delightful island lifestyle filled with beauty, community, and adventure. Come experience the magic of Hillcrest – your paradise awaits!

Newest Listings in Hillcrest

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 202614621 MLS ⋅ FS - Fee Simple Tenure ⋅ 40 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 ⋅ 68 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.