Hillcrest Homes for Sale

Welcome to Hillcrest, a hidden gem nestled in the heart of Kailua, Oahu. This enchanting neighborhood offers a unique blend of serene island living and vibrant community spirit, making it the perfect place to call home. Hillcrest is characterized by its lush landscapes, friendly neighbors, and a strong sense of community, making it ideal for families, retirees, and everyone in between.

The charm of Hillcrest lies not only in its picturesque surroundings but also in its proximity to some of Oahu's most stunning beaches and outdoor activities. Just a short drive away, you’ll find the pristine sands of Kailua Beach and Lanikai Beach, perfect for sunbathing, swimming, and water sports. For those who enjoy hiking, the nearby Olomana Trail offers breathtaking views of the island and is a favorite among locals.

When it comes to homes for sale in Hillcrest, you'll discover a diverse range of properties that cater to various lifestyles and budgets. From cozy single-family homes with tropical gardens to spacious modern residences with ocean views, there’s something for everyone. Many homes feature open floor plans, updated amenities, and outdoor spaces perfect for entertaining or enjoying the gentle island breezes.

Living in Hillcrest means embracing a relaxed lifestyle while still being close to Kailua’s vibrant town center, which boasts an array of shops, cafes, and restaurants. With a strong sense of community and a laid-back atmosphere, Hillcrest is not just a neighborhood; it's a place where memories are made and cherished. Come explore the homes for sale in Hillcrest and discover your own slice of paradise in Oahu!

Newest Hillcrest Homes for Sale

$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.