Hillcrest Real Estate

Welcome to Hillcrest, a charming neighborhood nestled in the heart of Kailua, Oahu! This idyllic community is a hidden gem that perfectly blends the beauty of nature with a vibrant, laid-back lifestyle. Known for its lush landscapes and friendly atmosphere, Hillcrest offers residents a unique island experience that is both serene and inviting.

One of the standout features of Hillcrest is its stunning views of the Koʻolau Mountains, which serve as a picturesque backdrop for daily life. The neighborhood is characterized by its well-maintained homes, many of which boast spacious yards and tropical gardens, creating a peaceful retreat just minutes from the beach. Residents enjoy easy access to Kailua’s pristine shores, where you can soak up the sun, take part in water sports, or simply relax with a good book.

Hillcrest is also conveniently located near a variety of local shops, restaurants, and parks, making it easy to enjoy everything Kailua has to offer. Whether you're grabbing a morning coffee at a local café or exploring the vibrant farmers' market, you’ll find that the community fosters a strong sense of connection among its residents.

Families will appreciate the excellent schools in the area, along with numerous recreational activities available for all ages. From hiking trails to community events, there’s always something happening in Hillcrest.

In summary, Hillcrest is more than just a neighborhood; it's a lifestyle. With its stunning natural beauty, welcoming community, and convenient amenities, it’s the perfect place to call home in Kailua, Oahu. Come discover the magic of Hillcrest and experience island living at its finest!

Newest Listings in Hillcrest

$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.