Hillcrest Real Estate

Welcome to Hillcrest, a charming neighborhood nestled in the heart of Kailua, Oahu. Known for its tranquil ambiance and picturesque landscapes, Hillcrest offers a unique blend of island living and community spirit. With its lush greenery, stunning mountain views, and proximity to some of Hawaii's most beautiful beaches, this neighborhood is a haven for those seeking both relaxation and adventure.

Hillcrest is characterized by its friendly atmosphere, where neighbors know each other by name and community events foster a strong sense of belonging. The residential streets are lined with well-maintained homes, many featuring tropical gardens and outdoor spaces perfect for enjoying the island's year-round sunshine. Families and individuals alike are drawn to the area for its safe environment and welcoming vibe.

Convenience is at your doorstep in Hillcrest, with local shops, cafes, and restaurants just a short drive away. Enjoy a morning stroll to the nearby Kailua Town, where you can indulge in delicious local cuisine or browse unique boutiques. For outdoor enthusiasts, the neighborhood is ideally situated close to hiking trails, parks, and the stunning Kailua and Lanikai beaches, perfect for swimming, kayaking, or simply soaking up the sun.

Education is also a priority in Hillcrest, with access to reputable schools and community resources that support families. Whether you’re looking to raise a family, retire, or simply enjoy the beauty of island life, Hillcrest offers a slice of paradise that feels like home. Come and discover the charm of Hillcrest, where every day feels like a vacation!

Newest Listings in Hillcrest

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 202614621 MLS ⋅ FS - Fee Simple Tenure ⋅ 42 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 ⋅ 70 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.