Hillcrest Homes with Fee Simple Land tenure

Welcome to Hillcrest, a hidden gem nestled within the beautiful city of Kailua on Oahu, Hawaii. This enchanting neighborhood is renowned for its tranquil atmosphere and stunning natural beauty, making it a perfect haven for families, retirees, and anyone seeking a slice of paradise. Hillcrest boasts a unique blend of lush landscapes, friendly neighbors, and a strong sense of community, all while being just a stone's throw away from the pristine beaches that Kailua is famous for.

The homes in Hillcrest are characterized by their charming architecture and spacious layouts, offering a perfect balance of comfort and style. One of the standout features of this neighborhood is the availability of Fee Simple land tenure, which means homeowners have full ownership of their property, providing peace of mind and long-term investment potential. Whether you’re looking for a cozy single-family home or a modern townhouse, Hillcrest has something to suit every taste and budget.

Residents of Hillcrest enjoy easy access to a variety of local amenities, including quaint shops, delightful eateries, and vibrant community parks. The nearby Kailua Beach, with its soft sands and turquoise waters, is perfect for sunbathing, surfing, and paddleboarding, making every day feel like a vacation.

If you’re searching for a welcoming community with a laid-back lifestyle and breathtaking surroundings, Hillcrest in Kailua is the ideal place to call home. Discover the charm of this neighborhood and experience the best of island living!

Newest Hillcrest Homes with Fee Simple Land tenure

$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

Start Your Search

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.