Hillcrest Homes with Fee Simple Land tenure

Welcome to Hillcrest, a hidden gem nestled in the picturesque town of Kailua on the stunning island of Oahu, Hawaii. This charming neighborhood is renowned for its lush landscapes, friendly community, and proximity to some of the most breathtaking beaches in the world. Hillcrest offers a unique blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone seeking a slice of paradise.

One of the standout features of Hillcrest is its array of homes with Fee Simple land tenure. This means homeowners enjoy full ownership of their property and the land it sits on, providing a sense of stability and investment that is hard to find elsewhere. The homes in Hillcrest are often characterized by their inviting designs, spacious yards, and stunning views of the surrounding mountains and ocean. Whether you’re looking for a cozy single-family home or a more expansive property, Hillcrest has something to suit every lifestyle.

The neighborhood is not just about beautiful homes; it’s also a vibrant community. Residents take pride in their friendly atmosphere, where neighbors become friends and community events bring everyone together. With nearby parks, excellent schools, and a variety of local shops and restaurants, Hillcrest provides all the amenities you need for a fulfilling lifestyle.

For those who love the outdoors, the nearby beaches offer endless opportunities for surfing, paddleboarding, and sunbathing, while the lush hiking trails promise adventure and stunning vistas. Discover the charm of Hillcrest, where every day feels like a vacation in paradise!

Newest Hillcrest Homes with Fee Simple Land tenure

$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

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.