Hillcrest Homes with Fee Simple Land tenure

Welcome to Hillcrest, a hidden gem nestled in the heart of Kailua, Oahu. This charming neighborhood is known for its serene atmosphere, lush landscapes, and a strong sense of community. Hillcrest offers a perfect blend of island living and suburban tranquility, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat in paradise.

One of the standout features of Hillcrest is its diverse array of homes, many of which come with Fee Simple land tenure. This means that homeowners in this delightful community enjoy complete ownership of their property, providing a sense of security and investment that is highly sought after in Hawaii. With well-maintained yards and inviting curb appeal, the homes here reflect the warm and welcoming spirit of the neighborhood.

Residents of Hillcrest take advantage of the area's natural beauty, with nearby beaches, parks, and hiking trails just a stone's throw away. The stunning Kailua Beach, known for its white sands and crystal-clear waters, is a short drive away, offering a perfect escape for sunbathing, swimming, and water sports. Additionally, the vibrant town center of Kailua is filled with local shops, dining options, and community events that foster a strong neighborhood bond.

Whether you're looking for a place to raise a family or a tranquil retreat to unwind, Hillcrest in Kailua offers a unique blend of comfort, community, and island charm. Come discover your dream home in this idyllic paradise, where every day feels like a vacation!

Newest Hillcrest Homes with Fee Simple Land tenure

$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.