Diamond Head Homes with Cul-De-Sac Lot Features

Welcome to Diamond Head, one of Honolulu's most sought-after neighborhoods, where breathtaking views meet a vibrant community spirit. Nestled on the southeastern coast of Oahu, this iconic area is renowned for its stunning volcanic crater, picturesque beaches, and lush landscapes. With a rich blend of natural beauty and urban convenience, Diamond Head offers residents an unparalleled lifestyle.

As you explore the charming streets of Diamond Head, you'll discover a variety of homes that cater to diverse tastes and preferences. Among the most desirable features are properties situated on serene cul-de-sacs, providing a peaceful retreat from the hustle and bustle of city life. These cul-de-sac homes not only offer added privacy and reduced traffic but also foster a sense of community, making them perfect for families and those seeking a tranquil living environment.

The neighborhood boasts easy access to world-class amenities, including trendy cafes, boutique shops, and the iconic Diamond Head State Monument, where outdoor enthusiasts can hike to panoramic vistas that showcase the beauty of the Pacific Ocean. Additionally, with nearby beaches like Kaimana and Sans Souci, residents can enjoy sun-soaked days and vibrant sunsets just moments from their doorstep.

Living in Diamond Head means embracing a lifestyle that combines luxury, leisure, and a strong sense of community. Whether you're sipping coffee on your porch or taking a leisurely stroll through the neighborhood, you'll find that this enchanting area truly feels like home. Discover the charm of Diamond Head and explore the inviting cul-de-sac homes that await you in this tropical paradise!

Newest Diamond Head Homes with Cul-De-Sac Lot Features

$17,500,000

5 Beds ⋅ 7 Baths ⋅ 202609193 MLS ⋅ FS - Fee Simple Tenure ⋅ 95 DOM

This magnificent Diamond Head “Cove Area” beachfront masterpiece harmoniously fuses traditional Hawaiian architectural elements with an open modern lifestyle floorplan. Located on a quiet lane off Diamond Head Road, this home is truly a treasure to behold. The grand reception areas lead out to extensive wraparound lanai areas, a covered grill space, and a beachside seating area—perfect for enjoying sunsets and drinks while taking in the endless views of the Pacific Ocean. The upper level boasts a large primary ocean view bedroom, two additional en-suite bedrooms, elevator, gas generator and an unmatched office with ocean views that you’ll never want to leave. Refreshing pool, lush private landscaping, and unmatched location, style, comfort, and distinction define this Diamond Head gem.

218 Kaalawai Place, Honolulu

$5,990,000

4 Beds ⋅ 6 Baths ⋅ 202604465 MLS ⋅ FS - Fee Simple Tenure ⋅ 130 DOM

Experience refined island luxury living in this executive-style 4-bedroom, 5.5-bath residence ideally positioned on the slopes of iconic Diamond Head. Encompassing nearly 5,900 sq ft of interior space on an 11,752 sq ft lot, this impressive home captures beautiful ocean and sunset views while offering exceptional indoor-outdoor living. Expansive lanai areas, complemented by a heated pool and spa, create a private retreat designed for effortless entertaining. Soaring ceilings enhance the home’s grand scale and invite abundant natural light throughout. The chef’s kitchen anchors the main living spaces, while separate guest quarters with a private entrance provide flexibility and privacy. Remodeled by Jeff Long in 1995, this distinguished property blends timeless design with a premier location just moments from Kapiolani Park, the Gold Coast, world-famous beaches, and renowned shopping and dining of Waikiki. A rare offering in one of Honolulu’s most prestigious neighborhoods.

2999 Makalei Place, Honolulu

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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.