Diamond Head Homes with Canal Frontage

Welcome to Diamond Head, a breathtaking enclave nestled on the southeastern coast of Oahu, Hawaii. Renowned for its iconic volcanic crater, this vibrant community offers a unique blend of natural beauty, rich history, and modern convenience. With its stunning views of the Pacific Ocean and lush landscapes, Diamond Head is a haven for outdoor enthusiasts and those seeking a serene lifestyle.

One of the most captivating features of Diamond Head is its charming homes with canal frontage. Imagine waking up each day to the gentle sounds of water lapping at your doorstep, surrounded by swaying palms and vibrant tropical gardens. These properties provide not only a picturesque view but also direct access to the tranquil canals, perfect for kayaking, paddleboarding, or simply enjoying a peaceful afternoon by the water.

The homes in this area reflect a diverse architectural style, from classic Hawaiian bungalows to modern luxury estates, each blending seamlessly with the stunning natural surroundings. Residents enjoy a tight-knit community atmosphere, complemented by nearby amenities such as boutique shops, delightful eateries, and stunning beaches. The famous Diamond Head State Monument is just a stone's throw away, offering hiking trails that reward adventurers with panoramic views of the island.

Living in Diamond Head means embracing a lifestyle characterized by relaxation, recreation, and connection to nature. Whether you’re sipping coffee on your canal-front deck or exploring the vibrant local culture, this enchanting region invites you to experience the true essence of Hawaiian living. Discover your dream home in Diamond Head and immerse yourself in the beauty of island life!

Newest Diamond Head Homes with Canal Frontage

$675,000

3 Beds ⋅ 2 Baths ⋅ 202611462 MLS ⋅ FS - Fee Simple Tenure ⋅ 9 DOM ⋅ Regency Park BLDG.

Welcome to Regency Park! Motivated and ready to sell this rarely available 3 bedroom 2 bath home with over 1200 sq ft of living with treetop views of the canal in the preferred Makai side of building! Unit offers comfort, value and convenience in one of Honolulu's most central locations. Freshly painted, with brand new carpeting in all the bedrooms, and includes two assigned covered parking stalls. Residents enjoy an array of amenities including a swimming pool, recreation room, tennis & pickleball courts, fitness center, private 2-acre park with basketball courts, bbq area and disc golf, onsite manager, 20 guest stalls and 24-hour security. Regency park is located near Waialae avenue restaurants and cafes, supermarkets, boutique shops and freeway access. This home is just minutes from University of Hawaii and walking distance to Chaminade University and Saint Louis School, making it an excellent opportunity for homeowners and investors alike. Building is pet-friendly, buyer to do their own due diligence to confirm the buildings pet policy. Competitively priced and offering exceptional value for the location and amenities, this is an opportunity you won't want to miss!

3138 Waialae Avenue Unit 226, Honolulu

$675,000

2 Beds ⋅ 2 Baths ⋅ 202614239 MLS ⋅ FS - Fee Simple Tenure ⋅ 27 DOM ⋅ Regency Park BLDG.

Rarely available condo with private yard/garden area- an uncommon find in Honolulu condo living! Pet-friendly 2-bed, 2-full-bath w/2 covered parking. Split a/c, and a beautifully renovated kitchen w/Quartz countertops, stainless-steel appliances, abundant cabinetry, and generous workspace. The unit opens directly to its own enclosed green space, complete with low-maintenance synthetic lawn, tropical landscaping, a sprinkler system, gardening storage, & a dedicated surfboard rack. Whether relaxing outdoors, entertaining friends, gardening, or creating a peaceful retreat for pets, this unique space offers the feel of a home with the ease of condominium living. Gated entry, known for its expansive park-like grounds and impressive amenities, including a private two-acre park, swimming pool, tennis & basketball courts, fitness center, rec room, BBQ and picnic areas, walking paths, pet area, guest parking, and 24-hour security. Conveniently located near Kaimuki’s popular restaurants, cafés, shopping, schools, & everyday conveniences. Near UH & Chaminade, easy access to Waikiki & H-1. Rare opportunity combining privacy, outdoor space, excellent amenities, and a central Honolulu location.

3138 Waialae Avenue Unit 109, Honolulu

$508,000

2 Beds ⋅ 2 Baths ⋅ 202611469 MLS ⋅ FS - Fee Simple Tenure ⋅ 68 DOM ⋅ Regency Park BLDG.

Welcome to Regency Park! This fee simple 2-bedroom, 2-bathroom high-rise unit offers 802 sq ft of interior living space plus 129 sq ft of lanai/patio area—perfect for indoor-outdoor island living. Situated on the 9th floor, this unit features a panoramic city skyline view and beautiful sunset views and bonus views of the Waikiki Friday night fireworks. Amenities include a swimming pool, tennis court, volleyball/basketball court, party room, exercise gym and a private 2-acre park with picnic areas. 2 parking stalls are attached to the property plus 20 plus guest parking stalls. Regency Park is conveniently located in the vibrant Kaimuki area featuring nearby shopping and dining AND Waikiki. Recent renovations include an open kitchen, easy care flooring, remodeled bathrooms with the primary bathroom featuring a walk-in shower. The living room lanai features automated aluminum shades plus split AC in the bedrooms and window mount ac in the living room.

3138 Waialae Avenue Unit 904, Honolulu

$1,350,000

5 Beds ⋅ 3 Baths ⋅ 202607891 MLS ⋅ FS - Fee Simple Tenure ⋅ 122 DOM

Attention investors and buyers looking for a great opportunity: this five-bedroom, two-and-a-half-bath home in Aina Haina offers incredible potential. The property includes an attached 2-bedroom, 1-bath ‘ohana unit that is in good condition—ideal for multi-generational living or rental income. The main home requires extensive remodeling, with the entire interior ready for a full update—perfect for buyers looking to build equity or create a home tailored to their family’s lifestyle.

523 Kiholo Street, 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.