Diamond Head Homes with Canal Frontage

Welcome to Diamond Head, one of the most iconic and picturesque neighborhoods in Honolulu, Hawaii. Nestled on the southeastern coast of Oahu, this vibrant community is renowned for its breathtaking views, stunning beaches, and rich cultural heritage. The majestic Diamond Head crater stands as a sentinel over the area, providing a stunning backdrop for outdoor enthusiasts and nature lovers alike. With its proximity to world-famous beaches and lush hiking trails, residents enjoy an active lifestyle amidst the natural beauty of the Hawaiian landscape.

One of the most appealing features of Diamond Head is the availability of homes with canal frontage. Imagine waking up to the gentle sounds of water lapping against the shore, with the sun glistening on the surface of the canal. These properties offer not only a unique waterfront living experience but also a rare opportunity to embrace the tranquil lifestyle that Hawaii is known for. Canal-front homes provide direct access to serene waterways, perfect for kayaking, paddleboarding, or simply enjoying the view from your private lanai.

The neighborhood boasts a rich blend of historic charm and modern conveniences, with a variety of dining, shopping, and entertainment options just a stone's throw away. Whether you're looking for a cozy bungalow or a luxurious estate, Diamond Head's real estate market caters to diverse tastes and lifestyles.

Discover the allure of Diamond Head and experience the perfect blend of natural beauty and vibrant community life. Your dream home awaits in this Hawaiian paradise!

Newest Diamond Head Homes with Canal Frontage

$1,699,000

202615208 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

Discover an incredible multi-dwelling opportunity nestled in the scenic Kuliouou Valley. This spacious parcel is situated at the end of a quiet street and features an original house alongside a permitted duplex. The duplex boasts 5 bedrooms, 3 bathrooms, and two kitchens, with separate entrances for each level, along with an internal staircase connecting them. Renovated in 2025, the duplex has been vacant and is ready for new occupants. Each unit includes its own electric and water meters, as well as a washer, dryer, carports, and front and back yards, offering ample open space. Conveniently located near shopping centers in Hawaii Kai and Koko Marina, as well as schools and medical facilities, this property is a must-see. Schedule your viewing today! Please note that the front house is the original structure and requires significant repairs or may need to be torn down. The property is being sold as-is.

6163 Kawekiu Place, Honolulu

$675,000

3 Beds ⋅ 2 Baths ⋅ 202611462 MLS ⋅ FS - Fee Simple Tenure ⋅ 14 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 ⋅ 32 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

$1,350,000

5 Beds ⋅ 3 Baths ⋅ 202607891 MLS ⋅ FS - Fee Simple Tenure ⋅ 127 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.