Diamond Head Real Estate

Diamond Head Real Estate

Welcome to Diamond Head, one of the most iconic and picturesque neighborhoods in Honolulu, Hawaii. Nestled on the southeastern coast of Oahu, this stunning area is renowned for its breathtaking natural beauty, rich history, and vibrant community atmosphere. The centerpiece of Diamond Head is the majestic volcanic crater that rises 760 feet above sea level, offering panoramic views of the Pacific Ocean and the vibrant cityscape of Honolulu.

As a resident of Diamond Head, you’ll enjoy a unique blend of outdoor adventure and urban convenience. The area is a paradise for outdoor enthusiasts, with hiking trails that lead you to the summit of the crater, where you can witness mesmerizing sunrises and sunsets. The nearby beaches, such as Kaimana Beach and the famous Waikiki, provide endless opportunities for swimming, surfing, and sunbathing.

Beyond its natural wonders, Diamond Head is steeped in history. The area was once a military lookout and is now a designated National Natural Landmark, preserving its unique geological features. The charming residential neighborhoods are characterized by a mix of historic homes and modern condos, making it an attractive place for families, retirees, and professionals alike.

Culinary delights await you in Diamond Head, with a variety of local eateries that showcase the rich flavors of Hawaiian cuisine. From fresh poke bowls to delectable shave ice, there’s something to satisfy every palate.

With its stunning landscapes, vibrant culture, and welcoming community, Diamond Head is not just a place to live; it’s a lifestyle. Discover your dream home in this enchanting paradise and experience the magic of island living!

Newest Listings in Diamond Head

$1,180,000
3 Beds ⋅ 2 Baths ⋅ 202614454 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity in desirable Palolo Valley! This versatile home offers flexible living and convenient in-town access. The main level features 3 bedrooms (with hardwood floors throughout) and 1 full bath, while the finished lower level includes a spacious storage area with a half bath—ideal for a workshop, home office, hobby space, or extra storage. A studio-style suite with a full bath was created by expanding the former laundry area and includes a refrigerator with space for a potential induction cooktop. The addition was completed without building permits; buyers are advised to conduct their own due diligence regarding the improvements and permitted uses. The paved front yard accommodates 2 vehicles, plus a tandem 2-car carport. Enjoy outdoor laundry facilities, cooling trade winds, and a mature mango tree in the backyard. Conveniently located near Hapa Local Market & Grill, Kaimuki's popular cafés, restaurants, and boutiques, Kahala Mall, the University of Hawai?i at Manoa, Kapahulu, Waikiki, parks, schools, beaches, and convenient H-1 freeway access. Enjoy the best of island living just minutes from town. Move right in or update to match your personal style.

3279 HOANOHO Place, Honolulu

Listing courtesy of The Agency-Oahu.

$2,750,000
202613984 MLS ⋅ FS - Fee Simple Tenure
Build your legacy in the heart of Honolulu. Rarely does an opportunity like this become available. Set in Wilhelmina, this exceptional 13,246 sf vacant parcel offers breathtaking 180-degree views of Diamond Head, the Pacific Ocean, sparkling city lights, and unforgettable sunset vistas. This premier estate lot provides the perfect canvas for an exceptional custom estate. The generous lot size and favorable development potential allow for your dream lifestyle residence. The design allows for 3 -5 car garage plus, room for 6+ cars in the driveway A separate dwelling can also be built if desired. Conceptual plans and architectural renderings by local, award-winning architect Jim Schmit are available; the permitting process is underway. Buyers may obtain the plans and continue the process toward bringing this extraordinary vision to life. Enjoy a sought-after scenic island lifestyle that combines privacy, prestige, and convenience, just minutes from the vibrant dining, shopping, cafés, and beaches. This is a rare chance to secure a landmark property and build a legacy home. Includes TMKs 1-3-3-032-031-0001 and 1-3-3-032-031-0002.

3950 Sierra Drive, Honolulu

Listing courtesy of Caron B Realty.

$2,088,000
3 Beds ⋅ 2 Baths ⋅ 202614277 MLS ⋅ FS - Fee Simple Tenure ⋅ Regency At Kahala BLDG.
Rarely available three-bedroom residence in the prestigious Regency at Kahala, one of Honolulu's most sought-after luxury condominiums. With only four residences per floor, this premier building offers an exceptional level of privacy and exclusivity. This spacious home offers an exceptional floor plan with generous living areas and an enclosed lanai that expands your usable space. This corner unit sits on the Mauka/Koko Head side with expansive views from the mountains to the ocean. Enjoy the full-service amenities, including 24-hour security, resident manager, heated swimming pool, fitness center, guest parking, and beautifully landscaped grounds. Ideally located next to Kahala Mall, Whole Foods, restaurants, shopping, and entertainment, with convenient access to Kahala Beach, Waialae Country Club, Waikiki, and downtown Honolulu. This is a rare opportunity to enjoy the perfect combination of space, privacy, luxury, and the coveted Kahala lifestyle.

4340 Pahoa Avenue Unit 7A, Honolulu

Listing courtesy of Forward Realty.

$3,900,000
4 Beds ⋅ 4 Baths ⋅ 202610734 MLS ⋅ FS - Fee Simple Tenure
Welcome to elevated island living in Black Point, one of Honolulu’s most coveted gated communities. This extensively renovated residence captures panoramic Pacific Ocean views stretching east toward Koko Head and Koko Crater, creating a stunning backdrop for everyday living. The main level offers desirable single-level living and was originally designed as a 3-bedroom, 2.5-bath layout. It is currently configured as a spacious 1-bedroom, 1.5-bath residence, with two former bedrooms incorporated into a living area and a separate bedroom used as part of an apartment currently rented for $2,100 per month. A private studio on the lower level provides additional flexibility for visiting family, guests, extended living, or rental use. Seller improvements include luxury vinyl plank flooring throughout, a renovated kitchen, updated bathrooms, new split air conditioning in the living room, and a spa-inspired wet room in the primary bath. The primary suite also features breathtaking ocean views and a private balcony overlooking the coastline. A rare opportunity to enjoy privacy, flexibility, and panoramic views in an exclusive gated setting.

4145 Akulikuli Terrace, Honolulu

Listing courtesy of Coldwell Banker Realty.

$1,737,000
7 Beds ⋅ 3 Baths ⋅ 202614441 MLS ⋅ FS - Fee Simple Tenure
GREAT SCHOOL DISTRICTS! WAIKIKI ELEMENTARY/ KAIMUKI MIDDLE/KALANI HIGH! MULTI-DWELLING IN KAPAHULU! Front house is a 2 story-- 2/1 upper & 2/1 lower. Back house is a 3/1. It has 3 electric meters & 3 gas meters. All tenants occupied. Renovated in 2022 includes new kitchens, bathrooms, flooring and paint. Please don't walk on property or disturb tenants.

3429 Wela Street, Honolulu

Listing courtesy of Realty Prime LLC.

$1,737,000
202614436 MLS ⋅ FS - Fee Simple Tenure
GREAT SCHOOL DISTRICTS! WAIKIKI ELEMENTARY/KAIMUKI MIDDLE/KALANI HIGH!!! MULTI-DWELLING IN KAPAHULU! Front house is a 2-story--2/1 upper & 2/1 lower. Back house is a 3/1. It has 3 electric meters & 3 gas meters. All tenants occupied. Renovated in 2022 includes new kitchens, bathrooms, flooring and paint. Please don't walk on property or disturb tenants.

3429 Wela Street, Honolulu

Listing courtesy of Realty Prime LLC.

$1,400,000
4 Beds ⋅ 3 Baths ⋅ 202613838 MLS ⋅ FS - Fee Simple Tenure ⋅ Kalani Iki Estates BLDG.
Rarely available in Kalani Iki Estates, this spacious 4-bedroom, 2.5-bath residence offers approximately 2,230 square feet of interior living space and the comfort of a 2 car enclosed garage, 2 more parking stalls in front, and the convenience of guest parking and the amenities nearby. The generous 2.5 level floor plan provides excellent separation between the living & private areas with plenty of room for entertaining, working from home, and everyday island living. The large 174 sqft outdoor lanai just off the living room offers ocean views and space dine outdoors. Surrounded by approximately 20 acres of lush tropical landscaping, Kalani Iki Estates offers a peaceful low-density setting with community amenities including a recreation center, swimming pool, tennis court, basketball court, and Pickleball court. Enjoy the privacy and space of a residential home with the conveniences of condominium living with a low maintenance fee that include landscaping, cable, internet, all in a desirable East Honolulu location with easy access to Kahala, shopping, dining, and major roadways. A wonderful opportunity to personalize a distinctive home in one of Honolulu’s most desirable communities!

1593 Kalaniuka Circle Unit 84, Honolulu

Listing courtesy of Compass.

$1,400,000
4 Beds ⋅ 3 Baths ⋅ 202613839 MLS ⋅ FS - Fee Simple Tenure ⋅ Kalani Iki Estates BLDG.
Rarely available in Kalani Iki Estates, this spacious 4-bedroom, 2.5-bath residence offers approximately 2,230 square feet of interior living space and the comfort of a 2 car enclosed garage, 2 more parking stalls in front, and the convenience of guest parking and the amenities nearby. The generous 2.5 level floor plan provides excellent separation between the living & private areas with plenty of room for entertaining, working from home, and everyday island living. The large 174 sqft outdoor lanai just off the living room offers ocean views and space dine outdoors. Surrounded by approximately 20 acres of lush tropical landscaping, Kalani Iki Estates offers a peaceful low-density setting with community amenities including a recreation center, swimming pool, tennis court, basketball court, and Pickleball court. Enjoy the privacy and space of a residential home with the conveniences of condominium living with a low maintenance fee that include landscaping, cable, internet, all in a desirable East Honolulu location with easy access to Kahala, shopping, dining, and major roadways. A wonderful opportunity to personalize a distinctive home in one of Honolulu’s most desirable communities!

1593 Kalaniuka Circle Unit 84, Honolulu

Listing courtesy of Compass.

$150,000
2 Beds ⋅ 2 Baths ⋅ 202614285 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.
This spacious, garden-view gem in prestigious Kahala is beautifully renovated and move-in ready! Featuring 2 bedrooms, 2 baths, 1 covered parking stall, an open floor plan, and an enclosed lanai, this home is just steps from a sandy beach, Kahala Mall, and the iconic Kahala Hotel. Enjoy direct beach access with a protective offshore reef, offering calm waters for swimming, snorkeling, diving, and paddleboarding. Experience the best of island living. Lease expires July 15, 2027.

4999 Kahala Avenue Unit 422, Honolulu

Listing courtesy of REMAX Hawaii.

$495,000
3 Beds ⋅ 3 Baths ⋅ 202614329 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.
Experience luxury BEACHFRONT living in prestigious KAHALA! This stunning 3b/3b residence offers direct beach access w/a protective offshore reef, creating calm waters ideal for swimming, snorkeling, diving & paddleboarding. Enjoy unobstructed OCEAN & KOKO HEAD views from the spacious enclosed lanai. Highlights incl: HARDWOOD floors, soaring ceilings, custom cabinetry, central A/C, Sub-Zero & Bosch appliances, wine refrigerator, built-in bookshelves & speakers, Toto toilets, dual water heaters & Water Guard sensors. Rare opportunity to own this beachfront paradise! Lease expires July 15, 2027.

4999 Kahala Avenue Unit 472, Honolulu

Listing courtesy of REMAX Hawaii.

$1,625,000
3 Beds ⋅ 3 Baths ⋅ 202614187 MLS ⋅ FS - Fee Simple Tenure
Commanding panoramic, unobstructed city and ocean views protected by the Board of Water Supply property below. Extensively remodeled over the years (1997, 2015, and 2019. Effective Year Built 1970). At the heart of the home is a beautifully renovated island kitchen that opens seamlessly to the house-wide deck and main living areas where panoramic vistas are the backdrop for everyday living and memorable gatherings. Desirable floor plan features a primary suite on the main living level w/private office & TV/den/reading room and separate entry to side yard. Lower level includes two bedrooms, spacious living area, wet bar, Wine Cellar, separate entry - ideal for extended family, guests, multigenerational or assisted living. Rare parking includes a two-car carport, driveway parking for two additional vehicles, plus coveted street parking. Just minutes from UH, freeway access, shopping, dining, and beaches. Experience the perfect blend of breathtaking views, versatile living, and exceptional convenience.

1516 Alencastre Street, Honolulu

Listing courtesy of Coldwell Banker Realty.

$775,000
3 Beds ⋅ 1 Baths ⋅ 202614249 MLS ⋅ FS - Fee Simple Tenure

1739 9th Avenue Unit A, Honolulu

Listing courtesy of Dream Home Realty Hawaii LLC.

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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.