Diamond Head Homes with City View

Welcome to Diamond Head, a breathtaking neighborhood nestled on the southeastern coast of Oahu, Hawaii, and part of the vibrant city of Honolulu. Known for its iconic volcanic crater, Diamond Head offers a unique blend of natural beauty and urban convenience, making it one of the most desirable places to call home.

As you explore this stunning region, you'll be captivated by the panoramic views that stretch across the sparkling Pacific Ocean and the lush greenery that surrounds the area. Homes in Diamond Head are not just residences; they are gateways to a lifestyle enriched by breathtaking city views, serene beaches, and an array of outdoor activities. Imagine waking up to the sun rising over the ocean, casting a warm glow on the vibrant cityscape below.

Real estate in Diamond Head features a variety of options, from charming single-family homes to luxurious condos, many of which boast expansive windows and spacious balconies designed to maximize those stunning views. Whether you're looking for a cozy retreat or a modern masterpiece, you'll find properties that cater to every taste and lifestyle.

Beyond the homes, Diamond Head is a haven for outdoor enthusiasts. The nearby Diamond Head State Monument offers hiking trails that reward adventurers with unparalleled views from the summit. Additionally, the pristine beaches, local eateries, and cultural attractions in Honolulu are just a stone's throw away, providing a vibrant community atmosphere.

Experience the magic of Diamond Head, where the beauty of nature meets the energy of city life. Your dream home with a view awaits in this enchanting Hawaiian paradise!

Newest Diamond Head Homes with City View

$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). 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, 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.

$1,298,000

3 Beds ⋅ 3 Baths ⋅ 202612198 MLS ⋅ FS - Fee Simple Tenure

Cooled by gentle mountain breezes & blessed with sweeping coastline views stretching toward Diamond Head, this exceptional 3-unit property offers the kind of island lifestyle people dream about. Upstairs, a spacious covered lanai becomes the heart of the home, a place to greet the morning with a cup of coffee as the sun rises over the Pacific, to gather with friends for leisurely meals, or unwind in the evening while watching mesmerizing sunsets paint the sky in shades of gold & pink. The well-appointed kit flows effortlessly to the outdoor living space, making entertaining and dining al fresco both easy & enjoyable. Whether preparing a casual breakfast or hosting a sunset dinner, everything is designed to embrace the HI indoor-outdoor way of life. The upstairs residence features 2 comfortable bedrooms & 1 bathroom, creating a peaceful retreat where the sights, sounds & breezes of the islands are never far away. The downstairs 1 bedroom unit has a generous sized living area leading out to the covered lanai. Easy walking distance to Waialae Avenue with numerous restaurants & boutique shops. Small studio also included in the offering.

4137 Sierra Drive, Honolulu

Listing courtesy of Coldwell Banker Realty.

$1,425,000

3 Beds ⋅ 2 Baths ⋅ 202613311 MLS ⋅ FS - Fee Simple Tenure

Welcome to 1568 Halekoa Drive in desirable Waialae Nui Ridge! Ideally located in town and not too far up the hill, this well-maintained 3-bedrm, 2-bath family home has been cared for by the same owner over the years and is ready for its next chapter. Freshly painted interior and ceilings give the home a clean, bright feel while allowing the next owner to update and personalize. Enjoy tradewind breezes and peekaboo ocean and Diamond Head views from the balcony, front of the home, and select windows. Designed for everyday living, the floor plan includes a living room, rumpus room, kitchen, enclosed utility/washroom area, and large basement/flex area with stairs—ideal for storage, hobbies, home office, game room, study area, or creative space. A rare bonus for hillside living, the property offers a level yard, 2-car carport/garage with storage, generous under-house storage, and workshop area. Front yard has red and yellow hibiscus; backyard has coconut, mango, and lychee trees providing afternoon shade. Roof replaced in 2010 and recently tented with transferable warranty. Convenient to Kahala Mall, Kaimuki, schools, parks, restaurants, and freeway access. 1st OH Sunday, 7/19, 2-5pm.

1568 Halekoa Drive, Honolulu

Listing courtesy of REMAX Hawaii.

$1,350,000

6 Beds ⋅ 2 Baths ⋅ 202613125 MLS ⋅ FS - Fee Simple Tenure

Rare opportunity to secure a premier redevelopment site in the prestigious Wilhelmina Rise neighborhood. Situated on an expansive 11,017 sq. ft. lot with breathtaking panoramic views of the city skyline, ocean, mountains, sunsets, and iconic Diamond Head, this property is a true value-add opportunity for investors, builders, developers, and contractors. The existing 6-bedroom, 2-bath residence (approximately 2,532 sq. ft., built in 1962) is in very poor condition, with the structure conveying zero value and offered strictly As-Is. Bring your vision and explore the possibilities to reimagine this exceptional homesite in one of Honolulu's most established neighborhoods. Conveniently located near parks, restaurants, shopping, grocery stores, and everyday conveniences. CAUTION: Property may present safety hazards. Interior access is limited and not recommended without appropriate precautions. Do not enter or access the property without prior approval. Buyer to conduct their own due diligence. Opportunities like this are rare—contact your REALTOR® today for more information.

4326 Sierra Drive, Honolulu

Listing courtesy of ENRG Realty.

$1,488,000

14 Beds ⋅ 6 Baths ⋅ 202613187 MLS ⋅ FS - Fee Simple Tenure

The property features five separate residential units, in beautiful Palolo Valley, providing immediate income and a compelling value-add investment opportunity. Priced to reflect its current condition, including existing water intrusion and significant repair needs, this offering provides investors the opportunity to acquire a multi-unit asset at a substantial discount. With renovation and repositioning, the property offers meaningful upside through increased rental income and long-term appreciation.

2001 10th Avenue, Honolulu

Listing courtesy of CBI Residential Advisory Svcs..

$3,499,500

4 Beds ⋅ 4 Baths ⋅ 202613054 MLS ⋅ FS - Fee Simple Tenure

Rim lot. Stunning view. Refrigerator, washer and dryer, dishwasher, two split air conditioner, salt water pool, two water heaters, two ceiling fans, remote controlled window coverings, remote controlled garage door, Photovoltaic system with two back up Tesla batteries. Sold "as is"

1728 Kumakani Loop, Honolulu

Listing courtesy of Young Hawaii Homes, Inc..

$1,750,000

5 Beds ⋅ 2 Baths ⋅ 202613079 MLS ⋅ FS - Fee Simple Tenure

Discover a rare opportunity in the highly desirable St. Louis neighborhood! This versatile 5-bedroom property features a legal, permitted ADU, offering flexibility for multi-generational living, extended family, guests, or potential rental income! Enjoy the ocean and Diamond Head views from your upper lanai while sipping your morning coffee. The remodeled lower level showcases modern finishes and updated living spaces, while the home's functional layout provides room for a variety of living arrangements. Whether you're looking for additional privacy, space to work from home, or an income-producing opportunity, this property delivers. Back side of the backyard borders State land, providing an added sense of privacy with no neighboring home along that boundary. Conveniently located to UH Manoa, Waikiki, Kaimuki, shopping, dining, parks, and freeway access, you'll enjoy neighborhood charm and town convenience. Don't miss the chance to own this unique St. Louis home with endless possibilities!

1938 Bertram Street, Honolulu

Listing courtesy of Century 21 Island Homes.

$2,200,000

3 Beds ⋅ 3 Baths ⋅ 202612638 MLS ⋅ FS - Fee Simple Tenure

Perched on the highly coveted Waialae Nui Ridge, one of Honolulu's most desirable ridge communities, this beautifully renovated home offers the perfect blend of comfort, convenience, and breathtaking views. Enjoy Diamond Head, city skyline, and stunning sunset vistas from the spacious lanai, all while living just minutes from the Honolulu metro area, shopping at Kahala Mall, dining, beaches, and much more. Situated along a relatively flat street in a walkable area of the ridge, this 3-bedroom, 2.5-bath residence offers a thoughtfully designed living space featuring exposed beam ceilings, a spacious kitchen, and an open inviting layout. Recent upgrades include luxury vinyl plank flooring throughout, updated appliances, Taj Mahal quartz kitchen countertops, California Closets storage, fresh interior and exterior paint, and low-maintenance Trex decking. Energy-efficient features include an owned 10-panel photovoltaic system on Net-Metering, and a solar hot water heater. Complete with a spacious yard, two-car garage, and access to the Waialae Ridgeline community center with pool, this exceptional home truly has it all.

2544 Halekoa Drive, Honolulu

Listing courtesy of Paradise Real Estate Brokers.

$1,825,000

5 Beds ⋅ 3 Baths ⋅ 202611287 MLS ⋅ FS - Fee Simple Tenure

Most homes trade elevation for the view—climb higher, live farther from everything. This Halekoa Drive home rewrites that story: nearly 180 degrees of open ocean and Diamond Head from every level, perched low enough to keep daily life close. Four bedrooms sit upstairs; below, a detached rental unit with its own entrance, bath, and wet bar gives you a flexible lower level - an income offset, a guest suite, or extra room for your Ohana. Sixteen owned solar panels and solar hot water run on net metering, putting the energy math in your favor. A neighborhood park sits just a few blocks off, and the address lands in some of Honolulu's most sought-after public school districts. This house is built for the buyer who wants the unobstructed views without the climb. The home has been tastefully maintained with contemporary flooring, spacious bedrooms, and an EV equipped garage you can pull into after a long day at the beach. You can count on one hand how many homes on the hill like this come to market. Don't miss your chance to stand in this space and feel the tranquility it holds. Call your favorite realtor today for a private showing, and welcome home.

1492 Halekoa Drive, Honolulu

Listing courtesy of Real Broker.

$1,725,000

5 Beds ⋅ 5 Baths ⋅ 202612360 MLS ⋅ FS - Fee Simple Tenure

PRICE IMPROVEMENT! Where else in St. Louis Heights will you find potential for three separate living areas, two separate driveways, and an ocean view? Multigenerational living, rental income, or both this home has the flexibility for it all. A two-car garage plus two separate driveways keeps parking handled no matter how you configure it. This gently sloped lot has no stairs to the front door, and out back, a usable yard opens up for evening gatherings as the sky turns gold over the horizon. Major upgrades already done: full electrical rewire, structural foundation reinforcement, renovated sewer line & an owned 8-panel PV solar system. Both kitchens and bathrooms have been renovated for true move-in-ready living, and each level comes with its own washer and dryer, so nothing has to be shared. Enjoy panoramic ocean, city, and sunset views from the primary living room, kitchen, and private lanai. Multiple serene outdoor spaces surrounded by mature fruit trees create a tropical retreat perfect for relaxing or entertaining. Set on a 7,854 sq. ft. R-5 corner lot in St. Louis Heights, with easy freeway access & minutes from UH Manoa, Kahala Mall, and some of Kaimuki's best restaurants.

1766 St Louis Drive, Honolulu

Listing courtesy of Keller Williams Honolulu.

$2,950,000

5 Beds ⋅ 5 Baths ⋅ 202612377 MLS ⋅ FS - Fee Simple Tenure

Stunning Ocean and Diamond Head views highlight this residence located halfway up the prestigious and highly sought after Waialae Iki ridge. Offering 5bedrooms, 5 baths plus a den/office. This spacious home features 3 primary suites with breathtaking views. The thoughtful layout includes 2 primary suites on the upper level, 2 additional bedrooms and a den/office on the main level and a private in-law suite with it's own separate entrance, wet bar and living area. With nearly 4,200 sqft of interior space, this home represents exceptional value. Enjoy the convenience to Kahala Mall, Waialae Country Club, Kahala resorts, shops and restaurants, all just minutes away. Recent improvements enhance the value and appeal of this house, including a brand new roof, picture frame windows, and new flooring throughout. The updates provide added peace of mind, and a fresh modern feel, move in ready for the next owner.

1717 Palaau Street, Honolulu

Listing courtesy of Locations LLC.

$2,999,000

5 Beds ⋅ 4 Baths ⋅ 202611449 MLS ⋅ FS - Fee Simple Tenure

Breathtaking Diamond Head, ocean views and soaring high ceilings greet you entering this luxury residence. The spacious and light filled five bedroom, four bath island retreat located on the slopes of Wilhelmina Rise is perfectly positioned to capture cooling trade winds and beautiful island views. The well appointed kitchen features custom kitchen cabinetry and Bosch appliances. The kitchen connects effortlessly to the inside and outside entertaining areas. There are three bedrooms located on the upper floor including a separate laundry area. The expansive and elegant primary suite connects to a sophisticated primary bathroom including a soaking tub. The lower level features another large living and dining area as well as a covered lanai. Two bedrooms, two bathrooms and another separate laundry area are perfect for multigenerational living options. The lower floor also has its own entrance. The lowest floor serves as a very versatile and fun recreational room. It also has its own entrance and very large covered lanai. Reinforced concrete walls and footings set deep into the rock just show the level of craftsmanship and detail used in this custom built home.

1717 Iwi Way, Honolulu

Listing courtesy of DM Luxury Homes 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.