Location & Geography

Diamond Head is strategically positioned on the southeastern shore of Oahu, bordered by Waikiki to the west, Kapahulu and Kaimuki to the north, Kahala to the east, and the Pacific Ocean to the south. The neighborhood wraps around the iconic Diamond Head Crater (called "Leahi" meaning "brow of the tuna" by ancient Hawaiians) and provides convenient access to major areas: 5-10 minutes to Waikiki, 10-15 minutes to Downtown Honolulu, and 15-20 minutes to Hawaii Kai.

Major MLS Neighborhoods & Market Statistics

The Diamond Head area encompasses several distinct MLS neighborhoods, each with unique characteristics and inventory levels:

1. Diamond Head Proper

• The core neighborhood surrounding Diamond Head Crater
• Includes the Gold Coast along Kalakaua Avenue and Kapiolani Park
• Bordered by Monsarrat Avenue, Diamond Head Road, and surrounding streets including Kaimanahila, Hakaka, Papu Circle, and Kaikoo Place
• Approximately 650 exclusive homes represent some of the finest, most sought after real estate in Honolulu
• Home to notable properties including Doris Duke's famous Shangri La estate

Dining & Activities in Diamond Head Proper:

• Diamond Head State Monument: The area's crown jewel - a hiking trail leading to spectacular panoramic views of Waikiki and Honolulu (approximately 1.6 miles round trip)
• Diamond Head Beach Park: A quiet, uncrowded beach perfect for those seeking solitude, though not ideal for swimming. Prime surf spots are located offshore
• Diamond Head Lighthouse: Historic lighthouse marking Oahu's southernmost point, offering scenic coastal views
• Kaimana Beach: Technically in Waikiki borders but beloved by Diamond Head residents - less touristy, dog-friendly, and excellent for swimming

2. Kahala

• Approximately 1,200 homes in this sought-after beachfront neighborhood
• In April 2025, home prices were up 40.3% compared to last year, selling for a median price of $2.2M
• Homes sell after 138 days on the market compared to 71 days last year, with 34 homes sold in April this year
• Features large flat lots averaging around 9,000 square feet
• Known as the "Beverly Hills of Hawaii"

Dining, Shopping & Activities in Kahala:

• Kahala Mall: The area's premier shopping destination featuring Whole Foods (for groceries), Macy's department store, Apple Store, Starbucks, a modern movie theater, and numerous restaurants
• The Kahala Hotel & Resort: Luxury oceanfront resort featuring fine dining at Arancino (upscale Italian cuisine with multi-course pasta meals and patio dining)
• Waialae Country Club: Historic golf course (almost 100 years old) that hosts the annual Sony Open PGA tournament - one of the most prestigious golf events in Hawaii
• Kahala Beach: Beautiful white sand beach with multiple public access points along Kahala Avenue, perfect for swimming, beach walks, and water activities
• Olive Tree Cafe (near Kahala Mall): Beloved local Greek & Mediterranean restaurant famous for falafel, baba ganoush, and tabouleh - cash only and BYOB, expect a wait due to popularity
• Several high-end boutiques and specialty shops within the mall and surrounding areas

3. Kahala-Black Point

• 31 residences situated behind the gated secured Black Point entry
• Price range for Active listings is from $2,500,000 to $9,950,000
• Features a world-famous saltwater infinity pool built into the cliff side, available only to residents
• Located between Diamond Head and Kahala, elevated on an oceanside black lava rock knoll

Activities & Amenities in Black Point:

• Private Ocean Access: Exclusive access to pristine coastline for swimming, surfing, and fishing directly from residents' yards
• Cliffside Salt Water Pool: Unique infinity pool built into the ocean's edge, available only to gated community residents
• World-Class Surf Breaks: Close proximity to renowned surf spots including "Mansions," "Cliffs," and "Lighthouse" breaks
• Secluded Beach Areas: Private coves and rocky coastline perfect for solitude and ocean activities
• Panoramic Ocean Views: Unobstructed views of Kahala's gold sand beaches and the Pacific Ocean

4. Kaimuki

• About 600 single-family homes in this eclectic neighborhood
• Known for mom-and-pop shops along Waialae Avenue
• Features restaurants, yoga studios, and diverse local businesses
• One of Honolulu's first planned neighborhoods maintaining suburban charm

Dining, Shopping & Activities in Kaimuki:

• Waialae Avenue: The neighborhood's main thoroughfare dubbed "restaurant row" by locals, offering incredible diversity from boutique coffee shops to craft breweries
• Leila: Chef Chris Kajioka opened this refined taste of Morocco with a focus on a journey through varied flavors. "Omakase menu", with dishes beautifully plated and perfectly balanced. Reviews mention a $85 fixed three-course menu.
• 3660 On the Rise: Upscale dining known for Ahi Katsu appetizer and excellent steaks like Grilled Kiawe Smoked Beef Tenderloin
• Cafe Miro: Unique French-Japanese-Mediterranean fusion offering 3 & 4 course dining experiences
• Koko Head Cafe: Celeb chef Lee Anne Wong runs this poopular brunch stop for breakfast udon, congee & other Pan-Asian eats, usually packed throughout the week
• Pipeline Bakeshop & Creamery: Local bakery known for its Hawaiian treats with signature island flavors and Malasadas
• The Breadshop: Amazing local bakery for fresh bread and pastries, perfect for morning coffee rituals
• Bean About Town: Bean About Town is a premier micro roaster specializing in wholesale coffee for businesses across Honolulu and Hawai'i. We offer a curated selection of espresso blends, single origins, and award-winning Kona coffee, all freshly roasted locally.
• Kaimuki Shopping Center: Local conveniences including Times Supermarket, Longs Drugs, banks, and various restaurants
• Pu'u o Kaimuki Mini Park (locally called "Christmas Tree Park"): Offers panoramic views of Manoa, Kahala, Honolulu, and Hawaii Kai - perfect for picnics and the annual Christmas tree lighting ceremony
• Kaimuki Community Park: Family-friendly park with playground, basketball courts, tennis courts, and indoor gym
• Saturday Farmers Market: Weekly market at nearby Kapiolani Community College for fresh produce and artisanal goods

5. Kapahulu

• Primarily single-family homes and some condominiums
• Close proximity to Ala Wai Golf Course and Waikiki
• Easy freeway access and central location

Dining & Activities in Kapahulu:

• Ala Wai Golf Course: Popular and economically priced public 18-hole golf course next to the Ala Wai Canal with club rentals - one of the most accessible courses in Honolulu
• Leonard's Bakery: World-famous for malasadas (Portuguese donuts) - a must-try local treat that's been a Hawaii favorite since 1952
• Sushi Ginza Onodera: Authentic sushi experience offering premium Japanese dining
• Yakiniku Futago: Upscale Korean-Japanese steak restaurant featuring tableside cooking and signature Hamideru Kalbi
• Side Street In on da Strip: Since opening its first location in 1992 in the heart of Honolulu, Side Street Inn has garnered a multitude of awards and accolades for its inviting atmosphere and award-winning “gourmet comfort food.” 
• Tenkaippin Ramen: Highly regarded for some of the best ramen in the city
• Rainbow Drive-In: Local institution serving classic Hawaiian plate lunches since 1961
• Kapahulu Avenue: Main strip with diverse dining options, from casual local eateries to upscale restaurants
• Close proximity to Waikiki Beach and Kapiolani Park for easy beach and park access

6. Palolo

• About 600 single-family homes lies along the steep hills overlooking Honolulu
• Many of the single-family homes are older with long-time residents, with some built as early as the 1920s
• Located between St. Louis Heights and Kaimuki neighborhoods
• Features the 272-unit Regency Park condominium complex

Activities & Amenities in Palolo:

• Palolo Valley District Park: Large community park with recreational facilities and green space
• Mau'umae Trail: Challenging hiking trail with steep inclines leading to panoramic views of Kaimuki and the ocean - popular among experienced hikers
• Close proximity to Waialae Avenue: Easy access to Kaimuki's restaurant scene and shopping
• Chaminade University: Small private university located at the base of the neighborhood near Regency Park condominiums
• Residential tranquility: Quiet hillside living with spectacular city and ocean views from elevated properties
• Easy freeway access: Convenient location for commuting throughout Oahu

7. Additional Subdivisions

• Puu Panini: Small neighborhood with only 27 homes available, built in the 1950s with large lots
• Waialae Iki: Ridge neighborhood with views of Diamond Head Crater and Waialae Country Club
• St. Louis Heights: Hillside community with original and remodeled single-family homes
• Maunalani Heights: Properties with panoramic views and proximity to hiking trails

Activities & Amenities in Additional Subdivisions:

• Puu Panini: Features a private park with tennis and paddleball courts exclusively for residents' use - unique among Honolulu neighborhoods
• Waialae Iki: Close proximity to Waialae Country Club and golf course activities; elevated locations offer excellent views for residents
• St. Louis Heights: Access to multiple hiking trails and elevated living with cooler temperatures and scenic vistas
• Maunalani Heights:
  • Maunalani Circle: Popular neighborhood walking loop with beautiful homes and mature landscaping
  • Ridge hiking trails: Direct access to Ko'olau mountain trails leading into pristine Hawaiian wilderness
  • Sierra Drive: Some of the highest residential elevations in the area with commanding views
  • Cool mountain breezes: Natural air conditioning from elevation and trade wind exposure

Educational Institutions

The Diamond Head area is served by highly-rated public schools:

Elementary Schools:

• Waikiki Elementary School: Named 2020 National Blue Ribbon School, serves students depending on their location within the Diamond Head area
• Kahala Elementary School: Serves eastern portions of the Diamond Head area

Middle Schools:

• Kaimuki Middle School: A State Blue Ribbon School of Excellence earning a Niche A-minus

High Schools:

• Kalani High School: Earns an A-minus on Niche
• Kaimuki High School: As of the 2023-2024 school year, the school has an enrollment of 620 students

Private School Options:

• Punahou School: Located 10-15 minutes away with over 3,700 students
• 'Iolani School: Located 10 minutes away, recruits teachers from across the world
• La Pietra: All-girls college preparatory school for grades 6-12

Dining & Shopping

Monsarrat Avenue Dining:

• 13 food options along this "restaurant row, with every culture around"
• Diamond Head Market & Grill: Local Chef Kelvin Ro's famous for gourmet deli, house roasted meats, signature Blueberry Cream Cheese Scones, and award-winning breakfasts
• South Shore Grill: Known for "Hawaii's best fish tacos" and upscale local Hawaiian fare
• Bogart's Cafe: Popular for breakfast bagels and omelets
• ARS Cafe: Coffee, tea, and homemade gelato in a relaxed cafe with a rotating art gallery.
• Cafe Morey's: Casual local cafe founded in 2018
• Barefoot Beach Cafe @ Queen's Surf Beach: Outdoor cafe has Hawaiian plates & standard American fare, plus live music & a weekend beach BBQ.

Major Shopping Centers:

• Kahala Mall: Features Whole Foods, Macy's, movie theater, Apple Store, and various restaurants
• Kaimuki Shopping Center: Includes Times Supermarket, Longs Drugs, banks, and restaurants
• Proximity to Ala Moana Center (15 minutes) and various Waikiki shopping destinations

Recreation & Amenities

Parks & Recreation:

• Kapiolani Park: 300-acre park, the largest park in the state of Hawaii, featuring the Honolulu Zoo, Waikiki Shell, and Waikiki Aquarium
• Diamond Head State Monument: Iconic hiking destination with panoramic views
• Multiple Beach Access Points: Including Diamond Head Beach Park, Kaimana Beach, and Kahala Beach
• Waialae Country Club: Almost 100 years old, home to the annual Sony Open
• Ala Wai Golf Course: in Waikiki but a short distance for a Public 18-hole course with club rentals

Fitness & Wellness:

• Multiple yoga studios and fitness centers along Monsarrat Avenue
• Tennis and basketball courts at various community parks
• Ocean access for surfing, swimming, and water sports

Transportation & Accessibility

The Diamond Head area provides excellent connectivity with multiple route options to avoid traffic delays:

• Downtown Honolulu: 5-20 minute commute depending on route and traffic
• Waikiki: 10-15 minutes
• Hawaii Kai: 15-20 minutes
• Honolulu Airport: Approximately 30 minutes
• Public Transportation: Served by TheBus, Honolulu's public bus system
• Proximity to H-1 Freeway: Easy access for island-wide travel

Historic Architecture & Development

Diamond Head features a diverse collection of architectural styles spanning nearly two centuries. The area includes charming historic homes dating back to the 1920s and 1930s, with many properties featuring:

• 1830s cottages representing some of the earliest residential structures
• 1920s Sears Craftsman bungalows showcasing classic American architectural elements
• Plantation-style homes reflecting Hawaii's agricultural heritage
• Colonial and vintage designs with Asian flair reminiscent of early Chinese and Japanese immigrants
• Modern oceanside estates with palatial gates and contemporary luxury features

The Chinatown fire in 1900 spurred development of the Diamond Head neighborhood, as the fire left many immigrants homeless, and many headed to the Diamond Head area for a new start. In 1898, Theodore Lansing and A.V. Gear purchased land from Dr. Trousseau and sold small lots, creating Honolulu's first subdivision.

The Kawamoto Legacy in Kahala

The Diamond Head area, particularly Kahala, was significantly impacted by the investment activities of Japanese billionaire Genshiro Kawamoto during the late 1980s Japanese economic bubble and subsequent decades.

Kawamoto's Acquisition Period: Kawamoto purchased hundreds of homes across Honolulu during the Japanese bubble, including 28 homes along prestigious Kahala Avenue over a 15-year period with an assessed value of approximately $150 million. These acquisitions represented some of the most valuable oceanfront real estate in Hawaii.

The Deterioration Issue: Unfortunately, due to neglect and lack of proper maintenance, Kawamoto's properties lost their exceptional luxury appearance over time. Many of these once-magnificent estates were left vacant and unmaintained, which diminished some of the fine appearance that Kahala Avenue once had. This situation created concern among residents and local officials about the impact on the neighborhood's character and property values.

Resolution and Restoration: Kahala residents celebrated when A&B Properties (Alexander & Baldwin), a reputable Hawaii developer, purchased 27 of the Kawamoto properties along Kahala Avenue in September 2013 for just under $100 million. This acquisition represented a significant step toward restoring the area's prestige and ensuring proper maintenance and development of these premium oceanfront properties.

The Kawamoto situation serves as an important case study in luxury real estate stewardship and highlights the significance of active property maintenance in preserving neighborhood character and values in Hawaii's premier residential areas.

Market Characteristics

For-sale housing inventory in the Diamond Head area is typically low, so competition in the area is strong. When a house is listed for sale, it usually is under contract within a short time of being listed. The average single-family home and condo values in the Diamond Head area are some of the highest on Oahu.

The neighborhood attracts both full-time residents and second-home owners, creating a unique blend of luxury living with convenient access to urban amenities, world-class beaches, and recreational opportunities. The area's historic significance, combined with its modern amenities and prime location, continues to make it one of the most desirable places to live in Hawaii.