View All Diamond Head HI Mid-Century Modern Homes Listings
Live the Gold Coast dream at the iconic Diamond Head Ambassador! This desirable 1-bedroom, 1-bathroom residence places you steps away from world-class surf, pristine beac...
- 1 Beds
- 1 Baths
- 202613177 MLS
- FS - Fee Simple Tenure
- Diamond Head Ambassador C Bldg.
- 13 DOM
Get ready to find your dream home with this stunning Mid Century Modern home designed by Alfred Preis, the renowned Arizona Memorial Architect. Located just a stone's thr...
- 4 Beds
- 4 Baths
- 202611048 MLS
- FS - Fee Simple Tenure
- 45 DOM
Breathtaking ocean views await from every room of "Maluhia," a sanctuary of quiet luxury perched at the edge of Diamond Head. Located within the prestigious Diamond Head ...
- 2 Beds
- 2 Baths
- 202610380 MLS
- FS - Fee Simple Tenure
- Diamond Head Apts Ltd Bldg.
- 55 DOM
Set on a level lot along coveted Papu Circle, this residence is a refined expression of Mid-Century modern design, defined by clean lines, thoughtful proportions, & a sea...
- 4 Beds
- 4 Baths
- 202607421 MLS
- FS - Fee Simple Tenure
- 54 DOM
Located in the desirable Kuliouou/east Honolulu neighborhood, this substantial mid-century home presents a unique opportunity for those seeking space, versatility, and lo...
- 8 Beds
- 4 Baths
- 202604120 MLS
- FS - Fee Simple Tenure
- 97 DOM
Charming and well-maintained 3-bedroom, 2-bath residence located in desirable Maunalani Heights. This mid-century gem is located on a quiet street at the end of Pakahi Pl...
- 3 Beds
- 2 Baths
- 202601193 MLS
- FS - Fee Simple Tenure
- 71 DOM
BIG PRICE CHANGE~A "DO NOT MISS" CHANCE! For Solid, mid-century custom designed Home in the "Carlos Long" subdivision of Palolo! Property emanates a tropical Country-like...
- 5 Beds
- 2 Baths
- 202600101 MLS
- FS - Fee Simple Tenure
- 201 DOM
This mid century modern style home awaits your personal touch. Expansive lanais, patio areas and large sliding glass doors create a seamless flow between indoor and outd...
- 3 Beds
- 3 Baths
- 202524108 MLS
- FS - Fee Simple Tenure
- 68 DOM
RARE, VINTAGE, MINT, BEACHFRONT OSSIPOFF GEM! Experience timeless Hawaii luxury in this exquisite 3-bedroom, 2.5-bathroom single-level home, meticulously crafted by reno...
- 3 Beds
- 3 Baths
- 202523545 MLS
- FS - Fee Simple Tenure
- 285 DOM
Discover this mid-century modern single-level home with mountain views perfectly situated on a spacious corner lot. Thoughtfully designed for both style and comfort, the...
- 3 Beds
- 3 Baths
- 202515657 MLS
- FS - Fee Simple Tenure
- 53 DOM
Experience sweeping ocean vistas and iconic Diamond Head views from the comfort of your spacious covered lanai, perfectly situated on a prized rim lot along highly desira...
- 3 Beds
- 2 Baths
- 202518823 MLS
- FS - Fee Simple Tenure
- 62 DOM
An exceptional mid-century residence offering sweeping ocean views in the prestigious Diamond Head area. Designed in 1959 by acclaimed architect Vladimir Ossipoff, this h...
- 6 Beds
- 8 Baths
- 202512547 MLS
- FS - Fee Simple Tenure
- 207 DOM
Welcome to your forever home in highly sought after Niu Valley! Just moments from the shoreline, this single level 4BD/3BA mid-century modern home embodies the effortless...
- 4 Beds
- 3 Baths
- 202516177 MLS
- FS - Fee Simple Tenure
- 42 DOM
Nestled in one of Honolulu’s most sought-after neighborhoods, this rare opportunity perched on the highest elevation point of Elepaio Street invites you to reimagine isla...
- 2 Beds
- 3 Baths
- 202513816 MLS
- FS - Fee Simple Tenure
- 70 DOM
Discover the epitome of Waialae Iki ridge living. 1782 Laukahi St is perched high offering some of the most incredible views one could buy. Thoroughly remodeled in 2025, ...
- 4 Beds
- 2 Baths
- 202509547 MLS
- FS - Fee Simple Tenure
- 73 DOM
'ELE 'ELE HOUSE (Black House) Architectural 3 bed/3 bath single family Waialae Nui Ridge home with open living concept and indoor outdoor flow that effortlessly floats ab...
- 3 Beds
- 3 Baths
- 202509544 MLS
- FS - Fee Simple Tenure
- 98 DOM
Mid-Century Modern Masterpiece with breathtaking views, designed by renowned architect Valdimar Ossipoff. This home perfectly embodies his signature style of seamlessly b...
- 5 Beds
- 3 Baths
- 202505741 MLS
- FS - Fee Simple Tenure
- 57 DOM
Aina Haina mid-century gem on a large level lot. Warm curb appeal, knotwood fencing and a custom paved driveway. Through secured side gates discover a completely fenced e...
- 5 Beds
- 3 Baths
- 202505485 MLS
- FS - Fee Simple Tenure
- 44 DOM
BACK ON MARKET! Ideally located on the slopes of Diamond Head in a gated community with security guards, this beautiful mid-century modern residence exudes warmth & timel...
- 2 Beds
- 3 Baths
- 202505650 MLS
- FS - Fee Simple Tenure
- La Pietra Bldg.
- 153 DOM
UNIMAGINABLE views await you from this mid-century modern home perched on the corner of a canyon! Discover this beautifully remodeled home featuring 3 spacious bedrooms...
- 5 Beds
- 3 Baths
- 202504790 MLS
- FS - Fee Simple Tenure
- 41 DOM
4546 Kolohala Street awaits a new chapter to this seasoned home where a large family enjoyed life at its best. This home designed by Takashi Anbe is an authentic Mid-Cent...
- 3 Beds
- 3 Baths
- 202426288 MLS
- FS - Fee Simple Tenure
- 116 DOM
WELCOME HOME to this charming single-family home within the highly desired "Flower Streets" of Palolo Valley. Enjoy the spectacular Diamond Head views from your bedroom, ...
- 3 Beds
- 2 Baths
- 202324089 MLS
- FS - Fee Simple Tenure
- 52 DOM
Nestled amidst lush mature landscaping lies a timeless gem of mid-century modern architecture, a tranquil oasis where a seamless fusion of indoor-outdoor living invites y...
- 4 Beds
- 3 Baths
- 202409224 MLS
- FS - Fee Simple Tenure
- 38 DOM
Situated on the ocean's edge, calling all thalassophiles / lovers of the ocean! Ground level unit in the iconic mid century Diamond Head Ambassador on the coveted Gold Co...
- 1 Beds
- 1 Baths
- 202317290 MLS
- FS - Fee Simple Tenure
- Diamond Head Ambassador A Bldg.
- 34 DOM
Your mid-century dream has come true in Kahala! Wide, quiet Kuana Street is only one curving block long, and close to the beach. It has sidewalks, underground utilities...
- 3 Beds
- 2 Baths
- 202321272 MLS
- FS - Fee Simple Tenure
- 71 DOM
An incredible opportunity to own a piece of paradise on Oahu's famous Gold Coast! The location of these 42 apartments is truly desirable, situated just beyond Famous Waik...
- 1 Beds
- 1 Baths
- 202324164 MLS
- FS - Fee Simple Tenure
- 2987 Kalakaua Bldg.
- 134 DOM
Comfort, convenience & charm! Welcome to this mid-century, delightful, well-loved home that awaits your personal touches. Blending modern amenities with the neighborhood'...
- 5 Beds
- 4 Baths
- 202311505 MLS
- FS - Fee Simple Tenure
- 106 DOM
Greeted by the sweet sounds of swaying coconut trees and the gentle lull of surf, this DIRECT OCEANFRONT, NEWLY RENOVATED 6th floor unit welcomes you with its LUXURY MODE...
- 1 Baths
- 202328480 MLS
- FS - Fee Simple Tenure
- Tropic Seas Inc Bldg.
- 47 DOM
Honolulu’s Kapua or Gold Coast is a beautiful stretch of coastline that runs from the edge of Waikiki through Kapiolani Park to the slopes of Diamond Head. The Diamond He...
- 2 Beds
- 2 Baths
- 202311746 MLS
- FS - Fee Simple Tenure
- Diamond Head Ambassador* Bldg.
- 157 DOM
Unparalleled Panoramic Views… This exquisite contemporary 5-BD home located on a premier street in iconic Diamond Head, offers spectacular views of the Pacific Ocean & pa...
- 5 Beds
- 5 Baths
- 202412239 MLS
- FS - Fee Simple Tenure
- 388 DOM
JUST LISTED!! This mid-century Kahala home is a must-see! Located on Kolohala St., in the premier section of Kahala/Diamond Head, this 4-bedroom, 3-bathroom residence is ...
- 4 Beds
- 3 Baths
- 202328173 MLS
- FS - Fee Simple Tenure
- 37 DOM
Amazing and sweeping ocean view and mauka to makai Aina Haina valley views from this ideally situated and elevated hillside rim lot!!! Must see to appreciate this beautif...
- 3 Beds
- 2 Baths
- 202317398 MLS
- FS - Fee Simple Tenure
- 26 DOM
Perched atop Maunalani Heights like the crown jewel on Her Majesty, this could be your once-in-a-lifetime opportunity to own a unique Ossipoff home in a highly sought-aft...
- 3 Beds
- 2 Baths
- 202416465 MLS
- FS - Fee Simple Tenure
- 140 DOM
Welcome to the Diamond House. A Mid-Century masterpiece born from the vision of famed architects Wimberly and Cook, this stunning A-frame is not to be missed. The archite...
- 4 Beds
- 2 Baths
- 202302993 MLS
- FS - Fee Simple Tenure
- 140 DOM
Welcome to unobstructed views through the lens of unparalleled master architect Vladimir Ossipoff. Start your day inspired in this private Mid Century gem situated in the...
- 3 Beds
- 3 Baths
- 202404779 MLS
- FS - Fee Simple Tenure
- 40 DOM
Just Listed in Chaminade Terrace! An impressively preserved Mid-Century Modern home with Japanese influence. Mid-way up Kaminaka Drive, this 3 bedroom, 2 bathroom home de...
- 3 Beds
- 2 Baths
- 202421846 MLS
- FS - Fee Simple Tenure
- 57 DOM
Experience unparalleled tranquility & breathtaking views in this Maunalani Heights gem. Located on a private drive, this unique property offers stunning vistas stretching...
- 3 Beds
- 3 Baths
- 202416841 MLS
- FS - Fee Simple Tenure
- 370 DOM
VIEWS, PRIVACY & SERENITY!! Welcome home to this beautifully renovated residence that is ideally perched on over 10k sqft of land in Aina Haina and provides spectacular v...
- 3 Beds
- 2 Baths
- 202403540 MLS
- FS - Fee Simple Tenure
- 36 DOM
Private and secluded property just minutes from town sits a single level home on a sprawling 47,000 square foot property. Stroll through the beautifully manicured lawn, s...
- 5 Beds
- 6 Baths
- 202222456 MLS
- FS - Fee Simple Tenure
- 337 DOM
Perched atop prestigious Maunalani Heights, this exceptional home stands as a beacon of architectural brilliance, crafted by the renowned Alfred Preis, and celebrated for...
- 5 Beds
- 3 Baths
- 202401152 MLS
- FS - Fee Simple Tenure
- 97 DOM
This Level 10,000 sq. ft lot is a true rarity in Kahala offering endless possibilities for creating a dream estate. The existing tiled pool sets the stage and is the cen...
- 5 Beds
- 3 Baths
- 202421180 MLS
- FS - Fee Simple Tenure
- 111 DOM
Sunday Open House November 3rd - 2:00pm to 5:00pm. Don't miss this opportunity to own a spacious, single-level mid-century home on a generous 10,000+ sqft lot in the PRE...
- 4 Beds
- 3 Baths
- 202415091 MLS
- FS - Fee Simple Tenure
- 56 DOM
Location Location! This mid century home sits on a corner lot in sought after lower Waialae Iki! Single level floor plan offers many opportunities to renovate and make th...
- 3 Beds
- 2 Baths
- 202418250 MLS
- FS - Fee Simple Tenure
- 17 DOM
Visionary Wanted! Restore This Mid-Century Masterpiece in Maunalani Heights. Welcome to 5136 Maunalani Heights, where opportunity meets breathtaking views and timeless de...
- 5 Beds
- 2 Baths
- 202420545 MLS
- FS - Fee Simple Tenure
- 74 DOM
Welcome to a charming piece of history nestled in the heart of Aina Haina! Built in 1958, this timeless home captures the essence of mid-century architecture, offering a ...
- 3 Beds
- 2 Baths
- 202412054 MLS
- FS - Fee Simple Tenure
- 27 DOM
Relish the Ocean and Diamond Head views from the spacious lanai of your mid-century modern Ossipoff & Snyder Architects designed home on the highly desirable neighborhood...
- 3 Beds
- 3 Baths
- 202424367 MLS
- FS - Fee Simple Tenure
- 49 DOM
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.
Diamond Head, HI · Curated MLS Search
Mid-Century Modern Homes in Diamond Head, HI
An editorially curated view of every active mid-century modern homes listing in Diamond Head, HI. Updated in real time from the local MLS, presented without the noise.
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