Diamond Head, HI · Curated MLS Search
Country Homes in Diamond Head, HI
An editorially curated view of every active country homes listing in Diamond Head, HI. Updated in real time from the local MLS, presented without the noise.
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Live MLS data — Diamond Head vs. Country Homes
Country Homes in Diamond Head: Market Data
Data as of (MLS snapshot; listings below update live)
KEVIN PEDERSEN | RS-77808's review of MLS data as of October 20, 2026 shows 10 active listings for Diamond Head country homes. That is about 5% of the 209 active listings in Diamond Head across every property type. At the time, 2 more were pending, and 9 sold in the past six months.
| Measure | Value |
|---|---|
| Active listings | 10 |
| All active listings in Diamond Head, every property type | 209 |
| Under contract | 2 |
| Sold, past six months | 9 |
Country Homes in other areas
- Waianae: 19 active, median $680,000
- Kailua: 9 active
- Honolulu: 8 active
- North Shore: 8 active
- Kahala: 5 active
Market questions
How many Diamond Head country homes are on the market?
There were 10 Diamond Head country homes for sale as of October 20, 2026, based on KEVIN PEDERSEN | RS-77808's review of MLS data.
How do Diamond Head country homes compare with other areas?
As of October 20, 2026, there were 10 Diamond Head country homes for sale. In the same search, Waianae had 19 country homes for sale at a median list price of $680,000, Kailua had 9 country homes for sale and Honolulu had 8 country homes for sale.
How many Diamond Head country homes sold in the past six months?
9 Diamond Head country homes sold in the six months before October 20, 2026.
How many Diamond Head country homes are pending?
As of October 20, 2026, 2 Diamond Head country homes were under contract.
How do Diamond Head country homes compare with all active listings in Diamond Head?
As of October 20, 2026, there were 10 Diamond Head country homes for sale, out of 209 active listings in Diamond Head across every property type.
Listing data courtesy of HiCentral MLS, Ltd.
Next Steps in Diamond Head, HI
View All Diamond Head HI Country Homes Listings
DESIGNED FOR THE WAY WE LIVE IN HAWAI‘I. This beautifully appointed 5 bedroom home in the heart of Kahala offers a spacious floor plan, light-filled interiors, contempora...
- 5 Beds
- 4 Baths
- 202619416 MLS
- FS - Fee Simple Tenure
- 7 DOM
Perched on a coveted rim lot in prestigious Waialae Iki, this spacious home captures sweeping views of the Pacific Ocean, iconic Diamond Head, and the lush fairways of Wa...
- 4 Beds
- 4 Baths
- 202616211 MLS
- FS - Fee Simple Tenure
- 55 DOM
A rare opportunity to own a newer, custom-designed home on Analii Street in lower Waialae Iki, just minutes from Waialae Iki Neighborhood Park. The upper level features 4...
- 5 Beds
- 5 Baths
- 202613840 MLS
- FS - Fee Simple Tenure
- 56 DOM
RARE OPPORTUNITY ON KOLOA STREET IN KAHALA. Priced below tax assessed value, this is your chance to acquire a substantial estate on one of Kahala's most beloved streets. ...
- 5 Beds
- 5 Baths
- 202615601 MLS
- FS - Fee Simple Tenure
- 63 DOM
Directly fronting the 7th hole fairway of Waialae G/C (home of the PGA Sony Open), this classic country-style Honolulu home offers a timeless island retreat on generous l...
- 4 Beds
- 5 Baths
- 202615121 MLS
- FS - Fee Simple Tenure
- 63 DOM
RARELY AVAILABLE - LOWER WAIALAE IKI NEXT TO THE PARK!! This renovated 3bed/3bath home is located in desirable Waialae Iki and features an open floorplan, panoramic ocean...
- 3 Beds
- 3 Baths
- 202615383 MLS
- FS - Fee Simple Tenure
- 69 DOM
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 floo...
- 3 Beds
- 2 Baths
- 202614277 MLS
- FS - Fee Simple Tenure
- Regency At Kahala Bldg.
- 90 DOM
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 p...
- 5 Beds
- 5 Baths
- 202612377 MLS
- FS - Fee Simple Tenure
- 76 DOM
PRICED $60,000 BELOW APPRAISED VALUE!!! w/ ELEVATOR from garage. Perched on the ridge above Kahala on a quiet dead-end street, this beautifully reimagined 3-bedroom, 2-ba...
- 3 Beds
- 2 Baths
- 202609835 MLS
- FS - Fee Simple Tenure
- 157 DOM
A Rare Opportunity in Coveted Kahala! Welcome to 608 Kuana Street a true single level 3-bedroom, 2-bath island home, nestled in the heart of Kahala, where luxury living a...
- 3 Beds
- 2 Baths
- 202608064 MLS
- FS - Fee Simple Tenure
- 21 DOM
Come experience this move-in ready 2,312 sq ft home offering 4 bedrooms, 2 baths, and a 2-car carport—perfectly blending a country-like feel with the convenience of being...
- 4 Beds
- 2 Baths
- 202602135 MLS
- FS - Fee Simple Tenure
- 56 DOM
RARELY FOUND IN KAHALA...this newly renovated property offers a versatile, multi-dwelling layout presenting an island estate where flexibility and luxury lifestyle conver...
- 5 Beds
- 6 Baths
- 202607921 MLS
- FS - Fee Simple Tenure
- 59 DOM
This beautifully remodeled single-family home offers stunning ocean views and is designed for both comfort and entertaining. Featuring 4 bedrooms and 4.5 bathrooms, the s...
- 4 Beds
- 5 Baths
- 202607298 MLS
- FS - Fee Simple Tenure
- 189 DOM
Welcome to 1116 Kealaolu Ave. a charming executive single-level home located near Waialae Country Club with tasteful architectural features that include stained concrete ...
- 4 Beds
- 4 Baths
- 202605306 MLS
- FS - Fee Simple Tenure
- 179 DOM
Nestled in the prestigious Waialae Iki neighborhood, 1708 Kumakani Loop offers an ideal blend of comfort, privacy and timeless Hawaii living. This well-maintained home sh...
- 3 Beds
- 3 Baths
- 202604841 MLS
- FS - Fee Simple Tenure
- 151 DOM
Discover a rare and extraordinary offering—over 45,000 square feet of prime buildable land along prestigious Kahala Avenue. This expansive oceanfront property, comprised ...
- 202604171 MLS
- FS - Fee Simple Tenure
- 242 DOM
NEW LISTING IN WAIALAE IKI!! This completely renovated 5bed/4bath home is located in desirable Waialae Iki and features an open floorplan, panoramic ocean views, quartz c...
- 5 Beds
- 4 Baths
- 202604007 MLS
- FS - Fee Simple Tenure
- 62 DOM
Situated on one of the most desired streets, in one of Honolulu’s most prestigious neighborhoods, 4781 Aukai Ave presents a rare opportunity to own a residence moments aw...
- 3 Beds
- 4 Baths
- 202600839 MLS
- FS - Fee Simple Tenure
- 47 DOM
Kahala luxury living in this highly upgraded, single-level ground floor residence with over 2,000sf. This renovated 3 bedroom, 2 bath home is located in sought after ocea...
- 3 Beds
- 2 Baths
- 202601168 MLS
- LH - Leasehold Tenure
- Kahala Beach Bldg.
- 278 DOM
Solid, mid-century custom designed Home in the "Carlos Long" subdivision of Palolo! Property emanates a tropical Country-like feel while remaining close to the amenities ...
- 5 Beds
- 2 Baths
- 202600101 MLS
- FS - Fee Simple Tenure
- 160 DOM
An award-winning residence in the prestigious Kahala neighborhood finely constructed with attention to detail and quality. This single level home of 3-bedrooms, 2 full ba...
- 3 Beds
- 4 Baths
- 202528545 MLS
- FS - Fee Simple Tenure
- 165 DOM
A rare opportunity to create a legacy estate in one of Honolulu’s most prestigious neighborhoods. Set on an expansive 20,021-square-foot parcel along coveted Kahala Avenu...
- 202527707 MLS
- FS - Fee Simple Tenure
- 322 DOM
Rare find, a great buy! Welcome to Kahala View Estate, 4-bedroom (4th bedroom has no closets) , 2.5-bath split-level townhome offering spectacular Diamond Head, ocean, mo...
- 4 Beds
- 3 Baths
- 202524595 MLS
- FS - Fee Simple Tenure
- Kahala View Estate Bldg.
- 75 DOM
Live a resort lifestyle in Kahala’s Only Beachfront Condominium! Located in Building 1 next to Waialae Country Club (home of the Sony Open) this 3rd Floor unit (out of 4 ...
- 2 Beds
- 2 Baths
- 202526410 MLS
- LH - Leasehold Tenure
- Kahala Beach Bldg.
- 53 DOM
Welcome to Kahala Beach 332, a rare oceanfront residence with direct, unobstructed ocean views, swaying palms, and gorgeous vistas of Koko Head. This expansive, beautiful...
- 3 Beds
- 3 Baths
- 202521077 MLS
- LH - Leasehold Tenure
- Kahala Beach Bldg.
- 20 DOM
Historic Charm Meets Endless Possibility in Kahala Set over 13,500 square feet on Kahala Avenue, this rare and charming 1931 Tudor home awaits your vision. 4354 Kaha...
- 3 Beds
- 1 Baths
- 202519633 MLS
- FS - Fee Simple Tenure
- 50 DOM
Serene Kahala Oasis- This spacious newer Kahala home is located across the street from world famous Waialae Golf Course, and offers 6 bedrooms, 5.5 bath (3 ensuite) on 2 ...
- 6 Beds
- 6 Baths
- 202517331 MLS
- FS - Fee Simple Tenure
- 83 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
Unbeatable Location Near Beaches, Golfing, and More… This spacious 5-bedroom 4-bath residence is located on one of Kahala’s most desirable streets. Rich hardwood floors a...
- 5 Beds
- 4 Baths
- 202512860 MLS
- FS - Fee Simple Tenure
- 127 DOM
Experience the pinnacle of island living in this immaculately maintained 4 bdrm + den/4 bath executive style residence in the highly coveted Kahala neighborhood. With alm...
- 4 Beds
- 4 Baths
- 202510141 MLS
- FS - Fee Simple Tenure
- 190 DOM
Welcome to 4837 Kolohala Street, where luxury and island living blend together in perfect harmony. The main layout of the home features 3 bedrooms and 3.5 bathrooms, with...
- 4 Beds
- 5 Baths
- 202507668 MLS
- FS - Fee Simple Tenure
- 82 DOM
First OPEN HOUSE on SUNDAY 3/30 2-5PM! Experience resort-style living in Kahala. This charming home offers over 5,000 sq. ft. of interior space, with the main house featu...
- 5 Beds
- 6 Baths
- 202507710 MLS
- FS - Fee Simple Tenure
- 44 DOM
Modern Living in a Prime Kahala Location. An exceptional opportunity to own on prestigious Kahala Avenue, home to some of Honolulu’s most distinguished residences. This e...
- 3 Beds
- 6 Baths
- 202506825 MLS
- FS - Fee Simple Tenure
- 74 DOM
Country living on 2.92 acres in town! A very rare opportunity in Palolo valley! 3 bed, 2 bath, single level home, surrounded by lush greenery, breathtaking views, endless...
- 3 Beds
- 2 Baths
- 202505777 MLS
- FS - Fee Simple Tenure
- 47 DOM
This home is a real treat. Up the hill in St Louis, above Honolulu, and away from the city, you’ll find a wonderful cozy SINGLE level home with 3br/2ba and 3 lanais. Fea...
- 3 Beds
- 2 Baths
- 202504787 MLS
- FS - Fee Simple Tenure
- 52 DOM
Do not be fooled by the square footage! There are enclosed lanai spaces here that feel like living space, making this a much bigger home. Here is your life in town, but a...
- 3 Beds
- 2 Baths
- 202502799 MLS
- FS - Fee Simple Tenure
- 80 DOM
Rarely Available: DIRECT OCEANFRONT KAHALA BEACH with EV Charging! A 2 bedroom, 2 bath condo with a twist- owner converted the dining room into a spare bedroom for added ...
- 2 Beds
- 2 Baths
- 202427467 MLS
- LH - Leasehold Tenure
- Kahala Beach Bldg.
- 22 DOM
A fully renovated and expanded single level home is ready for its new owner in Kahala! A wonderful floorplan showcases four bedrooms and three full bathrooms, plus two ex...
- 4 Beds
- 3 Baths
- 202407201 MLS
- FS - Fee Simple Tenure
- 55 DOM
Charming island home in the heart of Kahala! This large 4 bedroom, 3 bath home has been renovated and features high ceilings, split ACs, a new kitchen and bath, and upgra...
- 4 Beds
- 3 Baths
- 202324088 MLS
- FS - Fee Simple Tenure
- 73 DOM
Prime Kahala Avenue location – this expansive estate-sized lot spans over 20,000 square feet and is ready for you to create your dream home. The generous space offers a r...
- 202415567 MLS
- FS - Fee Simple Tenure
- 21 DOM
Fabulous Island Retreat… Situated on a desirable street in Kahala, this wonderful 3-BD + separate Den/exercise room, 3.5 BA home exudes privacy amidst lush tropical lands...
- 3 Beds
- 4 Baths
- 202316866 MLS
- FS - Fee Simple Tenure
- 164 DOM
Highly Desired and Convenient Location in Kahala!! This 2 bedrooms, 2 full baths, 1 reserved parking (street parking available) townhouse strategically located for home, ...
- 2 Beds
- 2 Baths
- 202326097 MLS
- FS - Fee Simple Tenure
- Tropic Gardens 1 Bldg.
- 29 DOM
Discreetly tucked away behind a tall mock orange hedge and redwood fence, sits this spacious, remodeled single-level ranch-style home that has just about everything one c...
- 4 Beds
- 5 Baths
- 202406439 MLS
- FS - Fee Simple Tenure
- 54 DOM
Discover the pinnacle of modern indoor/outdoor luxury living with beautiful natural elements in this stunning 5-bedroom, 3.5-bathroom home in the coveted Kahala neighborh...
- 5 Beds
- 4 Baths
- 202408861 MLS
- FS - Fee Simple Tenure
- 67 DOM
Large vacant lot on the prestigious Kahala Avenue is now available for you to build your dream home in paradise. This property is within walking distance to beach access ...
- 202320830 MLS
- FS - Fee Simple Tenure
- 116 DOM
Overlooking a peaceful stream with serene tropical surroundings, enjoy the allure of a quintessential Hawaiian country residence with the modern conveniences of a new hom...
- 3 Beds
- 4 Baths
- 202321506 MLS
- FS - Fee Simple Tenure
- 106 DOM
Location, Location, Location!!! A rare opportunity to own a single-family home in the highly desirable Waialae Nui-lower neighborhood. Bring your architect and your contr...
- 3 Beds
- 1 Baths
- 202326441 MLS
- FS - Fee Simple Tenure
- 45 DOM
Classical-contemporary single-level architecture harmonizes with urban sophistication in this breathtaking AIA Hawaii Award-winning retreat in Kahala. Drawing inspiration...
- 3 Beds
- 3 Baths
- 202418688 MLS
- FS - Fee Simple Tenure
- 235 DOM
Seize your opportunity to own a single level home on a large, level lot in one of Kahala's prime locations! This 5 bedroom + 3 bath house has been well-maintained over t...
- 5 Beds
- 3 Baths
- 202316801 MLS
- FS - Fee Simple Tenure
- 172 DOM
Experience luxe island living from this spacious residence in lower Waialae Iki with ocean and park views. This 5-bedroom, 3-bath home offers versatility and convenience,...
- 5 Beds
- 3 Baths
- 202328527 MLS
- FS - Fee Simple Tenure
- 80 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.