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Search Leeward Coast, HI Luxury Homes

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Newest Leeward Coast, HI Luxury Homes For Sale

87-912 Hakimo Road, Waianae image
87-912 Hakimo Road, Waianae $1,200,000

Amazing Opportunity in Maili on Hakimo Road featuring 4 bedrooms and 2 full bathrooms. Built in 1992 this property sits on 1 acre of Country 56 zoned land. Perfect for ke...

  • 4 Beds
  • 2 Baths
  • 202619824 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 3 DOM
87-579 Farrington Highway, Waianae image
87-579 Farrington Highway, Waianae $4,900,000

Konishiki Hale is a one-of-a-kind beachfront estate built by Hawaii-born sumo legend Konishiki Yasokichi. Set across two oceanfront parcels on Oahu’s Leeward Coast, the p...

  • 5 Beds
  • 5 Baths
  • 202618611 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 21 DOM
86-401 Kuwale Road, Waianae image
86-401 Kuwale Road, Waianae $2,000,000

Welcome to an exceptional and rare opportunity presenting a sprawling farm estate in Waianae. Spread across an expansive 11.9 acres and available for sale for the first t...

  • 12 Beds
  • 4 Baths
  • 202616888 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 26 DOM
84-581 Upena Street, Waianae image
84-581 Upena Street, Waianae $2,483,000

Oceanfront 5 bedroom each with its own private exterior entrance; 6 bathrooms; 2-car garage; laundry room; pool; covered carport; expansive yard; beach sand area; large w...

  • 202616618 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 40 DOM
87-1406 Farrington Highway Unit A, Waianae image
87-1406 Farrington Highway Unit A, Waianae $1,249,000

Welcome to your new home! This beautiful, newly built property offers stunning ocean views and modern living, with everything fresh and ready for its new owners. The main...

  • 5 Beds
  • 4 Baths
  • 202617701 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 40 DOM
87-1055 Hakimo Road, Waianae image
87-1055 Hakimo Road, Waianae $1,350,000

Multi-family property on 3 acre lot. Needs repair. Selling As-Is. Buyer to do their own Due Diligence. 3 homes on property all tenant occupied.DO NOT disturb tenants. ...

  • 202617537 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 42 DOM
87-201 Paakea Road, Waianae image
87-201 Paakea Road, Waianae $1,690,000 ▼

A unique opportunity for the right buyer — motivated sellers!  This nearly 3-acre agricultural estate offers over 57,000 sq ft of greenhouse space used as an Orchid farm...

  • 6 Beds
  • 5 Baths
  • 202616373 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 55 DOM
84-581 Upena Street, Waianae image
84-581 Upena Street, Waianae $2,483,000

Ultimate Beach House 5/6/10+ Must tour OCEANFRONT property & experience perfect location/parcel. Pie-shaped lot w/ small, discreet street front, & huge backyard w/pool & ...

  • 5 Beds
  • 6 Baths
  • 202616617 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 55 DOM
84-1330 Maunaolu Street, Waianae image
84-1330 Maunaolu Street, Waianae $2,398,000

Discover an exceptional opportunity in the prestigious Makaha Valley Estates. Set on an expansive 64,469-square-foot lot, this impressive 4-bedroom, 3.5-bath Estate offer...

  • 4 Beds
  • 4 Baths
  • 202612344 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 76 DOM
84-84 Maiola Place, Waianae image
84-84 Maiola Place, Waianae $1,550,000

Experience elevated island at Cottages at Mauna Olu, a desirable dated community offering privacy, comfort, and a relaxed island lifestyle. This exceptional former devel...

  • 3 Beds
  • 2 Baths
  • 202615228 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 80 DOM
84-425 Makaha Valley Road, Waianae image
84-425 Makaha Valley Road, Waianae $1,589,999 ▼

**PRIVATE • NO HOA • 1.35 ACRES OF AGRICULTURAL LAND • TWO HOMES • A RARE HAWAIIAN RETREAT!** Opportunities like this are almost impossible to find on Oahu. Hidden within...

  • 5 Beds
  • 3 Baths
  • 202614991 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 83 DOM
84-916 Hanalei Street, Waianae image
84-916 Hanalei Street, Waianae $1,400,000 ▼

Rare investment opportunity featuring four detached single-family homes on an R-5 zoned lot. Ideal for investors, 1031 exchange buyers, or multi-generational living, this...

  • 10 Beds
  • 4 Baths
  • 202614927 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 83 DOM
84-916 Hanalei Street, Waianae image
84-916 Hanalei Street, Waianae $1,400,000 ▼

Rare investment opportunity featuring four detached single-family homes on an R-5 zoned lot. Ideal for investors, 1031 exchange buyers, or multi-generational living, this...

  • 202614924 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 83 DOM
87-1087 Apuupuu Road, Waianae image
87-1087 Apuupuu Road, Waianae $2,900,000

RARE OPPORTUNITY! Discover the endless possibilities with this over 12-acre level agricultural-zoned property featuring two well-built single-family homes, perfect for mu...

  • 7 Beds
  • 5 Baths
  • 202613633 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 103 DOM
87-1087 Apuupuu Road, Waianae image
87-1087 Apuupuu Road, Waianae $2,900,000

RARE OPPORTUNITY! Discover the endless possibilities with this over 12-acre level agricultural-zoned property featuring two well-built single-family homes, perfect for mu...

  • 202613635 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 103 DOM
87-134 Kahau Street, Waianae image
87-134 Kahau Street, Waianae $1,500,000

Rare Investment Opportunity - 5 houses on R-5 Zoned Lot. Dont miss your chance to own a multi-family property. Ideal for investors or multi-generational living! Tenant p...

  • 202613418 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 108 DOM
84-980 Kaulawaha Road, Waianae image
84-980 Kaulawaha Road, Waianae $1,689,000

Step through the private gates and discover a place where time seems to slow down. Nestled on just over an acre of landscaped grounds, this charming country property has ...

  • 3 Beds
  • 2 Baths
  • 202611459 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 121 DOM
86-116 Puhawai Road Unit A, Waianae image
86-116 Puhawai Road Unit A, Waianae $1,399,999 ▼

Imagine a place where your lifestyle, business, and opportunity grow together! Set on 2 acres, this residence offers the freedom to create a life centered around what mat...

  • 5 Beds
  • 4 Baths
  • 202611931 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 126 DOM
85-824 Lihue Street, Waianae image
85-824 Lihue Street, Waianae $1,600,000 ▼

Great investment property. Four houses on over 1/2 acre lot. Five rental units. Convenient location. Next to public park and elementary school. Walking distance to shops,...

  • 15 Beds
  • 6 Baths
  • 202612022 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 128 DOM
85-1570 Waianae Valley Road, Waianae image
85-1570 Waianae Valley Road, Waianae $1,498,000

Rare opportunity to own two adjacent TMK1-8-5-004-101-0000 & 1-8-5-004-102-0000 parcels in the highly desirable AG-2 agricultural zone on the West Oahu (Waianae) coast. ...

  • 5 Beds
  • 3 Baths
  • 202611556 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 135 DOM
87-154 Kakalena Street Unit CPR 2-7, Waianae image
87-154 Kakalena Street Unit CPR 2-7, Waianae $1,950,000 ▼

Exceptional investment opportunity to acquire a six-unit residential portfolio consisting of six individual CPR units under separate TMKs (TMK 1-8-7-001-016: Units #2 thr...

  • 202611506 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 137 DOM
84-808 Moua Street, Waianae image
84-808 Moua Street, Waianae $1,499,000 ▼

Tropical oasis just moments from the Sunset Shoreline in Makaha's coveted Moua Beach Loop with Beach Access right Across, Ocean View from your Window & Aki's Beach. Expan...

  • 3 Beds
  • 2 Baths
  • 202611204 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 136 DOM
87-250 Kulaaupuni Street, Waianae image
87-250 Kulaaupuni Street, Waianae $1,350,000

3 acres of flat and clear land in Maili! Zoned AG2 and ready to be made your own. This property features a large house with two bedrooms, two bathrooms, and two additiona...

  • 2 Beds
  • 2 Baths
  • 202609399 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 166 DOM
85-720 Farrington Highway, Waianae image
85-720 Farrington Highway, Waianae $1,680,000

RARE redevelopment opportunity in Waianae. Large R-5 zoned parcel of approximately 40,266 sqft. List price is for 85-720 Farrington Hwy only; adjoining parcel 85-718 Farr...

  • 14 Beds
  • 6 Baths
  • 202609226 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 168 DOM
85-1020 Mill Street Unit A & B, Waianae image
85-1020 Mill Street Unit A & B, Waianae $1,575,000

Brand new multi-family opportunity in the heart of Waianae! This property features two separate 3-bedroom, 2-bath units, each offering approximately 1,200 sq ft of interi...

  • 202605176 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 234 DOM
84-816 Maiola Street Unit 40, Waianae image
84-816 Maiola Street Unit 40, Waianae — Cottages At Maunaolu $1,399,000

Incredible Active Legal Short Term Rental in a Gated Resort Community just 4 minutes from Makaha Beach! The Cottages at Mauna‘Olu, tucked in Makaha Valley, has a Security...

  • 3 Beds
  • 2 Baths
  • 202608622 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • Cottages At Maunaolu Bldg.
  • 179 DOM
84-956 Hanalei Street, Waianae image
84-956 Hanalei Street, Waianae $1,765,000

ATTENTION INVESTORS – STRONG CASH FLOW OPPORTUNITY! Multi-unit income-producing property in Waianae generating $11,271/month in rental income with a current 6.9% CAP rate...

  • 202606722 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 208 DOM
84-945 Alahele Street, Waianae image
84-945 Alahele Street, Waianae $2,795,000

Exceptional value in gated Mauna‘Olu Estates. Set on over 2 acres, this modern retreat offers ocean and mountain views, privacy, and indoor-outdoor living. Open-concept d...

  • 4 Beds
  • 4 Baths
  • 202606539 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 210 DOM
84-814 Maiola Street Unit 39, Waianae image
84-814 Maiola Street Unit 39, Waianae — Cottages At Maunaolu $1,456,800 ▼

Experience the mana of Makaha Valley as you enter this majestic, LEGAL SHORT-TERM RENTAL in the gated community of Mauna’Olu Estates. A desirable single-level 3-bed, 2-ba...

  • 3 Beds
  • 2 Baths
  • 202606337 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • Cottages At Maunaolu Bldg.
  • 213 DOM
87-879 Apuupuu Road, Waianae image
87-879 Apuupuu Road, Waianae $1,450,000 ▼

Rare opportunity to own almost 4 1/2 acre of prime land in Waianae, Hawaii, offering exceptional flexibility for a private island lifestyle. This expansive property featu...

  • 5 Beds
  • 2 Baths
  • 202528275 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 300 DOM
87-879 Apuupuu Road, Waianae image
87-879 Apuupuu Road, Waianae $1,450,000 ▼

Rare opportunity to own nearly four and a half acres of prime land in Waianae, Hawaii, offering exceptional flexibility for a private island lifestyle with mountain views...

  • 202528273 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 300 DOM
84-1036 Noholio Road, Waianae image
84-1036 Noholio Road, Waianae $1,450,000 ▼

Nestled on a 1-acre lot between the mountains and the ocean, this LIKE NEW property offers the best of island living—space, serenity, and stunning natural surroundings. T...

  • 8 Beds
  • 4 Baths
  • 202528276 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 308 DOM
84-781 Moua Street, Waianae image
84-781 Moua Street, Waianae $1,300,000

OCEANFRONT! PERMITTED SEAWALL!!! This is a rare opportunity to purchase an oceanfront property on over 14,000 sq. ft. of land with an existing Quonset Hut home, permitted...

  • 3 Beds
  • 1 Baths
  • 202506666 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 594 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.

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Elizabeth La Riva is a real estate team affiliated with Compass. Compass is a licensed real estate broker with a principal office in Oahu, Hawaii, and abides by all applicable equal housing opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit property already listed. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

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