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$1,949,000
6 Beds ⋅ 4 Baths ⋅ 202616413 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 DOM
Introducing private, duplex-style living in this exceptional 6-bedroom, 4-bath residence in Kaaawa. This oceanfront estate with a rare attached guesthouse offers spacious, and thoughtfully designed floor plans, each with seamless indoor-outdoor flow and custom windows capturing ocean and dramatic mountain views. Each residence features a well-appointed kitchen with ample storage, movable island, and dedicated dining areas. One side enjoys breezy oceanfront living with sunrise views, beach access, and a grandfathered seawall, while the other offers stunning Koolau mountain vistas. Additional highlights include 120 owned solar shingle panels, a new solar water heater, serviced split ACs, and expansive outdoor living with a pergola-covered lanai, firepit, and grassy yard leading directly to the beach, ideal for entertaining. Enjoy snorkeling just steps away, views of Chinaman’s Hat, and frequent sightings of turtles, monk seals, and seasonal whales. Set in a quiet location adjacent to the iconic Kualoa Ranch, this property presents a rare opportunity for multigenerational living, rental income, or a private coastal retreat.

49-797 Kamehameha Highway Unit A, Kaaawa
$1,949,000
202616396 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 DOM
Introducing private living in this exceptional 6-bedroom, 4-bath duplex in Kaaawa. Each unit having 3 beds, 2 baths. This rare oceanfront estate offers spacious, and thoughtfully designed floor plans, each with seamless indoor-outdoor flow and custom windows capturing ocean and dramatic mountain views. Each residence features a well-appointed kitchen with ample storage, movable island, and dedicated dining areas. Both sides enjoys breezy oceanfront living with sunrise views, beach access, and a grandfathered seawall, while the front of the homes offer stunning Koolau mountain vistas. Additional highlights include 120 owned solar shingle panels (60 per side), a new solar water heater, serviced split ACs, and expansive outdoor living with a pergola-covered lanai, firepit, and grassy yard leading directly to the beach, ideal for entertaining. Enjoy snorkeling just steps away, views of Chinaman’s Hat, and frequent sightings of turtles, monk seals, and seasonal whales. Set in a quiet location adjacent to the iconic Kualoa Ranch, this property presents a rare opportunity for multigenerational living, rental income, or a private coastal retreat.

49-797 Kamehameha Highway Unit A, Kaaawa
$1,995,000
5 Beds ⋅ 4 Baths ⋅ 202615876 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 DOM
Discover a rare tropical retreat where the majestic Koolau Mountains meet the sparkling waters of Kalaeoio Beach Park. Situated on an expansive 13,949 sq. ft. lot directly across from the beach, this beautifully renovated 5-bedroom, 4-bath residence captures the essence of Hawaii living with breathtaking mountain and ocean views, soaring ceilings, and seamless indoor-outdoor living. Expansive covered lanais and disappearing glass doors invite cool trade winds and create the perfect setting for entertaining or relaxing in paradise. A natural freshwater stream and charming bridges wind through the lush tropical landscape, creating a private island oasis rarely found on Oahu. The generous lot offers exceptional flexibility with room to expand the existing home or explore the potential for a second dwelling. The spacious lower level is ideal for guests or multi-generational living. The adjoining parcel may also be available for purchase with the home, offering a rare opportunity to create an extraordinary legacy estate with even more land and privacy. This is a rare opportunity to own one of Oahu's truly unique coastal retreats.

51-244 Kamehameha Highway, Kaaawa
$1,850,000
4 Beds ⋅ 5 Baths ⋅ 202606847 MLS ⋅ FS - Fee Simple Tenure ⋅ 157 DOM
PRICE REDUCTION!!! Rare opportunity in Kaaawa with sweeping ocean, sunrise, and mountain views just steps from the water. This 4-bed, 4.5-bath home blends island living with upscale finishes, featuring open-beam wood ceilings, a grand Ipe staircase, and seamless indoor-outdoor flow. The open kitchen and living area is built for entertaining with dual islands, granite countertops, double ovens, and a wine fridge. Multiple en-suite bedrooms, including a spacious primary with a soaking tub and panoramic views. Wraparound deck, plantation-style lanai, split AC, and quality finishes throughout. Turnkey coastal living with direct access to swimming, paddling, and fishing.

51-408 Kamehameha Highway, Kaaawa

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.