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$2,100,000

Welcome home to a thoughtfully designed space where comfort, connection, and everyday living come naturally. Located in the prestigious Portlock neighborhood of Hawaii Kai, this 5-bedroom, 3-bathroom home offers the perfect blend of functionality, space, and island living. Boasting over 2,000 square feet of interior living area, the home's unique open-concept floor plan provides generous living and dining spaces ideal for both everyday living and entertaining. Spacious bedrooms provide flexibility for family, a home office, or multigenerational living, while three separate gated yard areas offer private outdoor spaces off each wing of the home. Step outside to your own private tropical retreat featuring a swimming pool and beautifully landscaped yard, creating the perfect setting for outdoor dining, relaxation, and year-round enjoyment. From the spacious gathering areas to the private backyard, this home was made for making memories. Located in one of East Honolulu's most coveted neighborhoods and just moments from both Hawaii Kai's shopping centers and desirable beach access points, this Portlock home offers the lifestyle, space, and comfort you've been searching for.

5 Beds ⋅ 3 Baths ⋅ 202611728 MLS ⋅ FS - Fee Simple Tenure ⋅ 54 DOM

Welcome home to a thoughtfully designed space where comfort, connection, and everyday living come naturally. Located in the prestigious Portlock neighborhood of Hawaii Kai, this 5-bedroom, 3-bathroom home offers the perfect blend of functionality, space, and island living. Boasting over 2,000 square feet of interior living area, the home's unique open-concept floor plan provides generous living and dining spaces ideal for both everyday living and entertaining. Spacious bedrooms provide flexibility for family, a home office, or multigenerational living, while three separate gated yard areas offer private outdoor spaces off each wing of the home. Step outside to your own private tropical retreat featuring a swimming pool and beautifully landscaped yard, creating the perfect setting for outdoor dining, relaxation, and year-round enjoyment. From the spacious gathering areas to the private backyard, this home was made for making memories. Located in one of East Honolulu's most coveted neighborhoods and just moments from both Hawaii Kai's shopping centers and desirable beach access points, this Portlock home offers the lifestyle, space, and comfort you've been searching for.

7081 Kalanianaole Highway, Honolulu

$3,000,000

Tucked within a canopy of mature fruit trees and lush tropical landscaping, this vintage island style estate carries the warmth and authenticity that define classic Hawaii living while set in one of East Honolulu's most coveted addresses. Located on a private, expansive lot in the highly sought-after Portlock neighborhood, the main residence offers 3 bedrooms, 3 bathrooms, and the kind of character that simply cannot be built new — with ocean access just steps away across the street. Privately situated toward the rear of the property, a legal custom-built cottage adds remarkable versatility. Featuring approximately 768 sq. ft. of living space and an impressive lofted living area perfect for extended family, guests, or a private retreat of your own. Properties like this where privacy, tropical beauty, and proximity to the Pacific converge rarely come to market in East Honolulu. A true legacy property.

3 Beds ⋅ 4 Baths ⋅ 202607683 MLS ⋅ FS - Fee Simple Tenure ⋅ 103 DOM

Tucked within a canopy of mature fruit trees and lush tropical landscaping, this vintage island style estate carries the warmth and authenticity that define classic Hawaii living while set in one of East Honolulu's most coveted addresses. Located on a private, expansive lot in the highly sought-after Portlock neighborhood, the main residence offers 3 bedrooms, 3 bathrooms, and the kind of character that simply cannot be built new — with ocean access just steps away across the street. Privately situated toward the rear of the property, a legal custom-built cottage adds remarkable versatility. Featuring approximately 768 sq. ft. of living space and an impressive lofted living area perfect for extended family, guests, or a private retreat of your own. Properties like this where privacy, tropical beauty, and proximity to the Pacific converge rarely come to market in East Honolulu. A true legacy property.

380 Portlock Road, Honolulu

$14,250,000

Spectacular beachfront estate ..two separate parcels seamlessly combined.Stroll through immaculately landscaped grounds with soothing waterfalls throughout and a separate guest studio.Fully walled for privacy.Step into this architectural masterpiece designed by well known architect Jeff Long with grand foyer directly looking out to breathtaking beach, ocean, and Diamond Head Views!! Three primary suite-sized bedrooms..one suite on the main level...all enjoying Diamond Head and ocean views. Two other primary suites on the upper level with "Romeo and Juliet" balconies looking down to the foyer.Open floor plan with soaring ceilings ... finished with the finest materials..hardwood floors,wood trim in bedroom ceilings,etched glass touches,floor to ceiling sliding glass doors..close to island themed restaurants by the marina, shopping, Hanauma Bay, Sandy Beach..Your own Private Hawaiian Paradise..Simply STUNNING!! Both TMK's are being sold together for a total purchase price of $14,250,000. This spectacular dream retreat is also a Celebrity Home ... having been featured in multiple episodes of Hawaii Five-O. Your chance to own a piece of Hollywood and paradise all in one !!

6 Beds ⋅ 8 Baths ⋅ 202604666 MLS ⋅ FS - Fee Simple Tenure ⋅ 165 DOM

Spectacular beachfront estate ..two separate parcels seamlessly combined.Stroll through immaculately landscaped grounds with soothing waterfalls throughout and a separate guest studio.Fully walled for privacy.Step into this architectural masterpiece designed by well known architect Jeff Long with grand foyer directly looking out to breathtaking beach, ocean, and Diamond Head Views!! Three primary suite-sized bedrooms..one suite on the main level...all enjoying Diamond Head and ocean views. Two other primary suites on the upper level with "Romeo and Juliet" balconies looking down to the foyer.Open floor plan with soaring ceilings ... finished with the finest materials..hardwood floors,wood trim in bedroom ceilings,etched glass touches,floor to ceiling sliding glass doors..close to island themed restaurants by the marina, shopping, Hanauma Bay, Sandy Beach..Your own Private Hawaiian Paradise..Simply STUNNING!! Both TMK's are being sold together for a total purchase price of $14,250,000. This spectacular dream retreat is also a Celebrity Home ... having been featured in multiple episodes of Hawaii Five-O. Your chance to own a piece of Hollywood and paradise all in one !!

255 & 257 Portlock Road, Honolulu

$6,900,000

Rarely will you find a home that evokes quintessential Hawaii living at its finest. This SINGLE LEVEL oceanfront home is located on a LARGE 15,000+lot on prestigious Portlock Rd. It has everything: a beautifully designed Ossipoff home, off-shore breezes, & rare double WIDTH private lane entrance. The local property Owner is the founder of the surf company, Local Motion. He says the area PORTLOCK has the BEST WEATHER IN THE WORLD, the location has direct West exposure w-off-shore breezes, slower living away from the hustle-bustle. Raised in Kailua, the seller has also lived in different areas of Hawaii & chose this area. ONLY a few homes on Portlock Rd. have private land in front, this is one of them. This home sits on the ocean but has NO SAND that attracts people, no music, trash or hanging around. Hawaii Kai has everything needed: 5 surfing areas in front (beginners-advanced), ranked schools, public golf, recreation pools & shopping conveniences. Private & separate entry for Guest room for family or care giving. Hawaii living at its finest; unpretentious, you deserve to live the dream. Rob is a Hawaiian Local & raised in Hawaii all his life & will provide his BIO if asked.

3 Beds ⋅ 4 Baths ⋅ 202528103 MLS ⋅ FS - Fee Simple Tenure ⋅ 216 DOM

Rarely will you find a home that evokes quintessential Hawaii living at its finest. This SINGLE LEVEL oceanfront home is located on a LARGE 15,000+lot on prestigious Portlock Rd. It has everything: a beautifully designed Ossipoff home, off-shore breezes, & rare double WIDTH private lane entrance. The local property Owner is the founder of the surf company, Local Motion. He says the area PORTLOCK has the BEST WEATHER IN THE WORLD, the location has direct West exposure w-off-shore breezes, slower living away from the hustle-bustle. Raised in Kailua, the seller has also lived in different areas of Hawaii & chose this area. ONLY a few homes on Portlock Rd. have private land in front, this is one of them. This home sits on the ocean but has NO SAND that attracts people, no music, trash or hanging around. Hawaii Kai has everything needed: 5 surfing areas in front (beginners-advanced), ranked schools, public golf, recreation pools & shopping conveniences. Private & separate entry for Guest room for family or care giving. Hawaii living at its finest; unpretentious, you deserve to live the dream. Rob is a Hawaiian Local & raised in Hawaii all his life & will provide his BIO if asked.

469 A Portlock Road, Honolulu

$6,500,000

Tucked behind a private gate in prestigious Portlock, this extensively rebuilt residence offers rare privacy and peacefulness. Thirty-foot sliding glass doors and ceilings open to a large covered lanai and backyard featuring a 50-foot saltwater pool and spa. Mature palms along the property line create a natural privacy buffer. Step through the front door into expansive open living spaces with marble-like Italian porcelain flooring and soaring ceilings. The layout includes five bedrooms with two primary suites — each with a private lanai — plus a versatile bonus room with private entrance and an in-home sauna. Designed by award-winning architect James McPeak and reimagined in recent years, the home features dramatic floor-to-ceiling windows and spa-inspired bathrooms. Set on a 13,000+ sq ft lot with ¼ shared ownership in a nearby beach access walkway. Recent improvements include a new custom roof (2021), updated windows (2022, excluding select doors), and a solar system subject to a power purchase agreement. Just minutes to Costco, Hawaii Kai shopping centers, and dining. A rare offering in one of O?ahu's most established coastal neighborhoods.

5 Beds ⋅ 6 Baths ⋅ 202528543 MLS ⋅ FS - Fee Simple Tenure ⋅ 220 DOM

Tucked behind a private gate in prestigious Portlock, this extensively rebuilt residence offers rare privacy and peacefulness. Thirty-foot sliding glass doors and ceilings open to a large covered lanai and backyard featuring a 50-foot saltwater pool and spa. Mature palms along the property line create a natural privacy buffer. Step through the front door into expansive open living spaces with marble-like Italian porcelain flooring and soaring ceilings. The layout includes five bedrooms with two primary suites — each with a private lanai — plus a versatile bonus room with private entrance and an in-home sauna. Designed by award-winning architect James McPeak and reimagined in recent years, the home features dramatic floor-to-ceiling windows and spa-inspired bathrooms. Set on a 13,000+ sq ft lot with ¼ shared ownership in a nearby beach access walkway. Recent improvements include a new custom roof (2021), updated windows (2022, excluding select doors), and a solar system subject to a power purchase agreement. Just minutes to Costco, Hawaii Kai shopping centers, and dining. A rare offering in one of O?ahu's most established coastal neighborhoods.

235 Portlock Road, Honolulu