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$3,000,000
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

$4,485,000
3 Beds 6 Baths 202605472 MLS FS - Fee Simple Tenure 106 DOM
Situated on one of Oahu’s most treasured streets in one of the most private, yet convenient neighborhoods, this mid-century contemporary home combines architectural integrity, character and functionality all dressed in a palate of solid and evocative materials. Thin mullioned French windows, brick and custom tile conspire to create a home that is warm, timeless and very much aligned with today’s living. 12 Lumahai St. is a landmark 1975 custom estate representing a compelling renovation opportunity. Set on 15,577 sq. ft. of land, this home offers 3,881 sq. ft. of interior living space and includes a thoughtfully designed main home as well as a separate guest cottage — offering flexibility for multi-generational living, guest accommodation or home gym or office. The home’s terraced architecture cascades toward a stunning pool and deck, framing breathtaking, unobstructed ocean views. Original brick archways, soaring ceilings and bold contemporary lines speak to the craftsmanship of its era and remain ready to anchor a world-class modern renovation. The property invites transformation as few properties on O'ahu offer this combination of scale, privacy, location, views and opportunity.

12 Lumahai Street, Honolulu

$1,395,000
2 Beds 2 Baths 202608318 MLS FS - Fee Simple Tenure 106 DOM
Nestled in the vibrant Kapahulu neighborhood of Honolulu, 3252 Esther Street is a charming single-family home that seamlessly blends modern updates with classic Hawaiiana character. Built in 1930, this residence has been thoughtfully renovated to offer contemporary comforts while preserving its original appeal. 2 spacious bedrooms, including a newly added primary suite featuring a walk-in shower and walk-in closets. 2 full bathrooms, both updated with modern fixtures. Equipped with new cabinets, countertops and appliances, including a gas range. Tankless gas water heater split air conditioning units and updated lighting fixtures throughout. Electronic gate and fencing for added privacy and security. This home offers unparalleled access to Honolulu's best attractions. Experience the best of Honolulu living, combining modern comforts with a prime location!

3252 Esther Street, Honolulu

$1,425,000
202607989 MLS FS - Fee Simple Tenure 112 DOM
Well located in town apartment building featuring a desirable mix of two 2 bedroom units and one 4 bedroom unit, offering flexible rental options and strong income potential. All units are generously sized with functional layouts, washer/dryer hook ups, separate electrical meters, good natural light, and on site parking, making them easy to lease and simple to manage. Tenants enjoy quick access to shopping, bus lines, schools, and major commuter routes, supporting stable demand and low vacancy in this central location. Ideal for an investor seeking steady cash flow or an owner occupant looking to live in one unit and rent the others to offset the mortgage. Plumbing was upgraded and building painted prior to listing.

2221 Fern Street, Honolulu

$3,250,000
4 Beds 5 Baths 202607298 MLS FS - Fee Simple Tenure 113 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 spacious layout includes an expansive living room and a large, updated kitchen that is perfect for gatherings. Enjoy beautiful sweeping views of the ocean from the living room and bedrooms. Recent upgrades include new flooring, fresh interior paint, and various modern improvements throughout. The expansive kitchen features Bosch appliances and a Thermador fridge. Enjoy outdoor living with a private pool and ample space to host guests. Conveniently located near Kahala Mall, Waialae Country Club, the beach and more! There are many fruit trees including but not limited to: fig, lemon, white dragon fruit, soursop, guava and more! Two brand new (installed 2025) Tesla charging battery / charging station is included. The house also has 43 owned Panasonic solar panels. Property details does not match tax records. Buyer to verify and to conduct their own due diligence.

1632 Ihiloa Loop, Honolulu

$2,042,250
9 Beds 6 Baths 202607482 MLS FS - Fee Simple Tenure 119 DOM
Rare Kakaako live-work opportunity in the centrally located Kakaako Community Development District. Situated on approximately 6,000 sq. ft. of level land, this versatile property features three separate living areas offering exceptional flexibility for owner-occupants, remote professionals, shared living arrangements, guest accommodations, or supplemental rental income. The spacious floor plans and generously sized rooms are ideal for home offices, consulting spaces, creative studios, study areas, wellness rooms, or other personal workspaces while maintaining comfortable residential living. Three distinct living areas create privacy and separation, making it easy to balance living, working, and hosting on one property: Upstairs: 3-bedroom, 2-bath residence (~1,241 sq. ft.); Downstairs: a move-in ready 3-bedroom, 2-bath unit (~1,201 sq. ft.); above the carport: 3-bedroom, 2-bath ADU built in 1997 (~1,128 sq. ft.).A rare urban convenience, this property also offers a 6-car tandem carport and long driveway. Thre is the opportunity to combine with the neighboring duplex (additional 6,000 sq. ft. lot) for future redevelopment potential or a larger multigenerational compound.

1128 Alohi Way, Honolulu

$1,725,000
4 Beds 4 Baths 202606994 MLS FS - Fee Simple Tenure 125 DOM
Nestled in the sought-after hillside community of St. Louis Heights, this fully renovated, turn-key home offers the perfect blend of modern design and flexible multi-generational living. Spanning two distinct living areas plus a wet bar, the layout is as functional as it is impressive. The home features two luxurious primary suites, two additional bedrooms, and two full bathrooms — all thoughtfully updated with contemporary finishes throughout. A one-car garage plus driveway parking adds everyday convenience. Step outside onto two expansive lanais and take in sweeping city views that make every evening unforgettable. Whether you’re entertaining or simply unwinding, this home delivers an exceptional Hawaii lifestyle. Move-in ready. Nothing to do but enjoy.

2234 St Louis Drive, Honolulu

$2,200,000
6 Beds 5 Baths 202603875 MLS FS - Fee Simple Tenure 125 DOM
Nestled in the lush and prestigious Manoa Valley, this expansive single-family residence offers a rare blend of space, comfort, and timeless island charm. Featuring 6 bedrooms and 4.5 bathrooms, the home spans 3,588 square feet of living area on a 6,860 square foot lot, providing exceptional flexibility for multigenerational living, extended family, or home office needs. Thoughtfully designed, the spacious floor plan includes generously sized bedrooms, multiple living areas, and abundant natural light throughout. The kitchen and common areas flow seamlessly, ideal for both everyday living and entertaining. Well-appointed bathrooms and ample storage enhance functionality, while the home's layout offers privacy and versatility - Rental opportunity on Lower Level. Set against the tranquil backdrop of Manoa's verdant mountains, this property enjoys a peaceful residential setting while remaining conveniently close to the University of Hawaii, top schools, shopping, dining, and freeway access. Just minutes from town yet surrounded by nature, this is a unique opportunity to own a substantial home in one of Honolulu's most.

2742 Manoa Road, Honolulu

$5,990,000
4 Beds 6 Baths 202604465 MLS FS - Fee Simple Tenure 130 DOM
Experience refined island luxury living in this executive-style 4-bedroom, 5.5-bath residence ideally positioned on the slopes of iconic Diamond Head. Encompassing nearly 5,900 sq ft of interior space on an 11,752 sq ft lot, this impressive home captures beautiful ocean and sunset views while offering exceptional indoor-outdoor living. Expansive lanai areas, complemented by a heated pool and spa, create a private retreat designed for effortless entertaining. Soaring ceilings enhance the home’s grand scale and invite abundant natural light throughout. The chef’s kitchen anchors the main living spaces, while separate guest quarters with a private entrance provide flexibility and privacy. Remodeled by Jeff Long in 1995, this distinguished property blends timeless design with a premier location just moments from Kapiolani Park, the Gold Coast, world-famous beaches, and renowned shopping and dining of Waikiki. A rare offering in one of Honolulu’s most prestigious neighborhoods.

2999 Makalei Place, Honolulu

$6,900,000
7 Beds 8 Baths 202601735 MLS FS - Fee Simple Tenure 136 DOM
PRICE REDUCED! MOTIVATED SELLER. This luxury home was taken nearly to the studs and rebuilt a few years ago, and it shows. Unobstructed ocean views are framed by 30-foot windows and ceilings spanning the entire front of the house, opening to oversized decks. A rooftop deck adds sweeping views of the coastline, Diamond Head, and the ocean. Quiet, private setting two blocks from Diamond Head Road and a short distance to the beach. Seven bedrooms and six full baths plus two half baths. Includes a separate studio with its own private entrance — one bedroom, one bath, full kitchenette — ideal for multigenerational living, guests, or rental income. Owned 27-panel photovoltaic system keeps energy costs low. Seller financing may be available.

3849 Poka Street, Honolulu

$1,680,000
3 Beds 3 Baths 202601029 MLS FS - Fee Simple Tenure 136 DOM
Nestled in lush Tantalus, above the Honolulu cityscape, this 3BD/3BA retreat offers privacy, nature, & modern comfort on a 0.40-acre lot surrounded by tropical greenery. Built in 1975 & updated in 1987, the home features soaring ceilings, rich redwood walls, & warm wood tones throughout. Its flexible layout includes an open kitchen & 3 living rooms, one on each level, making this property ideal for single family or multi-family living. Sunlight pours through large windows, showcasing stunning views, while 31 PV panels with battery backup provide energy efficiency. Sip your morning coffee on one of three wrap-around covered lanais, enjoy your fenced garden patio, or play on your flat, terraced yard space—rare for the area—supported by beautiful, newly-engineered rock retaining walls. The detached 2-car garage adds convenience, & the forested setting enhances the serene ambiance of this home. Explore the terrain on your own lot or venture out. You're minutes from Pu'u 'Ualaka'a State Park & hiking trails, yet still close to downtown and schools. This home perfectly balances seclusion & accessibility. A true sanctuary to embrace Hawaii’s beauty & island living!

4142 Round Top Drive, Honolulu

$4,980,000
5 Beds 7 Baths 202528395 MLS FS - Fee Simple Tenure 137 DOM
Perfectly situated on one of the prettiest tree-lined drives in Honolulu, known for its refined estates, this gorgeous classic treats you to panoramic Diamond Head, ocean, and mountain views. From the luxurious porte-cochere, a lovely hall opens to elegant living and dining rooms with high ceilings. The generous covered lanai and spacious pool overlook the landscaped lawn and magnificent views. You’ll be proud to entertain guests in museum-quality spaces or simply enjoy your serene, indoor-outdoor lifestyle. A desirable ground floor bedroom suite, family room, breakfast room, kitchen and plentiful storage complete the expansive main level. Upstairs are three more large bedroom suites, each with its own bath. A separate cottage provides flexible options for guests or extended living. Attributed to architect C. W. Dickey, who designed the original Halekulani Hotel and other island-style treasures, this home is on the Hawaii Register of Historic Places with property taxes of only $25/month. Lovingly maintained and upgraded with PV and more, the residence offers masterful design, privacy, and views in a stellar location.

2475 Makiki Hts Drive, Honolulu

$1,950,000
3 Beds 2 Baths 202606137 MLS FS - Fee Simple Tenure 137 DOM
Perched in the prestigious Waialae Nui Ridge, this exceptional Ossipoff-designed single-family residence offers breathtaking panoramic views of Diamond Head and the sparkling coastline. Designed with a spacious open floor plan, the home seamlessly blends indoor and outdoor living, creating an inviting atmosphere ideal for both relaxing and entertaining. Large windows and open living areas capture natural light and showcase the stunning scenery from multiple vantage points. Enjoy the tranquility and privacy of this sought-after neighborhood, all while being conveniently located just minutes from shopping, dining, beaches, and top-rated schools. A rare opportunity to own in one of East Honolulu’s most desirable communities.

1627 Halekoa Drive, Honolulu

$1,695,000
4 Beds 3 Baths 202605317 MLS FS - Fee Simple Tenure 153 DOM
NEW PRICE! Tucked away in a private, forested mountainside enclave, this rare architectural estate by noted architect Charles Chamberland offers a striking blend of mid-century modern heritage and smart, flexible living. Enveloped by trees and a stunningly peaceful setting this 4-bedroom, 3-bath gem provides nearly 3,000 sq. ft. of living space masterfully designed to accommodate multi-generational families with separate private entrances. Refreshed with new paint and carpet, the upper levels feature an expansive open floor plan anchored by soaring ceilings and floor-to-ceiling windows that perfectly frame the lush, verdant surroundings. The gourmet kitchen combines timeless mahogany cabinetry with elegant marble floors, leading up to a loft-style primary suite. The first-level layout provides the perfect separation of space, allowing for potential rental, secured with hurricane shutters. The estate features world-class botanical grounds that flow seamlessly into the forest, offering peaceful sitting areas, winding trails, and tranquil water features. Unwind on the scenic third-level landing with peek-a-boo ocean views. Your ultimate, flexible nature retreat awaits. Sold as is.

156 Forest Ridge Way, Honolulu

$1,500,000
5 Beds 4 Baths 202604150 MLS FS - Fee Simple Tenure 155 DOM
Rare opportunity to own two separate homes on one lot. Two Electrical meters The front home offers 3 bedrooms and 2 bathrooms, remodeled in 2015 and well maintained over the years. Comfortable layout, move-in ready, and easy for everyday living. The detached rear home features 2 bedrooms and 2 bathrooms with 1 bedroom and 1 bath upstairs and 1 bedroom and 1 bath downstairs. There is also an open patio with extra space for outdoor use. Parking for up to 5 vehicles on the property provides good separation and privacy between the two homes. Great option for extended family or rental income while living in the main home. Plenty of parking on the property plus easy street parking nearby. Flexible layout suitable for multi-generational living or investment. Convenient location close to hospitals, markets, and bus routes with easy access to daily necessities. Must see to appreciate.

709 Twin View Drive, Honolulu

$1,400,000
5 Beds 4 Baths 202605116 MLS FS - Fee Simple Tenure 158 DOM
The Giving House - A truly rare offering on highly desired St. Louis Drive in Honolulu. Commanding sweeping ocean views from its prized east-west orientation, this exceptional residence is designed to capture natural light and refreshing trade winds throughout the day. Architectural surprises and thoughtful details are found throughout, adding warmth and character to every level. The flexible floor plan features 4 bedrooms and 2.5 baths upstairs, creating generous space for living and entertaining, while a separate one-bedroom, one-bath downstairs offers ideal potential for multi generation guests, or long-term rental income. Step outside to an abundant edible yard with mature plantings, offering both beauty and bounty. With versatility, view, and income potential combined in one property, this is truly the house that keeps on giving - a rare opportunity to own a distinctive island retreat in a highly desirable Honolulu location.

1834 St Louis Drive, Honolulu

$5,500,000
5 Beds 6 Baths 202604792 MLS FS - Fee Simple Tenure 163 DOM
Hawaii Loa Ridge is one of Oahu’s most prestigious residential enclaves. Privately positioned within the secluded gated community of The Pointe, this remarkable estate captures commanding ocean vistas and sweeping panoramas stretching toward Koko Head Crater. Designed by architect Mark Lively, the five-bedroom, five-and-a-half-bath Mediterranean masterpiece reflects timeless architectural elegance and exceptional craftsmanship throughout. The main level unfolds with a gracious formal dining room, an expansive family room, and a sumptuous primary suite retreat. A grand living room opens seamlessly to the resort-style pool terrace, where shimmering ocean views create an unforgettable backdrop. Upstairs, an additional en-suite bedroom, a secondary lounge, and two adjoining bedrooms provide both comfort and flexibility. A private maid’s quarters is discreetly integrated for added convenience. An extraordinary offering in one of Honolulu’s most coveted neighborhoods, this residence epitomizes elevated island living — where scale, privacy, and breathtaking horizons converge in effortless sophistication. Property to be conveyed "As Is".

525 Moaniala Street, Honolulu

$14,250,000
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

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.