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$6,350,000
5 Beds ⋅ 6 Baths ⋅ 202611061 MLS ⋅ FS - Fee Simple Tenure
This remarkable Estate on 21,832 sq ft lot. 4,577 sq ft of living space all on one level, including swimming pool. This 5 bedroom 5.5 bath has sweeping panoramic views of Diamond Head, Ocean, Mountains and the seasonal Whales, December thru March. Architectural elegance and exceptional craftsmanship throughout. Property to be conveyed "as is".

28 Moloaa Street, Honolulu

Listing courtesy of Tomoko Realty.

$1,895,000
15 Beds ⋅ 8 Baths ⋅ 202610829 MLS ⋅ FS - Fee Simple Tenure
PRICE ADJUSTMENT! RARE 4-PERMITTED-UNIT INVESTMENT OPPORTUNITY IN MAKAHA! Situated on approximately 1 acre, this unique income-producing property features 4 permitted residential units, all extensively renovated, offering a turnkey opportunity for investors, multi-generational living, or an owner-occupant seeking rental income. Approximately 4,384 SQ FT, 15 bedrooms, 7.5 bathrooms, and parking for approximately 14+ vehicles. Currently generating approximately $9,900/month, with projected gross rental income of approximately $13,500/month ($162,000/year) when fully occupied. Four permitted units + 1 acre + extensive renovations + strong income potential - a rare combination on Oahu. Must see to appreciate the value and possibilities this property offers!

84-290 Makaha Valley Road, Waianae

Listing courtesy of SC Realty, LLC.

$1,880,000
8 Beds ⋅ 8 Baths ⋅ 202610511 MLS ⋅ FS - Fee Simple Tenure
Welcome to 609 Olomana Street, a newer-built residence in the highly desirable Coconut Grove neighborhood of Kailua. Constructed in 2022 this expansive property offers 8 bedrooms, 6 full bathrooms, and 2 half bathrooms, including a permitted Accessory Dwelling Unit (ADU) —providing exceptional flexibility for multigenerational living, guest accommodations, or potential rental income. The home features approximately 2,960 square feet of living area on a level 5,000-square-foot lot, with split air conditioning throughout for year-round comfort. Modern finishes, and a functional floor plan create an inviting environment for both everyday living and entertaining. Outside, the paved frontage provides ample parking. Ideally located just minutes from Kailua's world-famous beaches, shopping, dining, schools, parks, and recreation, this property offers the perfect combination of island lifestyle and investment potential. Pictures uploaded completed right after construction in 2022. (2) HECO Electric meters.

609 Olomana Street, Kailua

Listing courtesy of Island Life Homes.

$12,400,000
5 Beds ⋅ 6 Baths ⋅ 409793 MLS ⋅ Fee Simple Tenure
In 2015, a family from Idaho built this home for one purpose: to bring everyone together on the ocean in Maui. A place where children and grandchildren could land, spread out, and stay awhile. A decade later, it is offered for the first time. Fee simple, sandy beachfront on the quiet end of Halama Street, built by Smith Builders Maui with materials chosen to outlast the people who chose them. Inside, the craftsmanship is deliberate and quiet. Douglas fir wainscoting, artisan wallpaper, Rocky Mountain hardware. Five ensuite bedrooms, so everyone has their own space and no one is underfoot. The primary suite claims the entire upper level: dual closets, a dedicated office, its own laundry, and an oversized covered lanai exclusive to the upper floor. Ocean views to the front, mountain and garden views beyond. Whoever owns this home can host the whole family and still have somewhere to breathe. The kitchen, dining, and living spaces open directly to the coast. Pool, lawn, palms, then sandy beach, then ocean. The Pacific is not a backdrop here. It is the reason for all of it. The 3-car garage includes an upstairs ohana, ready for an onsite caretaker or extended family overflow. Monier tile roof, Hardie siding, copper gutters: a home that locks, leaves, and waits without complaint. Quiet enough to feel removed. Close enough to Kihei’s dining and conveniences that proximity is never a question. This is what multigenerational ownership looks like on Maui.

1536 Halama St, Kihei

Listing courtesy of Island Sotheby's International Realty(M).

$26,500,000
6 Beds ⋅ 6 Baths ⋅ 409734 MLS ⋅ Fee Simple Tenure
THE ULTIMATE MAUI DREAM . .The most sophisticated are no longer asking where to live . .They are asking, “Where can we breathe?” Welcome to The Makena Generational Oceanside Retreat offering resort-style living with smart-home technology, unobstructed ocean & sunset views, Haleakala sunrise views situated on a professionally landscaped one-acre gated and walled tropical estate.The fully operational compound is ready for occupancy offering a vast combination of energy efficiency, self-sufficiency and refined comfort featuring the largest residential Tesla Solar Roof in the US installed in 2024. A unique opportunity to own a private Maui sanctuary of this stature where luxury, wellness and sustainability coexist in harmony. The indoor-outdoor lifestyle is designed for multigenerational living, executive retreats and legacy ownership. In a world moving faster than ever, it is intentionally crafted for life to slow down. Extensively upgraded under the current owner with substantial infrastructure, aesthetic and technology enhancements, the property is now offered well below current replacement cost. The Makena community remains one of Maui’s most coveted luxury destinations. The current property manager creates effortless luxury living with lock-and-leave convenience. The luxurious amenities are endless. The privately separated interior living areas offer exceptional craftsmanship, premium wood finishes, floor-to-ceiling bifold glass doors, elevator, gourmet kitchen, exercise area, massage room, sauna, and steam shower. The dramatic custom water features include a puka lava entry waterfall with pond and interior floor-to-ceiling water feature at the base of the floating staircase. The additional luxury oceanside pool home with its oversized heated pool includes its own gourmet kitchen, Italian brick pizza oven and rear projection entertainment system. Combined with many additional features, the estate offers a total of 8b-8b comfortably accommodating up to 16 guests. Parking is a breeze with a 4+car garage and generous additional parking areas.

7505 Makena Rd, Kihei

Listing courtesy of Compass-W.

$4,925,000
7 Beds ⋅ 7 Baths ⋅ 202610108 MLS ⋅ FS - Fee Simple Tenure
The most extraordinary remodel transformation you’ll ever see! This stunning 7 bedroom, 6.5 bath residence spans over 6,000 square feet on a generous 14,125-square-foot lot, just a short stroll from Kailua’s iconic 3 mile sandy beach. Completely reimagined, the home feels brand new, fresh, modern, and thoughtfully designed for today’s island lifestyle. Two expansive primary suites anchor the home, each featuring spa-level amenities with private saunas, oversized walk-in showers, washer/dryer's and luxurious soaking tubs. A large rumpus room offers the perfect retreat for the little’s or additional entertaining, while the yard is surrounded by new areka palms that will give total privacy in the near future and a prized mango tree. Plenty of room for a pool too. The kitchen is a showpiece, centered around a 14-foot quartzite island, complemented by striking windows, doors, stone flooring, and two architectural staircases. A rare 2,000-square-foot rooftop deck delivers flexibility for entertaining or relaxing under the stars. Additional highlights include an au-pair suite with kitchenette, a stunning porte-cochère, and an unbeatable location close to the heart of Kailua.

125 N Kalaheo Avenue, Kailua

Listing courtesy of eXp Realty.

$9,500,000
6 Beds ⋅ 6 Baths ⋅ 409677 MLS ⋅ Fee Simple Tenure
Welcome to 1949 W Kuiaha Rd: a rare opportunity to acquire a one of a kind, legacy Maui country estate within one of the most beautiful microclimates of all the Hawaiian islands. On 39 acres of pristine land, two skillfully crafted homes look out onto expansive, gently sloping green pastures with full panoramic ocean views.  Enjoy tranquil ocean, garden & mountain views from the entire downstairs great room as well as from the 818 sq ft covered lanai of the 4 bed 3.5 bath main home. Notable features are massive beam construction, Venetian plaster walls, a 1050 sq ft Primary suite with a fireplace, clawfoot tub & its own 756 sq ft private Ipe deck with incredible ocean views, a 659 sq ft multipurpose room with its own stairwell entrance, a 200 sq ft office, a 1933 sq ft garage, 531 sq ft of storage & an owned PV system. Just beyond the bamboo grove is a quaint 2 bed/2.5 bath, 1495 sq ft cottage which features a stunning 586 sq ft covered lanai & Ipe deck offering prime ocean views, Monkeypod slab counters in the kitchen & living room, a fireplace, 2 offices, semi outdoor shower & a gorgeous vaulted cupola roof. In addition, there are 4 fenced pastures, 2 partially enclosed sheds totaling 782 sq ft, 1 garden shed, 3 additional loafing sheds & a hitching post. The impressive array of fruit & ornamental trees, Rainbow Eucalyptus & Cook Pine forests, 2 acre garden, a seasonal stream, 3 property entrances, inspiring Haleakala, Giggle Hill, West Maui mountain & Pacific ocean views, incredible privacy, immersion in nature, general potential & future value that this property offers is unlike any other. There is much to explore, enjoy & create. This property is an equestrian’s and rancher's dream. 1949 W Kuiaha Rd is well-positioned in Haiku Pauwela with close proximity to Haiku, Makawao & Paia towns, Baldwin beach, Twin falls, exceptional schools, the best farmer’s markets on the island, private & international airports.  This property is a gem & must be seen in person to appreciate.  Seller is open to selling all or part of the property: A four unit CPR is in progress. Once completed, individual lots will be available to purchase separately at an elevated value. Seller may be open to trades. Contact Listing agent for more information. Listing agent is related to Seller.

1949 W Kuiaha Rd, Haiku

Listing courtesy of Hawaii Life (MA).

$30,000,000
5 Beds ⋅ 6 Baths ⋅ 202609850 MLS ⋅ FS - Fee Simple Tenure ⋅ Park Lane BLDG.
A Rare Grand Penthouse Residence—An Exclusive Privilege Reserved for the Select Few. It is your own private sanctuary, undisturbed by the outside world. Here, a unique vista and living space unfold—a setting found nowhere else on earth. The yacht harbor and Waikiki skyline, bathed in the glow of the morning sun. Ahead lies the lush greenery of Ala Moana Beach Park, stretching toward an endless expanse of blue sky and ocean. As day turns to dusk, the sea begins to shimmer, shifting to hues of crimson and gold—ushering in that magical, radiant moment just before the sun dips below the horizon. A breathtaking vista, framed as if it were your own personal work of art. Spanning an expansive 5,700 sqft living space , this residence is a true masterpiece—a harmonious fusion of residential grandeur and cutting-edge luxury. Situated in the heart of Honolulu, it offers absolute privacy, allowing you to savor the profound serenity and liberation typically found only in a private villa.

1388 Ala Moana Boulevard Unit 6800, Honolulu

Listing courtesy of Shimizu Gateways Inc.

$3,600,000
6 Beds ⋅ 6 Baths ⋅ 202609253 MLS ⋅ FS - Fee Simple Tenure
Get ready for Old Pali living in the modern era! Feast your eyes on this 2022 remodel on a massive 20,000+ squarefoot lot gated for privacy. The main home features 4 bedrooms, 4.5 bathrooms, and offers luxury living. Each bedroom has its own en suite bathroom, walk in closet and all but one are on the main floor, which features luxury vinyl plank flooring. Gourmets will adore the expansive kitchen featuring an 8-burner gas stove, Viking appliances and an island for extra prep space. There's also an adjacent bonus pantry space off the laundry/mud room. This home is perfect for entertaining as there's tons of parking, a great room, a sunken living area with a fireplace and a gigantic outdoor covered lanai. Enjoy indoor outdoor living in Nuuanu with ample yard space. Although it's typically cooler, you can also close everything up and run the split AC and dehumidifiers were cleverly built into the remodel. The property also contains a separate 2-bedroom, 1-bathroom cottage, perfect for visitors or multi-generational living. With its fenced yard, this home is a perfect sanctuary for your furry friends. Must see to appreciate and shown to qualified buyers upon request.

14 Hakumele Place, Honolulu

Listing courtesy of Harcourts Island Real Estate.

$1,100,000
9 Beds ⋅ 7 Baths ⋅ 202609159 MLS ⋅ FS - Fee Simple Tenure
Discover a RARE and VERSATILE investment opportunity in Waianae! This UNIQUE multi-unit property features FOUR SEPARATE UNITS, offering incredible flexibility for investors or multi-generational living. Two units are currently VACANT, providing immediate potential for rental income or owner-occupancy, while the other two units have tenants in place for BUILT-IN CASH FLOW. Each unit offers functional living spaces with the opportunity to enhance and maximize value. Enjoy a LARGE LOT with room for outdoor living, entertaining, or future improvements. Conveniently located near BEAUTIFUL WEST SIDE BEACHES, shopping, dining, and schools, this property blends lifestyle and income potential. Whether you're looking to HOUSE HACK, expand your portfolio, or create the perfect OHANA compound, this is a SMART and SPACIOUS opportunity you don’t want to miss! Actual number of rooms and tax records do not match.

87-876 Ehu Street, Waianae

Listing courtesy of Coldwell Banker Realty.

$1,680,000
14 Beds ⋅ 6 Baths ⋅ 202609226 MLS ⋅ FS - Fee Simple Tenure
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 Farrington Hwy is listed separately under MLS #202609228 and is intended to be sold together with this property. Existing improvements are in major repair condition, and the property is being sold strictly As Is. Sewer capacity was previously approved for 8 units for the combined parcels, and seller has explored a possible multi-home development concept. Buyer to conduct own due diligence regarding zoning, sewer, permitting, development potential, and all property conditions. Please do not enter or walk onto the property without permission. **Showings are contingent upon an accepted offer.

85-720 Farrington Highway, Waianae

Listing courtesy of Central Pacific Properties Inc.

$17,500,000
5 Beds ⋅ 7 Baths ⋅ 202609193 MLS ⋅ FS - Fee Simple Tenure
This magnificent Diamond Head “Cove Area” beachfront masterpiece harmoniously fuses traditional Hawaiian architectural elements with an open modern lifestyle floorplan. Located on a quiet lane off Diamond Head Road, this home is truly a treasure to behold. The grand reception areas lead out to extensive wraparound lanai areas, a covered grill space, and a beachside seating area—perfect for enjoying sunsets and drinks while taking in the endless views of the Pacific Ocean. The upper level boasts a large primary ocean view bedroom, two additional en-suite bedrooms, elevator, gas generator and an unmatched office with ocean views that you’ll never want to leave. Refreshing pool, lush private landscaping, and unmatched location, style, comfort, and distinction define this Diamond Head gem.

218 Kaalawai Place, Honolulu

Listing courtesy of Coldwell Banker Realty.

$2,800,000
10 Beds ⋅ 6 Baths ⋅ 202609043 MLS ⋅ FS - Fee Simple Tenure
This exceptional beachfront property offers over 25,000 square feet of sandy beachfront land with over 100 linear feet of ocean frontage. Two TMKs, 91-373 & 91-373A, on Ewa Beach Road are being sold together, creating a versatile, long-term beachfront parcel. The property currently has six existing structures, including a cottage, two 2-bedroom/1-bath dwellings, one 3-bedroom/1 full and 1 half-bath dwelling, a detached carport, and a beachfront pavilion. Located near well-known fishing, swimming, and surf areas, this property captures island living and offers possibilities for its next owner. Whether envisioned as a private seaside retreat, a multigenerational family compound, or a long-term beachfront investment, this offering stands out as a rare opportunity to secure a prized stretch of Oahu shoreline with enduring value and exceptional potential.

Ewa Beach

Listing courtesy of The Agency-Oahu.

$4,895,000
4 Beds ⋅ 6 Baths ⋅ 409534 MLS ⋅ Fee Simple Tenure
Located within the coveted acreage community of Wailuku Country Estates, 2150 Kamaile Street offers a rare combination of privacy, scale, and resort-style living across approximately 2.78 acres. The main residence spans approximately 3,175 square feet and is designed to capture the essence of indoor-outdoor island living. Generous living spaces flow effortlessly to the surrounding grounds, creating an inviting setting for both everyday comfort and elevated entertaining. A detached two-bedroom, two-bathroom Ohana of approximately 1,000 square feet enhances the compound feel of the property. Complete with an oversized garage, this separate residence offers privacy and versatility while remaining integrated into the overall estate design. Recent enhancements have transformed the outdoor experience into a private retreat. A newly constructed resort-style pool and spa anchor the property’s recreational amenities, complemented by an expanded pool deck ideal for gatherings. A tranquil water feature and private putting green further elevate the grounds, creating a curated setting designed for relaxation and enjoyment. The detached barn structure has been thoughtfully upgraded and finished, adding substantial flexibility to the estate. Whether utilized as a studio, gym, office, creative space, or extended entertaining area, it contributes meaningful utility and enhances the property’s overall functionality. With nearly three acres of usable land, multiple structures, and newly added resort-level amenities, 2150 Kamaile Street presents a compelling opportunity to own a private lifestyle compound in one of Central Maui’s most desirable estate communities. This is a property designed not only as a residence — but as a destination.

2150 Kamaile St, Wailuku

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$2,790,000
11 Beds ⋅ 8 Baths ⋅ 202608921 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity with great potentials, for either own family living or rental investment, easy to afford mortgage! Located only a few houses away from world-famous Waimanalo white sand beach! Ideal for own living to enjoy lots of space in highly desirable beach neighborhood. 5704sf living space, 6 private entrances on 11,250sf lot. This 2-story house, 3811sf was newly built in 2015. Plus 1-story Ohana unit, 1893sf. This gated & spacious property offers 11 bedrooms, 8 full bathrooms, idyllic office space. Stunning, unobstructed Ko’olaumountain views. Total of 2 kitchens, 2 wet bars and plus. Huge sizes for all living rooms, kitchens, bedrooms, etc. 11ft tall ceiling for main living room; 9ft tall for other areas. Tons of upgrades: lanai, auto metal gate, natural stones, metal roof, solid wood cabinets & double-door entries, hardwood floor, granite & quartz countertops, Quartz staircase, etc. If for rental, since so close to beach, high rental demands paying good price to generate good incomes.

41-51 Hinalea Street, Waimanalo

Listing courtesy of eXp Realty.

$15,950,000
6 Beds ⋅ 7 Baths ⋅ 202606829 MLS ⋅ FS - Fee Simple Tenure ⋅ North Shore Club Residences BLDG.
North Shore Club | Penthouse Residence | Now Previewing. The final direct beachfront Penthouse in Phase I offers a rare opportunity to acquire a signature legacy residence at the North Shore Club. This premier 6 bedroom, 6.5 bath residence offers over 7,820 livable square feet with 6,029 interior and 1,791 panoramic lanai space, a private pool, and sweeping ocean views. Designed for effortless island living, the residence showcases a grand-scale great room, bespoke finishes, and a seamless indoor-outdoor flow. Floor-to-ceiling openings frame uninterrupted Pacific vistas, while curated materials and architectural detailing create a timeless modern coastal aesthetic. Pre-construction design selections remain available, allowing for personalized interior finishes. Members enjoy world-class amenities including championship golf, resort pools, spa and wellness experiences, state-of-the-art fitness facilities, and curated dining. A truly irreplaceable beachfront legacy offering in one of Hawaii’s most coveted coastal settings, located walking distance to the Ritz-Carlton, O'ahu Turtle Bay Resort.

57-275 Kamehameha Highway Unit 1/5, Kahuku

Listing courtesy of Compass.

$1,450,000
7 Beds ⋅ 7 Baths ⋅ 202608719 MLS ⋅ FS - Fee Simple Tenure
Great multi-generational and investment opportunity with this spacious 7-bedroom, 6.5-bath home designed for flexibility and privacy. Thoughtfully configured across multiple living areas, the property offers three distinct spaces with separate entrances, ideal for extended family living or rental income potential. Also well-suited for home care arrangements. The ground level features 3 bedrooms, 2.5 baths, and a dedicated laundry area with private access. The second level offers 3 bedrooms and 3 full bathrooms, enhanced by a pass-through connection to a studio with kitchenette, full bath, private entrance, and its own laundry area. The property is equipped with leased photovoltaic panels and three Tesla Powerwall batteries, providing energy efficiency and long-term utility savings. A private shared driveway leads to a 2-car garage and additional carport parking, offering convenience and functionality. A versatile layout allows for owner-occupancy with supplemental income, or comfortable accommodation for extended household living.

2802 Numana Road, Honolulu

Listing courtesy of Century 21 Island Homes.

$3,330,000
6 Beds ⋅ 6 Baths ⋅ 202608303 MLS ⋅ FS - Fee Simple Tenure
| Seller Financing Available | Offering over 5,000 square feet of interior living space on more than an acre of land, this expansive estate delivers space, privacy, and potential rarely found on Oahu. Enjoy the best of both worlds with sweeping ocean and mountain views, all from the comfort of your own private compound. Surrounded by lush landscaping and enclosed by a full rock wall, the property offers a true sense of retreat and seclusion. Designed for both everyday living and entertaining, the home features multiple living areas, a chef’s kitchen equipped with high-end commercial-grade appliances, and a separate guest quarters with its own entrance. The grounds include a private tennis court and expansive open space, offering endless possibilities to create your ideal outdoor setting.

84-940 Moaelehua Street, Waianae

Listing courtesy of Compass.

$2,295,000
9 Beds ⋅ 7 Baths ⋅ 202608473 MLS ⋅ FS - Fee Simple Tenure
Two homes, one lot, endless flexibility. Live in one, rent the other, and let the income work for you every month. The front home is built for space: six bedrooms, four bathrooms, and 4-car parking, with 32 solar panels keeping utility costs low. It's the kind of layout that draws serious, long-term tenants. Tucked behind it, the back home offers a quieter footprint: three bedrooms, two and a half bathrooms, a 2-car garage, and 23 solar panels of its own. Private, comfortable, and easy to fill. Live in either one and the other starts generating income from day one. Minutes from downtown Honolulu, with strong rental demand and short commutes in every direction, 2134 Kanealii St offers two well-appointed homes and a rare kind of flexibility in this market.

2134 Kanealii Avenue, Honolulu

Listing courtesy of Agora Hawaii.

$2,788,000
15 Beds ⋅ 10 Baths ⋅ 202608364 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity to own two newer homes on a spacious lot, ideal for investors, multigenerational living, or potential daycare use. This versatile property features 2 dwellings with separate kitchens, offering excellent flexibility for extended families or generating strong rental income. Constructed with solid materials and quality craftsmanship, these homes reflect pride of ownership and are built for long-term durability. The property also offers ample front yard space, perfect for additional parking or outdoor entertaining. Located in Halawa with convenient access to all parts of the island, this property is well-suited for both owner-occupants and tenants. Close proximity to Tripler, Fort Shafter, Pearl Harbor, Hickam, Camp Smith, and major freeways enhances its appeal, supporting strong rental demand and easy commuting. Whether you’re looking to accommodate multiple generations under one roof or secure a high-potential investment property with abundant living space, this is a unique opportunity you won’t want to miss.

99-438 Ulune Street, Aiea

Listing courtesy of Soldier To Soldier HI Realty.

$8,740,000
5 Beds ⋅ 6 Baths ⋅ 409447 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
Wailea Point Residence 802 & 804 is an exquisite, rare, double residence featuring 5 bedrooms and 6 full bathrooms. Enjoy unobstructed panoramic ocean and sunset views from four ocean-view lanais or from inside the expansive great room, enhanced by the upgraded, dual-mitered glass bay “aquarium” windows that dramatically enhance the vistas and whale watching (in season). This turnkey purchase—fully furnished, legacy property, created by thoughtfully combining two elegant units—lives like a luxurious single-family home, while retaining lock-and-leave condominium convenience. It includes elegant designer furniture, all kitchen appliances (including 2 frigs, 2 dishwashers, 3 wine frigs), china, linens and more. The residence offers soaring ceilings, 4-zone central air conditioning, a terrific owner’s home office/den, privately located adjacent to the primary bedroom with ocean views, and a separate and large double garage, with built-in storage and two of the wine frigs. Seamless indoor-outdoor living is complemented by the four spacious lanais that open directly onto lush, manicured gardens and the oceanfront setting. Meticulously maintained, this home represents exceptional value as the best price per square foot in Wailea Point (less than $1,780 per gross interior sq ft) and a unique opportunity to own or create your own personal, multi-generational retreat in one of Maui’s most distinguished condominium communities—a must-see. Wailea Point was designed to be Hawaii’s premier residential condominium. The development offers very low density (just over 4 units per acre), high-quality construction, and a serene garden environment. Residents enjoy 24-hour gated and roving security, two pool pavilions with 4 pools (including a 25-meter lap pool), 2 whirlpool spas, fully equipped kitchens, a lighted tennis court, 2 pickleball courts (1 lighted), a fully air-conditioned fitness gym, barbecue areas, fruit and herb gardens, ample parking, and a golf-cart friendly domain. Located next to the Four Seasons and Fairmont Kea Lani Hotels; and within 100 yards of the famous and long Wailea Beach shorefront walkway; great for early morning or sunset walks. There are two magnificent, ocean beaches adjacent to Wailea Point. Shopping, fine restaurants, outstanding golf courses and graceful streets all surround the acclaimed development. In a 7/15/26 ruling, the Appeals Court changed the minimum rental period at Wailea Point BACK to 30 days. An Association Board of Directors Bulletin dated 7/22/26 states, “Consistent with the appellate court's decision, the minimum rental period is being administered as 30 consecutive days."

4000 Wailea Alanui Dr Unit 802 & 804, Kihei

Listing courtesy of Wailea Point Realty, Inc..

$2,300,000
4 Beds ⋅ 6 Baths ⋅ 202604724 MLS ⋅ FS - Fee Simple Tenure
Open House on 07/19 2-5pm! Perched in the gated community of Kumulani at Makakilo, this expansive 4-bedroom, 4.5-bath residence offers over 3,600 sq ft of interior living space. Tucked away on a quiet, low-traffic street, the home enjoys added privacy and a peaceful neighborhood setting. Enjoy cool breezes and sweeping panoramic views of the ocean, coastline, and Diamond Head from the upper level, creating a serene retreat above it all. The thoughtfully designed floor plan features a bedroom and full bath on the main level—ideal for multi-generational living or guests—along with generous living and dining areas. Upstairs, a spacious family room provides the perfect setting for gatherings, entertaining, or a secondary living space. Extensively upgraded with nearly $300,000 in improvements, this home features 22 owned solar panels with 2 batteries (installed July 2022), a remodeled kitchen and bathrooms, and a leveled backyard with a retaining wall—enhancing both functionality and outdoor enjoyment. Kumulani stands out for its larger interior layouts, gated privacy, and well-planned design—offering a rare combination of space, comfort, and convenience in Upper Makakilo.

92-243 Hoalii Place, Kapolei

Listing courtesy of Keller Williams Honolulu.

$3,985,000
3 Beds ⋅ 6 Baths ⋅ 202605472 MLS ⋅ FS - Fee Simple Tenure
Price Reduction! 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 int. 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. Inviting transformation as few properties on O'ahu offer this combination of scale, privacy, location, views and opportunity.

12 Lumahai Street, Honolulu

Listing courtesy of Compass.

$12,900,000
5 Beds ⋅ 8 Baths ⋅ 409428 MLS ⋅ Fee Simple Tenure
Nestled withing the prestigious enclave to Kapalua Place, this extraordinary oceanview estate on over 1 landscaped acre offers an unparalleled blend of luxury, privacy, and island elegance. Encompassing over 10,000 square feet of living space, the magnificent five bedroom, 7.5 bath residence is designed to capture the essence of refined Hawaiian living. Thoughtfully crafted with an expansive open floor plan, the home flows seamlessly from grand interior living spaces to breathtaking outdoor spaces perfect for effortless entertaining and relaxed island living. Walls of glass frame panoramic ocean vistas while inviting natural light and gentle trade winds throughout the residence. The open chef's kitchen with gorgeous granite countertops anchors the main living area and opens to generous living and dining areas for hosting both intimate dinners and large celebrations. Each of the 5 bedroom suites offers exceptional comfort and privacy creating a serene retreat for family and guests alike. Complete with an elevator. The resort style outdoor living spaces create a tropical sanctuary designed for both relaxation and entertaining. At the heart of the grounds is a spectacular swimming pool accented by a cascading waterfall evoking the ambiance of a five star luxury living in the Kapalua resort. There is a separate private spa. Set within Maui's most coveted enclaves, this remarkable property provides both exclusivity and proximity to the world-class amenities of Kapalua, including championship golf, pristine beaches, fine dining, and luxury resort experiences. A rare offering where timeless architecture, breathtaking ocean views, famous sunsets and the west maui mountains frame the views and the spirit of aloha come together in perfect harmony. Private gated enterance to the white sand beach at Oneloa Bay with views up the coastline to Honolua Bay.

8 Kapalua Pl, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$8,980,000
11 Beds ⋅ 12 Baths ⋅ 202607845 MLS ⋅ FS - Fee Simple Tenure ⋅ The Ritz-Carlton Residences Twr 2 - 383 Kalaimoku BLDG.
One of a kind. Owning the entire 27th floor at the Ritz-Carlton Residences Waikiki Beach, specifically in the Diamond Head Tower, represents a pinnacle of luxury retreat to Hawaii. With sweeping views of the Pacific Ocean, Diamond Head Crater, and the Waikiki Skyline, the residence is perfectly positioned to offer both sunrise and sunset vistas. This high-ceiling full-floor residence provides unmatched privacy and exclusivity, consisting of 10 separate units of studios,1 bedrooms & 2 bedrooms. Many of these homes are available fully furnished, making it effortless to move in, generate income through the hotel pool, or begin hosting guests. Beyond the residence, ownership comes with access to the Ritz-Carlton’s signature five-star service. This includes in-residence dining, daily housekeeping (in hotel pool), concierge services, valet parking, and access to world-class amenities like infinity pools, a fitness center, a full-service spa, and top-tier dining. The sale includes 10 units (CPR) 2701 (1BR 1BA), 2702 (0BR 1BA), 2703 (0BR 1BA), 2705 (1BR 2BA), 2706 (1BR 1BA), 2707 (0BR 1BA), 2708 (0BR 1BA), 2709 (0BR 1BA), 2710 (2BR 2BA), & 2711 (0BR 1BA).

2139 Kuhio Avenue Unit 2701-2711, Honolulu

Listing courtesy of Coldwell Banker Realty.

$6,998,000
5 Beds ⋅ 8 Baths ⋅ 202607760 MLS ⋅ FS - Fee Simple Tenure
This home is an exceptional buy for the Kahala market. Priced below replacement cost for this INCREDIBLE & RARE to see craftsmanship! Completed in 1993 & built from quality materials & impeccably detailed carpentry. The original décor & finishes of each room was created as a series of elaborate fantasies from Shakespeare to the travels of Napoleon. A dramatic entry boasts soaring ceilings impeccably detailed; a sweeping staircase highlighted by walls of glass; & an extensive use of fine marble & granite throughout. Wide pocketing glass doors joins the interior to the outdoor spaces & pool for relaxing in this splendid residence. The first level includes a grand dining area with a reflective mirrored ceiling, a service bar with a spacious lounge for social gatherings, a library/media room & two bedroom ensuites. On the second level is a billiard area with a step down cozy seating area for spectators to relax. To the right & left of the billiard room are two additional bedroom ensuites. The home includes a 3-car garage & lots of storage areas. Located across the street from the former Weinberg Estate & a direct access to sandy beach for a stroll along the ocean.

4504 Kahala Avenue, Honolulu

Listing courtesy of Hawaii Life.

$1,650,000
12 Beds ⋅ 6 Baths ⋅ 202607808 MLS ⋅ FS - Fee Simple Tenure
Welcome to "Hale Waiwai" The house of prosperity - a rare four-unit property nestled at the base of the majestic Koolau mountains. This is the Windward lifestyle at its purest: vibrant green winters, dramatic cliffs that feel close enough to touch, and summers filled with days out on Kaneohe Bay. Enjoy sandbar picnics, paddling adventures, and the kind of natural beauty most people only dream of experiencing. This property has a level of flexibility that is extremely hard to find on Oahu. Whether you envision living in one unit and renting the others, bringing your whole Ohana together, or adding a Class A + powerful income-producing asset to your portfolio, this home gives you options for every chapter of life. Financially, it’s already a standout: strong cash-flow potential from day one, with rental configurations that appeal to both long-term tenants and multi-family living. Even better, there is still room to enhance the property over time, giving you a rare double advantage - immediate monthly income plus value-add opportunities. This is more than a home; it’s a legacy property and a wealth-building opportunity that can impact your family for generations.

47-325 Ahuimanu Road, Kaneohe

Listing courtesy of Real Broker.

$2,042,250
9 Beds ⋅ 6 Baths ⋅ 202607482 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Island Prop.

$3,999,000
5 Beds ⋅ 6 Baths ⋅ 409285 MLS ⋅ Fee Simple Tenure
Situated on two privately fenced and gated acres in Haiku, Holokai Hale is a North Shore estate designed for indoor-outdoor living. More than 1,600 square feet of covered space includes lanais, walkways, and multiple areas to relax. Plumeria and puakenikeni line the grounds, with partial ocean views through the canopy. The home offers five bedrooms, six bathrooms, and over 5,000 square feet. The main residence centers on a chef’s kitchen with a large island, butler’s pantry, and direct access to covered lanais for dining and entertaining. Interior and exterior spaces connect seamlessly. The grounds include a saline pool and spa, sauna, cold plunge, and established landscaping with raised garden beds, papaya trees, banana and ginger groves, citrus, lei flowers, and a mature soursop tree. You will find vaulted ceilings and Brazilian Tiger wood floors and each bedroom includes an en-suite bathroom with the primary bedrooms Italian White Carrara Marble bathroom and extra large dressing suite. A separate guest suite provides privacy for extended stays. Additional structures include a detached workshop, an air-conditioned studio with its own sink, and a bonus room above the garage which also has a dumbwaiter. The property is supported by a 52-panel photovoltaic system, solar hot water, split air conditioning, and a whole-home backup generator. Holokai Hale is a flexible property suited for a primary residence, extended family living, or a private retreat.

65 N Holokai Rd, Haiku

Listing courtesy of Keller Williams Realty Maui-Ki.

$4,100,000
10 Beds ⋅ 6 Baths ⋅ 202607262 MLS ⋅ FS - Fee Simple Tenure
Live your Hawaii dream in this gated oceanfront compound, perfectly situated on the serene Naupaka Peninsula of Laie Point. This sale includes 2 OCEANFRONT HOMES (10 bedrooms, 6 bathrooms) on a large 16,875 sq ft lot. With approximately 100 linear feet of unobstructed ocean frontage, enjoy stunning panoramic views of clear blue ocean, Laie Bay, and the majestic Ko'olau Mountains. Both homes were recently renovated. 55-060 Naupaka Street includes an approximately 1,478 sq ft 3 bedroom 2 bath home + a 1 bedroom 1 bath ohana unit. The larger 55-064 Naupaka Street includes an approximately 3,258 sq ft 7 bedroom 4 bath home & a 2 car garage. Both homes have their own separate individual Tax Map Key (TMK). Rare opportunity to own two adjacent oceanfront homes on the very desirable Laie Point. Very close to BYU, the Polynesian Cultural Center, North Shore beaches, Waimea Bay, Pipeline, & the 5-Star Turtle Bay Resort, farm-to-table restaurants, world class golf, oceanfront horseback riding, walking trails, and helicopter tours. Approximately an hour drive to Honolulu by car or 15 minutes by helicopter from Turtle Bay's Heliport. Very easy to view on short notice! Welcome home to paradise!

55-060 & 55-064 Naupaka Street, Laie

Listing courtesy of HomeSmart Island Homes.

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