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$5,100,000
4 Beds ⋅ 4 Baths ⋅ 728773 MLS ⋅ ['Fee Simple'] Tenure
This Kauai vacation rental is located within the exclusive Kukui’ula resort community on Kauai’s sunny South Shore, offering refined island living in one of the island’s most sought-after neighborhoods. Situated on the second fairway of the private Kukui’ula Golf Course, this 4-bedroom, 3.5-bathroom home comfortably hosts your guests. Golf course views are captured from every room, while the upper level offers distant ocean and mountain vistas. Designed in a modern plantation style, the home features a spacious open floor plan and seamless indoor-outdoor living. The chef’s kitchen includes Wolf and Sub-Zero appliances, custom cabinetry, and a breakfast nook. Three lanais extend living areas for dining and relaxation. The upper level includes the primary suite, guest suite, and media room. The lower level offers a second suite, guest bedroom, and main living area centered around a covered dining lanai. The backyard is an entertainer’s dream with a pool, spa, sun deck, BBQ, and outdoor dining area. Equipped with climate control, a 32-panel photovoltaic system, and irrigation control, the home is comfortable and energy efficient. Located in the VACATION DESTINATION AREA and offered fully turnkey, it is a short walk to the Kukui’ula clubhouse with spa, fitness, tennis, pickleball, farm, events, and golf amenities. Renovations include: • New master bathroom & built out new office in 2023 • Renovated living room fireplace in 2023 • New backyard, including a large lanai, pool, spa, outdoor kitchen, outdoor shower, outdoor eating area, landscaping, & landscape lighting in 2023 • Repainted the exterior in 2023 with three tones: soffits, siding & window trim, & doors • $1M in renovations done in 2023/24 • All renovations are permitted, including the backyard & pool/spa • Upgraded kitchen nook light fixture & dining • $150,000 Plantation Membership fee to The Club at Kukui’ula is mandatory. Welcome Home to Kukui’ula!

2739 Uluwehi St, KOLOA

Listing courtesy of Keller Williams Honolulu.

$5,090,000
5 Beds ⋅ 4 Baths ⋅ 202610282 MLS ⋅ FS - Fee Simple Tenure
Open House Cancelled 7/26/26 Nestled in the prestigious Hawaii Loa Ridge, this exceptional residence at 399 Puuikena offers breathtaking 180-degree panoramic views spanning the sparkling Pacific Ocean, coastline, and lush mountain ridges. Enjoy true island luxury with a stunning pool perfectly positioned to capture sunrise, sunset, and sweeping vistas. The elevated setting provides privacy, cooling tradewinds, and a serene atmosphere above the city. Designed for seamless indoor-outdoor living, the home features spacious open living areas, expansive lanais, and large windows that frame the incredible views from nearly every room. Whether relaxing poolside or entertaining guests, this property delivers an unforgettable Hawaii lifestyle experience. Located in a gated, secure community known for its exclusivity, scenic surroundings, and convenient access to beaches, shopping, and dining, this is a rare opportunity to own in one of East Oahu's most sought-after neighborhoods.

399 Puuikena Drive, Honolulu

Listing courtesy of Keller Williams Honolulu.

$5,000,000
4 Beds ⋅ 3 Baths ⋅ 202616764 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity in one of Oahu’s most coveted locations with spectacular ocean views. This distinctive property is Lot 3 of Leahi Estates. Gated private access driveway. No HOA, no CCRs, no board, no fees. Directly across street from Leahi Beach Park; easy walk to Diamond Head, Makalei and Kaimana Beaches, Kapiolani Park, and iconic South Shore surf breaks. A truly exceptional Diamond Head location offering privacy, ocean views, and easy access to some of Oahu’s best beaches, parks, and surf.

3200 Diamond Head Road, Honolulu

Listing courtesy of OahuRE.com.

$5,000,000
730220 MLS ⋅ ['Fee Simple'] Tenure ⋅ North Shore Preserve Oceanside Ranch BLDG.
Oceanside Ranch 49 is a beautiful homesite within North Shore Preserve, an exceptional residential community by Discovery Land Company. Surrounded by lush tropical landscapes and conveniently located near the clubhouse, Oceanside Ranch 49 presents an incredible opportunity to create a private and tranquil custom island retreat with potential for ocean, mountain, and sunrise views. The property features a cleared building envelope of approximately 41,841 square feet and offers ample space for a thoughtfully designed residence of up to 6,000 square feet of conditioned living area, along with an additional 2,500 square feet of unconditioned and covered exterior space to fully embrace Kaua‘i’s seamless indoor-outdoor lifestyle. Purchase of the property includes an invitation to apply (acceptance not guaranteed) to the private club, featuring Discovery’s signature family-focused amenities and experiences, including the newly renovated golf course and comfort stations, wellness and fitness offerings, farm-to-table dining, and endless outdoor adventures designed to connect families with the natural beauty of Kaua‘i’s North Shore.

3693 Kuula Pl Unit 49, KILAUEA

Listing courtesy of Discovery Makena Realty LLC.

$5,000,000
1 Beds ⋅ 2 Baths ⋅ 730960 MLS ⋅ ['Fee Simple'] Tenure ⋅ Secret Cove BLDG.
Perched above Kauai’s most iconic stretches of North Shore coastline, this extraordinary 1.3-acre property offers the rare privilege of private access to legendary Secret Beach. The 2,076-sq-ft residence, built just 12 yrs ago and meticulously maintained by its original owner, is nestled within a lush botanical sanctuary of tropical plantings, fruit trees, and tranquil water features. At the upper level, ocean and sunset views stretch across the horizon, while expansive stone lanais and sliding glass doors welcome the island’s gentle trade winds and blur the line between indoors and out. Sapele wood flooring flows throughout the home, including the open kitchen with its custom breakfast bar. Bathrooms are finished in natural stone and tile, and a striking Sapele wood and glass spiral staircase rises beneath a dramatic pyramid skylight, creating a sculptural focal point at the heart of the home. Designed for comfort and self-sufficiency, the home is fully air-conditioned and equipped with a whole-house water filtration system, tankless water heater, and a 14-panel owned photovoltaic system. Highlights include a dedicated dance and exercise studio; a tropical outdoor shower off the half bath; copper gutters and trim, and generous storage throughout. Custom teak and Sapele furnishings are included, allowing the home to be enjoyed immediately as a refined island retreat. The property also offers exceptional flexibility for the future. Infrastructure is in place to support expansion, including underground electrical for a spa and pool. An attached 446-square-foot garage and covered carport provide ample space for vehicles and outdoor equipment suited to Kauai’s adventurous lifestyle. Offered fully turnkey, this home includes everything from a fully appointed kitchen to a well-maintained Nissan Juke housed in the garage. Concept plans created by the original designer, an established local Kauai architect, are available to expand the home into 3-bedrooms, 3.5-baths.

2874-A Kauapea Rd, KILAUEA

Listing courtesy of Hawaii Life.

$5,000,000
4 Beds ⋅ 4 Baths ⋅ 409679 MLS ⋅ Fee Simple Tenure
Welcome to the Resort in Maui Meadows — an extraordinary private estate where jaw-dropping panoramic ocean views, unforgettable sunsets, and elevated island living converge in one of South Maui’s most coveted neighborhoods. Perfectly positioned above the coastline, this exceptional residence captures sweeping vistas stretching across the Pacific Ocean to the neighboring islands, creating a breathtaking backdrop from nearly every room. By day, enjoy sparkling turquoise waters and endless horizon views; by evening, experience Maui’s legendary sunsets illuminating the sky in spectacular color. Designed to live like a private luxury resort, the property is an entertainer’s dream. Expansive indoor-outdoor living spaces flow seamlessly onto oversized lanais and gathering areas curated for unforgettable sunset dinners, cocktail parties, celebrations, and relaxed evenings beneath the stars. The open-concept design invites effortless hosting while maximizing the stunning ocean vistas and cooling island trade winds throughout the home. The chef’s kitchen anchors the residence with premium appliances, generous prep and serving areas, and elegant finishes designed for both intimate dining and large-scale entertaining. Spacious guest accommodations provide comfort and privacy for family and friends, while the primary suite offers a tranquil retreat with spa-inspired luxury and mesmerizing ocean views. Surrounded by lush tropical landscaping and an atmosphere of complete serenity, the Resort in Maui Meadows delivers a rare sense of escape while remaining just moments from Wailea’s world-class beaches, golf courses, fine dining, and luxury resorts. This is more than a home — it is a destination, a retreat, and a lifestyle defined by breathtaking beauty, privacy, and unforgettable entertaining in the heart of South Maui.

557 Kupulau Dr, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$5,000,000
2 Beds ⋅ 3 Baths ⋅ 202609461 MLS ⋅ FS - Fee Simple Tenure ⋅ Kainalu BLDG.
Awesome direct oceanfront double unit (combined 5B & 5C) at Kainalu offering panoramic views of crystal-clear waters where fish and coral are visible from your living room. From this 5th floor, enjoy front-row seats to multiple surf breaks filled with traditional longboarders and foil surfers, along with sailboats gliding across the horizon. Open the expansive wall of windows to welcome cooling trade winds and sweeping vistas stretching from Diamond Head to Waikiki and beyond. Whether dining or relaxing, breathtaking sunsets become part of everyday living in this spacious coastal retreat. The exceptional trophy residence features 2 bedrooms (could be three), 3 bathrooms, and 73 feet of beach/ocean frontage with access to a small private beach. Located in a quiet residential area just below DH on the Goldcoast with close proximity to Waikiki, Kapiolani Park, beaches, fine dining, shops & so much more! Additional highlights include air conditioning, elegant limestone flooring, a resident manager, and two covered secured parking stalls. Experience the best of oceanfront luxury island living.

2801 Coconut Avenue Unit 5 B/C, Honolulu

Listing courtesy of List Sotheby's Int'l Realty.

$5,000,000
409381 MLS ⋅ Fee Simple Tenure
Welcome to Kapalua Farms, a remarkable opportunity to own over 35 acres of agricultural land perched above Napili Bay at the gateway to Kapalua. Imagine waking up to sweeping, panoramic ocean views that create a breathtaking backdrop for this unique property. With access from both Honoapiilani Highway and the Lower Road, convenience and tranquility come together in this stunning location. This expansive property is nestled near the Pineapple Hill community and the scenic Kapalua Golf Course, offering a perfect blend of natural beauty and limitless potential. Whether you're envisioning a private retreat, a working farm, or something entirely your own, the possibilities here are as vast as the views. Opportunities like this are rare—don’t let it pass you by. Kapalua Farms is ready for your vision.

Kapalua Farms Hui Rd F Rd, Lahaina

Listing courtesy of Compass.

$5,000,000
727323 MLS ⋅ ['Fee Simple'] Tenure ⋅ Hokulia Phase 2 BLDG.
Hokulia Phase 2, Lot 63 is an exceptional 1.64-acre second-row homesite, fully graded and ready for construction, with all utilities stubbed at the property frontage. Set against the open Pacific, this rare offering invites the creation of a legacy estate, with space to breathe, privacy to retreat, and unparalleled ocean views. Hokulia is a luxury residential community spanning 1,260 uncrowded acres along Hawaii Island's famed Kona Coast. With three miles of elevated, west-facing shoreline, the property is set away from the island's densely populated resort bubbles. Hokulia offers members access to an award-winning Jack Nicklaus Signature golf course and best-in-class amenities including an exquisitely designed clubhouse, Pavilion restaurant, ocean adventures, sports-courts, & aquatic activities. One of the most coveted amenities is the spectacularly designed Jack Nicklaus Signature golf course, which was masterfully planned to maximize the dramatic ocean views at nearly every tee box and green. Sheltered from the strong winds that affect golfers in many other areas of Hawaii, the course enjoys gentle ocean breezes & warm temperatures year-round. Consistently ranked among the best private golf courses in Hawaii, the impeccably designed fairways follow the gentle slopes and naturally undulating topography of Hokulia. The Developer is offering a rare opportunity with the purchase of a Hokulia Phase 2 Lot — a Hokulia Equity Golf Membership will be included in the purchase price, upon closing. Additionally, as part of a limited time and amount offering, the sale will also include a Charter Membership, providing the property owner with two memberships. A Charter Membership allows the member to maintain a membership after the transfer or sale of their Equity Golf Membership for the duration of their life or can be relinquished at any time before then. Dues for the Charter Membership are not payable until the Charter membership is activated.

Hawaii Loa Drive, KEALAKEKUA

Listing courtesy of Hawaii Life.

$5,000,000
5 Beds ⋅ 4 Baths ⋅ 202521091 MLS ⋅ FS - Fee Simple Tenure
Experience exceptional beachfront living on coveted Papailoa Road along Oahu's world-famous North Shore. This private 5-bedroom, 3.5-bath residence boasts 119 feet of sandy ocean frontage with panoramic views from Ka?ena Point to Waimea Bay. Lush tropical landscaping, a wraparound lawn, and meandering garden paths create a peaceful island retreat. Step from your lanai onto the beach to swim with sea turtles, enjoy breathtaking sunsets, or dine under the stars. Designed for flexibility, the home features two interconnected living areas, each with its own kitchen, making it ideal for multi-generational living, guests, or rental opportunities. Enjoy direct access to renowned surf breaks including Laniakea and Himalayas, with surfing, snorkeling, kayaking, paddleboarding, kite surfing, and wing foiling just outside your door. A gated electric entry and fenced perimeter provide privacy, while historic Hale?iwa Town's shops, cafés, art galleries, and restaurants are just a scenic one-mile stroll along the shoreline. This rare legacy property offers the perfect blend of tranquility, adventure, and timeless island elegance in one of Oahu's most sought-after beachfront communities.

61-707 Papailoa Road, Haleiwa

Listing courtesy of eXp Realty.

$5,000,000
202404884 MLS ⋅ FS - Fee Simple Tenure
Do you desire to expand your growing investment portfolio with a centrally-located multiunit property? Check out the possibilities of 1254 Lunalilo Street! Tucked away in an extremely convenient area is this 15-unit concrete multiunit building featuring a desirable 1:1 parking ratio, separate electric meters, and a secured laundry area with two washers, two dryers, and a utility sink. Boasting 12-one bedroom units and 3-two bedroom units, the property allows for maximum resident comfort. Each unit features an open layout, neutral interior paint, a spacious living/dining area, storage closets, and a fully-equipped kitchen with a gas stove, pantry, and ample cabinets. Bedrooms are well-sized with generous closet space, while each full bathroom includes a shower/tub combo, medicine cabinet, and a storage vanity. Outdoor relaxation is a breeze with all units featuring a cozy balcony. Tenants will enjoy easy access to transportation, shopping, restaurants, entertainment, and Makiki Park. NOI is actual. Please contact Listor with additional questions. Interior showings will be subjected to accepted offer. Please submit offers using the Commercial PSA. DO NOT DISTURB tenants.

1254 Lunalilo Street, Honolulu

Listing courtesy of Real Estate Specialists.

$4,999,999
2 Beds ⋅ 3 Baths ⋅ 409543 MLS ⋅ Fee Simple Tenure
Discreetly positioned off Kula Highway, the approach reveals very little. A winding drive. A narrowing road. Then, through the trees, a freshly painted 1933 guest cottage quietly appears, a subtle introduction to what lies ahead. A whisper of what came before. Keep driving. The landscape begins to unfold. And then you arrive. A refined modern architectural private retreat. Exposed beams. Oak floors. Walls of Andersen windows drawing the landscape inward from every direction. Once cattle ranch land, these twenty-two rolling acres of open pasture and mature eucalyptus and jacaranda have evolved into one of Maui’s most distinctive private estates. Deer move effortlessly through the golden afternoon light. Birdsong replaces background noise. The silence here feels restorative, the kind that settles into you. The former owner named it Pheasant Ridge for good reason. Originally built in 2001 and thoughtfully reimagined in 2019, the main home was designed for a deeply intentional way of living. The open-concept kitchen, dining, and living spaces flow together in one expansive, light-filled room anchored by a fireplace and framed entirely by the land beyond. The primary suite faces Haleakala. The guest suite offers its own en-suite bath and soaking tub worthy of a primary retreat. This is not beach Maui. The air is cooler. The light lingers longer. Life moves at its own pace. Evenings call for the warmth of a fireplace, and there will be evenings worthy of it. A Pilates studio occupies the garage. A separate she - shed is settled into the surrounding landscape. AG zoning and open pasture invite horses, livestock, or simply the freedom of open land returning to its natural purpose.

8515 Kula Hwy, Kula

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

$4,999,999
3 Beds ⋅ 4 Baths ⋅ 408222 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
Discover luxury resort living in this exceptional ocean-view Villa located within the prestigious gated community of Ho'olei in Wailea. It is ideally positioned near world-class resorts, fine dining, luxury shopping, championship golf courses, and Maui's best beaches. The Villa features 3 bedrooms and 3.5 bathrooms, in a two-story townhome-style, encompassing 2,426 square feet. There is an additional 596 square feet of covered lanais across two levels. Each bedroom includes a private ensuite bath, offering comfort and privacy for owners and guests alike. Thoughtful design elements include a private elevator, an attached garage, a covered carport, and an outdoor storage closet. Floor-to-ceiling sliding glass doors and retractable screens open almost 30 feet onto the expansive lanai, embracing Maui's indoor/outdoor lifestyle. The lanai is ideal for entertaining and is equipped with a Wolf 36" grill, a Sub-Zero under-counter refrigerator, and custom cabinets. The Villa features polished travertine floors, recessed lighting, high tray ceilings, surround sound, a security system, and a 2-zone central air conditioning system. The Chef's kitchen includes premium appliances by Sub-Zero, Wolf, Thermador, and Bosch. A touch of elegance is added with the Snaidero Italian custom cabinetry. You can enjoy ocean views from high above the resort pool. Ho'olei's amenities include a lagoon-style pool with cascading waterfalls and grottos, a sandy beach entry, two hot tubs, a massage cabana, an outdoor kitchen with covered pavilion, and a fully equipped, air-conditioned fitness center with sauna, locker rooms, and showers. Offered fully furnished, the Villa is truly turn-key & has been meticulously maintained. The property is hotel-zoned, allowing use as a short-term vacation rental, private residence, or a combination of both. Successfully operated as a vacation rental since 2007, the Villa has received over 150 five-star reviews. The owner is willing to continue marketing the property or assist with a smooth transition to new management. This remarkable Ho'olei Villa presents a rare opportunity to own a luxury, hotel-zoned home in paradise.

81 Makakehau St Unit Apt H-2, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$4,999,000
4 Beds ⋅ 4 Baths ⋅ 733281 MLS ⋅ ['Fee Simple'] Tenure
Set behind the coveted “Makai” ocean side gates of the legendary Mauna Kea Resort, Fairways North #22 is a sanctuary crafted for those who value privacy and design, on Hawaiʻi’s most storied coastline. Just moments from the iconic Mauna Kea Beach Hotel and the white sands of Kaunaʻoa Bay, this residence enjoys one of the most desirable locations in the resort. • Host with style in the gourmet kitchen and expansive open-concept living spaces • Unwind by to a private pool, cedar sauna and two outdoor showers or soak beneath the stars in the serene tub. • Offer guests the comfort of a separate pool house complete with kitchenette • Appreciate interior finishes of marble, hardwood and basalt stone • Savor panoramic views of the Pacific, Maui, Kohala Mountains, and the Mauna Kea Golf Course Meticulously maintained by Mauna Kea Residences, the on-site management team. Ownership includes the opportunity to join the Club at Mauna Kea, granting privileged access to 2 championship golf courses, oceanfront tennis, fine dining, and two of Hawaiʻi’s favorite beaches, This opportunity comes at a pivotal moment: the resort itself is undergoing a $240+M reimagining, to be unveiled in late 2025. The transformation includes redesigned guest rooms and suites, revitalized dining venues—including the legendary Manta restaurant—and the debut of a world-class destination spa with infinity pool, open-air treatment rooms, a full-service salon, and enhanced fitness center. The famed Mauna Kea Golf Course has also being re-envisioned, to elevate the resort's enduring legacy as one of Hawaii's premier destinations.

62-3459 Aloalii Pl, KAMUELA

Listing courtesy of Aloha Sotheby's Intl Realty - Hawai'i.

$4,999,000
4 Beds ⋅ 4 Baths ⋅ 731176 MLS ⋅ ['Fee Simple'] Tenure
Seller says let's get this SOLD with a very bold price reduction. Experience the essence of oceanfront living in the prestigious Kohala Waterfront community. Where golden sunsets, gentle trade winds, and the rhythmic sound of the Pacific set the tone for everyday life, this private, gated enclave offers a rare blend of serenity and accessibility to the Kohala Coast’s most celebrated beaches, golf courses, and luxury resorts. Designed to embrace Hawaii’s quintessential indoor-outdoor lifestyle, this 4-bedroom, 4-bath residence spans 3,113 square feet, opening effortlessly to a resort-style pool and spa, expansive lanai areas, and lush, custom landscaping by Bioscape Hawaii. The interiors, curated by Peggy Chestnut, pair refined finishes with a relaxed, sophisticated atmosphere. The chef’s kitchen—equipped with premium Hestan appliances and a walk-in pantry—flows into open living areas perfectly suited for both grand entertaining and quiet moments. The primary suite serves as a true sanctuary, featuring private lanai access, a spa-inspired bath, and a secluded outdoor shower garden enveloped in tropical greenery. Each guest suite is thoughtfully designed for comfort and privacy. Additional highlights include an integrated outdoor BBQ entertainment area, automated window shades, a fully owned solar system, and an attached garage. Offered turnkey furnished, this exceptional property invites you to step into a fully realized island lifestyle.

59-121 Kihi Kihi Pl, KAMUELA

Listing courtesy of Hawaii Luxury Real Estate.

$4,999,000
408462 MLS ⋅ Fee Simple Tenure
Also listed as Single Family - MLS# 408461. Best Mixed Use, Turnkey business/residential complex, Landmark & Iconic Maui, HI property. $26K/mo. existing & diversified residential & commercial rental income with 5,000sf commercial space and 1800sf residential space currently leased with 100% occupancy. Multiple very profitable business opportunities grossing over $1.2mil/yr. Additional rental and business income being added. This property is way less than free!! Subdividable and CPRable. Exceptional, 360 deg views in perfect weather, very affluent Lower Kula area of $2-15mil homes. This growing area needs more business development with a huge upside potential in the near future. Destined to be a possible $40mil project-mixed use condos, medical plaza, hotel/restaurant, or Kula Town Center. Purchase now at a high cap rate and realize your future income ambitions with this unique offering in Paradise. Almost an acre, all utilities, 2 water meters, level and all useable. Over $150K in repairs/upgrades recently. Owner or SBA financing with best terms available. 1031 Exchange, Sale Leaseback, or Lease Option possible. More info/pics at Loopnet.com and Bizbuysell.com. Do Not Disturb businesses/tenants. Shown by appt only. Beware!! Vicious guard dog on site 24/7. You will not find a better, more lucrative deal Anywhere!

3135 Lower Kula Rd, Kula

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

$4,999,000
2 Beds ⋅ 1 Baths ⋅ 408461 MLS ⋅ Fee Simple Tenure
Also listed as Commercial-For sale - MLS# 408462. Best Mixed Use, Turnkey business/residential complex, Landmark & Iconic Maui, HI property. $26K/mo. existing & diversified residential & commercial rental income with 5,000sf commercial space and 1800sf residential space currently leased with 100% occupancy. Multiple very profitable business opportunities grossing over $1.2mil/yr. Additional rental and business income being added. This property is way less than free!! Subdividable and CPRable. Exceptional, 360 deg views in perfect weather, very affluent Lower Kula area of $2-15mil homes. This growing area needs more business development with a huge upside potential in the near future. Destined to be a possible $40mil project-mixed use condos, medical plaza, hotel/restaurant, or Kula Town Center. Purchase now at a high cap rate and realize your future income ambitions with this unique offering in Paradise. Almost an acre, all utilities, 2 water meters, level and all useable. Over $150K in repairs/upgrades recently. Owner or SBA financing with best terms available. 1031 Exchange, Sale Leaseback, or Lease Option possible. More info/pics at Loopnet.com and Bizbuysell.com. Do Not Disturb businesses/tenants. Shown by appt only. Beware!! Vicious guard dog on site 24/7. You will not find a better, more lucrative deal Anywhere!

3135 Lower Kula Rd, Kula

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

$4,999,000
202600059 MLS ⋅ FS - Fee Simple Tenure
Two. Gated, Ocean-Front Properties for sale with 4 houses, 1. TMK:1-9-1-023-023-0000 (A&C Houses on 12,3 sq f lot) 2. TMK:1-9-1-023-106-0000 (C&D Houses on 12,482 sq ft lot) On a Beautiful, White Sandy Beach with Diamond Head View. Large open grassy area. Security System. $9,600.00 total rental income.

91-249 Ewa Beach Road, Ewa Beach

Listing courtesy of West Oahu Realty, Inc..

$4,999,000
9 Beds ⋅ 4 Baths ⋅ 202600054 MLS ⋅ FS - Fee Simple Tenure
Two, Gated, ocean front properties for sale with 4 houses. 1. TMK:1-9-1-123-106-0000 (B&D houses on 12,482 sq ft lot) 2. TMK: 1-9-1-023-023-0000 (A&C) houses on 12,382 sq ft) 4 Houses are rented for $9,600.00 per month total rent. On a beautiful, white sandy beach with Diamond Head View Large, open grassy area. Security System, Pavilion Area.

91-249 Ewa Beach Road, Ewa Beach

Listing courtesy of West Oahu Realty, Inc..

$4,995,000
3 Beds ⋅ 2 Baths ⋅ 410634 MLS ⋅ Fee Simple Tenure
OCEANFRONT LIVING, NORTH SHORE STYLE. Some oceanfront homes give you a view. This one makes the ocean part of everyday life. Set beside Tavares Bay, just minutes east of Paia, 465 & 467 Hana Hwy combine an oceanfront main residence, private guest cottage and additional approx. 6,000 SF adjacent parcel into one exceptional North Shore retreat. From the moment you enter, the Pacific draws you through the home, filling the living and dining spaces with blue water, horizon and light. The Pacific is the backdrop, the surf is the soundtrack, and the home creates an effortless connection between indoor and outdoor living. Treasured as the owner’s retreat for over twenty years, the light-filled, furnished, single-level main residence offers 2,072 sq. ft. with 3 bedrooms and 2 baths. Imagine waking to the sea and ending the day to the gentle lull of the waves. Vaulted natural wood ceilings, crisp white enameled beams and travertine floors create a warm, natural palette throughout the home, complemented by granite counters, soft-close cabinetry, stainless-steel appliances and central A/C. Renovated in approximately 2005 and updated in 2018, expansive windows keep the ocean ever present throughout the home. The ocean-facing primary suite opens to a private outdoor seating area. Its spacious en-suite bath features a walk-in closet, floor-to-ceiling stone-tiled open shower, private outdoor shower and soaking tub. Outside, the grounds have been artfully nurtured over time. Mature tropical landscaping, including ginger, heliconia, plumeria and abundant foliage, creates privacy and the feeling of an established Hawaiian garden. Panoramic Pacific, West Maui Mountain, Molokai and Sunset Color views surround the property. Here, the ocean becomes part of the rhythm of the day. Look toward Tavares Bay to see what the swell is bringing, head down to the beach, or simply stay home and watch the ocean change throughout the day. A separate guest cottage, thoughtfully divided into two independent studio accommodations, adds another dimension to the property. Studio One features a wet bar and full bathroom, while Studio Two includes a full kitchen and full bathroom. The cottage creates inviting possibilities for guests or extended family while maintaining comfortable separation from the main residence. Together, the two parcels total 19,079 sq. ft., nearly half an acre adjacent to Tavares Bay. The included adjacent vacant parcel has its own water meter and expands the possibilities of the property, offering additional space to shape it around your own vision for the future. Two parcels. A private guest cottage. Nearly half an acre beside Tavares Bay. Thoughtfully established tropical grounds. And at the heart of it all, a home where the Pacific is part of how you live.

465 & 467 Hana Hwy, Paia

Listing courtesy of Maui Real Estate Advisors LLC.

$4,995,000
731710 MLS ⋅ ['Fee Simple'] Tenure
Rarely does an opportunity of this scale become available along Hawaiʻi Island’s Hāmākua Coast. Encompassing approximately 470 acres above Papaikou, this exceptional fee simple property offers tremendous versatility, extraordinary privacy, and sweeping ocean and mountain views. The property is predominantly open pastureland and is currently fenced with multiple paddocks throughout, making it well suited for ranching, grazing, diversified agriculture, or the establishment of a substantial agricultural operation. Adding to the character of the property are two active streams that run along major boundaries of the land. Along their course are multiple waterfalls and natural pools, creating a landscape that feels distinctly Hawaiian and setting this property apart from more typical large acreage offerings. Beyond its agricultural potential, the sheer scale and natural beauty of the property open the door to a much broader vision. It could serve as a private ranch or estate, conservation oriented holding, family legacy property, agricultural enterprise, or long term investment in Hawaiʻi land. From its elevated setting above Papaikou, the property captures impressive views across the surrounding countryside and toward the Pacific while remaining within convenient reach of Hilo. Nearly 470 contiguous acres with pasture, streams, waterfalls, natural pools, privacy, and tremendous views. For buyers seeking a significant landholding on Hawaiʻi Island, this is a truly uncommon opportunity. Information herein deemed reliable but not guaranteed. Buyer and buyers agent to do their own due diligence on all pertinent facts.

27-640 La Rd, PAPAIKOU

Listing courtesy of Better Homes and Gardens Real Estate Hank Correa Realty.

$4,995,000
5 Beds ⋅ 4 Baths ⋅ 409257 MLS ⋅ Fee Simple Tenure
Welcome to perfection in Upcountry Kula. Imagine a private retreat spanning 2.367 acres, surrounded by the abundant natural beauty of the land, combined with pristine bi-coastal ocean views reaching to Moloka’i and Lana’i. A legacy estate of this caliber defines tranquil upcountry living at its best, creating a home to celebrate life’s landmarks. Resting at 2,200 feet on Haleakala’s western slope, this unique residence enjoys the best of the mild upcountry climate. Kula residents appreciate year-round Springtime with gentle Pacific breezes and consistently comfortable temperatures. Panoramic views of the Pacific greet you throughout the home’s interiors. Oversized picture windows in the living room and primary suite frame these reach-out-and-touch unequaled vistas, changing throughout the day as the light does. The main residence’s light-filled, lofty spaces seamlessly meld together with 5 bedrooms and 3.5 baths, spanning 3,644 square feet. The home's custom Mediterranean architecture and local craftsmanship embrace simplicity, which defines the unique upcountry lifestyle. In addition to those ocean views, there are forty native fruit trees (avocado, mango, citrus, mangosteen, star apple, lychee, peach, nectarine, star fruit), honoring the land and the year-round outdoor living experience. A separate suite with a private entrance is the perfect flex space for a creative studio, work-from-home office, full-size gym with infrared sauna, second kitchen, full bathroom, private deck, and yard. The main residence has brand-new Wolf appliances, including an induction range, refrigerator, and dishwasher. Custom new white oak hardwood flooring throughout is the canvas for your personal design statement. Discover the custom yurt with 20ft ceilings, including ocean and unequaled Haleakala’s views. Walking trails wind throughout the property's landscape, with ocean views at every turn, and are a natural amenity to this perfect retreat. The redesigned pool and spa are the home’s centerpiece, boasting a 40-foot saltwater pool with solar heating. Imagine experiencing the best of Kula from sunrise to sunset, 365 days a year. Visit this Upcountry Kula home, and you will discover it is exactly where you are meant to be.

1260 Naalae Rd, Kula

Listing courtesy of Compass-W.

$4,995,000
4 Beds ⋅ 5 Baths ⋅ 404626 MLS ⋅ Fee Simple Tenure
Elevated design meets serene island living in this architectural triumph within the esteemed double-gated Lanikeha community in the Ka'anapali Golf Estates. This 4-bedroom, 5-bathroom residence spans 3,710 square feet of interior space, offering a harmonious blend of contemporary luxury and timeless Hawaiian elegance. From the moment you enter, you'll be captivated by the expansive, light-filled layout. High ceilings and wide-plank white oak flooring create a seamless flow throughout the home. The gourmet kitchen boasts a Miele refrigerator, a Wolf range, dual dishwashers, and a thoughtfully designed pass-through window connecting to the outdoor kitchen and BBQ—a feature crafted for effortless entertaining. Nearly 1,000 square feet of covered lanai beckons you to savor meals and tranquil moments while soaking in panoramic ocean and outer-island views. Just beyond, the stunning in-ground pool boasts a Baja shelf and an oversized hot tub—a true retreat designed for relaxation and indulgence. Practicality meets luxury with features such as a three-car garage, two-zone central air conditioning, and Hana Hou Builders' signature attention to detail. Each element of the home has been meticulously curated to enhance your elegant living experience, including the landscaped grounds that complement the home's modern aesthetic. You are within 5 minutes of Kaanapali Beach and Whalers Village shops. You are also a stone's throw away from the Ka'anapali Golf Courses, while the PGA Plantation Course in Kapalua is just a 15-minute drive. Lanikeha owners also enjoy access to a fabulous community clubhouse with a fitness center, billiards, and a beautiful infinity-edge pool. This move-in ready, new luxury residence exemplifies elegant contemporary island design. Its flawless design, functionality, and perfect location make it an extraordinary opportunity to open the door to the ultimate Ka'anapali resort-style living.

837 Anapuni Loop, Lahaina

Listing courtesy of Welcome Hawaii Properties.

$4,990,000
4 Beds ⋅ 5 Baths ⋅ 729953 MLS ⋅ ['Fee Simple'] Tenure
This oceanfront four-bedroom, four-bathroom residence within Kona Bay Estates offers 3,490 sq ft of interior living space on a 12,020 sq ft parcel. Designed by Lucky Bennett, the home reflects a deliberate alignment of architecture, climate, and coastline within a guard-gated community with 24-hour security, direct shoreline access, and proximity to Kailua Pier, Ali‘i Drive, and a nearby community park with pickleball courts. Set along a coastline historically associated with the Royal Compound of King Kamehameha I, the property is grounded in both cultural and geographic continuity. Just steps away, Keiki Beach/Queen Bath provides rare sandy, swimmable access. This oceanfront enclave includes only eight homes with direct sandy beach frontage, and the property features its own private sandy beach area. Designed for indoor-outdoor living, the open-concept layout allows a seamless transition between interior and covered lanais, where the two merge fluidly. The orientation captures both sunrise and sunset year-round, with expansive ocean views from the main living areas and multiple bedrooms. A true oceanfront dining area sits directly along the coastline. The home is arranged across multiple levels to maximize airflow, views, and natural light. A central courtyard anchors the design, featuring a shaded pool positioned beneath the main living structure, creating a naturally cooled environment that contrasts with the open ocean exposure. Interior features include koa wood cabinetry in the kitchen and bathrooms, and a primary suite with central air conditioning and two air-conditioned walk-in closets. Additional living spaces support flexible use and gatherings, with a layout designed for connection and flow. The oceanfront setting provides ongoing visibility of marine life, with whales and dolphins frequently observed offshore, integrated into the daily coastal experience.

75-5506 Kona Bay Dr, KAILUA KONA

Listing courtesy of COMPASS.

$4,985,000
4 Beds ⋅ 4 Baths ⋅ 202616140 MLS ⋅ FS - Fee Simple Tenure
Conveniently located near Kahala Mall, this beautiful property sits on a 12,117 approx sqft lot with a spacious 3,860 approx sqft interior. On the market for the very first time, the home showcases high ceilings, open living spaces, and a refined design throughout. The first floor offers a guest suite, bonus room, and an oversized laundry room. A dramatic staircase connects the first and second floors with an elegant open-to-above design, enhancing the sense of space while inviting an abundance of natural light in the home. The upstairs primary suite features high ceilings and a luxurious layout, while the additional bedrooms are designed with a peaceful ambiance, offering comfort and privacy. Surrounded by mature trees and lush tropical landscaping, this residence enjoys a rare sense of an exclusive setting while still being on a main street. A truly unique opportunity in the highly desirable Kahala neighborhood.

4363 Kilauea Avenue, Honolulu

Listing courtesy of Associated Real Estate Advisor.

$4,980,000
5 Beds ⋅ 7 Baths ⋅ 202528395 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

$4,975,000
4 Beds ⋅ 5 Baths ⋅ 409156 MLS ⋅ Fee Simple Tenure
Located within the prestigious gated enclave of Pineapple Hill in the world-renowned Kapalua resort, 620 Silversword Drive represents a rare offering in one of Maui’s most exclusive communities. This impeccably maintained 4-bedroom, 4.5-bath residence has been substantially remodeled and is in flawless, move-in-ready condition, including a new roof with photovoltaic and Tesla battery. Perfectly positioned to capture unobstructed panoramic vistas, the home showcases breathtaking sunset views that stretch across the Pacific, widely considered among the finest in Kapalua. The seamless indoor-outdoor living experience is designed to embrace Maui’s natural beauty, with large backyard ideal for entertaining or quiet relaxation. Residents enjoy privileged access to Kapalua’s top-notch amenities, including championship golf course, full-service spa, tennis and pickleball facilities, and a collection of exceptional dining experiences. Pineapple Hill is known for its privacy, elegance, and elevated lifestyle, making it one of Maui’s most sought-after luxury communities. This is a rare opportunity to own a turnkey home in a premier location, where refined island living meets unmatched views and world-class resort amenities

620 Silversword Dr Unit 26, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$4,950,000
3 Beds ⋅ 3 Baths ⋅ 410375 MLS ⋅ Fee Simple Tenure
Perched within the prestigious double-gated enclave of Lanikeha in the Ka‘anapali Golf Estates, this exceptional fully furnished single-level residence was thoughtfully designed to showcase one of West Maui’s most captivating panoramas. Framed by breathtaking views of the Pacific Ocean, the neighboring islands of Lana'i and Moloka'i, and spectacular sunsets throughout the year, the home offers an effortless blend of timeless craftsmanship, modern technology, and the relaxed elegance that defines luxury island living. From the moment you enter, soaring vaulted Tigerwood ceilings, exquisite Sapele wood trim, and impressive 8-foot solid Mahogany doors create an immediate sense of warmth, scale, and refinement. Every finish has been carefully selected, resulting in a residence that feels both sophisticated and inviting. An integrated whole-home audio system provides the perfect soundtrack whether enjoying a quiet evening or entertaining family and friends. Designed for those who appreciate both beauty and functionality, the gourmet kitchen features premium Bosch appliances, a Liebherr refrigerator and freezer, and an open-concept layout that keeps the spectacular ocean views front and center. Whether preparing a casual breakfast or hosting sunset dinners, the surrounding scenery becomes part of every experience. The primary suite serves as a private sanctuary, offering a spa-inspired bath complete with both indoor and outdoor showers. The outdoor shower is a true work of art, highlighted by an extraordinary solid granite slab that transforms a daily routine into a uniquely luxurious experience. Modern convenience is seamlessly integrated throughout the home with Legrand smart lighting and fan controls, voice-activated motorized lanai screens, multi-zone air conditioning, and advanced home automation. Sustainability is equally impressive, with 33 owned photovoltaic solar panels paired with three Tesla Powerwalls, providing exceptional energy efficiency and peace of mind without sacrificing comfort. Beyond the residence itself, Lani?keha offers one of Maui’s most desirable lifestyles. Situated behind two private gated entrances within a golf cart-friendly community, owners enjoy the convenience of leaving the car behind for many of life’s daily pleasures. A short golf cart ride leads to world-renowned Ka‘anapali Beach, Whalers Village, championship golf, oceanfront dining, upscale shopping, tennis and pickleball facilities, luxury resorts, and countless recreational activities. West-facing and perfectly positioned between the islands of Lana'i and Moloka'i, the home captures mesmerizing sunsets nearly every evening, while seasonal whale watching becomes part of everyday life during the winter months. Combined with West Maui’s remarkably temperate climate—widely regarded as one of the finest anywhere in the world—this extraordinary property offers an unparalleled opportunity to experience the very best of island living.

24 Lolii Pl, Lahaina

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$4,950,000
5 Beds ⋅ 5 Baths ⋅ 202606798 MLS ⋅ FS - Fee Simple Tenure
Oceanfront residence on one of Oahu's most beautiful stretches of coastline. 5811 Kalanianaole Highway is a contemporary oceanfront residence where the remodel and the setting work together. Thoughtfully remodeled with a contemporary design sensibility, every detail has been considered and every space elevated. The open plan kitchen anchors the main living area with a large island, upgraded appliances, and a flow that makes it as comfortable for quiet mornings as it is for entertaining. Generous lanai space leads to the lawn and the ocean beyond. Morning coffee with the sunrise over the Pacific, afternoon barbecues on the lawn with the water right in front of you. The second-floor primary suite is designed to maximize the setting. Ocean and mountain views from the primary bedroom, ocean views from the bath, and a dedicated space that works equally well as a home office or art studio, all facing the water. Five bedrooms, four full baths, and a half bath across 3,300 square feet of living on 8,674 square feet of fee simple land. The first floor includes a full bedroom suite. A pool provides a private retreat in back. Two-car garage. Photovoltaic owned. Direct ocean access.

5811 Kalanianaole Highway, Honolulu

Listing courtesy of Compass.

$4,950,000
2 Beds ⋅ 2 Baths ⋅ 729851 MLS ⋅ ['Fee Simple'] Tenure
Steps to the sand - low priced in Hanalei. This is a fixer upper ready for you to put your personal stamp on your own piece of Hanalei. The location on the corner of Weke Road and Hee Road can't be beat. A 60 second stroll puts your feet on the sandy shore of Hanalei Bay. Experience world class surfing in the winter, gentle boogie-board combers in the summer. Need groceries, looking for dinner out? Three blocks away brings you into Hanalei town. Hanalei is the place to be. Don't miss this opportunity. Property sold AS IS, WHERE IS. All offers must include an AS IS Addendum. Sellers reserve the right to structure this sale as a 1031 Tax Deferred Exchange, at no cost to the buyer. Price is set to attract offers.

5404 Weke Rd, PRINCEVILLE

Listing courtesy of Na Pali Properties, Inc..

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.