Waikiki Beach Real Estate Search

Waikiki Beach 5 Bedroom Properties for Sale

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Newest Waikiki Beach 5 Bedroom Properties for Sale

$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).

$1,395,000
5 Beds 4 Baths 409651 MLS Fee Simple Tenure
Also listed as Single Family with Detached Ohana or Cottage - MLS 407568 - Situated on nearly one acre, the 3-bedroom, 3-bath main home and detached 2-bedroom, 1-bath cottage enjoy sweeping ocean views, sunrise and moonrise vistas, and the tranquility of indoor/outdoor living from the expansive wraparound covered lanai — the ideal spot to watch whales breach and ships sail by. Set against a lush backdrop of tropical landscaping, yet just a short drive from town, this beautifully renovated property offers the perfect blend of island luxury, comfort, and versatility. The main residence was thoughtfully renovated in 2018, showcasing vaulted open-beam ceilings, upgraded lighting fixtures, Australian eucalyptus wood and travertine flooring, and abundant windows that bathe the interiors in natural light. The gourmet kitchen is a chef’s dream, featuring granite countertops, soft-close cherry wood cabinetry, and top-of-the-line Viking stainless steel appliances, including a custom panel side-by-side refrigerator, gas stove with hood, built-in microwave, convection oven, and a separate pantry. The spa-inspired bathrooms offer marble countertops, river rock and mosaic tile shower floors, and a soaking tub in the primary suite — perfect for unwinding after a day in paradise. Additional upgrades include a new roof, windows, and doors (2018), and updated electrical and plumbing systems and interior and exterior paint (2020). Downstairs, a bonus finished basement adds versatility with a full bath, wet bar, and concrete-stained flooring— ideal as a media room, game room or home office. The main home has hot water on demand from its propane tankless water heater. The detached cottage, renovated in 2022, features 2 bedrooms, 1 bath, a 1-car carport, vinyl plank flooring, updated kitchen cabinets, countertops, and appliances. Thoughtfully positioned to allow for privacy, it’s a perfect income opportunity, guest space, or multigenerational living option. The property has two county water meters and two electric meters. Don’t miss the chance to own this unique island retreat — a rare opportunity to enjoy serene tropical living with modern upgrades, flexible living spaces, and unforgettable ocean views.

2609 Kahekili Hwy, Wailuku

Listing courtesy of Carol Ball & Assocs.

$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..

$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.

$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.

$4,995,000
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.

$1,850,000
5 Beds 3 Baths 408994 MLS Fee Simple Tenure
Welcome to a rare Moloka?i oceanfront estate property offering space, privacy, and sweeping island views. Situated on a .59-acre lot with an additional adjoining vacant parcel, this impressive property combines luxury living with the relaxed lifestyle Moloka?i is known for. The main estate home features 5 bedrooms, 2.5 bathrooms, and approximately 2,925 square feet of interior living space, complemented by an attached three-car garage and a roundabout driveway with a private automatic entry gate. Designed to take full advantage of its waterfront setting, the home features a large tiled oceanfront lanai, perfect for enjoying views across the channel to Lanai, seasonal humpback whale sightings, and spectacular winter sunsets, all while benefiting from Moloka?i’s year-round cooling trade winds. Inside, the spacious layout includes a great-room style kitchen with a large island, seated bar, tiled counters, double ovens, and a full walk-in pantry. The kitchen flows into both a formal dining area and an oceanfront breakfast nook, ideal for morning coffee with expansive ocean views. The home also includes a comfortable living room with hardwood floors and beachfront vistas. The primary bedroom suite captures panoramic ocean views right from the bed and includes a luxurious bathroom with a soaking tub and walk-in ice cube shower. Guest bedrooms also enjoy beautiful ocean and garden views. In addition to the main residence, the estate includes a separate 681 sq ft one-bedroom, one-bath ohana cottage, ideal for extended family, guests, or potential rental use. The property is being sold with an additional adjoining vacant lot totaling approximately 15,581 sq ft, complete with its own water meter, offering possibilities for future development, expanded privacy, or additional garden space. The grounds feature spacious lawns, fenced areas, a small greenhouse, and a variety of tropical plants and fruit trees, creating a peaceful island retreat. With no neighbors directly on either side, the property offers exceptional privacy while still being just a short walk to One Ali?i Beach Park. This is a unique opportunity to own a large oceanfront estate with additional buildable land along Moloka?i’s scenic coastline—combining privacy, space, and breathtaking island views in one exceptional property.

2160 Kamehameha V Hwy, Kaunakakai

Listing courtesy of Molokai Vacation Properties.

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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.