Waikiki Beach Real Estate Search

Waikiki Beach 5 Bedroom Properties for Sale

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Newest Waikiki Beach 5 Bedroom Properties for Sale

$4,500,000
5 Beds 4 Baths 409863 MLS Fee Simple Tenure
E Komo Mai to Your Own Private Paradise Above Wailea As you pass through the gates at 3264 Keha Drive, a lush tropical landscape unfolds before you. Spread across nearly three-quarters of an acre in the heart of Maui Meadows, this private sanctuary welcomes you home. Every detail of this incredible multi-family estate has been designed to embrace the beauty and peacefulness of island living, while delivering the comforts and amenities of a private luxury retreat. Cascading waterfalls and a tranquil koi pond greet you upon arrival, and from the very first moment, the stage is set for an immersive Maui experience. Perched high above Wailea on the sun-warmed slopes of Haleakala, this estate commands a 180-degree panoramic view that stops you in your tracks every single time. The Pacific stretches endlessly before you, with Kaho'olawe rising from the sea to the left and Lana'i to the right, two islands framing a horizon that transforms at golden hour into something that simply cannot be described, only witnessed. This is the view that Maui is famous for, and it belongs to this home. Life here is lived looking outward from every vantage point the estate offers. Mornings begin slowly, coffee in hand, the ocean laid out below you. Evenings end with the sun dropping toward the horizon as the sky ignites in brilliant color, the trade winds moving through, each sunset an original. You will never see the same one twice. The estate is rare in both scale and versatility, offering significant square footage and a multi-structure configuration that opens up genuine possibilities. The main residence, complete with two living rooms and generous proportions, is complemented by an attached private guest suite, a separate two-bedroom rental, and an additional private guest suite. For a multi-generational family, it is the perfect gathering place. For the investor, it is an income-producing property with the rental infrastructure already in place. Outside, resort-caliber living awaits. A sparkling pool anchors the outdoor space, with a sauna, steam room, full outdoor bar, and poolside television all within reach, thoughtfully designed for quiet mornings and unforgettable gatherings alike. These spaces don't just complement the Maui lifestyle; they embody it. Over 72 solar panels paired with integrated smart home technology run quietly in the background, dramatically reducing energy costs and delivering the kind of efficiency a property of this caliber deserves. A fully electric Nissan Leaf and dedicated charging station are included, making the transition to island living as seamless as it should be. This estate is offered fully furnished and completely turnkey, perfectly suited for the island family ready to settle into something exceptional, the buyer watching another winter roll in somewhere far from here, or the investor seeking a property that works as beautifully as it looks. Bring your suitcase. Everything else is already waiting. Opportunities like this are rare. The elevation, the views, the scale, the versatility, all within one of Maui's most coveted neighborhoods. This kind of property doesn't come around often, and when it does, it doesn't last. Resort Living. Island Privacy. Endless Possibilities.

3264 Keha Dr, Kihei

Listing courtesy of eXp Realty.

$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.

$1,695,000
5 Beds 4 Baths 202605605 MLS FS - Fee Simple Tenure
Rare opportunity to own a spacious 5-bedroom, 3.5-bath residence in the highly sought-after Salt Lake neighborhood. The interior square footage is 2,768 sq ft on a 8,597 sq ft lot. Designed for comfortable living, the primary level offers 4 bedrooms and 2.5 bathrooms, while the enclosed unfinished basement area includes an additional bedroom and full bath ideal for guests, multi-generational living, or flexible use space. Step outside to your fully fenced backyard retreat featuring an in-ground swimming pool perfect for entertaining and enjoying Hawaii’s year-round sunshine. The home is also equipped with photovoltaic (PV) solar panels for enhanced energy efficiency. Conveniently located within the Moanalua Elem, Moanalua Inter, and Moanalua HS public school districts, and just minutes from shopping, dining, freeway access. A fantastic opportunity to personalize and make this home your own in one of Honolulu’s most desirable neighborhoods. Tax records show the home as a 5-bedroom 4 baths, actual is 5 bedrooms 3.5 baths. Monthly property based on 2025 property assessed values. Sqft Liv includes the 898 sq ft "unfinished basement" in the tax​​‌​​​​‌​‌​​​​‌‌​​‌‌​‌‌​​‌​​​‌​‌ records.

1360 Ala Puumalu Street, Honolulu

Listing courtesy of Coldwell Banker 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..

$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.

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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.