Waikiki Beach Real Estate Search

Waikiki Beach 5 Bedroom Properties for Sale

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Newest Waikiki Beach 5 Bedroom Properties for Sale

$1,649,000
5 Beds 4 Baths 410140 MLS Fee Simple Tenure
Nestled along a peaceful country road in highly sought-after Kula, this beautifully remodeled 5-bedroom, 3.5-bath residence offers the perfect blend of modern comfort, Upcountry charm, and breathtaking natural beauty. Backing expansive pastureland, the property enjoys exceptional privacy and panoramic views stretching from the Pacific Ocean to majestic Haleakala. Set amidst lush, manicured grounds, the property is a true tropical retreat featuring mature jacaranda trees, swaying palms, bamboo, and an abundance of fruit trees including avocado, lemon, and orange. Enjoy cool Upcountry breezes while harvesting fresh fruit from your own backyard and taking in the stunning scenery. Filled with natural light, the open-concept interior showcases warm wood flooring and thoughtfully updated finishes throughout. The inviting kitchen features crisp white cabinetry, generous counter space, and a functional layout designed for both everyday living and effortless entertaining. The kitchen and living room are perfectly positioned to capture sweeping views of rolling pastureland, while the seamless indoor-outdoor design creates an airy, open atmosphere throughout the home. The main level offers four spacious bedrooms, along with a versatile bonus room that can easily serve as a media room, home office, playroom, or second living area. Two of the bedrooms enjoy private access to outdoor spaces, providing exceptional flexibility for guests, extended family, or multigenerational living. Large windows throughout the home frame lush tropical greenery, bringing vibrant natural beauty and a sense of tranquility into every room.Occupying the entire upper level, the primary suite serves as a private sanctuary complete with spectacular mountain and coastal views. Enjoy a spa-inspired ensuite features a soaking tub perfectly positioned beneath a picture window, creating the ultimate setting to relax and unwind. Outdoor enthusiasts will appreciate the custom rock-climbing wall and close proximity to Haleakala's world-class hiking and biking trails. A two-car garage and utility shed provide additional storage and workspace. Offering privacy, functionality, and the quintessential Upcountry Maui lifestyle, this exceptional property captures the beauty and tranquility that make Kula one of Maui's most coveted communities. Contact your favorite Realtor to schedule a private showing.

506 Kolohala Dr, Kula

Listing courtesy of Keller Williams Realty Maui-Ki.

$16,950,000
5 Beds 6 Baths 410130 MLS Fee Simple Tenure
Perched on Maui’s coveted west side, this extraordinary 8-bedroom private estate offers a level of luxury, privacy, and craftsmanship rarely seen in Hawai'i. More than a home, this is a legacy estate, an irreplaceable Maui sanctuary designed for those who accept nothing less than extraordinary. Located in the coveted Plantation Estates at Kapalua community on the incredible 16th hole of the world-class Plantation Course, the property commands unmatched sweeping panoramic views across the Pailolo Channel framed by the stunning views of the outer islands of Lana'i and Moloka'i. Designed without compromise, the 2-acre estate encompasses more than 8,200 square feet across two separate residences, creating a private retreat unlike any other. Resort-caliber amenities include an infinity-edge pool and dual spas, private office, theater and fitness center. The 7,200 square foot 5-bedroom 5.5 bath main residence seamlessly blends indoor and outdoor living through expansive custom pocket sliding doors that open to reveal breathtaking ocean vistas and unforgettable sunsets. Rich natural materials, custom African Mahogany millwork, exotic stone, and world-class finishes define every space, from the chef’s kitchen and grand great room to the spectacular primary suite. A fully appointed three-bedroom guest cottage with its own pool, fire-pit and Palapa set over a koi pond provides exceptional accommodations for family, guests, or staff while maintaining complete privacy. Aside from world-class golf, the Kapalua resort offer the utmost in amenities including award-winning spa, tennis and pickleball, exquisite dining options and some of the finest beaches: Fleming Beach, Oneloa Bay and Kapalua Bay, which was rated as the Best Beach in America by Conde Nast Travel Magazine.

706 Mokuleia Pl Unit 6, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$3,600,000
5 Beds 4 Baths 410070 MLS Fee Simple Tenure
NOW AVAILABLE AS A UNIQUE OPPORTUNITY: Three beautifully positioned CPR units with more than 26,300 sq ft of combined land—offering generous space, flexible options, and lasting value for years to come. Experience breathtaking panoramic ocean views from this stunning Unit B of a 3 unit CPR, newly remodeled 2-story home offering 3,064 sq ft of modern coastal living. The open floor plan, with soaring vaulted ceilings, creates a bright, spacious ambiance that's ideal for relaxing or entertaining, connecting the kitchen to the dining and living areas, which flow seamlessly to the private wrap-around lanai. With 5 bedrooms and 4 bathrooms, there's ample space for guests and a home office. The flexible layout includes the possibility of a split unit downstairs, which could be accessible via an interior staircase or a separate outside entrance, perfect for multi-generational living, guest quarters, or long-term rental potential. Included, we are offering Unit A (TMK 2-2-1-018-085-0001) and Unit C (TMK 2-2-1-018-085-0003) for added value. Unit A an allocation for a 720 sq ft cottage on approximately 11,369 sq ft of land. The current zoning for unit C (6,000+ sq ft) allows an 840 sq ft ADU on the back side of the main house, offering a great opportunity to add value to this beautiful property (see attached preliminary site plans). Don't miss your chance to own this exceptional property that combines luxury, versatility, and spectacular views! This beautiful home is perched at the top of the prestigious Maui Meadows neighborhood, just minutes from the beach, world-class restaurants, golf courses, and everything that South Maui has to offer. This is a Residential CPR.

3435 Hookipa Pl Unit A - B - C, Kihei

Listing courtesy of Equity One Real Estate Inc (M).

$1,495,000
5 Beds 4 Baths 410056 MLS Fee Simple Tenure
Located in the desirable Keonekai neighborhood of South Kihei, this beautifully maintained multi-unit property has a very flexible floor plan to host a large family and/or create a comfortable rental revenue stream. The upstairs level is a 3-bedroom/2-bath home with soaring vaulted open beam/wood ceilings, fresh paint, abundant natural light, beautiful woodwork, the space feels open, airy, and welcoming. The front lanai opens through large sliding glass doors, extending the living area and creating a seamless indoor-outdoor experience with an additional 264 sq ft of living space. Tile flooring throughout adds to the spacious feel and ease of maintenance with washer/dryer upstairs. Enjoy cooking in a chef’s kitchen complete with custom cabinetry with newer stainless steel appliances. Multiple wall-mounted A/C units throughout the home keep the space cool and comfortable year-round. The expansive primary suite features a private ensuite bathroom with dual sinks and its own lanai—perfect for morning coffee or evening relaxation. On the ground level, there is a one-bedroom unit and an additional space with multiple possible uses. A large storage area lies between the two downstairs spaces and a bonus 2 car garage. Each of the two downstairs spaces have separate entrances. Washer/Dryer room established for downstairs. One water meter for the entire property. Separate electric meters for the upstairs and the downstairs. This is a great income producing property or live in one and offset your mortgage payment with the rental income. Property has a large peaceful back yard with fruit trees. Located very close to the South Maui boat ramp, shopping and dining opportunities in Kihei, and is only a few minutes away from accessing the world class beach resorts found in Wailea and Makena.

2735 Panepoo St, Kihei

Listing courtesy of PKR Realty.

$1,995,000
5 Beds 5 Baths 409973 MLS Fee Simple Tenure
Beautiful Hana- ON THE BEACH. Walk out your front door right on to beautiful Waikoloa black sand beach. The only home for sale ON THE BEACH!!! Millions below homes on the beach in other parts of Hawaii. Here it is. Almost 3/4 acres! Hear the waves crash all day and night. This property is listed under its appraised 4/6/25 appraised value of $3,000,000! Are you interested? If you are read on.... It's pure serenity in Hana! This legacy property consists of a spacious lot. Charles Lindberg, George Harrison, Pat Benatar, Jim Nabors, Vincent Price and others have chosen Hana for its peace and beauty. This spacious remodeled home, caretaker area and workshop are a short bike ride to town! The 5 bedroom 5 bath home has Starlink internet and has been lovingly remodeled. There are travertine tile floors, granite countertops, custom cabinets and stainless steel appliances and Koa accents. There is even a studio area off the garage which may be perfect for a caretaker or visitors! This property overlooks a restored Hawaiian fishpond. There is a new lava rock wall surrounding the property. The 448 square foot workshop area is plumbed and wired. The home boasts a solar array. It even has a 22k generator with a 100 gallon propane tank. Hana is the perfect escape. Live an idyllic life -- walk the bay or bike to Hana town. Appreciate the cultural significance of the heiau and fishpond. Discover why Hana is Hawaii’s best secret.

140 Waikoloa Rd, Hana

Listing courtesy of Deep Blue HI.

$675,000
5 Beds 3 Baths 409947 MLS Fee Simple Tenure
Charming cul-de-sac retreat with ocean and mountain views! Nestled at the quiet end of a cul-de-sac, this spacious 5-bedroom, 3-bathroom, 1,600-square-foot home offers the perfect blend of functionality and relaxed island living. Originally built with a cozy footprint, the home underwent a significant professionally built extension in 2011, thoughtfully adding 3 bedrooms and 2 bathrooms to effortlessly accommodate a growing household, guests, or a dedicated home office setup. Enjoy stunning panoramic views of the mountains and ocean from the expansive front and back lanai spaces, which are ideal for morning coffee, evening sunsets, or breezy outdoor entertaining. Inside, the bright, open-concept main living area seamlessly transitions into a large kitchen featuring expansive countertops, a built-in pantry, and dual skylights that flood the space with beautiful natural light. Stay cool year-round with efficient split-system air conditioning units and multiple ceiling fans positioned throughout the home. Low-maintenance living is a breeze here, thanks to durable ceramic tile flooring that spans the entire interior. The impressive indoor-outdoor flow continues outside with a charming wood-plank front deck and a fully tiled back lanai complete with extra utility storage closets. Boasting great curb appeal, the exterior features a wide driveway with a spacious covered carport and a beautifully terraced, low-maintenance yard accented by a classic volcanic rock retaining wall. Full of potential and ready for its next chapter, this unique property is a must-see!

405 Palapalae Pl, Kaunakakai

Listing courtesy of Molokai Realty LLC.

$6,950,000
5 Beds 6 Baths 409921 MLS Fee Simple Tenure
Sunlight and ocean breezes flow through 21 feet of bi-folding floor-to-ceiling glass doors, complemented by soaring 14-foot ceilings that blur the boundaries between home and horizon. Step into this South Maui beachfront estate, where elegant stone columns welcome you to a true masterpiece. The open-concept spaces unfold effortlessly, anchored by a chef's kitchen featuring custom white oak cabinetry with an interior finish that adds warmth and depth, quartzite countertops, tumbled Belgian limestone tile accents, hand-scraped French oak flooring, professional-grade appliances, and a generous breakfast bar— the perfect hub for shared meals, laughter, and connection. A floating staircase leads upstairs to the bedrooms, where the primary suite awaits as a serene sanctuary for the soul. It includes a spa-inspired soaking tub, dual vanities, a spacious walk-in closet, and a private ocean-view lanai ideal for morning reflections. Each additional guest suite has been thoughtfully designed to soothe the senses, with layouts and features that prioritize comfort, including ensuite bathrooms for ultimate privacy. Outside, your personal coastal retreat beckons. Lounge poolside in the saltwater pool, host gatherings under a canopy of stars, or savor a cocktail as the sky blazes with sunset hues. A detached guesthouse with a full bathroom and a two-car garage offer flexible additional space, while integrated smart home technology blends modern convenience into this tranquil, soul-nourishing haven. The adjacent lot is also for sale by the same seller. (MLS #409920, 892 S Kihei Rd) and can be purchased together.

860 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

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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.