Wailea/Makena Homes with Ocean Frontage

Welcome to the stunning Wailea/Makena area, a true gem on the enchanting island of Maui, Hawaii. Nestled within the vibrant city of Kihei, this picturesque neighborhood is renowned for its breathtaking oceanfront properties that offer unparalleled views and a lifestyle of luxury and tranquility.

Wailea/Makena is celebrated for its pristine beaches, where golden sands meet the azure waters of the Pacific Ocean. Imagine waking up to the soothing sounds of waves crashing against the shore, with the sun rising over the horizon, painting the sky in brilliant hues of orange and pink. This idyllic setting is perfect for those who appreciate nature's beauty and seek a serene escape.

The community boasts a rich cultural heritage, with a welcoming atmosphere that embodies the spirit of Aloha. Residents enjoy access to world-class amenities, including upscale shopping, fine dining, and renowned golf courses. Whether you’re indulging in a gourmet meal at one of the ocean-view restaurants or exploring the scenic coastal trails, Wailea/Makena offers an unparalleled lifestyle that is both active and relaxing.

For those in search of oceanfront homes, this area truly shines. Properties here feature expansive lanais that invite you to bask in the sun, while floor-to-ceiling windows provide unobstructed views of the ocean's splendor. Whether you're looking for a luxurious estate or a cozy beach bungalow, the oceanfront homes in Wailea/Makena promise a life of elegance and serenity, making every day feel like a vacation.

Discover the allure of Wailea/Makena and let this beautiful community welcome you home.

Newest Wailea/Makena Homes with Ocean Frontage

$29,900,000

5 Beds ⋅ 6 Baths ⋅ 407766 MLS ⋅ Fee Simple Tenure

Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living. Designed by world-renowned architect Guy Dreier, the home is a livable work of art, featuring soaring ceilings, dramatic architectural lines, and an innovative floor plan. Step through the entryway into an entertainer’s paradise. The expansive great room flows effortlessly through large pocket doors to the oceanfront deck, where a stunning infinity-edge pool appears to spill into the sea—ideal for sunset gatherings or peaceful mornings with coffee in hand. Multiple living and dining areas, along with a dedicated service area, create an unparalleled setting for both intimate dinners and large-scale celebrations. The exquisite primary suite and three guest suites each offer private ocean-view lanais, providing serene retreats with panoramic vistas. A beautifully appointed attached Ohana unit adds exceptional flexibility for guests, extended family, or a caretaker. Move-in ready and designed for effortless hospitality, this is more than a home—it’s a true Makena masterpiece blending modern coastal luxury with the timeless beauty of Maui’s south shore.

5050 Makena Rd, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$9,000,000

2 Beds ⋅ 4 Baths ⋅ 408876 MLS ⋅ Fee Simple Tenure

Over an acre of direct beachfront in Makena is an exceptional rarity — and 4584 Makena Road stands as one of the most compelling value opportunities along Maui's coastline. Positioned on Poolenalena Beach, the property offers expansive grounds, exceptional privacy, and irreplaceable beach frontage. The existing residence requires renovation, making this an ideal opportunity for investors or end users seeking to add value in a location where land alone commands a premium. With limited beachfront inventory in Makena, the ability to renovate or reimagine a home on a parcel of this size represents a strategic acquisition. Peaceful and secluded, yet within walking distance of the Wailea Beach Path and celebrated resorts including Fairmont Kea Lani, Four Seasons, Grand Wailea, and Andaz, this offering combines lo-cation, land, and long-term upside in one of Hawaii’s most prestigious enclaves.

4584 Makena Rd, Kihei

Listing courtesy of Island Sotheby's Int'l Rlty(W).

Start Your Search

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.