Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Listing photo for 5050 Makena Rd, Wailea/Makena, HI
Previous View the Previous slide Next View the next slide

5050 Makena Rd,

Wailea/Makena, HI

$29,900,000

5 Beds
5½ Baths
9,176 Sqft
0.51 Acres
2006
Year Built

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.

Facts & Features
MLS® # 407766
Price $29,900,000
Bedrooms 5
Bathrooms 5.50
Square Footage 9,176
Acres 0.51
Year Built 2006
Type Residential
Sub-Type Single Family Residence
Land Tenure Fee Simple
Status Active
Community Information
Address 5050 Makena Rd
Area Wailea/Makena
State HI
Zip Code 96753
Amenities
Parking Garage
# of Garages 2
View Ocean
Is Waterfront Yes
Waterfront Ocean Front
Has Pool Yes
Pool In Ground
Interior
Cooling Central Air
Additional Information
Date Listed November 14th, 2025
Days on Market 303
Short Sale No
RE / Bank Owned No
Description Land Tenure Fee Simple
Listing Details
Office Discovery Makena Realty LLC
Office Contact Cell: 808-870-8000
Photo of Anita L. White RB-21022

Anita L. White RB-21022

Office: 808-665-1166
Cell: 808-345-7654

Listings provided courtesy of the REALTORS® Association of Maui.

IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

What's Your Home Worth? Find out now, for Free.

Let's Go