5050 Makena Rd, Wailea/Makena, HI

$29,900,000

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5

Beds

Baths

9,176

Square feet

0.51

Acres

About 5050 Makena Rd

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.

Features of 5050 Makena Rd

MLS® # 407766
Price $29,900,000
Bedrooms 5
Bathrooms 5.50
Square Footage 9,176
Land Tenure Fee Simple
Acres 0.51
Year Built 2006
Type Residential
Sub-Type Single Family Residence
Status Active

Community Information

Address 5050 Makena Rd
Area Wailea/Makena
City 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
Fireplace No

Additional Information

Date Listed November 14th, 2025
Days on Market 277
Short Sale No
RE / Bank Owned No
Vacation Rental No
Pets Allowed N
Land Tenure Fee Simple

Listing Details

OfficeDiscovery Makena Realty LLC
Contact InfoCell: 808-870-8000

Listing Map

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