Wailea Real Estate For Sale

Photo of Listing #408944

63 Wailea Gateway Pl 5103

$2,100,000
  • 2 Beds
  • 2.00 Baths
  • 1,248 SqFt
Keala O Wailea 5-103 offers panoramic Pacific Ocean views from one of Wailea's premier hillside communities. This single-level 2-bedroom, 2-bathroom residence spans approximately 1,248 square feet and was built in 2018, with updates completed in 2025...
Residential
Photo of Listing #410693

30 Waikai St

$2,199,000
  • 3 Beds
  • 2.50 Baths
  • 2,129 SqFt
Welcome to Wailea Kai, where privacy, luxury, and effortless island living come together in one of Wailea’s most desirable gated communities. This immaculately maintained 3-bedroom, 2.5-bath residence feels both refined and relaxed, with soaring va...
Residential
Photo of Listing #410718

3150 Waiea Pl

$2,295,000
  • 3 Beds
  • 3.00 Baths
  • 2,032 SqFt
Tucked behind your own personal gate within the exclusive, gated neighborhood of Wailea Kai, 3150 Waiea Pl is a completely private tropical oasis just across the street from the stunning white sands of Keawakapu Beach. Set on one of the largest lots ...
Residential
Photo of Listing #410122

3236 Pikai Way

$2,350,000
  • 4 Beds
  • 3.00 Baths
  • 1,894 SqFt
Welcome to 3236 Pikai Way, an exceptional single-level residence nestled within the exclusive gated enclave of Wailea Kai, just across the street from the golden sands of world-famous Keawakapu Beach. Situated on a quiet private cul-de-sac in Little ...
Residential
Photo of Listing #411008

384 Kualono Pl Lot 596

$2,490,000
  • 3 Beds
  • 2.00 Baths
  • 2,187 SqFt
Welcome to this beautifully appointed single-level residence in the prestigious gated community of Wailea Pualani Estates. Ideally positioned at the end of a peaceful cul-de-sac, it offers unmatched privacy and quiet. Designed for effortless island l...
Residential
New
Photo of Listing #411084

173 Holokahiki Ln 10b

$2,495,000
  • 3 Beds
  • 3.00 Baths
  • 1,802 SqFt
Experience modern coastal luxury living at Makalii at Wailea #10B. Centrally tucked away from any road awareness yet only moments from Polo Beach and Fairmont Kea Lani, this 2021-built 3-bedroom, 3-bathroom townhome features the gated community's lar...
Residential
Photo of Listing #410251

139 Waaula Way

$2,499,000
  • 3 Beds
  • 2.50 Baths
  • 2,788 SqFt
Welcome to 139 Waaula St, a stunning single-family home in the gated Wailea Kai community, just one block from Keawakapu Beach. Set on a large 10,000-square-foot lot, this multi-level residence lives large, with generous indoor and outdoor spaces des...
Residential
Photo of Listing #408470

3142 Waiea Pl

$2,500,000
  • 3 Beds
  • 2.50 Baths
  • 1,902 SqFt
Wailea Kai is one of the closest communities to the beach! 3 BR 2.5 BA with a pool and easy walking distance to Keawakapu Beach. This recently updated home offers a unique living style with the master on the main level and 2 bedrooms tucked away sepa...
Residential
Photo of Listing #409467

100 Poailani Pl 29

$2,595,000
  • 4 Beds
  • 4.00 Baths
  • 2,129 SqFt
Also listed as Residential MLS# 409490. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-level residence offers the community’s most desirable floor plan. Located in an ex...
Residential
    

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