Information About Living in Wailea


Situated on the slopes of Haleakala on the east side of Maui, Wailea is most prominently recognized as the home of the Grand Wailea Resort and Spa. However, the city and its almost 6,000 residents find that the area’s upscale and extravagant architecture and planning provide for the perfect living environment. Residents of real estate homes or condominiums for sale benefit from the local resorts’ complimentary services that many residents can take advantage of. Accordingly, Wailea provides an affluent community for residents to enjoy the beauty of Maui and nature from the safety of a secure neighborhood with the amenities of any world-class town.

A nice feature of Wailea is the placement of all utilities underground and landscaped roadways. Originally built to serve the upper class clientele of the beachfront resorts, residents of Wailea also enjoy the well-kept area roads, beaches, and resources. The Shops At Wailea provide one of the greatest selections of stores in Maui with the likes of Gucci and Fendi but also local jewelry stores and other favorite eateries. Nearby are championship golf courses, tennis courts, and other recreational facilities. Wailea also hosts the annual Maui Film Festival and Maui Writers Conference.

Because of Wailea’s prominent location along the leeward side of the island, many water sports and tours originate in Wailea, including an armada of ships destined for snorkeling charters to the offshore crescent island of Molokini. Additionally, a variety of other activities including whale watch cruises, Haleakala bike tours, and historical walking tours begin in Wailea. Residents typically enjoy the upscale feeling of the area and the amenities that come with such status. Although upscale, residents and visitors both appreciate how Wailea has maintained its island charm and sense of community through years of development and change.

Wailea Makena Real Estate Listings

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$18,500,000

3076 S Kihei Road, Kihei

This beautiful oceanfront, two story, contemporary Hawaiian designed home is situated on the best beach on Maui. The gorgeous, five bedroom, 5 bathroom and two half bath...

  • Beds 5
  • Baths 5.0

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$17,300,000

7155 Makena Road, Kihei

First offering of this rare Makena Estate, highlighting contemporary Asian design Created with privacy in mind, the 7,600 square foot home stretches over two acres in a o...

  • Beds 4
  • Baths 4.5

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$13,000,000

3190 S Kihei Road, Kihei

THE LAST OF ITS KIND! A ready for construction beachfront lot on the most private and broadest part of Keawakapu Beach. Seven tenths of an acre with an impressive 133 lin...

  • Beds
  • Baths

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$12,995,000

37 Ualei Place, Kihei

Breathtaking panoramic ocean & outer island views & warm tropical breezes intoxicate the senses & renew the spirit. An easy walk to Palauea Beach & the many world-class ...

  • Beds 6
  • Baths 7.0

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$12,800,000

5510 Makena Road, Kihei

One of the largest oceanfront lots in South Maui. Prime location within the secluded neighborhood of Black Sand at Makena. Only seven luxury homes make up this private ...

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  • Baths

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$11,888,000

4950 Makena Road, Kihei

Beachfront luxury residence at its finest. Professionally furnished and decorated, this elegant beachfront residential condominium offers the ultimate in Makena. Maui b...

  • Beds 4
  • Baths 4.5

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$9,950,000

5550 Makena Road, Kihei

Only the finest materials were used when creating this estate. Residence Five is perched on 1 acre of land overlooking Black Sand Beach and the nature preserve of Pu’u Ol...

  • Beds 5
  • Baths 5.5

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$9,950,000

4950 Makena Road, Kihei

An oceanfront Gem in the Makena Resort on Maui, the undisputed playground of Hawaii!! Set back only 40' from the Crystal Blue Pacific, this four bedroom four and one-hal...

  • Beds 4
  • Baths 4.5

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$9,900,000

4950 Makena Road, Kihei

Rare and wonderful this is the jewel placed on the point at Makena Place. Beautifully designed with 4 bedrooms, 3.5 baths, and open kitchen leading to over sized lanai w...

  • Beds 4
  • Baths 3.5

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$8,795,000

4950 Makena Road, Kihei

Steps away from a secluded sandy beach with dramatic outer island views and fiery sunsets is this unique property with 7 bedrooms and 7.5 baths. In the sought after resid...

  • Beds 7
  • Baths 7.5

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