Search all Upcountry Real Estate

Affinity Real Estate Group features the best Upcountry Maui real estate MLS search for homes, condos and land available. We have worked hard to ensure this is the only site you will ever need. It is easy to use and navigate through Upcountry Maui real estate searches.

A Few Facts About Upcountry

Upcountry Maui is one of the most beautiful and least-well known parts of the island. Upcountry Maui is generally understood to include the towns of Paia, Makawao, Kula, and Ulapalakua, although it also encompasses numerous historic sites, smaller communities, and scenic outlooks. Upcountry is warm and pleasant, with excellent tropical weather throughout the year and, in many cases, great views of the coastline and the ocean. Upcountry Maui was heavily influenced by the sugar plantation industry, which used to drive the economy of the islands, but has since evolved into a haven for recreation, culture, and history.

Upcountry is home to a number of turn-of-the-century buildings in addition to local favorite restaurants, souvenir shops, and boutiques. Some parts of Upcountry Maui are known for being the last havens for the paniolo, or Hawaiian cowboy, especially the town of Makawao, which prides itself upon this tradition. The Alii Kula Lavender Farm is worth a visit, as Ulupalakua Ranch, the Tedeschi Vineyards, Ulupalakua Ranch Store, the Surfing Goat Dairy, and a number of beautiful beaches and surfing spots. Upcountry Maui also boasts tropical rain forests, views of Haleakala, stunning sunsets, golf courses, and luxurious accommodations.

Upcountry Featured Properties

property photo

$660,000

63 Pukalani Street, Pukalani

Enjoy beautiful ocean views from this half acre corner lot in Pukalani. Ideal for extended family living or use the ohana as a mortgage helper. Conveniently located near ...

  • Beds 3
  • Baths 2.0

property photo

$675,000

2778 Omaopio Rd, Kula

Omaopio Estates is a 20 lots subdivision with minimum 2-acre agricultural lot located on Omaopio Road, Kula, Maui considered to be the most desirable place to live becaus...

  • Beds 3
  • Baths 1.0

property photo

$1,810,000

88 Kawehi Pl, Kula

Allow yourself to be surrounded by lush tropical flowers, cool breezes, night full of stars, and sunsets that go on forever. This 5.26 acre estate is situated in a highl...

  • Beds 3
  • Baths 2.5

property photo

$848,000

2255 Lower Kula Road, Kula

Wonderful plantation style home in great condition. There are super ocean views as well as other island views. The home is very well constructed and features bamboo floor...

  • Beds 3
  • Baths 2.0

property photo

$999,999

25 Kau St., Kula

Incredible price reduction!!!!!! !!!!!!!!! Spectacular views from this custom designed kula kai home. Upstairs luxurious 2500 s.F living area with 3br 2.5 Bth w/ f...

  • Beds 5
  • Baths 4.0

property photo

$400,000

867 Paniolo Place, Makawao

Seller's lender will NOT accept any offers LOWER than $400,000.00 Approved Short Sale. Very easy to show on short notice. Please enjoy Visual Tour to get a complete unde...

  • Beds 5
  • Baths 2.5

property photo

$985,000

1530 Piiholo Road, Makawao

House and two cottages on 5 acres off the newly paved Piiholo Road in Olinda. Both cottages were remodeled in 2008 with new kitchens, baths, paint, flooring and lighting...

  • Beds 2
  • Baths 1.5

property photo

$1,295,000

893 Middle Road, Kula

Magical Gardens……… Surround yourself with 2 acres of total privacy, extraordinary views and possibly the most beautiful garden estate in Kula. These gardens rival Kula’s...

  • Beds 3
  • Baths 2.0

property photo

$2,900,000

83 Ikena Kai Place, Kula

This is the famous Kula Waterfall House in the pastoral, gated neighborhood of Omaopio Ridge now available for resale. Don't miss this second chance to own the most exci...

  • Beds 3
  • Baths 3.5

property photo

$2,300,000

201 Waipoli Road, Kula

Exceptional Upcountry Estate on four pastoral acres with amazing panoramic ocean and mountain views! Beautiful custom home with versatile floor plan offers 6 bedrooms, 4...

  • Beds 6
  • Baths 4.0

Free Daily Email Updates

  • Automated home searches
  • Save searches
  • Email updates
  • And much more…

Upcountry Neighborhoods