Our website features the best real estate search for homes with an ohana guest house available for sale in Upcountry Maui on the beautiful island of Maui, Hawaii. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s Association Of Maui database every 15 minutes.
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100 Kalelemuku is a newly completed (2025) architectural estate set within Kula I'o, a gated enclave that redefines upcountry luxury. This landmark estate is fully fenced...
Listing courtesy of Welcome Hawaii Properties.
Situated on Maui’s Upcountry serene landscape, this Legacy Estate offers stunning panoramic ocean and mountain views across 22.25 acres of pristine pastoral land. The fir...
Listing courtesy of Island Sotheby's International Realty(M).
A truly rare offering in coveted Keokea. This exceptional Upcountry estate is perfectly positioned between Kula and Ulupalakua, presenting an unparalleled living experien...
Listing courtesy of Compass-W.
Discreetly positioned off Kula Highway, the approach reveals very little. A winding drive. A narrowing road. Then, through the trees, a freshly painted 1933 guest cottage...
Listing courtesy of Island Sotheby's International Realty(M).
This 10 acre Piiholo property at 4,000' elevation borders a 41-acre State forest and has incredible ocean and mountain views. The very distinctive and extraordinary main ...
Listing courtesy of Coldwell Banker Island Prop(P).
Set across two fully usable acres in one of Kula most desirable microclimates, this exceptional agricultural-zoned estate presents a rare fusion of refined luxury, privac...
Listing courtesy of Berkshire Hathaway Maui Prop-L.
Endless horticultural possibilities await on this rare AG-zoned, turnkey property, with the potential for SELLER FINANCING. Complete with a valuable 2-inch water meter, t...
Listing courtesy of Coldwell Banker Island Prop(P).
If home is where your horse is, try imagining yourself on this 9.618-acre ranch in the heart of Maui's cowboy town, Makawao! With a 16-stall horse barn and a climate-cont...
Listing courtesy of Equity One Real Estate Inc (M).
Crest the rolling hills and you’ll discover this breathtaking Upcountry Maui estate: a one-of-a-kind property with a rare combination of privacy, expansive space, and tim...
Listing courtesy of Coldwell Banker Island Prop(S).
This Kula property consists of THREE separate homes on 2.736 acres with a combined living area of over 6,000 square feet. Located at approximately 3,000 feet elevation, t...
Listing courtesy of Compass-W.
Wow! Bi-coastal views from Molokini to Paia! This perfectly positioned home and ohana on 1/2 acre of land, in the highly desirable Kula Mala neighborhood, features privac...
Listing courtesy of Haleakala Realty, LLC.
This unique multi-unit property (4 structures, 8 units) offers a rare opportunity for investors seeking strong cash flow and long-term upside. There are 5 one bedroom uni...
Listing courtesy of eXp Realty.
Enjoy the best of Upcountry Maui from this beautifully maintained Kula Kai residence offering spectacular bi-coastal ocean views, comfortable single-level living, and exc...
Listing courtesy of Compass-W.
Spacious, private, and full of character, 25 Lumahai Place, just off Olinda Road, sits on 2.88 acres with sweeping ocean and West Maui mountain views, cool fresh air, and...
Listing courtesy of Compass-W.
Tucked just off coveted Polipoli Road in Kula, this remarkable Upcountry estate is a rare blend of artistic legacy, architectural pedigree, and timeless Maui beauty. Once...
Listing courtesy of ENRG Realty.
This newly refreshed Kula retreat pairs a beautifully updated main residence with a detached cottage, offering the flexibility that makes this property truly exceptional....
Listing courtesy of Island Sotheby's International Realty(M).
Welcome to 1199 Freitas Place in Makawao town — a well-cared-for home that combines functional design with classic island living. This is truly one of the best values in ...
Listing courtesy of Compass-W.
This property really is a little gem. It has been well cared for and ready for a buyer that wants a turnkey move in experience. The location is super convenient with eas...
Listing courtesy of Welcome Hawaii Properties.
Looking for a home with multi-generational living options or a mortgage helper? Look no further than 191 Alohilani. This two-bedroom, two-bath home and two-bedroom, one-a...
Listing courtesy of The Maui Real Estate Team Inc.
Your whole family will have space in this energy efficient, turnkey, Bungalow Style, multi-level "Mini Mansion" It's nestled Upcountry on Haleakala. Walking distance to ...
Listing courtesy of Nathalie Mullinix Rlty Universal Inc.
Welcome to 40 Kalihi Pl, Kula, HI 96790—a rare opportunity to own a versatile multi-family property in one of Upcountry Maui’s most desirable areas. Situated on a quiet ...
Listing courtesy of Tri-Isle Rlty & Dev Co Inc.
AS-IS sale. Rare opportunity in Pukalani, located next to Old Haleakala Highway. This approximately quarter-acre (11,155 sq ft) property features two dwellings. The main ...
Listing courtesy of eXp Realty.