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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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).
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.
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).
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).
Endless horticultural possibilities await on this rare AG-zoned, turnkey property, with the potential opportunity to acquire an established, successful business. Complete...
Listing courtesy of Coldwell Banker Island Prop(P).
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).
3 1/2 acres of fertile farm ground with 1 1/2" water meter and bonus buildings. Seller may Carry Owner Financing with large down and fair terms. (2) 2 Bedroom 1 bath ho...
Listing courtesy of Pacific Shores Realty.
Also listed under Multi-Dwelling (MLS 409725). This unique multi-unit property (4 structures, 8 units) offers a rare opportunity for investors seeking strong cash flow an...
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.
Expansive ocean and island views take center stage from this spacious 3-bedroom, 2.5-bath, 3,034 sq. ft. home near the top of popular Kula Kai. The open main level is fil...
Listing courtesy of Island Sotheby's International Realty(M).
Welcome to 85 Ulana Street, a versatile Upcountry property located in the desirable Maui Uplands neighborhood of Makawao. Situated in a peaceful residential setting, the ...
Listing courtesy of Commercial Prop of Maui LLC.
Unique on Maui, and nestled in the sought-after Upcountry community of Pukalani, this multi-unit property presents a rare chance to own a plantation style home, inviting ...
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 is it! A super convenient location, a house and ohana, heated swimming pool and best of all… The seller is offering a 4.25% Assumable VA loan…and yes, non-veterans a...
Listing courtesy of Welcome Hawaii Properties.
House and cottage! Now offering a $20,000 buyer credit at closing. The main home has two-bedrooms, with a bonus room that could be used as a third bedroom. The cottage ha...
Listing courtesy of The Maui Real Estate Team Inc.
Up country living at its best downtown Makawao. Lightfilled 3 bed, 2 bath one story home, new vinyl windows throughout. Expansive living room that moves into a large e...
Listing courtesy of Chris Bakeman Realty LLC.
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.