Makawao/Olinda/Haliimaile real estate in Upcountry, Maui is our specialty. Our team is committed to making the buying and selling of real estate in Makawao/Olinda/Haliimaile, Upcountry Maui a pleasurable and rewarding experience. Our website allows you to search all active Makawao/Olinda/Haliimaile homes for sale. It is easy to use and navigate through property searches. You can also save searches and get daily email alerts of new listings as they become available.
Over two acres on Makawao Avenue, held by the same owners for generations. The property sits up on a rise in the band between Pukalani and Makawao, with Haleakala above i...
Listing courtesy of Keller Williams Realty Maui-Ka.
Discover the possibilities with this captivating 2-bedroom, 1-bathroom cottage situated on a little over half an acre of flat, fully usable land. Built in 2013, this well...
Listing courtesy of Shore To Shore Realty, Inc..
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.
Sold before listed.
Listing courtesy of REMAX Hawaii Maui.
Welcome home to 742 Kekona Place, tucked into the heart of Makawao. If you love the charm of country living, the sense of community that comes with a small town, & the co...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Tucked privately at the top of a cul-de-sac, this beautifully appointed 3-bedroom, 3-bath home plus office is a Makawao residence that offers a rare combination of thoug...
Listing courtesy of Equity One Real Estate Inc (P).
Bring your vision and a contractor to this unique Makawao opportunity. Situated to capture a partial ocean view, this property offers a rare setup featuring a one-bedroom...
Listing courtesy of Compass-W.
Welcome to 30 Paha‘a Place, a beautifully updated and exceptionally versatile Upcountry Maui home tucked away on a flag lot at the end of a quiet cul-de-sac in Pukalani. ...
Listing courtesy of Keller Williams Realty Maui-Ka.
Warm 4-bedroom, 2-bath home in the heart of Makawao! Conveniently located within walking distance to schools, parks, shopping, and local restaurants, this property offers...
Listing courtesy of Tri-Isle Rlty & Dev Co Inc.
Set atop a quarter-acre lot across from the 12th fairway in Pukalani Terrace, 185 Hololani Street offers the rare combination of move-in-ready comfort and future potentia...
Listing courtesy of Coldwell Banker Island Prop(S).
Secluded at the top of Olinda and surrounded by state forest, 115 Alaluana Road offers privacy and profound quiet above Makawao town. Set on 1.4 agricultural acres, this ...
Listing courtesy of Compass-W.
One of the most turnkey development opportunities in Upcountry Maui. This 1.8-acre vacant lot comes with its own three rare 5/8" county water meters and county-approved b...
Listing courtesy of Coldwell Banker Island Prop-Ku.
In the Hawaiian language, Iini means "to desire, yearn for, or long for"—a fitting introduction to this tastefully renovated 4-bedroom, 3.5-bath home with a new shingle r...
Listing courtesy of Equity One Real Estate Inc (M).
Exceptional multi-generational living or investment opportunity in the heart of Pukalani! Situated on a generous 10,000 sq. ft. lot overlooking the 13th hole of the Pukal...
Listing courtesy of Compass.
Follow the country road to the very top of Piiholo Road, where peaceful Upcountry living, privacy, and breathtaking surroundings await. Nestled on this exceptional 3 Acre...
Listing courtesy of Coldwell Banker Island Prop(P).
Nestled on a private road, 37 Pukiki Place offers the peace, privacy, and tranquility that define Upcountry Maui living. This recently renovated single-level residence is...
Listing courtesy of Coldwell Banker Island Prop(S).
Tucked away on a peaceful private road, 35 Pukiki Place presents a rare opportunity to enjoy the best of Upcountry Maui living in one of the island’s most desirable micro...
Listing courtesy of Coldwell Banker Island Prop(S).
Be the first to call this brand-new home, completed in 2026, your own! Located in the very sought out Kualono subdivision, this thoughtfully designed 3-bedroom, 3.5-bath ...
Listing courtesy of Keller Williams Realty Maui-Ka.
Hollow tile house and cottage on a 1/2-acre lot in Pukalani. Both need EXTENSIVE work including but not limited to new roofs. This is a "contractor special". Both homes h...
Listing courtesy of Island Sotheby's International Realty(M).
Wonderful opportunity in the desirable Pukalani area! This charming 984 sq. ft. home is situated on a level half-acre lot, offering ample space and potential for expansio...
Listing courtesy of Shore To Shore Realty, Inc..
Perched along desirable Alaluana Road in Olinda, this exceptional vacant parcel offers breathtaking mountain and ocean views in one of Upcountry Maui's most scenic locati...
Listing courtesy of Hawaii Life (MA).
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).
Perched just above Makawao Town, 1131 Kehau Place captures the essence of Upcountry living with sweeping ocean and West Maui Mountain views, cool trade winds, and the con...
Listing courtesy of Compass-W.
This super charming 5-bedroom, 2.5-bathroom home in Pukalani is set on nearly 14,000 sq.ft., the property showcases sweeping 180-degree ocean and mountain views from its ...
Listing courtesy of eXp Realty.
Great opportunity to own a beautiful property in Makawao, priced to sell quickly! A precious 3 bed, 3 bath home on a 1/2 acre lot with close to 400 sq ft lanai, and larg...
Listing courtesy of Keller Williams Realty Maui-Ka.
Experience the best of Upcountry Maui with this beautifully updated single-level home overlooking the Pukalani Golf Course. Brand new flooring, interior paint, stylish li...
Listing courtesy of Island Sotheby's International Realty(M).
Wake up in the heart of Makawao in this charming 1,404 sq. ft 4-bedroom, 3-bath home. Under high ceilings, this thoughtfully designed upgraded kitchen features beautiful ...
Listing courtesy of Equity One Real Estate Inc (M).
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.
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.
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.
Spanning 19.5 acres of rolling countryside on coveted Olinda Road, this remarkable Upcountry Maui property feels like a step back to a simpler time. Framed by expansive o...
Listing courtesy of Island Sotheby's International Realty(M).
Experience a true time capsule sanctuary in the cool climate of Pukalani. This beautifully preserved 1961 “island on an island” estate perfectly captures the essence of c...
Listing courtesy of Island Sotheby's International Realty(M).
Rare opportunity to own one of the only vacant land offerings in Lower Olinda. Ideally located just 5 Mins from charming Makawao Town, this exceptional 2-acre parcel offe...
Listing courtesy of Compass-W.
Lovingly cared for by original owners, this property offers an abundance of storage/worksheds, carports, and endless possibilities. Situated on a spacious 18,700 sq. ft....
Listing courtesy of Chris Bakeman Realty LLC.
Sold Before Listed
Listing courtesy of Coldwell Banker Island Prop(S).
Some properties are simply beautiful. Others leave you feeling something long after you’ve gone. Perched along the breathtaking slopes of Olinda Road on over 2 private a...
Listing courtesy of Keller Williams Realty Maui-Ka.
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.
Perched in coveted Upcountry Maui, this original Plantation-style 3-bedroom home captures breathtaking north and south shore views, sweeping across the entire Central Val...
Listing courtesy of Corcoran Pacific Properties.
2756 Leolani Place offers a unique opportunity to own a single-level home in the heart of Upcountry Maui. Situated on approximately 11,630 square feet, this 3-bedroom, 2-...
Listing courtesy of Hawai'i Modern Realty.
Nestled in the heart of charming Makawao town, 7 Hoolai St is a private sanctuary that blends island living with modern comfort. Surrounded by lush, tall hedges and secur...
Listing courtesy of Compass-W.
Step into the charm of 270 Pau Hana Road, nestled in the peaceful heart of Makawao, Maui. This beautifully designed, contemporary 2-bedroom, 1-bathroom home effortlessly ...
Listing courtesy of Compass-W.
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).
Welcome to Maui Uplands, often considered the gem of Makawao. This quality-built 3-bedroom, 2-bath home, along with a separate 2-bedroom, 1-bath detached cottage, is set ...
Listing courtesy of REMAX Hawaii Maui.
Pukalani Fairway Estates – Unit #5 offers a rare blend of Upcountry charm, privacy, and natural beauty in one of Pukalani’s most desirable communities: 24 homes nestled o...
Listing courtesy of REMAX Hawaii Maui.
Enjoy cool, clean air and Upcountry living in this meticulously maintained residential condominium in the Cottages at Kulamalu. This 4-bedroom, 3-bathroom home features o...
Listing courtesy of Hawaii Life (W).
Also listed as Single Family Home, MLS #409194 Beautiful golf course home—your opportunity to step into island living with this move-in ready retreat. The charming backya...
Listing courtesy of Hawaiian Style Realty LLC.
Now offered at an exceptional new price, this beautifully maintained single-level home is an incredible opportunity to own on a quiet cul-de-sac in the heart of Makawao. ...
Listing courtesy of Compass.
Sophistication and simplicity do a remarkable tango together at this rarely offered upcountry condo. Located between Makawao and Pukalani, this elegant courtyard style gr...
Listing courtesy of Hawaii Life (MA).
On the fairway at Pukalani Country Club, with Cook pines lining the edges and the ocean visible on the horizon, 272 Hololani Street is the kind of Upcountry address that ...
Listing courtesy of Island Sotheby's International Realty(M).
Welcome to Maui Uplands! This beautiful 2-bedroom, 2-bath home with views of the West Maui mountains was fully renovated in 2023. Luxury vinyl flooring, custom bathrooms,...
Listing courtesy of Pacific Image Properties.
Front Row on the 15th! Situated at the end of the 15th hole of Pukalani Golf Course, with impressive bi-coastal and fairway views, this 4-bedroom, 3-full bath split-leve...
Listing courtesy of Keller Williams Realty Maui-Ka.
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.
Set above a picturesque gulch in desirable Pukalani, this home captures sweeping North Shore ocean views. Wildlife is frequently seen in the valley below, adding to the e...
Listing courtesy of Island Sotheby's International Realty(M).
Welcome to 3584 Baldwin Avenue in the heart of Makawao—where Upcountry charm meets thoughtful design and everyday comfort. This beautifully finished single-level 3-bedroo...
Listing courtesy of Compass-W.
Upcountry Maui living with many thoughtful upgrades and flexible space! 34 Alaluana Rd #B offers approximately 2,500 sq ft under roof, including a 960 sq ft upper level w...
Listing courtesy of Real Broker.
Nestled in the prestigious gated community of Kulamalu Hilltop in Pukalani, Maui, this stunning residence is a true sanctuary of luxury and comfort. Soaring vaulted ceili...
Listing courtesy of Compass-W.
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.
$30,000 Seller-credit to Buyer at close of escrow!!! This is the Upcountry Maui home you have been waiting for! Situated in Pukalani, close to shopping, dining, great pu...
Listing courtesy of Island Sotheby's International Realty(M).
Discover a rare investment opportunity just steps away from the charming town of Makawao! This diverse property features 3 livable structures. A main house built in 1964,...
Listing courtesy of Island Sotheby's International Realty(M).
Sold before listed.
Listing courtesy of Coldwell Banker Island Prop(P).
“Pending Continue To Show” Sellers accepting back up offers. Perched in the serene elevations of Upcountry Maui, this property combines breathtaking views with privacy an...
Listing courtesy of Ihu Properties LLC.
Bring your vision to this peaceful Upcountry property nestled just below the cool cloud line of Upper Piiholo. Set on two (2) beautifully established acres, this three (...
Listing courtesy of Coldwell Banker Island Prop(Ka).
Welcome to 1072 Aala Place, a charming upcountry property tucked away on a quiet cut-de-sac in the heart of Makawao and experience the perfect blend of comfort, privacy, ...
Listing courtesy of Real Broker.
Nestled in the heart of charming Makawao, this versatile Maui home offers the perfect blend of space, privacy, and island lifestyle. Situated on a generous 10,000+ sq. ft...
Listing courtesy of Maui Property Managers LLC.
Welcome to this thoughtfully upgraded 4-bedroom, 3-bath home in desirable Pukalani, offering the perfect blend of comfort, quality construction, and the Upcountry lifesty...
Listing courtesy of Coldwell Banker Island Prop(Ka).
Multi-generational residence on the 9th tee of the Pukalani Country Club golf course. No flooding, no leaking, no problems during the recent storms. This 2476 square foot...
Listing courtesy of Romvari Realty Ltd.
Also listed under 'Commercial' MLS 408225 TWO large commercial lots totaling 1.65 acres present a rare offering in a highly desirable corner location in Pukalani's Kula...
Listing courtesy of Equity One Real Estate Inc (P).
A rare 5-acre offering along the highly desired upper stretch of Olinda Road, this property delivers the kind of views and setting that define Upcountry living. Positione...
Listing courtesy of Island Sotheby's International Realty(M).
Welcome to your luxury upcountry home, just a short stroll to Makawao Town but worlds apart. This 4 bedroom, 3 bath house is located at the bottom of a gated driveway ins...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Spectacular Golf Course Views from this exquisite remodel! In the heart of Pukalani, this charming estate offers the best of Upcountry living with comfort and flexibilit...
Listing courtesy of Century 21 Island Homes.
Welcome to your own slice of Hawaiian paradise at 50 Poha Place, nestled in the coveted Kula 200 community of Maui. This expansive estate spreads across a lush 2-acre can...
Listing courtesy of Compass-W.
Perched in the gentle hills of Pukalani, where cool Upcountry breezes meet sweeping island views, this newly reimagined estate captures the essence of modern Maui luxury ...
Listing courtesy of Keller Williams Realty Maui-Ki.
New price improvement! Price is below appraised value. Ready for new homeowners to complete. Majority of the renovations have been done. New appliances are also inclu...
Listing courtesy of HomeSmart Island Homes.
Discover modern Upcountry living in this fully renovated Pukalani home offering flexible space and room to grow. Ideally located in the heart of Upcountry Maui, this beau...
Listing courtesy of Berkshire Hathaway Maui Prop-L.
Welcome to true Upcountry Maui living in Makawao Ranch Acres! Tucked away at the end of a quiet cul-de-sac, this charming property features the main home, a detached cott...
Listing courtesy of Commercial Prop of Maui LLC.
Welcome to 1123 Kehau Place — a timeless 3-bedroom, 2-bath plantation-style home nestled on a peaceful hillside just above historic Makawao Town. This classic residence w...
Listing courtesy of ENRG Realty.
This is an amazing and RARE opportunity to own a SINGLE LEVEL home and POOL in Kula 200! Put your own touches and remodeling ideas together for this home with great bone...
Listing courtesy of Equity One Real Estate Inc (P).
Property is a flag lot with approximately 11,025 sf of land. It appears a large capacity septic tank is in place and recently installed roof on both the main and cottage....
Listing courtesy of East Gate Realty.
Welcome to 3576 Pahala Street, This charming 3-bedroom, 1-bath home with additional flexible living space. Just down the street from the boutiques and cafés of historic M...
Listing courtesy of Island Sotheby's Int'l Rlty(M).
Discover tranquility and ultimate privacy at this exceptional Upcountry Maui estate. Nestled on the slopes of Haleakala and bordered by a lush gulch, this 3,433 sqft resi...
Listing courtesy of Keller Williams Realty Maui-Ka.
Nestled in the desirable climate of lower Olinda, this newly completed CPR offers a gently sloping 2.5-acre pasture to build your Upcountry dream home. Unit B of the CPR ...
Listing courtesy of REMAX Hawaii Maui.
This home is exceptional. A craftsman build with loving care and his workmanship and craft is apparent un everything from the flooring to the fireplace. The primary sui...
Listing courtesy of Tri-Isle Rlty & Dev Co Inc.
Welcome to 10 Alohi Place – a rare Upcountry Maui opportunity featuring a 3-bedroom, 1 bath main home, and a 2-bedroom 1 bath detached cottage on an expansive 19,624 sq f...
Listing courtesy of HomeSmart Island Homes.
This home sits at a wonderful location, a corner ocean view lot on the golf course end of Haulani Street, on approximately .51 acres. This home is ready for new owners, ...
Listing courtesy of Keller Williams Realty Maui-Ka.
Discover the magic of Maui living in this sweet 2-bedroom, 1-bath plantation-style cottage, nestled on a truly special property bursting with fruiting trees. The efficien...
Listing courtesy of Coldwell Banker Island Prop(S).
Calling all cowboys! Come see this adorable retro rambler that has been owned by the same family for 55 years. Awesome location in Makawao Ranch Acres, walking distance t...
Listing courtesy of Equity One Real Estate Inc (M).
Beautiful and pristine Upcountry pastureland just outside of Makawao Town with large acreage at 11.883 acres. Conveniently located close to shops and restaurants but pri...
Listing courtesy of Big Wave Realty LLC.
Nestled in a peaceful and mature neighborhood, this 3-bedroom, 1-bath, 988 sq. ft. home offers a serene escape with convenient access to the best of Upcountry living. Jus...
Listing courtesy of Century 21 Island Homes.
Huge Opportunity, Seller is Highly motivated to find a buyer for this - Pukalani Gem, 3 bed 2 bath home can be used as a 3 bed 1 bath Main Area and the 520 square foot ad...
Listing courtesy of Keller Williams Realty Maui-Ka.
Amazing opportunity in a quiet, family-friendly Upcountry neighborhood. This 3-bedroom, 1-bath home on a spacious 10,074 sq ft lot is full of potential! The Main home pro...
Listing courtesy of Coldwell Banker Island Prop(S).
Welcome to the heart of historic Makawao Town! This delightful 2-bedroom, 1-bath home sits on a spacious, fully fenced lot-perfect for pets and room to grow. Nestled in M...
Listing courtesy of Coldwell Banker Island Prop-Ku.
Welcome to 609 Loulu Way. This fresh two-story residence on a quiet cul-de-sac offers contemporary living, detailed upgrades & exceptional flexibility while still offerin...
Listing courtesy of REMAX Hawaii Maui.
TERRIFIC Pukalani Golf Course VIEW home offers a wonderful and flexible floor plan with both upstairs and downstairs living areas! There are fabulous tradewinds that natu...
Listing courtesy of Equity One Real Estate Inc (P).
Welcome to 172 Ikea Place Unit C in lower Pukalani offering the best of Upcountry living with the ideal climate, stunning bicoastal ocean views, the majestic West Maui Mo...
Listing courtesy of Kokua Realty LLC.
New price as of 3/31/26, bring your offer! Interior remodeled to include all new light fixtures, electrical outlets, switches, toilets, paint, ceiling fans, quartz counte...
Listing courtesy of Keller Williams Honolulu.
Represented Buyer in purchase, Seller unrepresented.
Listing courtesy of General Public.
Excellent opportunity to personalize this classic home in sunny Pukalani! This charming single-level home is nestled on a generous 7,606 sq ft lot and consists of 3 bedro...
Listing courtesy of Coldwell Banker Island Prop(S).
Welcome to this recently renovated and versatile 4 bedroom, 3 bath home, thoughtfully converted into three separate living spaces with their own entrances. Perfect for mu...
Listing courtesy of Whalers Investment Group LLC.
Welcome to the Meadows at Makawao subdivision. 244 N Makaleha Pl offers a unique opportunity to own a piece of Upcountry Maui. This 1,774 sq ft, 3 bedroom 3 bath single-f...
Listing courtesy of Ihu Properties LLC.
Nestled just a stone's throw from Makawao Town, Burns Place offers the perfect blend of classic charm and modern convenience. This delightful neighborhood features 1950s ...
Listing courtesy of Emerald Club Realty Inc.