Upcountry Homes under $2.5 million

Upcountry Homes under $2.5 million

Welcome to Upcountry Maui, a hidden gem that perfectly encapsulates the charm and beauty of Hawaii's lush landscapes. Nestled in the hills above the bustling beach towns of the island, Upcountry offers a serene retreat that is both tranquil and vibrant. With its cooler temperatures, breathtaking views of the Pacific Ocean, and stunning sunsets, this region is ideal for those seeking a peaceful lifestyle while still being close to Maui's famous attractions.

Upcountry is known for its rich agricultural heritage, featuring picturesque farms, flower fields, and the renowned Kula Lavender Farm. Stroll through charming towns like Makawao and Pukalani, where you’ll find a delightful mix of local shops, art galleries, and eateries serving up delicious farm-to-table cuisine. The area is also a gateway to adventure, with easy access to hiking trails, horseback riding, and the majestic Haleakalā National Park, where you can experience the awe-inspiring sunrise above the clouds.

For those looking to call Upcountry home, there are fantastic opportunities available, with homes priced under $2.5 million. Whether you're in search of a cozy cottage, a sprawling estate, or a modern home with panoramic views, Upcountry offers diverse real estate options that cater to various lifestyles and preferences. Embrace the slower pace of life, surrounded by nature’s beauty, and discover why Upcountry Maui is not just a place to live, but a way of life. Come and explore the possibilities—your dream home awaits in this enchanting paradise!

Newest Upcountry Homes under $2.5 million

1175 Kamehameiki Rd, Kula
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 410974 MLS ⋅ Fee Simple Tenure
Coming soon. Currently tenant occupied.

1175 Kamehameiki Rd, Kula

Listing courtesy of Coldwell Banker Island Prop(Ka).

71 Makawao Ave Unit 3, Pukalani
$935,000
2 Beds ⋅ 3 Baths ⋅ 410936 MLS ⋅ Fee Simple Tenure ⋅ Gardens Upcountry BLDG.
These units rarely come on the market in this highly desirable small condo complex in Pukalani/Makawao. Built in a U shape around a very sweet courtyard and elegant park like setting, the complex has just 20 units and is very centrally located. The upcountry vibe and trade winds make for cooler and gentler living with easy access to Haleakala Hwy and just a 12 minute drive to Kahului. The unit is very gracious with high cathedral ceilings downstairs, and an open winding staircase to the two bedrooms with en-suite baths upstairs. The entrance leads into the main living area, including a half bath, with lots of windows for spectacular light, and the kitchen and dining area downstairs are in the back of the unit where there's a small yard and space to sit outside or grill on the bbq. The unit is tenant occupied and has been for some time; with rental income at $3,500/month.

71 Makawao Ave Unit 3, Pukalani

Listing courtesy of Keller Williams Realty Maui-Ka.

1199 Freitas Pl Pl, Makawao
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 410916 MLS ⋅ Fee Simple Tenure
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 entertainment room, & an additional room that leads to the covered patio. Enjoy the large fenced lot filled with an abundance of fruit trees, established hedge for privacy, & roomy tool shed. The main bath has been beautifully remodeled with custom tile, counter top, & storage. Kitchen boasts new countertops & tile backsplash. The original kitchen sink stainless steel with side boards, not to be missed. Huge 2 car garage with storage, laundry room & bath with furo. Detached cottage is approx. 660 st. ft with its own electric meter and carport. A blank canvas for you to make it your own. Easy to show. This location is close to the Makawao rest., shops, entertainment, famous Komoda Bakery, schools, gyms, and other amenities.

1199 Freitas Pl Pl, Makawao

Listing courtesy of Chris Bakeman Realty LLC.

328 Kaomi Pl, Makawao
$1,488,000
5 Beds ⋅ 3 Baths ⋅ 410913 MLS ⋅ Fee Simple Tenure
Two homes, over half an acre, and room for whatever you have in mind. Tucked at the end of a quiet cul de sac just off Haleakala Highway, 328 Kaomi Place in Makawao gives you the space upcountry is known for. Mature trees set the stage for a spacious backyard with plenty of room to garden, gather, or simply enjoy the cool upcountry air. The main home offers 5 bedrooms and 2.5 baths with a flexible floor plan, a two car garage, and additional flex space ready for storage, a home gym, a dance or art studio, a workshop, or whatever your needs may be. A separate detached 2 bedroom, 1 bath dwelling adds even more options, whether that's multigenerational living, rental income, or living in it yourself while renting out the main house. Easy access to Pukalani, Kahului, and the rest of the island without giving up the upcountry setting. Contact your favorite REALTOR to schedule a showing.

328 Kaomi Pl, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

245 Mokuahi St Unit Unit A, Makawao
$879,000
2 Beds ⋅ 1 Baths ⋅ 410881 MLS ⋅ Fee Simple Tenure
"Treetops Condominium" is a residential condo sale offerinng the Main dwelling (Unit A) with rights to expand the current footprint and/or build an additional cottage. You'll feel at home in this floor plan that offers comfort and charm. The spacious kitchen with granite countertops, cherrywood cabinets and stainless steel appliances opens to the living room where trees and plants fill every window. Koa laminate flooring connects the living spaces throughout and the generous primary bedroom offers a walk-in closet.The spacious, covered deck adds over 350 sq ft of outdoor entertainment and living space. Underneath the house, you have storage for all your toys, tools and gardening supplies.You’ll love the walkable location to Makawao town with its historical vibe, mixed with boutique shops and dining. From this location, you can be at the airport, shopping, and Baldwin Beach all under 15 minutes. There are no common area maintenance fees. The home is sited on just over 15,000 s.f. of Limited common area yard and serviced by a private cesspool and electric meter. Water usage is shared with the cottage (unit B). Be prepared to submit a pre-approval letter or proof of cash funds with any offer. Listor is Seller and part-owner of the property. Listing Broker/Agent is the Principal and a Sole-Proprietor.

245 Mokuahi St Unit Unit A, Makawao

Listing courtesy of Cheryl L Lee.

140 Kahala Pl, Kula
$2,495,000
2 Beds ⋅ 1 Baths ⋅ 410870 MLS ⋅ Fee Simple Tenure
3 1/2 acres of fertile farm ground with 1 1/2" water meter and bonus buildings. (2) 2 Bedroom 1 bath homes plus an addition 4480 sq ft bonus building with septic, electric and plumbing that can be used as farm operations building or you can apply for permit to make it the main house. 710 Sq ft Ohana has it's own cesspool and there is also another bonus stand alone octagonal office or yoga studio. 888 sq ft Main house also has a bonus office/ohana next to it and it's own cesspool. This property is a must see. Close to Makawao town and Pukalani. Only 20 minutes to north shore beaches and Paia. Perfect for Owner Farmer who needs housing for workers or Contractor who needs equipment storage and worker housing. Multiple Mango, Avocado, Lychee, Coconut and other mature fruit bearing trees. Dead end Street for safety and privacy. Seller may consider seller financing with acceptable terms.

140 Kahala Pl, Kula

Listing courtesy of Pacific Shores Realty.

1587 Polipoli Rd, Kula
$1,484,000
2 Beds ⋅ 2 Baths ⋅ 410825 MLS ⋅ Fee Simple Tenure
Breathtaking Multi-Island Views & Serene Upcountry Living on 2+ Acres! Welcome to your pristine retreat tucked away and perched in the cool Kula air with stunning, unobstructed vistas that stretch north to south shore and more. From the sweeping morning light dancing over the bi-coastal waters to the legendary, golden-hued sunsets, the ever-changing panoramic views are a daily masterpiece. Built in 1995, the thoughtfully designed interior features a comfortable, single-story floor plan with a spacious two-bedroom, two-bath layout finished with a cozy wood-burning fireplace that serves as the ideal gathering spot for crisp mountain evenings. The primary bedroom features an en-suite deluxe bath with an ocean view, soaking tub, separate shower and large closet. The living space flows effortlessly with windows framing the scenery and drawing the beauty of Upcountry indoors. Step outside to experience the rest of the magic of this property and enjoy the dream-view deck while soaking in the hot tub. The sloping verdant acreage, with a good variety of fruit trees, offers immense privacy. Complete with a 2-car garage, separate extra storage building, and an equestrian 3-stall barn, this estate is a rare opportunity to own a pristine slice of paradise with views you have to see to believe.

1587 Polipoli Rd, Kula

Listing courtesy of Island Sotheby's International Realty(M).

640 Makawao Ave, Makawao
$1,599,000
4 Beds ⋅ 2 Baths ⋅ 410773 MLS ⋅ Fee Simple Tenure
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 it and open sky in every direction. Cool mornings, usable ground, and a location that needs no explaining to anyone who knows upcountry. The parcel is zoned agricultural and largely open. Room for pasture, orchard, gardens, animals, or equipment, with space left over. A 4 bedroom, 2 bath home sits on the property and is ready to live in now. Makawao town and the shops and restaurants along Baldwin Avenue are minutes away, with Kahului a short drive down the hill. Over two acres fronting Makawao Avenue rarely becomes available, and property held this long tends to sell once and stay put. Come see it in person, since the size and the setting read differently on the ground than they do in photos. Contact your agent to schedule a private showing.

640 Makawao Ave, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

284 Alalani St, Makawao
$1,150,000
2 Beds ⋅ 1 Baths ⋅ 410747 MLS ⋅ Fee Simple Tenure
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-maintained property was thoughtfully updated in 2022 with a remodeled kitchen and luxury vinyl plank flooring throughout. Enjoy gorgeous ocean views from the patio and beautiful mountain views throughout the property. The cottage features stainless steel appliances, split A/C in the primary bedroom and living room, a solar water heater, and 25 owned photovoltaic panels for added energy efficiency. The expansive lot offers plenty of room to enjoy the outdoors while providing significant future potential. The property also includes a small wood-frame shed for additional storage. The high-capacity septic system was intentionally designed to accommodate the future addition of up to a 5-bedroom home, offering flexibility for expansion along with a concrete tank and leech field. There is ample room to add a main house and potentially another cottage, subject to County approvals, permitting, zoning, and applicable regulations. Recent improvements include new exterior paint, adding to the property's inviting appeal. Whether you're looking for a comfortable cottage, additional space for future development, or a property with room to grow, this unique offering provides an exciting combination of usable land, views, solar infrastructure, and potential. Some photographs have been virtually staged for illustrative purposes.

284 Alalani St, Makawao

Listing courtesy of Shore To Shore Realty, Inc..

190 Aliiolani St, Pukalani
$1,659,000
3 Beds ⋅ 2 Baths ⋅ 410729 MLS ⋅ Fee Simple Tenure
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 cottage, versatile workshop, and two separate flex spaces, all set on over 1/2 acre of fully fenced land. The main residence has just been updated with new interior paint, new vinyl plank flooring, and a revamped kitchen featuring beautiful quartz countertops. It is move-in ready with a bright, clean, fresh feel. Enjoy panoramic views of Haleakala and the West Maui Mountains by day and town lights by night as you unwind in the backyard fire pit area. Two strategically positioned flex space studios offer options for a home office, studio, extra storage, or a small business. The layout ensures privacy with generous spacing between the main house, cottage, and workshop, making it ideal for multi-generational living or rental opportunities. There's also potential for a CPR, offering added flexibility for future development or investment. Situated in one of Maui's most ideal climates, this property is minutes away from multiple schools, community parks, boutique shopping, a local golf course, and variety of favorite dining spots. Truly a must-see opportunity that cannot be fully appreciated from a drive-by. Please schedule a private tour through your realtor today.

190 Aliiolani St, Pukalani

Listing courtesy of Compass-W.

8 Paliuli Pl, Kula
$1,685,000
4 Beds ⋅ 4 Baths ⋅ 410722 MLS ⋅ Fee Simple Tenure
PRICE IMPROVEMENT! Experience the Upcountry lifestyle with this exceptional value in sought-after Kulamanu. Nestled on a large and private corner lot, this well-established 4-bedroom, 3.5-bath home offers a rare combination of space, comfort, flexibility, and beautiful mountain and ocean views. This home has 2,038 square feet of interior living space and is complemented by expansive open and covered decks, large lanai,and covered porch providing for exceptional indoor/outdoor living and entertaining. Enjoy added privacy, a fenced yard, garden space, and established landscaping with producing banana, coffee, and citrus trees.The versatile floor plan features an open kitchen, dining, and living room with wood burning fireplace for those cool Kula nights. Within this floor plan you’ll find two very spacious primary suites, each with its own ensuite bathroom, one on the main floor and one on the lower level making this home exceptionally well suited for multigenerational living, guests, or buyers seeking flexible use of space. The two-car garage provides convenient parking, laundry and additional storage. Underground utilities, enjoy the views of Molokai and Lanai on crisp, clear days, within close proximity to schools, farmers’ markets, dining, parks, and quaint Upcountry towns. Exterior painted in 2025. Some photos have been virtually staged.

8 Paliuli Pl, Kula

Listing courtesy of Kulamanu Realty.

1102 Mailuna Pl, Makawao
$1,569,500
3 Beds ⋅ 3 Baths ⋅ 410602 MLS ⋅ Fee Simple Tenure
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 thoughtful design, lush surroundings, private pool, intimate outdoor spaces, and an exceptionally flexible floor plan. The home feels both gracious and wonderfully easy to live in, with a sense of privacy and tranquillity that is increasingly difficult to find. Upstairs, an inviting living room is warmed by a cozy gas fireplace, while expansive windows draw in abundant natural light and frame the verdant surroundings. The kitchen and living spaces open naturally toward the home's vine-draped lanai on the lee side- the Owner's favorite place to gather, dine, and enjoy the sweet views toward Makawao sunsets. The spacious primary suite offers a private retreat, complete with built-in bookshelves and a serene sense of separation from the rest of the home. Downstairs feels like its own private world. Two additional bedrooms and an exceptionally generous second living room create a versatile configuration for guests, extended family, a home office, or live-in relatives. From the bedrooms, step directly onto your private lanai and toward the pool and gardens, creating an effortless connection to the outdoors. Outside, the beautifully landscaped grounds are designed for privacy and enjoyment. A fabulous intimate lap pool and cozy pool pavilion provides a peaceful focal point for this residence. For energy efficiency, the property is also equipped with 32 photovoltaic panels. The location is equally compelling. Enjoy the charm of Makawao town within walking distance, while Kahului and Baldwin Beach are approximately 20 minutes away. Here, thoughtful architecture, lush grounds, privacy, flexible living spaces, and an enviable Upcountry setting come together in a truly special property. A distinctive home with wonderful possibilities.

1102 Mailuna Pl, Makawao

Listing courtesy of Equity One Real Estate Inc (P).

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