Makawao/Olinda/Haliimaile Homes under $2.5 million

Makawao/Olinda/Haliimaile Homes under $2.5 million

Welcome to the enchanting district of Makawao, Olinda, and Haliimaile, nestled in the heart of Maui, Hawaii. This charming region is a delightful blend of rich history, vibrant culture, and breathtaking natural beauty, making it a sought-after destination for both residents and visitors alike.

Makawao, known for its paniolo (cowboy) heritage, offers a unique glimpse into Maui's past, with its rustic storefronts and welcoming community. Stroll through the quaint streets lined with art galleries, boutique shops, and delicious eateries that celebrate the local flavors of Hawaii. Just a short drive away, Olinda boasts stunning panoramic views of the island, with lush landscapes and cool breezes that make it a perfect retreat from the hustle and bustle of everyday life. Meanwhile, Haliimaile, with its charming plantation-style homes, is a hidden gem that captures the essence of Maui's agricultural roots.

For those looking to invest in this picturesque area, there’s an exciting range of homes available under $2.5 million. Whether you’re dreaming of a cozy cottage surrounded by vibrant gardens or a spacious family home with stunning mountain views, the real estate options here cater to various tastes and lifestyles. Each property reflects the unique character of the region, providing an inviting sanctuary amidst the lush greenery and serene atmosphere.

Embrace the spirit of Aloha and discover your dream home in Makawao, Olinda, or Haliimaile—where the beauty of Maui awaits you at every turn!

Newest Makawao/Olinda/Haliimaile Homes under $2.5 million

1160 Ehu Rd, Makawao
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 411002 MLS ⋅ Fee Simple Tenure
Enjoy the space, privacy and cooler climate of Upcountry living in this single-level 3-bedroom, 2-bath home set on 2.5 level, usable acres. High vaulted ceilings create an open, airy feel, while a wrap-around covered deck extends the living space outdoors and provides a comfortable setting to enjoy the peaceful surroundings. The fully fenced and gated property features an expansive green lawn with plenty of room to enjoy the acreage. A detached 2.5-car garage offers space for two vehicles plus a workshop, storage or hobby area. Privately situated yet easy to show, this Upcountry property combines comfortable single-level living with generous usable land and versatile outdoor space. Photos have been virtually staged. This is not a CPR. Zoning allows for 1 main house, a 2nd dwelling of up to 1,500 sf. (permitting conditions apply).

1160 Ehu Rd, Makawao

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

189 Hokupa St Unit Lot 36, Makawao
$1,525,000
4 Beds ⋅ 3 Baths ⋅ 410946 MLS ⋅ Fee Simple Tenure
Discover Hoku’ula in the charming town of Haliimaile, set on the mild slopes of Haleakala and overlooking Maui’s famous North Shore. Construction is underway, with an estimated completion date of November 2026. Expansive ocean and mountain views will greet you from this bottom row, two-story C floor plan home with 4 bedrooms and 2.5 bathrooms. Features include; 9 foot ceilings, open layout, covered lanai, and an attached two car garage. Notable amenities include; split air-condition, rain gutters, stainless-steel appliances, double paned windows, soft close cabinetry, upgraded carpet, upgraded LVP flooring, Kohler tubs, sinks and toilets. Located just minutes from Kahului’s modern conveniences and the quiet appeal of Paia and Makawao. This is truly a unique opportunity to own your piece of paradise on Maui, a wonderful place to call home. All renderings and floor plans are conceptual and are not intended to be an actual depiction of the home, driveway, or landscaping. Square footage and room sizes are approximate. Buyer and Buyer's Agent to conduct due diligence.

189 Hokupa St Unit Lot 36, Makawao

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

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.

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.

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..

1102 Mailuna Pl, Makawao
$1,475,000
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).

918 Hiilani St, Makawao
$750,000
3 Beds ⋅ 2 Baths ⋅ 410551 MLS ⋅ Fee Simple Tenure
Bring your vision and creativity to this fixer-upper opportunity in quaint Haliimaile town. The current structure will require renovation and repairs. Ideal for investors and contractors. Please DO NOT ENTER the property without an appointment. Don't miss the opportunity to transform this property into something special. Information may differ from County records.

918 Hiilani St, Makawao

Listing courtesy of Realty 1st Inc.

30 Pahaa Pl, Makawao
$1,095,000
4 Beds ⋅ 3 Baths ⋅ 410550 MLS ⋅ Fee Simple Tenure
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. Situated on approximately ¼ acre, this private property offers generous indoor and outdoor living, a flexible floor plan, mature landscaping and numerous recent improvements, including nearly 1000 additional square feet of bonus living space with beautiful ocean views from the backyard and Haleakala views from the front yard. The bright and refreshed main residence features new interior paint and numerous updated doors, fixtures and finishes. The well-appointed kitchen offers cherry cabinetry, granite countertops, stainless steel appliances and gas cooking. Photovoltaic solar panels, solar hot water and seven split-system A/C units add comfort and energy efficiency throughout the property. A converted garage now serves as a spacious bonus room/gym with Murphy bed, offering flexible possibilities for recreation, work or guests. The attached nohana space has also been substantially upgraded with a remodeled kitchen and bathroom, stacked washer/dryer and an enclosed former porch creating additional usable space. Outside, a newly stained deck and patio overlook the spacious, fully fenced yard shaded by mature fruit trees, with two sheds providing additional storage and garden space. Multiple avocado trees, fig, citrus, banana, lime, dragonfruit, pineapple and a bountiful spice garden offers options for additional income, or just to enjoy the bounties of island living. Conveniently located near Pukalani and Makawao shopping, schools, parks and Upcountry amenities, and approximately 15 minutes from Kahului and the North Shore, 30 Paha‘a Place offers the space, flexibility and relaxed lifestyle that make Upcountry Maui living so special. Private. Updated. Versatile. Energy-conscious. And ready for its next chapter.

30 Pahaa Pl, Makawao

Listing courtesy of Keller Williams Realty Maui-Ka.

29 Mikiola St, Makawao
$1,100,000
2 Beds ⋅ 1 Baths ⋅ 410471 MLS ⋅ Fee Simple Tenure
Large sunny easy to build one-half-acre lot with a two-bedroom one bath accessory dwelling. The location of the accessory dwelling towards the rear of the lot provides ample space for your new main dwelling and another accessory dwelling. Amazingly easy to build lot that is flat with multiple building sites to provide privacy and room for your desired home. Accessary dwelling is well maintained to allow living on site or rental income. Reroofed and deck repairs made. On the mauka side of Mikiola with some pine trees in the front, give you that country living feeling. Bearing trees on property include avocado, coconut, lime, and Lemon.

29 Mikiola St, Makawao

Listing courtesy of ZT Hawaii LLC.

3566 Kalua Pl, Makawao
$835,000
4 Beds ⋅ 2 Baths ⋅ 410447 MLS ⋅ Fee Simple Tenure
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 the charm of Upcountry living in a well-established neighborhood where neighbors know and care for one another. Situated on a quiet, private street, the home provides a peaceful setting while remaining close to everyday conveniences. This longtime family home has been expanded over the years, creating additional living space. The improvements were completed without permits, and county records do not reflect the current configuration. Buyers are advised to conduct their own due diligence regarding the property's condition, improvements, and county records. Property is served by county water, a cesspool, and county trash service. Open House: Sunday, August 9, from 10:00 AM to 2:00 PM. Come explore the possibilities this centrally located Makawao home has to offer!

3566 Kalua Pl, Makawao

Listing courtesy of Tri-Isle Rlty & Dev Co Inc.

185 Hololani St, Makawao
$1,239,000
3 Beds ⋅ 3 Baths ⋅ 410434 MLS ⋅ Fee Simple Tenure
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 potential. The home features 3 bedrooms, 2.5 baths, plus a versatile bonus room ideal as a dedicated office or fourth bedroom, abundant storage, a separate storage room or workshop, and two carports with covered parking for up to three vehicles. A rare private sewer connection enhances the property's long-term flexibility, allowing you to fully enjoy and maximize the land without the constraints of a cesspool or septic system. Whether you envision a future cottage or ADU, expanded living space, or simply the luxury of a generous yard, the possibilities are yours to explore (subject to County approval). Just minutes from Pukalani Country Club, shopping, parks, historic Makawao town, Kulamalu Town Center & food trucks, and some of Maui's most distinguished private schools, this is Upcountry living with room to imagine more.

185 Hololani St, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

Start Your Search