Maui Homes with Detached Ohana Cottage

5 Beds ⋅ 4 Baths ⋅ 411312 MLS ⋅ Fee Simple Tenure

For more information, see the duplicate listing at Multi Dwelling listing MLS #411313. Country living at its finest on 2 acres in Upcountry Maui, with sweeping views across green pastures and Giggle Hill and beyond to the ocean and Kahului Bay. The main home features high ceilings, wraparound windows, skylights, and a lovely deck where you can take in the tranquil views. Two additional homes, each with its own character and charm, also offer lovely views and have new roofs and new septic systems. Most of the kitchens on the property have been renovated. The houses and garage are currently set up as follows: Main House: a 3bed/2bath, 2/1 and 0/1. Garage: 2/1. Unit A (middle house): 3/1 and 2/1. Unit B (lower house): 3/2 and 1/1. A total of 8 units of which 7 bring in $12,500 a month in rental income. The grounds are a gardener's delight: about 10 avocado trees, several banana patches, lemon and lime trees, and abundant hibiscus and boganvilla, with tenants currently growing vegetables and herbs. Cooling trade winds in summer and plentiful rainfall keep the land lush. There's no irrigation system, and the water bill runs about $160 a month. An easy 6 minutes to Makawao or Haiku and just 10 minutes to Hookipa. Move into the main house and have the tenants and income already in place. Most tenants are on a Month toMonth lease. Or the property offers flexibility for a family compound or multigenerational living. Showings: Two units are shown at the first showing; all units at a second showing with 48 hours' notice. Buyers to do their due diligence as regards property permits and use. Contact your favorite REALTOR®.

2040 Kauhikoa Rd, Haiku

Listing courtesy of Keller Williams Realty Maui-Ka.

$3,200,000

3 Beds ⋅ 2 Baths ⋅ 411288 MLS ⋅ Fee Simple Tenure

Welcome to 170 Kee Road, a beautiful, versatile, and private 4.3-acre estate, nestled on a quiet country road at the fresh elevation of 1,600 feet, just a half mile from Makawao town. With two separate entrances, multiple structures, mature trees, a unique zoning, and a ¾" water meter, the property offers a multitude of possibilities. The paved main entrance ascends to a charming 3-bedroom 2-bath cottage, set against a neighboring pasture. The 2017 custom-built cottage enjoys a leeward lanai, private lawn area, separate electric meter, septic system, and ample parking. The Royal Palm-lined driveway continues past mature fruit trees, two flexible-use structures, and the former tack building with lanai and enclosed garage, to the current main home backing to a private pasture with unobstructed Haleakala views. The mowed and maintained pasture is framed by forest and organic fruit trees with a rain water filled water tank for landscaping. Comfortably separated from the other structures, the quaint 3-bedroom 2-bath home was fully renovated in 2018 and features high ceilings, quartz countertops, owned grid tied PV system and a spacious lanai that overlooks the pasture, small gulch, fruit trees with stunning mountain views. In this special setting, morning songbirds and nene geese are frequently seen and heard overhead. With Buyer's due diligence, some possibilities to explore: building an additional dwelling, CPR, re-creating an equestrian estate, multigenerational living and much more! At idyllic, yet convenient 170 Kee Road, envision and create a unique lifestyle of your own. Please see the plot map locating structures and a list of fruit trees on the property in the MLS Documents.

170 Kee Rd, Makawao

Listing courtesy of REMAX Hawaii Maui.

$16,500,000

4 Beds ⋅ 6 Baths ⋅ 411266 MLS ⋅ Fee Simple Tenure

Front-row sunsets. Remarkable architecture. Your own oceanfront retreat. At 1750 Halama Street, contemporary design meets the Pacific in a private, gated South Maui setting with approximately 75 feet of ocean frontage. Motorized Fleetwood glass doors open the living spaces to ocean views and coastal breezes. The two-story, steel-frame main residence offers four ensuite bedrooms and five-and-a-half baths, soaring Sapele wood ceilings, a sculptural floating staircase, marble tile and upstairs wood flooring. A commissioned 12-foot glass “wave” kitchen bar, custom gold-leaf cabinetry, two Sub-Zero refrigerators, Miele ovens and a butler’s pantry make the kitchen a distinctive centerpiece. A separate two-bedroom, one-bath ohana with marble tile flooring provides additional space for guests. Approximately 2,500 square feet of lanais, a glass-roof pool lounge, spa and waterfall create a memorable setting for sunset entertaining. Lutron smart-home controls, five-zone air conditioning, an air-conditioned two-car garage and 84 owned photovoltaic panels complete the experience. Walled grounds offer privacy, with South Maui restaurants, shopping and everyday amenities close at hand. Discover the craftsmanship. Feel the setting. Make the ocean part of your everyday life.

1750 Halama St, Kihei

Listing courtesy of Maui Luxury Real Estate LLC.

$10,995,000

5 Beds ⋅ 6 Baths ⋅ 411261 MLS ⋅ Fee Simple Tenure

Built in 2015, this exceptional oceanfront residence was designed with a clear vision: to create a place on Maui where generations could gather, relax, and enjoy time together. This fee-simple property sits directly on a sandy beach at the quiet end of Halama Street. Constructed by Smith Builders Maui, the home reflects thoughtful design, quality craftsmanship, and durable materials throughout. Interior finishes include Douglas fir wainscoting, artisan wallpaper, and Rocky Mountain hardware. Five ensuite bedrooms provide privacy and comfort for family and guests, while the primary suite occupies the entire upper level, complete with dual closets, a dedicated office, private laundry, and an expansive covered lanai overlooking the ocean. The main living areas, kitchen, and dining spaces open seamlessly to the outdoors, where a swimming pool, spacious lawn, and tropical landscaping lead directly to the sandy shoreline. Ocean, mountain, and garden views complement the property's exceptional coastal setting. A detached three-car garage with an upstairs ohana provides additional accommodations for extended family, guests, or an onsite caretaker. Built for longevity, the residence features a Monier tile roof, Hardie siding, and copper gutters. Conveniently located and just 10 minutes from Wailea and 25 minutes from the airport, this location is near restaurants, shopping, and amenities, yet tucked away in a peaceful beachfront setting. This is a chance to own a thoughtfully designed oceanfront estate created for multigenerational living and lasting enjoyment.

1536 Halama St, Kihei

Listing courtesy of Hawaii Life (W).

$1,889,000

3 Beds ⋅ 3 Baths ⋅ 411212 MLS ⋅ Fee Simple Tenure

Discover the relaxed elegance of island living at 20 Kaikane Place, a private Kihei retreat tucked away on a quiet cul-de-sac, less than a 10 minute stroll to the beach. Set on a spacious 10,000 SF lot, this versatile property features a 3-bedroom, 2.5-bath main residence that has been living like a four-bedroom home, thanks to an additional upstairs room ideal for a bedroom, office, or flexible living space. The backyard is landscaped for privacy as a tropical oasis, centered around an exceptional saline swimming pool, with a generous covered lanai for outdoor dining and a great grassy lawn for play and relaxation. Inside, vaulted ceilings, abundant natural light, central A/C, and island-inspired details create a comfortable, inviting atmosphere. The two-car garage has been transformed into an EPIC fun game room, offering a dedicated hangout for the younger ones, entertaining, or recreation, while retaining the flexibility to function as a garage. A charming detached 2-bedroom, 1-bath cottage adds another dimension of versatility, ideal for extended family, guests, or long term tenant income. Bright and open, the cottage features a full laundry room with a new split AC, new central A/C, and inviting outdoor spaces, including a garden area in front and a private area in back. A lengthy driveway accommodates multiple vehicles, while the property's convenient South Maui location places beaches, dining, shopping, Wailea, and Makena within easy reach. A rare combination of privacy, flexible living spaces, resort-style outdoor enjoyment, and walk-to-the-beach convenience, all in the heart of Kihei. Come see this gem!

20 Kaikane Pl, Kihei

Listing courtesy of Hawaii Life (W).

$12,900,000

4 Beds ⋅ 4 Baths ⋅ 411187 MLS ⋅ Fee Simple Tenure

There are properties that follow the landscape, and others that transform the way you experience it. Set across more than 18 acres of rolling green pastures in Haiku, this extraordinary modern retreat offers a remarkable intersection of architecture, art, and nature, with sweeping views from Haleakala to the Pacific Ocean. Designed by SEE Architecture and featured in Dwell, Wallpaper, and Maui Magazine, the residence draws inspiration from celebrated museums, mid-century modernism, and the understated elegance of contemporary retreat architecture. Its clean, minimalist exterior reveals a beautifully considered interior, where soaring glass walls frame the surrounding landscape and blur the distinction between indoors and out. The materials are as exceptional as the design itself. Vein-cut silver travertine, western red cedar, Italian porcelain tile, custom Henrybuilt cabinetry, Heath Ceramics tile, Waterworks fixtures, and a bronze-clad Honduran mahogany pivot entry door reflect an uncompromising attention to craftsmanship. A precision-engineered BONE Structure steel framing system forms the architectural foundation. Beyond the residence, more than two decades of thoughtfully cultivated landscaping have created a lush private setting. Mature tropical gardens, established orchards, expansive pastures, sculptural stone installations, and a sleek swimming pool complement the architecture while celebrating the natural beauty of Ha?iku. A separate two-bedroom guest cottage offers its own private retreat, complete with a full kitchen, covered lanais, and garden views. A 1,000 sq ft barn near a secluded eucalyptus grove provides additional utility and flexibility, while the property's fenced pastures and existing equestrian infrastructure invite a connection to the land. The result is something rarely encountered on Maui: a property where contemporary architecture, extraordinary craftsmanship, and the freedom of expansive acreage exist in remarkable harmony.

1642 W Kuiaha Rd, Haiku

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

$1,700,000

5 Beds ⋅ 3 Baths ⋅ 411184 MLS ⋅ Fee Simple Tenure

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 property features a spacious 5-bedroom, 3-bath main residence along with a detached 2-bedroom, 1-bath cottage, offering excellent flexibility for extended family, guests, a home office, or rental income. Mature landscaping and the generous outdoor space create a private Upcountry atmosphere with room to enjoy Maui’s year-round indoor-outdoor lifestyle. Maui Uplands is conveniently located between Makawao and Pukalani, providing easy access to schools, shopping, restaurants, and everyday conveniences while maintaining the quiet residential feel Upcountry is known for. Community amenities include a swimming pool, tennis court, and clubhouse. With a main residence and detached cottage, 85 Ulana Street presents a unique opportunity for those looking for additional living space, rental potential, or a flexible multi-generational property in one of Makawao’s established neighborhoods.

85 Ulana St, Makawao

Listing courtesy of Commercial Prop of Maui LLC.

$1,449,000

3 Beds ⋅ 3 Baths ⋅ 411172 MLS ⋅ Fee Simple Tenure

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 are eligible. This property has been well cared for and is ready for a buyer that wants a turnkey move-in experience. With a 2 to 3 minute drive to Pukalani Terrace and Pukalani Superette, and approximately a 15 minute drive to Kahului makes this property ideally located. The main house features many upgrades including, but not limited to, a 19-panel PV system with Enphase battery back-up, a full kitchen remodel, new flooring throughout, new window coverings, the interior walls are newly plastered, a tub to shower conversion in the main bath, and a beautifully retiled pool with heating system installed in 2026. The back deck overlooks the heated pool and is perfect for outdoor entertaining and year around swimming. The backyard is fully fenced for privacy and security. The 2nd home features a 19 panel PV system, solar water, newer appliances, new kitchen counter and large pantry, and easy access to a spacious back yard, with a covered lanai and gazebo for outdoor gatherings.

3260 Kihapai Pl, Makawao

Listing courtesy of Welcome Hawaii Properties.

$7,770,000

4 Beds ⋅ 3 Baths ⋅ 411096 MLS ⋅ Fee Simple Tenure

Situated along one of South Maui’s most coveted oceanfront streets, 1544 Halama Street presents a rare opportunity to create an extraordinary luxury estate, with years of architectural planning, engineering, and permitting already completed. Following approximately five (5) + years of planning and design, this exceptional property offers approved architectural plans, structural engineering, building permits, and Special Management Area (SMA) approval, allowing the next owner to move forward without starting the lengthy entitlement process from scratch. A particularly compelling aspect of this opportunity is the approved renovation’s ability to preserve much of the existing residence’s oceanfront footprint. Given today’s increasingly restrictive shoreline setback requirements and SMA regulations, achieving a comparable design, scale, and proximity to the ocean could be extremely challenging, if not impossible, through a new permitting process. The thoughtfully designed plans envision a spectacular private oceanfront compound featuring expansive indoor-outdoor living spaces, a beautifully reimagined main residence, a swimming pool, and a separate two-story structure with an upstairs ohana and garage parking below. The design emphasizes a seamless connection between the home and the ocean, creating an exceptional setting for entertaining, relaxation, and enjoying the Maui lifestyle. With the architectural vision established and major approvals in place, the next owner can bring this remarkable estate to life while personalizing the interior finishes to reflect their own style and preferences. Opportunities to acquire oceanfront property with this level of planning, design, and permitting are exceptionally limited. At 1544 Halama Street, the value extends well beyond the land itself—it lies in the opportunity to create a legacy oceanfront estate in a location where comparable development potential may no longer be attainable.

1544 Halama St, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$1,875,000

3 Beds ⋅ 3 Baths ⋅ 411090 MLS ⋅ Fee Simple Tenure

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 filled with natural light, with large windows framing the impressive views and sliding doors opening to a covered deck—an ideal extension of the living space and a wonderful place to enjoy the Upcountry setting. The main residence also features PV panels and an attached 2-car garage. Set on over one-third of an acre, the property includes a detached 1-bedroom cottage with its own driveway and carport, providing excellent flexibility for guests, extended living, a home office or potential rental use. Located in long-established Kula Kai, this property offers generous living space, versatility and truly remarkable views. All furniture and furnishings are either staged or virtually staged.

122 Ka Dr, Kula

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

$7,000,000

3 Beds ⋅ 3 Baths ⋅ 411041 MLS ⋅ Fee Simple Tenure

You have ARRIVED! Poised above Hana’s extraordinary coastline, sweeping ocean views unfold throughout the property, creating a dramatic backdrop for a thoughtfully reimagined main residence and private suite, complemented by a refreshed separate cottage. Connected by a covered breezeway and designed to embrace the surrounding landscape, the residences offer exceptional versatility while preserving privacy and an effortless connection to the beauty of Hana. This rare 2.28 acre legacy estate is defined by beauty, privacy, and an incomparable sense of place. Over $3 million in significant improvements have elevated the estate with careful attention to craftsmanship and quality. Rich mahogany wall paneling, Taj Mahal quartzite countertops, cherry wood cabinetry, stone-inspired tile flooring, Thermador appliances, new roofs, expansive Custom Marvin windows, and bespoke finishes have been thoughtfully selected to create interiors that feel sophisticated yet beautifully at home in their tropical surroundings. The grounds of Pu‘uiki Place are cultivated exclusively with Korean Natural Farming, a regenerative practice that treats soil as a living community. Nourished by inputs made from native plants and minerals gathered on the land itself, and free of synthetic chemicals, the gardens flourish in harmony with Hana’s rich, vibrant ecosystem. A newly designed pavilion provides an inspired setting for outdoor living and entertaining, or simply taking in the mesmerizing Ocean Views and ever changing Hana coastline. A masterfully sited stand-alone garage and additional storage further enhance the estate’s functionality without compromising its sense of retreat. There are also adjoining property ownership options to explore. Beyond the property, enjoy access to the coastal pathway leading toward Waioka, often known as Venus Pool, while renowned Hamoa Beach is just moments away.Rare in setting and exceptional in presence, Pu‘uiki Place offers the opportunity to steward a remarkable piece of Hana a legacy property where thoughtful design, expansive grounds, extraordinary ocean views, and the enduring character of East Maui come together. E Komo Mai to Pu‘uiki Place, Hana, Maui.

7127 Hana Hwy, Hana

Listing courtesy of Keller Williams Realty Maui-Ka.

$4,249,000

6 Beds ⋅ 6 Baths ⋅ 411038 MLS ⋅ Fee Simple Tenure

BALI IN MAUI! If tropical island living with Balinesian influence is what you crave, WAIT NO MORE! The estate located at 138 Awaiku Street consists of a single-level main home (6-bedroom, 6-bathroom) and ohana (2-bedroom, 2-bathroom) spread across 2 acres. You are surrounded by breath-taking ocean, islands and West Maui mountain views! Built with a Balinesian vision, the influence is felt throughout décor & layout (i.e. communal great room, intimate/private bedrooms retreats, pod-like segmentation of living areas, vaulted ceiling, furnishings, large picture windows/door, substantive balinesian doors, transition-bridge-walk ways). The property has been enjoyed and managed as licensed Bed & Breakfast estate (tax classification is currently 10- COMMERCIALIZED RESIDENTIAL). The B&B LICENSE IS NOT TRANSFERABLE. The Ohana is the perfect extended living area for family, friends or on-site care-taker. Sold furnished with exceptions. The compound at 138 Awaiku Street (Lot 22-B) is part of the Mahanalua Nui Subdivision within the agricultural zoned community of Launiupoko. This parcel has not been CPR’ed. Conveniently located in the heart of Launiupoko neighborhood, YOU are within walking distance of the Launiupoko walking trails, West Maui Mountains and the Launiupoko beach park. Information may not correspond to public records. Buyer(s)/Buyer(s)' Agent to confirm all information. One Seller has an in-active Hawaii real estate license that comes inactive on 10/26/26. Your Time Is Now.

138 Awaiku St, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

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