Maui Homes with Detached Ohana Cottage

2 Beds ⋅ 3 Baths ⋅ 410821 MLS ⋅ Fee Simple Tenure

Experience the Maui Meadows lifestyle where space, privacy, and relaxed island living come together in one of South Maui’s most desirable residential neighborhoods. Set on a generously sized lot in an exceptionally quiet setting, this unique property offers the flexibility to create a private Maui residence with potential rental income or an inviting multi-generational family compound with room for everyone to enjoy their own space. This residence features a distinctive brick exterior and tile roof, a combination that not only adds character but also helps keep the interior naturally cooler in Maui’s warm tropical climate. Two split-system air conditioners provide additional year-round comfort, while the home’s flexible layout lends itself beautifully to everyday island living. Adding even more versatility is the detached ohana, remodeled in 2021 with a new roof and water heater. The separation between the main residence and ohana creates wonderful possibilities for extended family, guests, a home office, additional private living space or rental income. Outside, the expansive grounds and outdoor living areas invite you to embrace the lifestyle Maui is famous for—morning coffee in the fresh island air, relaxed afternoons at home, and evenings spent outdoors under the Maui sky. The large fully fenced lot provides a sense of openness and privacy that can be increasingly difficult to find in South Maui. Maui Meadows is prized for its peaceful residential atmosphere, larger properties, and proximity to the best of South Maui. This private Estate is just minutes from world-famous beaches, Wailea and Kihei restaurants, shopping, championship golf courses, resorts, and countless opportunities to enjoy the ocean and outdoors. Whether you envision a private island retreat or a multi-generational Maui home with space to gather and room to spread out, this home offers a rare combination of location, flexibility, privacy, and the laid-back lifestyle that makes Maui Meadows so special.

818 Kumulani Dr, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$3,985,000

4 Beds ⋅ 3 Baths ⋅ 410782 MLS ⋅ Fee Simple Tenure

5 STRUCTURE OCEANFRONT COMPOUND | OFFERED AT $ 3,985,000. An exceptional opportunity to own a private oceanfront estate overlooking breathtaking Waipio Bay in beautiful Huelo. Set behind electronic gates and surrounded by a protective hedge on 2 acres, this fully permitted sanctuary offers the rare combination of privacy, expansive ocean views, multiple living spaces, lush tropical grounds and a remarkable degree of self-sufficiency. The main residence features 4 bedrooms/3 baths, beautiful teak flooring and a Primary Suite spa inspired bathroom with a private entrance to the pool. The Primary Suite entry doors and bed are custom made from Koa Wood, adding to the tropical elegance. A large gazebo next to the main house has a private ocean view deck, shower and spa as your guests will enjoy yoga, stargazing, whale watching or cocktails at sunset with the outdoor lifestyle Maui is known for. A beautifully renovated 2 bedroom/1 bath ohana provides a private retreat for guests, extended family or tenants, with its own patio and spa and expansive ocean views. A 4-car garage includes a 1 bedroom/1 bath apartment with a deck up above. A separate Garden Cottage with a kitchen adds yet another peaceful area for naps, personal seclusion or the perfect artist’s studio. You’ll find an abundance of fruit trees, tropical flowers and a large organic garden with a nearby equipment shed to support the property’s practical side. The grounds are a true delight with a pool and waterfall feature surrounded by mature tropical, low maintenance landscaping. Designed with 2 large capacity water catchment tanks and pump house, propane for hot water and cooking, security system and established hardscape walkways, while only 30 minutes to the airport and Costco. A property of this scale, privacy, oceanfront setting and versatility is rarely offered at this price point. Come experience it in person by appointment through your favorite Realtor.

311 Door Of Faith Rd, Haiku

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

$2,389,000

4 Beds ⋅ 3 Baths ⋅ 410769 MLS ⋅ Fee Simple Tenure

Sweeping ocean views, recent updates, and ultimate privacy define this custom hillside house and cottage tucked away on a quiet double cul de sac on desirable Kuaua Place in Maui Meadows. This unique property features a nicely refreshed 1,900 square foot main home designed for seamless indoor outdoor island living, alongside a separate detached 676 square foot cottage situated on low maintenance grounds. The main residence offers a flexible 4 bedroom, 3 bathroom layout with exposed beamed ceilings, an open and airy living area, and private lanais on both levels that invite year round sunsets and whale watching. Steps away, the charming 1 bedroom, 1 bath cottage has its own open beamed ceilings and private lanai, making it perfect for guests or rental income. Both dwellings feature split air conditioning. Additionally, the main home features an owned photovoltaic system. Located just minutes from Wailea’s world class beaches, resorts, shopping, and golf, this property offers the absolute best of South Maui living.

3375 Kuaua Pl, Kihei

Listing courtesy of Compass-W.

$1,350,000

3 Beds ⋅ 3 Baths ⋅ 410746 MLS ⋅ Fee Simple Tenure

For those who value privacy, peace, and a life removed from the busy pace of life, 2480 Upper Kanaio Road offers a rare opportunity to embrace the quiet beauty of Kanaio. Set on approximately 4 acres with expansive ocean views, this private gated property features a remodeled main residence, detached cottage, and a flexible lower-level living area—creating space for family, guests, extended living, or a private retreat. The main home is currently configured with two bedrooms on the primary level, while the lower level functions as a one-bedroom mother-in-law quarters with its own living space and breathtaking ocean views. A detached one-bedroom cottage with loft has also been partially remodeled as of July 2026, offering additional accommodations or creative space. Both residences enjoy sweeping views toward the Pacific and the surrounding natural landscape. Designed for comfortable island living, the main home features a tankless water heater, 33 photovoltaic panels with three Tesla Powerwall batteries, newer kitchen appliances, and thoughtful remodeling throughout. Electric and County water already hooked up. Separate private gated entry provides added privacy for both the main residence and the mother-in-law quarters. Here, the rewards are found beyond the walls of the home: quiet mornings, dramatic ocean horizons, cool trade winds, brilliant sunsets, and star-filled nights far removed from the distractions of urban life. Kanaio offers a rare sense of space and simplicity—where the pace slows, the landscape takes center stage, and the days are measured by nature rather than a schedule. For the buyer seeking something different—privacy over proximity, tranquility over traffic, and the authentic simplicity of rural Maui—this is an opportunity to create your own private sanctuary in one of the island’s most peaceful settings.

2480 Upper Kanaio Rd, Kula

Listing courtesy of The Agency Maui.

$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.

$1,050,000

3 Beds ⋅ 1 Baths ⋅ 410695 MLS ⋅ Fee Simple Tenure

19 Kameeui Place offers something a finished home cannot: the freedom to build on Maui's West Side, your way. This 10,942 square foot (0.25 acre) R-3 lot sits in Honokowai, north of Kaanapali, and comes with two legally permitted dwellings and county water, sewer, and electric already connected to the site. R-3 zoning allows for up to three dwellings on the lot. With two already permitted, there is room to shape the property around your own vision. Retain and renovate some of the existing improvements, renovate one structure to live in while you build the rest at your own pace, design and build a new primary home, or add a third dwelling such as an ohana or guest house. The two existing structures total 1,512 square feet: a 912 square foot dwelling and a separate 600 square foot dwelling. The front structure is likely not habitable, and the rear structure is in poor condition. Both are legally permitted, giving an investor, contractor, or creative buyer a head start a bare lot does not offer. How much of that head start you use is up to you. Offered fee simple and sold strictly as-is, this is an opportunity for a buyer who sees value not only in the land, but in what it can become. Buyer and buyer's agent to verify all zoning, permitting, utilities, flood designation, and development options with the County of Maui prior to offer.

19 Kameeui Pl, Lahaina

Listing courtesy of Keller Williams Realty Maui-Ka.

$4,650,000

4 Beds ⋅ 3 Baths ⋅ 410691 MLS ⋅ Fee Simple Tenure

Experience classic plantation style charm blended with modern island living at this stunning oceanfront residence on Halama Street. Set on a gated and private .46 acre lot, this home captures the essence of Maui with refreshing ocean breezes, sweeping multi island views, and direct oceanfront access right outside your door. The main residence is sold fully furnished and designed for effortless comfort, while the detached ohana offers flexibility for guests, extended family, or an onsite caretaker. A sparkling in ground pool surrounded by lush island landscaping creates the perfect setting for relaxation and entertaining. From sunrise to sunset, enjoy the ultimate Maui lifestyle in a home that combines timeless character with tropical tranquility. Make 1656 Halama Street your personal Maui oasis. A new asphalt shingle roof is scheduled for completion in September 2026.

1656 Halama St, Kihei

Listing courtesy of Compass-W.

$1,549,000

2 Beds ⋅ 2 Baths ⋅ 410684 MLS ⋅ Fee Simple Tenure

HEAVENLY HANA AWAITS! Nestled in a peaceful, private setting just minutes from Hana town, this beautiful home and separate cottage offer a rare blend of tropical serenity, comfort, and convenience. The main home features a treetop-inspired setting with an expansive deck, abundant windows, open living spaces, and lush tropical views. The spacious kitchen includes granite countertops, rich wood cabinetry, and a gas range. The primary suite offers a walk-in closet and spa-like en-suite bath with double sinks, a large shower, and separate soaking tub. Downstairs, flexible space provides storage, covered parking, or room for entertaining. The level yard is surrounded by mature fruit trees and tropical landscaping, with ample space to create an outdoor oasis or add a pool. The charming separate cottage includes an oversized covered porch and a comfortable 2-bedroom, 1-bath layout—perfect for guests, extended family, or additional living space. Near Hana town, pristine beaches, and Hana Airport, this property delivers privacy and timeless Old Hawaii charm with everyday convenience. Experience the special lifestyle that makes Hana one of Maui’s most treasured places.

143 Alalele Pl, Hana

Listing courtesy of Keller Williams Realty Maui-Ki.

$4,995,000

3 Beds ⋅ 2 Baths ⋅ 410634 MLS ⋅ Fee Simple Tenure

OCEANFRONT LIVING, NORTH SHORE STYLE. Some oceanfront homes give you a view. This one makes the ocean part of everyday life. Set beside Tavares Bay, just minutes east of Paia, 465 & 467 Hana Hwy combine an oceanfront main residence, private guest cottage and additional approx. 6,000 SF adjacent parcel into one exceptional North Shore retreat. From the moment you enter, the Pacific draws you through the home, filling the living and dining spaces with blue water, horizon and light. The Pacific is the backdrop, the surf is the soundtrack, and the home creates an effortless connection between indoor and outdoor living. Treasured as the owner’s retreat for over twenty years, the light-filled, furnished, single-level main residence offers 2,072 sq. ft. with 3 bedrooms and 2 baths. Imagine waking to the sea and ending the day to the gentle lull of the waves. Vaulted natural wood ceilings, crisp white enameled beams and travertine floors create a warm, natural palette throughout the home, complemented by granite counters, soft-close cabinetry, stainless-steel appliances and central A/C. Renovated in approximately 2004 and updated in 2018, expansive windows keep the ocean ever present throughout the home. The ocean-facing primary suite opens to a private outdoor seating area. Its spacious en-suite bath features a walk-in closet, floor-to-ceiling stone-tiled open shower, private outdoor shower and soaking tub. Outside, the grounds have been artfully nurtured over time. Mature tropical landscaping, including ginger, heliconia, plumeria and abundant foliage, creates privacy and the feeling of an established Hawaiian garden. Panoramic Pacific, West Maui Mountain, Molokai and Sunset Color views surround the property. Here, the ocean becomes part of the rhythm of the day. Look toward Tavares Bay to see what the swell is bringing, head down to the beach, or simply stay home and watch the ocean change throughout the day. A separate guest cottage, thoughtfully divided into two independent studio accommodations, adds another dimension to the property. Studio One features a wet bar and full bathroom, while Studio Two includes a full kitchen and full bathroom. The cottage creates inviting possibilities for guests or extended family while maintaining comfortable separation from the main residence. Together, the two parcels total 18,988 sq. ft., nearly half an acre adjacent to Tavares Bay. The included adjacent vacant parcel has its own water meter and expands the possibilities of the property, offering additional space to shape it around your own vision for the future. Two parcels. A private guest cottage. Nearly half an acre beside Tavares Bay. Thoughtfully established tropical grounds. And at the heart of it all, a home where the Pacific is part of how you live.

465 & 467 Hana Hwy, Paia

Listing courtesy of Maui Real Estate Advisors LLC.

$1,385,000

3 Beds ⋅ 2 Baths ⋅ 410591 MLS ⋅ Fee Simple Tenure

Aloha and welcome to 12 Nohokai St, a corner lot on the sunny side of South Maui! Multi-living options on a large lot with the potential to expand. The large lot and layout of the property exude a relaxed and spacious feel. The location of the property is well desired as it's across the street from Yee's Orchards, a block away from McDonald's, schools, shopping, dining out, a gym, Kihei Aquatic Center and oh yeah, don't forget the beach! The property has been well taken care of over the years! The main house has 3 bedroom, 2 baths with a large carport. There is a separate laundry room and a storage room off the carport. The main house was remodeled in 2024 with Formica countertops, wood cabinets, newer appliances and luxurious vinyl plank flooring. The detached cottage has 2 bedrooms with 1 bath and was remodeled in 2022. Each dwelling has their own driveways. If you're looking for a place to live and or an investment property, 12 Nohokai St is one to see! Added bonus!! This property is designated Business Community Plan. A relative of the Sellers holds an Active Hawaii Real Estate license. Buyer(s) to participate in Sellers 1031 Exchange at no cost to the Buyer(s). *Attention investors! Sellers are also selling the adjacent lot, 1164 S.Kihei Rd MLS #410589. Combined the two lots total 5 rental units on 23,714 sqft or 0.5444 acres. The property generates great rental income and is designated “Business/Commercial” on the Kihei Community Plan, opening up many possibilities for future development.

12 Nohokai St, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$1,295,000

3 Beds ⋅ 2 Baths ⋅ 410589 MLS ⋅ Fee Simple Tenure

Aloha and welcome to 1164 S.Kihei Rd on the sunny south side of Maui! Multi-living options on a large lot with the potential to expand. The large lot and layout of the property exude a relaxed and spacious feel. Great location of S.Kihei Rd, across the street from Yee's Orchards, a block away from McDonald's, shopping, dining out, schools, a gym, Kihei Aquatic Center and oh yeah, don't forget the beach! The property has been well taken care of over the years! The main house has 3 bedrooms with 2 baths, today it is utilized as 2 bedrooms with 1 bath and a 1 bedroom with 1 bath (size of a studio). The main house was remodeled in 2023 with Quartz countertops, wood cabinets, and luxurious vinyl plank flooring. The detached cottage has 2 bedrooms with 1 bath. The cottage was remodeled in 2022 with granite countertops, wood cabinets and luxurious vinyl plank flooring. The property offers lots of space for parking and each dwelling has their own covered carport. The yard is easy to maintain too! If you're looking for a place to live and or an investment property, 1164 S.Kihei Rd is one to see! Added bonus, his property is designated Business Community Plan. Licensed Hawaii Real Estate agent is part owner. Buyer(s) to participate in Sellers 1031 Exchange at no cost to the Buyer(s). *Attention investors! Sellers are also selling the adjacent lot, 12 Nohokai St. MLS # 410591. Combined the two lots total 5 rental units on 23,714 sqft or 0.5444 acres. The property generates great rental income and is designated “Business/Commercial” on the Kihei Community Plan, opening up many possibilities for future development.

1164 S Kihei Rd, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$2,100,000

5 Beds ⋅ 3 Baths ⋅ 410578 MLS ⋅ Fee Simple Tenure

Discover a rare property offering flexibility, privacy, and strong income potential. Situated on approximately 2 acres of agriculturally zoned land in Haiku, this unique estate features multiple dwellings—ideal for multi-generational living or rental use. Conveniently located just a short drive to Haiku Town, Makawao, the North Shore, and world-renowned surf at Ho‘okipa and Paia. The main residence offers 5 bedrooms, 3 bathrooms, and a 1-car garage with its own private yard. A second home includes 4 bedrooms, 3 bathrooms, and a 1-car garage, thoughtfully positioned to provide separation and privacy, with multiple private entrances for flexible use. At the rear of the property is an original plantation-style home with 4 bedrooms and 1 bathroom, along with an additional structure featuring expansive floor-to-ceiling glass panels—ideal for an office, studio, or creative workspace with mountain views. The grounds feature a variety of tropical fruit trees, including mango, mountain apple, loquat, lychee, and avocado, along with bamboo, palms, and flowering plants such as ginger and gardenia. There is ample space for farming, gardening, or future improvements. Additional features include two water meters, one cesspool, and one septic system. A versatile property with multiple use options. Contact your Realtor today to schedule a private showing

2615 Kaupakalua Rd, Haiku

Listing courtesy of Royal Realty LLC.

Maui Homes with Detached Ohana Cottage

Newest Maui Homes with Detached Ohana Cottage