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$29,900,000
5 Beds ⋅ 6 Baths ⋅ 407766 MLS ⋅ Fee Simple Tenure
Perched on one of Makena’s most coveted cliffside locations, this contemporary direct-oceanfront estate is perfectly situated along an intimate cove, offering breathtaking, unobstructed Pacific views from nearly every room. Set on over 22,190 sq. ft. of land, this two-story, five-bedroom, five-and-a-half–bath residence is a masterpiece of luxury and Hawaii’s signature indoor–outdoor living. Designed by world-renowned architect Guy Dreier, the home is a livable work of art, featuring soaring ceilings, dramatic architectural lines, and an innovative floor plan. Step through the entryway into an entertainer’s paradise. The expansive great room flows effortlessly through large pocket doors to the oceanfront deck, where a stunning infinity-edge pool appears to spill into the sea—ideal for sunset gatherings or peaceful mornings with coffee in hand. Multiple living and dining areas, along with a dedicated service area, create an unparalleled setting for both intimate dinners and large-scale celebrations. The exquisite primary suite and three guest suites each offer private ocean-view lanais, providing serene retreats with panoramic vistas. A beautifully appointed attached Ohana unit adds exceptional flexibility for guests, extended family, or a caretaker. Move-in ready and designed for effortless hospitality, this is more than a home—it’s a true Makena masterpiece blending modern coastal luxury with the timeless beauty of Maui’s south shore.

5050 Makena Rd, Kihei

Listing courtesy of Discovery Makena Realty LLC.

$1,285,000
5 Beds ⋅ 3 Baths ⋅ 410279 MLS ⋅ Fee Simple Tenure
Located in Ka Ono Ulu Estates, one of North Kihei's most desirable residential neighborhoods, this versatile single-level home is conveniently located just a short stroll to the beach. Offering a flexible floor plan with 5 bedrooms, 3 bathrooms and a loft, the home can be enjoyed as one spacious residence or configured into two connected living areas with an interior door. Each side features its own private entrance, central A/C system, and dedicated laundry area, making it ideal for multigenerational living, extended family, or added privacy. This home features durable stucco construction, soaring vaulted ceilings, a remodeled kitchen and bathrooms, a propane stove, and a large Daikin wall-mounted A/C unit in the main living room for added comfort. A beautiful custom gate designed by Padilla Designs enhances both privacy and curb appeal, while the oversized concrete driveway provides parking for up to 8 vehicles. Additional highlights include a garage bar, two large storage sheds, an irrigation system, a low-maintenance yard, and mature banana, orange, and avocado trees. Ideally located near beaches, shopping, dining, schools, and parks, this exceptional property offers the perfect blend of comfort, flexibility, and island living. Listor is Seller.

148 E Alulike St, Kihei

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

$3,600,000
5 Beds ⋅ 4 Baths ⋅ 410070 MLS ⋅ Fee Simple Tenure
NOW AVAILABLE AS A UNIQUE OPPORTUNITY: Three beautifully positioned CPR units with more than 26,300 sq ft of combined land—offering generous space, flexible options, and lasting value for years to come. Experience breathtaking panoramic ocean views from this stunning Unit B of a 3 unit CPR, newly remodeled 2-story home offering 3,064 sq ft of modern coastal living. The open floor plan, with soaring vaulted ceilings, creates a bright, spacious ambiance that's ideal for relaxing or entertaining, connecting the kitchen to the dining and living areas, which flow seamlessly to the private wrap-around lanai. With 5 bedrooms and 4 bathrooms, there's ample space for guests and a home office. The flexible layout includes the possibility of a split unit downstairs, which could be accessible via an interior staircase or a separate outside entrance, perfect for multi-generational living, guest quarters, or long-term rental potential. Included, we are offering Unit A (TMK 2-2-1-018-085-0001) and Unit C (TMK 2-2-1-018-085-0003) for added value. Unit A an allocation for a 720 sq ft cottage on approximately 11,369 sq ft of land. The current zoning for unit C (6,000+ sq ft) allows an 840 sq ft ADU on the back side of the main house, offering a great opportunity to add value to this beautiful property (see attached preliminary site plans). Don't miss your chance to own this exceptional property that combines luxury, versatility, and spectacular views! This beautiful home is perched at the top of the prestigious Maui Meadows neighborhood, just minutes from the beach, world-class restaurants, golf courses, and everything that South Maui has to offer. This is a Residential CPR.

3435 Hookipa Pl Unit A - B - C, Kihei

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

$1,495,000
5 Beds ⋅ 4 Baths ⋅ 410056 MLS ⋅ Fee Simple Tenure
Located in the desirable Keonekai neighborhood of South Kihei, this beautifully maintained multi-unit property has a very flexible floor plan to host a large family and/or create a comfortable rental revenue stream. The upstairs level is a 3-bedroom/2-bath home with soaring vaulted open beam/wood ceilings, fresh paint, abundant natural light, beautiful woodwork, the space feels open, airy, and welcoming. The front lanai opens through large sliding glass doors, extending the living area and creating a seamless indoor-outdoor experience with an additional 264 sq ft of living space. Tile flooring throughout adds to the spacious feel and ease of maintenance with washer/dryer upstairs. Enjoy cooking in a chef’s kitchen complete with custom cabinetry with newer stainless steel appliances. Multiple wall-mounted A/C units throughout the home keep the space cool and comfortable year-round. The expansive primary suite features a private ensuite bathroom with dual sinks and its own lanai—perfect for morning coffee or evening relaxation. On the ground level, there is a one-bedroom unit and an additional space with multiple possible uses. A large storage area lies between the two downstairs spaces and a bonus 2 car garage. Each of the two downstairs spaces have separate entrances. Washer/Dryer room established for downstairs. One water meter for the entire property. Separate electric meters for the upstairs and the downstairs. This is a great income producing property or live in one and offset your mortgage payment with the rental income. Property has a large peaceful back yard with fruit trees. Located very close to the South Maui boat ramp, shopping and dining opportunities in Kihei, and is only a few minutes away from accessing the world class beach resorts found in Wailea and Makena.

2735 Panepoo St, Kihei

Listing courtesy of PKR Realty.

$6,950,000
5 Beds ⋅ 6 Baths ⋅ 409921 MLS ⋅ Fee Simple Tenure
Sunlight and ocean breezes flow through 21 feet of bi-folding floor-to-ceiling glass doors, complemented by soaring 14-foot ceilings that blur the boundaries between home and horizon. Step into this South Maui beachfront estate, where elegant stone columns welcome you to a true masterpiece. The open-concept spaces unfold effortlessly, anchored by a chef's kitchen featuring custom white oak cabinetry with an interior finish that adds warmth and depth, quartzite countertops, tumbled Belgian limestone tile accents, hand-scraped French oak flooring, professional-grade appliances, and a generous breakfast bar— the perfect hub for shared meals, laughter, and connection. A floating staircase leads upstairs to the bedrooms, where the primary suite awaits as a serene sanctuary for the soul. It includes a spa-inspired soaking tub, dual vanities, a spacious walk-in closet, and a private ocean-view lanai ideal for morning reflections. Each additional guest suite has been thoughtfully designed to soothe the senses, with layouts and features that prioritize comfort, including ensuite bathrooms for ultimate privacy. Outside, your personal coastal retreat beckons. Lounge poolside in the saltwater pool, host gatherings under a canopy of stars, or savor a cocktail as the sky blazes with sunset hues. A detached guesthouse with a full bathroom and a two-car garage offer flexible additional space, while integrated smart home technology blends modern convenience into this tranquil, soul-nourishing haven. The adjacent lot is also for sale by the same seller. (MLS #409920, 892 S Kihei Rd) and can be purchased together.

860 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$4,500,000
5 Beds ⋅ 4 Baths ⋅ 409863 MLS ⋅ Fee Simple Tenure
E Komo Mai to Your Own Private Paradise Above Wailea As you pass through the gates at 3264 Keha Drive, a lush tropical landscape unfolds before you. Spread across nearly three-quarters of an acre in the heart of Maui Meadows, this private sanctuary welcomes you home. Every detail of this incredible multi-family estate has been designed to embrace the beauty and peacefulness of island living, while delivering the comforts and amenities of a private luxury retreat. Cascading waterfalls and a tranquil koi pond greet you upon arrival, and from the very first moment, the stage is set for an immersive Maui experience. Perched high above Wailea on the sun-warmed slopes of Haleakala, this estate commands a 180-degree panoramic view that stops you in your tracks every single time. The Pacific stretches endlessly before you, with Kaho'olawe rising from the sea to the left and Lana'i to the right, two islands framing a horizon that transforms at golden hour into something that simply cannot be described, only witnessed. This is the view that Maui is famous for, and it belongs to this home. Life here is lived looking outward from every vantage point the estate offers. Mornings begin slowly, coffee in hand, the ocean laid out below you. Evenings end with the sun dropping toward the horizon as the sky ignites in brilliant color, the trade winds moving through, each sunset an original. You will never see the same one twice. The estate is rare in both scale and versatility, offering significant square footage and a multi-structure configuration that opens up genuine possibilities. The main residence, complete with two living rooms and generous proportions, is complemented by an attached private guest suite, a separate two-bedroom rental, and an additional private guest suite. For a multi-generational family, it is the perfect gathering place. For the investor, it is an income-producing property with the rental infrastructure already in place. Outside, resort-caliber living awaits. A sparkling pool anchors the outdoor space, with a sauna, steam room, full outdoor bar, and poolside television all within reach, thoughtfully designed for quiet mornings and unforgettable gatherings alike. These spaces don't just complement the Maui lifestyle; they embody it. Over 72 solar panels paired with integrated smart home technology run quietly in the background, dramatically reducing energy costs and delivering the kind of efficiency a property of this caliber deserves. A fully electric Nissan Leaf and dedicated charging station are included, making the transition to island living as seamless as it should be. This estate is offered fully furnished and completely turnkey, perfectly suited for the island family ready to settle into something exceptional, the buyer watching another winter roll in somewhere far from here, or the investor seeking a property that works as beautifully as it looks. Bring your suitcase. Everything else is already waiting. Opportunities like this are rare. The elevation, the views, the scale, the versatility, all within one of Maui's most coveted neighborhoods. This kind of property doesn't come around often, and when it does, it doesn't last. Resort Living. Island Privacy. Endless Possibilities.

3264 Keha Dr, Kihei

Listing courtesy of eXp Realty.

$12,400,000
5 Beds ⋅ 6 Baths ⋅ 409793 MLS ⋅ Fee Simple Tenure
In 2015, a family from Idaho built this home for one purpose: to bring everyone together on the ocean in Maui. A place where children and grandchildren could land, spread out, and stay awhile. A decade later, it is offered for the first time. Fee simple, sandy beachfront on the quiet end of Halama Street, built by Smith Builders Maui with materials chosen to outlast the people who chose them. Inside, the craftsmanship is deliberate and quiet. Douglas fir wainscoting, artisan wallpaper, Rocky Mountain hardware. Five ensuite bedrooms, so everyone has their own space and no one is underfoot. The primary suite claims the entire upper level: dual closets, a dedicated office, its own laundry, and an oversized covered lanai exclusive to the upper floor. Ocean views to the front, mountain and garden views beyond. Whoever owns this home can host the whole family and still have somewhere to breathe. The kitchen, dining, and living spaces open directly to the coast. Pool, lawn, palms, then sandy beach, then ocean. The Pacific is not a backdrop here. It is the reason for all of it. The 3-car garage includes an upstairs ohana, ready for an onsite caretaker or extended family overflow. Monier tile roof, Hardie siding, copper gutters: a home that locks, leaves, and waits without complaint. Quiet enough to feel removed. Close enough to Kihei’s dining and conveniences that proximity is never a question. This is what multigenerational ownership looks like on Maui.

1536 Halama St, Kihei

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

$1,200,000
5 Beds ⋅ 3 Baths ⋅ 409688 MLS ⋅ Fee Simple Tenure
Situated in a desirable North Kihei neighborhood, 295 Kaihoi St offers the space, comfort, and convenience today’s families are looking for. This well-appointed 5-bedroom, 3-bath home features a spacious layout with multiple living areas, providing flexibility for everyday living, entertaining, or working from home. Large windows bring in abundant natural light, creating a warm and inviting atmosphere throughout the home. Step outside to enjoy the fully fenced yard, perfect for children, pets, backyard gatherings, or relaxing in your own private outdoor space. The home is also equipped with leased solar panels, helping to enhance energy efficiency and support Maui’s indoor-outdoor lifestyle. Ideally located in North Kihei, this property offers convenient access to all parts of the island, with nearby beaches, parks, schools, shopping, dining, and an easy commute to Central Maui, Wailea, and Lahaina. Combining comfort, functionality, and an excellent location, this home is a wonderful opportunity to enjoy the best of island living.

295 Kaihoi St, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$1,290,000
5 Beds ⋅ 4 Baths ⋅ 409681 MLS ⋅ Fee Simple Tenure
5 bedroom / 4 bath with 2693 sf living area, R-2 Zoned Single Family | Convenient North Kihei Location | Flexibility & Portfolio Opportunity — Rare opportunity to acquire an expansive property on a 7,885 sf R-2 lot with panoramic ocean views from the observation deck! The home features three individual living spaces with a versatile layout that naturally lends itself to extended family living, house-hacking, or a variety of owner-user/income hybrid strategies. R-2 zoning provides a meaningful long-term optionality layer, consistent with future redevelopment or lot utilization strategies as the market evolves. Located in a supply-constrained coastal submarket with limited new residential development, 255 Kaiolohia St delivers a highly desirable North Kihei address, strong tenant appeal, and the adaptability to serve multiple housing strategies over time. A scarce chance to secure a flexible, well-located R-2 asset with easy highway access to all major town centers and world famous beaches.

255 Kaiolohia St, Kihei

Listing courtesy of Kokua Realty LLC.

$8,740,000
5 Beds ⋅ 6 Baths ⋅ 409447 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
Wailea Point Residence 802 & 804 is an exquisite, rare, double residence featuring 5 bedrooms and 6 full bathrooms. Enjoy unobstructed panoramic ocean and sunset views from four ocean-view lanais or from inside the expansive great room, enhanced by the upgraded, dual-mitered glass bay “aquarium” windows that dramatically enhance the vistas and whale watching (in season). This turnkey purchase—fully furnished, legacy property, created by thoughtfully combining two elegant units—lives like a luxurious single-family home, while retaining lock-and-leave condominium convenience. It includes elegant designer furniture, all kitchen appliances (including 2 frigs, 2 dishwashers, 3 wine frigs), china, linens and more. The residence offers soaring ceilings, 4-zone central air conditioning, a terrific owner’s home office/den, privately located adjacent to the primary bedroom with ocean views, and a separate and large double garage, with built-in storage and two of the wine frigs. Seamless indoor-outdoor living is complemented by the four spacious lanais that open directly onto lush, manicured gardens and the oceanfront setting. Meticulously maintained, this home represents exceptional value as the best price per square foot in Wailea Point (less than $1,780 per gross interior sq ft) and a unique opportunity to own or create your own personal, multi-generational retreat in one of Maui’s most distinguished condominium communities—a must-see. Wailea Point was designed to be Hawaii’s premier residential condominium. The development offers very low density (just over 4 units per acre), high-quality construction, and a serene garden environment. Residents enjoy 24-hour gated and roving security, two pool pavilions with 4 pools (including a 25-meter lap pool), 2 whirlpool spas, fully equipped kitchens, a lighted tennis court, 2 pickleball courts (1 lighted), a fully air-conditioned fitness gym, barbecue areas, fruit and herb gardens, ample parking, and a golf-cart friendly domain. Located next to the Four Seasons and Fairmont Kea Lani Hotels; and within 100 yards of the famous and long Wailea Beach shorefront walkway; great for early morning or sunset walks. There are two magnificent, ocean beaches adjacent to Wailea Point. Shopping, fine restaurants, outstanding golf courses and graceful streets all surround the acclaimed development. In a 7/15/26 ruling, the Appeals Court changed the minimum rental period at Wailea Point BACK to 30 days. An Association Board of Directors Bulletin dated 7/22/26 states, “Consistent with the appellate court's decision, the minimum rental period is being administered as 30 consecutive days."

4000 Wailea Alanui Dr Unit 802 & 804, Kihei

Listing courtesy of Wailea Point Realty, Inc..

$1,199,000
5 Beds ⋅ 3 Baths ⋅ 409208 MLS ⋅ Fee Simple Tenure
Well-maintained North Kihei home offering flexible living just moments from the beach. Unit A of the Waiakoa Makai CPR includes approximately 1,726 sq ft of living area on a ~7,500 sq ft limited common element, with comfortable indoor spaces and a usable yard. The upper level is configured as a 3-bedroom, 2-bath layout with bright living areas and an updated kitchen. The lower level includes 2 additional bedrooms, bathroom, and separate entry, creating a great opportunity for extended living, multi-generational use, or added flexibility. Set among mature trees, the property feels tucked away with a sense of privacy while still being close to everything. Currently tenant-occupied; buyer to cooperate with existing lease in place. Conveniently located near Mai Poina Beach Park, with easy access to shopping, dining, and central Maui amenities. Photos are from prior to tenant occupancy; updated photos to be added. Contact your Realtor today to schedule a private showing.

442 Kenolio Rd Unit A, Kihei

Listing courtesy of West Maui Land Company Inc.

$1,649,000
5 Beds ⋅ 4 Baths ⋅ 408728 MLS ⋅ Fee Simple Tenure
Experience the essence of Maui coastal living and investment potential all in one. Located directly across from the beach on S. Kihei Road, this versatile property offers four separately rentable units for maximum income and flexibility. The main home is thoughtfully configured into three distinct living spaces—an upstairs 3-bedroom / 1.5-bath, and two separate 1-bedroom / 1-bath units downstairs. A detached 2-bedroom / 1-bath cottage provides additional income or ohana living options. Each dwelling enjoys its own yard space, beautifully landscaped with tropical flowers and fruit trees, and fully fenced for privacy. The main house includes a shared coin-operated laundry, while the cottage enjoys its own private laundry. With ample parking, no HOA or maintenance fees, and shared ownership of the access drive lot included in the sale, this property represents one of the best ROI opportunities in Kihei. Perfect for multi-generational living or as a fully occupied investment, this property is just minutes from Kihei’s charming town center, boutique shops, parks, and world-class ocean activities. Discover the rare combination of lifestyle, location, and long-term value—right here in the heart of South Maui. Photos have been virtually staged.

1011 S Kihei Rd Unit B, Kihei

Listing courtesy of Compass-W.

$24,500,000
5 Beds ⋅ 6 Baths ⋅ 408059 MLS ⋅ Fee Simple Tenure
Experience the pinnacle of oceanfront luxury in this stunning, 5 bedroom, 5 bath, plus 2 half bath, 7,244 sq. ft. home estate. This over a half-acre property is located within the ideal stretch of Keawakapu Beach, offering unparalleled access to Maui’s most coveted shoreline. This architectural triumph blends contemporary elegance and convenience with the island’s natural beauty, creating a private sanctuary of sophistication and rare serenity. This estate features 5 spacious en-suite bedrooms, multiple areas for relaxed socializing, and a seamless indoor-outdoor flow that embraces the home’s stunning pool courtyard and oceanfront experience. Every room gifts an extraordinary vantage point of paradise – between sweeping ocean views in three master suites or tranquil poolside perspectives from the guest suites. At the heart of the home, the expansive pool and courtyard form a striking focal point, linking the media room, main entry, and living areas in perfect harmony. A private poolside retreat ensures both security and discretion, ideal for intimate gatherings or large-scale entertaining. Landscaped gardens with numerous palm trees and second-level sundecks off the guest suites provide elevated spaces to soak in a front seat view of unforgettable sunsets. A spacious oceanfront lawn offers ultra-privacy, featuring a fire pit that creates an inviting ambiance, shielded from public view and accessible only through a discreet, gated beach entrance. Whether you seek a primary residence, a lavish vacation home, or an island retreat, this estate is designed for those who desire premium beachfront living with an ultimate feel of privacy. A rare opportunity to own the most memorable oceanfront lifestyle in Maui.

3254 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$6,999,000
5 Beds ⋅ 4 Baths ⋅ 408014 MLS ⋅ Fee Simple Tenure
A rare South Maui estate — 2.118 acres in the exclusive gated community of Kaimanu Estates. This private retreat feels like living in Hana and Old Hawai‘i, surrounded by hundreds of native and fruiting trees including avocado, citrus, banana, lilikoi, guava and many more. With 4,718 sq. ft. in the main residence and a detached studio ohana, the property offers unmatched privacy and opportunity rarely found in South Maui. Just minutes away are Wailea’s world-class golf courses, resorts, fine dining, boutique shopping, and some of the best beaches in the world. Here you’ll find the perfect balance of tropical seclusion and resort-side convenience.

135 Kaimanu Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$2,100,000
5 Beds ⋅ 4 Baths ⋅ 407071 MLS ⋅ Fee Simple Tenure
ORIGINAL OWNERS | FIRST TIME EVER ON THE MARKET | IMPECCABLE CONDITION! Welcome to THE MOANA ESTATES GEM . . . the largest 10,382 sf homesite gated and walled offering exceptional pride of ownership and is definitely move in ready. What is A Gem?...by definition, it refers to something valuable or unique;The property represents the crown jewel of the neighborhood. You will discover a meticulously maintained home that has been thoughtfully upgraded inside and out, reflecting true pride of ownership. Energy efficiency meets peace of mind with a 42-panel owned net metered PV solar system paired with a 100% Cummins backup generator powerful enough to run the entire home, including 2 zone A/C with UV lighting and the additional split garage A/C. The exterior shines with the new 40-year roof, fresh paint, seamless rain gutters, black powder-coated fencing with gates and an oversized stamped and resealed driveway. Quartzite-tiled lanais and walkways, professionally designed landscape lighting, and mature tropical landscaping complete the outdoor oasis. Inside, the residence has been fully refreshed with new interior paint and carpet in 2025. The newly polished Corian counter tops and custom closets by Maui Closet Systems bring modern comfort throughout. The kitchen features Bosch appliances, two refrigerators, a reverse osmosis water system with hot & cold dispenser and upgraded faucets & shower heads. Two complete laundry sets, an owned security system, surround sound wiring, and the four included wall mounted televisions enhance everyday convenience. Every detail of this home has been carefully maintained or newly improved, creating a residence that combines efficiency, beauty, and function. For those seeking a special property with enduring quality, this Moana Estates GEM is for you. Come preview a special property!

96 Moana Ave, Kihei

Listing courtesy of Compass-W.

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.