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$2,600,000
4 Beds ⋅ 4 Baths ⋅ 410606 MLS ⋅ Fee Simple Tenure
PERCHED HIGH ON THIS ELEVATED LOT. It is rare that a house in Wailea has an asking price less than the county assessed value with remarkably low real property taxes of only $3,975.84 for 2026. There is no better value in Wailea Resort at $890.10 PSF for 2,921 SF. This house has been vacant for nearly three years so allow for mechanical things not working due to non use. All the appliances need to be serviced and may not need replacing. The 13,491 SF lot is one of the largest in this section of Kialoa. Stucco exterior and Monier tile roof. Large pool/Spa. Water in pool and the patio furniture is Ai generated. Pool equipment may just need the pumps and motors primed and lubricated, maintenance and service. The pool plaster may just need a high quality two-part epoxy Pool-paint. Eight(8) large rooms. Commercial chef grade kitchen all granite clad with Viking appliances, double gas burning stoves/ovens. trash compactor, food warmer, Bosch dishwasher. Real Travertine floors on the entire main level and staircase. The living room travertine was under a large Persian rug and never saw the light of day and is literally brand new so when you look at the rest of the flooring CSI will make it look brand new too. Two bedrooms on the main level are being used as storage. Two fully remodeled bathrooms also on main level. Spacious and bright living room, dining room and large kitchen with huge center island with service sink and butler's prep kitchen. One of the downstairs bedrooms serves as an office with French doors and has a full bathroom and closets. It is being used for storage The architecture is classic and bold. The lush foliage makes this residence very private. Upstairs has a huge family room with real hard wood maple floors, wet bar and spectacular ocean views from the balcony from the west Maui mountains, Lanai, Kaho'olawe, Molokini, all the way to Ulupalakua. There is a huge wall perfect for a 100" flat screen tv. There are two full bathrooms upstairs. Art deco ceilings. The owner did a major renovation in 2005 to the kitchen, three of the four bathrooms and added the Travertine floors. The primary bedroom is en suite with a large walk in Travertine shower. Back-to-back closets. The irrigation system and electrical recently upgraded. The avocado tree bears fruit. The garage has 830 SF with storage rooms and is packed solid with restaurant equipment and misc stuff. This is truly an indoor/outdoor house with three ingress/egress from the L.R, D.R and kitchen out to the pool deck and pool/spa. Solar hot water tank is around 3-4 years old. The trellis can easily be converted to a porte-co-chere. For all intents and purposes this house is move in condition. The carpeting in the two upstairs bedrooms needs to be replaced. All the storage contents in the three bedrooms, garage and outside will be removed prior to closing. House is being sold unfurnished AS IS. Seller requires Proof of Funds or bank approval letter prior to showings. RECENT HOUSES SOLD IN WAILEA KIALOA WITH SIMILAR SIZE 195 E. Ikea Kai next door with 2,851 SF SOLD for $4,000,000, 12/20.2024. 171 W. Ikea Kai with 3,117 SF SOLD for $3,725,000, 10/27/2023. 175 W. Ikea Moku with 3,105 SF SOLD for $3,550,000, 12/24.2025. 206 Heleuma Place with 3,169 SF SOLD for $3,300,000 , 01/07/2026. 194 E. Panana Place with 3,024 SF SOLD for $3,240,000. 11/28/2025. 194 E. Panana Place with 3,024 SF SOLD for $2,400,000. 11/14/2023. 3133 Kikihi St with 1,955 SF SOLD for $2,565,000 03/11/2026. The Central Pacific Bank Nov. 2024 appraisal for 221 E. Ike indicates 3,190 SF interior. "The handwriting is on the wall" for 221 E. Ikea Kai. "Don't hesitate!" The closest comparable houses in Wailea with 2,788 SF in Wailea Kai with no view and on the road asking $2,499,000. The only comps in Wailea Kialoa have 2,582 SF no views asking $2,848,000 and 162 W. Ikea Kai with 2,843 SF asking $3,150,000. 221 E. Ikea Kai is the deal of the decade.

221 E Ikea Kai Pl, Kihei

Listing courtesy of eXp Realty.

$3,850,000
3 Beds ⋅ 4 Baths ⋅ 410561 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
Discover elevated luxury at Villa T-1, the best priced property and sole end-unit available today at Ho’olei. Boasting the community’s largest floor plan—the sought-after Hibiscus layout—this spacious split-level townhome blends 3,076 sq.ft. of exquisitely refreshed interior space with approximately 700 sq.ft. of covered lanai for seamless indoor-outdoor living. Positioned in a coveted front-row location, you are steps away from Ho’olei’s world-class amenities, featuring a lagoon-style pool with a dramatic 19’ waterfall, swim-in grotto, dual spas, fitness facility, and poolside entertaining pavilion. Just moments from Wailea Beach, fine dining, championship golf, and shopping, this beautifully furnished residence offers exceptional privacy, a place to call home in Maui, alongside a stellar, proven rental track record.

24 Hoolei Cir Unit T-1, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$20,500,000
3 Beds ⋅ 4 Baths ⋅ 410482 MLS ⋅ Fee Simple Tenure
Welcome to the quintessential Maui oceanfront estate, ideally situated on Keawakapu Beach—widely regarded as one of Maui’s most beautiful stretches of sand. This timeless Hawaiian residence embraces its unrivaled setting with approximately 2,500 square feet of covered outdoor living space, perfectly suited for beachfront lounging and entertaining. Designed with architectural integrity and island sensibility, the home features traditional Dickey rooflines topped with black glazed tiles imported from Japan. A electronic gate opens into a private, walled compound that includes the main residence, a detached two-bedroom guest cottage (Ohana), a two-car garage with workshop, and a beautifully landscaped courtyard with a pool and spa. The single level main home offers soaring 16 foot ceilings in the great room with a working fireplace serving as the centerpiece, complemented by an open-concept kitchen and expansive glass walls that frame breathtaking ocean views while preserving privacy. The main residence includes three bedrooms and four bathrooms, all designed with ease of access and comfort in mind. The detached two-bedroom, one-bath Ohana is finished to the same high standard, ideal for visiting family or guests. Set on 0.8 acres, the estate flows seamlessly from lush lawn to the beach, where a protective lava rock point cradles the property and collects soft white sand along this dramatic, crescent-shaped shoreline—one of the largest and most coveted on the island. A rare opportunity to own a true legacy property on Maui’s finest beachfront. **Disclosure** Some pictures have been Virtually Re-Staged and noted.

3146 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$7,800,000
3 Beds ⋅ 4 Baths ⋅ 410468 MLS ⋅ Fee Simple Tenure
Brand New Construction | Luxurious Estate Living at The Ridge, Wailea Welcome to a sprawling, brand-new estate at The Ridge in Wailea, where every detail has been curated for elevated island living. Terraced landscaping and hand-set rock walls guide you toward the hilltop entrance, offering a dramatic first glimpse of the infinity pool as you arrive. Step through the substantial solid walnut wood pivot door, flanked by bilateral side windows that flood the entry with natural light. Inside, the open-concept kitchen, dining, and living areas flow seamlessly past disappearing Fleetwood doors to a spacious lanai anchored by an infinity pool and spa. Beyond, sweeping views stretch across West Maui, Lanai, Kahoolawe, and Molokini. The lanai wraps to the south into an entertainer's dream — a full bar and BBQ area complete with a hidden large-screen TV — while a pool bath with full sauna delivers a true resort-at-home experience. The chef's kitchen is outfitted with a premium Thermador appliance suite, shaker and flat-front cabinetry, and granite countertops, plus a built-in white wine cooler and a sleek, temperature-controlled red wine storage room. Rounding out the first floor: a two-car garage, a large laundry room, a modern half bath, and a primary suite with direct lanai access, smart shower, smart toilet, double vanity, and a private outdoor soaking tub. Ascend the dramatic floating staircase, set off by a sleek modern chandelier and stone accent walls, to discover a hidden office and an open den with lanai access leading to an outdoor gathering area centered on an elegant fire pit — all framed by more sweeping ocean views. Two additional bedrooms complete the second floor: a guest suite with ensuite bath and lanai access, and a second primary suite featuring lanai access, a walk-in closet, an oversized smart shower, and a top-filling soaking tub. Home is offered fully furnished and situated on the highest elevated lot in Wailea. Quality and luxury abound — your perfect Wailea oasis awaits.

22 Halapa Pl, Kihei

Listing courtesy of Hawaii Life (W).

$9,195,000
4 Beds ⋅ 4 Baths ⋅ 410457 MLS ⋅ Fee Simple Tenure
Discover exceptional beachfront living at 1614 Halama Street. This stunning oceanfront residence offers unobstructed Pacific views, breathtaking sunsets, and direct access to the shoreline from your own backyard. Designed to embrace Maui's natural beauty, the open layout features abundant natural light, and seamless indoor-outdoor living. Enjoy unforgettable evenings from the expansive lanai or oceanfront infinity pool, with panoramic views, neighboring island vistas, and seasonal humpback whale sightings. A spacious primary suite, generous guest accommodations, and lush tropical landscaping create the perfect private retreat. A rare opportunity to own a premier beachfront property on one of South Maui's most coveted streets.

1614 Halama St, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$4,795,000
3 Beds ⋅ 4 Baths ⋅ 410334 MLS ⋅ Fee Simple Tenure ⋅ Papali Wailea BLDG.
Where do timeless design, ultimate privacy, and panoramic ocean vistas all converge in Wailea? Welcome to Papali #17. Perfectly positioned in the community’s premier location, this exquisite residence is being offered for the first time since the original developer release. This single-level three bedroom and three-and-a-half baths provides the comfort and presence of a private home with the carefree and secure lock and leave benefits of a luxury condominium lifestyle. Sweeping ocean and outer-island views are complemented by Papali’s award winning design, contemporary architecture, and distinctive copper rooflines. Set on over ten acres of beautifully maintained tropical landscaping, Papali offers an exclusive sense of serenity with only two homes per acre providing privacy, tranquility, and a spacious sense of place just moments from Wailea’s pristine beaches, golf, dining, and shopping. Inside highlights include soaring vaulted ceilings with Alaskan Yellow Cedar beams, rich African mahogany millwork, limestone flooring, and a gourmet kitchen with premium granite surfaces. Flooded with natural light, expansive glass doors, and open generous lanai spaces for seamless indoor-outdoor living. Perfect for sunset gatherings and relaxed island evenings under the stars. A private garage, abundant storage, and dual entry points complete this rare and remarkable offering - furnished for your turn-key Maui lifestyle. Papali #17 isn’t just a home – it’s a legacy. Wailea’s most extraordinary offering.

3100 Wailea Alanui Dr Unit 17, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$13,900,000
4 Beds ⋅ 4 Baths ⋅ 410182 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
Level One oceanfront at Wailea Point — Hawaii's finest residential condominium, nestled between Wailea Beach and Polo Beach on Maui's coveted Gold Coast. 3,820 SF · 4 bed · 4 bath · 180-degree unobstructed Pacific and island views · 46 feet above the shore. One bedroom functions as a den. From the moment the door opens, the reaction is immediate — an arrival that announces itself before a single detail is pointed out. The residence showcases nine-foot clear grade Cedar ceilings, travertine marble floors, Sub-Zero, Wolf, and Thermador appliances, an African Mahogany wet bar, and Big Island Koa entry doors — all of which convey with the sale. In 2025, it was further elevated with a fully automated lighting and shade system — controlled at the touch of a button — and custom engraved electrical covers throughout. All-new furnishings, including a custom Koa coffee table set on a driftwood base, also convey. A 2025 Jeep and premium golf cart may also be available to the purchaser — full details outlined in the Disclaimer below. Set within 30 acres at under 4 units per acre — one of the lowest density communities in Hawaii. Four resort-style pools · lighted tennis and pickleball · fitness center · 24-hour gated security. Immediate neighbors include the Four Seasons Resort Maui and the Fairmont Kea Lani — world-renowned luxury hotels. Their restaurants, spas, and beaches are part of daily life here. Private appointment only · Pre-qualified buyers exclusively. DISCLAIMER Purchase of this property includes mandatory membership in the Wailea Community Association (WCA), which is separate and distinct from the property's AOAO (Association of Apartment Owners). Buyers should independently review WCA governing documents, dues, and obligations as part of their due diligence. A 2025 Jeep and premium golf cart may be available to the purchaser under a separate bill of sale. These items are personal property, are not included in the real property purchase price, and will be transferred separately from the real estate transaction. This will be outside of escrow. Wailea Point's original governing documents prohibit rentals of fewer than 30 consecutive days. An amendment effective July 1, 2026 that sought to increase the minimum lease term to more than 365 days was held invalid. Buyers should independently review the current declaration, bylaws, house rules, AOAO notices, applicable governmental requirements, and any subsequent legal developments. No representation or guarantee is made regarding rental eligibility, rental income, or future rental restrictions.

4000 Wailea Alanui Dr Unit 101, Kihei

Listing courtesy of Engel & Volkers Maui.

$3,200,000
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).

$2,100,000
4 Beds ⋅ 4 Baths ⋅ 410011 MLS ⋅ Fee Simple Tenure
Welcome to one of the most desirable homes in Moana Estates, featuring the largest single-level floor plan in the neighborhood. This meticulously maintained 4-bedroom, 3.5-bath residence offers exceptional comfort, thoughtful upgrades, and timeless island-inspired style. Beautifully furnished and professionally designed, the home exudes a relaxed beach cottage ambiance with inviting, light-filled living spaces. New quartz countertops, engineered wood flooring throughout the main living areas, tile bathrooms, and custom white wood shutters create a refined yet casual coastal aesthetic. The spacious floor plan seamlessly connects indoor and outdoor living, opening to a private backyard oasis complete with a swimming pool, outdoor shower, fully fenced grounds, and a substantial rock privacy wall. Manicured landscaping and outstanding curb appeal enhance the home's welcoming presence. Additional features include a two-car garage, 24 photovoltaic panels with net metering for energy efficiency, and furnishings that make this home truly move-in ready. Every detail has been carefully maintained, creating a residence that is as functional as it is beautiful.

147 Moana Ave Unit Unit 39, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$3,785,000
4 Beds ⋅ 4 Baths ⋅ 409908 MLS ⋅ Fee Simple Tenure
Nestled within the prestigious Wailea Pualani community, 390 Pualoa Nani Place offers the essence of luxury island living with privacy, elegance, and the relaxed sophistication that defines Wailea. Surrounded by lush tropical landscaping and swaying palms, this beautifully designed residence welcomes you with a grand driveway entrance and exceptional curb appeal. Inside, the home blends comfort and functionality with spacious living areas, abundant natural light, and quality finishes throughout. The residence showcases magnificent views of the West Maui Mountains along with beautiful glimpses of the Pacific Ocean, creating a peaceful backdrop from multiple areas of the home. Recently enhanced with brand-new quartz countertops as well as upgraded flooring, the property reflects quality craftsmanship and modern island elegance. The expansive laundry and utility room provides generous storage and workspace, while the thoughtfully designed floor plan creates seamless indoor-outdoor living ideal for entertaining or peaceful everyday enjoyment. Adding to the uniqueness of this exceptional offering is a magnificent curated art collection that complements the home's sophisticated ambiance and tropical luxury setting. (Please see attached document with photos of the art pieces included in the sale.) This is also an extraordinary opportunity to own a home with exceptional energy independence and efficiency. The property is equipped with an impressive owned photovoltaic system featuring approximately 69 solar panels along with three Tesla Powerwall batteries, providing substantial renewable energy production, backup power capability, and long-term utility savings. This remarkable solar investment enhances both the value and sustainability of the property while supporting the Maui lifestyle with modern energy resilience. From the aerial perspective, the home's positioning captures privacy and tranquility with neighboring greenery and open space, creating a serene tropical environment. Located moments from world-class beaches, championship golf courses, luxury resorts, fine dining, and upscale shopping in Wailea, this exceptional residence offers the perfect blend of comfort, convenience, luxury, sustainability, and the coveted Wailea lifestyle.

390 Pualoa Nani Pl, Kihei

Listing courtesy of Engel & Volkers Maui.

$1,195,000
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.

$5,000,000
4 Beds ⋅ 4 Baths ⋅ 409679 MLS ⋅ Fee Simple Tenure
Welcome to the Resort in Maui Meadows — an extraordinary private estate where jaw-dropping panoramic ocean views, unforgettable sunsets, and elevated island living converge in one of South Maui’s most coveted neighborhoods. Perfectly positioned above the coastline, this exceptional residence captures sweeping vistas stretching across the Pacific Ocean to the neighboring islands, creating a breathtaking backdrop from nearly every room. By day, enjoy sparkling turquoise waters and endless horizon views; by evening, experience Maui’s legendary sunsets illuminating the sky in spectacular color. Designed to live like a private luxury resort, the property is an entertainer’s dream. Expansive indoor-outdoor living spaces flow seamlessly onto oversized lanais and gathering areas curated for unforgettable sunset dinners, cocktail parties, celebrations, and relaxed evenings beneath the stars. The open-concept design invites effortless hosting while maximizing the stunning ocean vistas and cooling island trade winds throughout the home. The chef’s kitchen anchors the residence with premium appliances, generous prep and serving areas, and elegant finishes designed for both intimate dining and large-scale entertaining. Spacious guest accommodations provide comfort and privacy for family and friends, while the primary suite offers a tranquil retreat with spa-inspired luxury and mesmerizing ocean views. Surrounded by lush tropical landscaping and an atmosphere of complete serenity, the Resort in Maui Meadows delivers a rare sense of escape while remaining just moments from Wailea’s world-class beaches, golf courses, fine dining, and luxury resorts. This is more than a home — it is a destination, a retreat, and a lifestyle defined by breathtaking beauty, privacy, and unforgettable entertaining in the heart of South Maui.

557 Kupulau Dr, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$2,848,000
3 Beds ⋅ 4 Baths ⋅ 409610 MLS ⋅ Fee Simple Tenure
A private Wailea Kialoa retreat, where chic island elegance meets effortless living. This custom single-level 3-bedroom, 3.5-bath residence offers an open and thoughtfully crafted floor plan with seamless indoor-outdoor living. The expansive great room connects to a covered lanai through retractable pocket doors, creating an ideal setting for everyday living and entertaining. The well-appointed chef’s kitchen features striking granite surfaces, paired with timeless wood finishes throughout, custom wood cabinetry, and premium appliances including Viking, Bosch, and Sub-Zero, along with a large dine-in bar and adjacent dining area. The serene primary suite includes a secluded lanai, large walk-in closet, and an en-suite bath with spa inspired dual vanities, soaking tub, and walk-in shower. Two additional guest bedrooms each offer en-suite baths and direct outdoor access, providing privacy and flexibility. Outdoor amenities include a lagoon-style pool and spa, tropical landscaped yard, and mature trees, foliage and lava rock wall for your own private sanctuary. Additional features include a spacious 2-car garage with workroom/storage area. Conveniently located near Wailea’s white sandy beaches, award winning golf courses, world class dining, and shopping.

230 E Panana Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$2,595,000
4 Beds ⋅ 4 Baths ⋅ 409490 MLS ⋅ Fee Simple Tenure
Also listed as Condo MLS# 409467. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-level residence offers the community’s most desirable floor plan. Located in an exclusive gated enclave of just 38 detached residential condominiums, this beautifully appointed 4-bedroom, 4-bath home blends luxury, privacy, and effortless island living. The 2,129 sq. ft. interior features an open-concept design filled with natural light and quality finishes like Hunter Douglas interior blinds and remote exterior blinds. The recently remodeled kitchen features top-of-the-line appliances like Wolf and Sub-Zero. Modern upgrades include the latest Wi-Fi system, a multi-zone Sonos sound system throughout, and a security system for added convenience and peace of mind. Two true primary suites offer spacious walk-in closets and large double-vanity baths, each remodeled with Toto Washlets. A third bedroom is located in the main living area with a full bath just across the hall, while the fourth bedroom and bath are privately situated off the courtyard—ideal for guests or extended family. Offered fully furnished and turn-key, the home includes a complete inventory of housewares and essentials, making it ready for immediate enjoyment or effortless second-home ownership. Lovely ocean views with dreamy sunsets from your large, private lanai, and the ease of lock-and-leave ownership make this home especially appealing. Association-maintained landscaping enhances the carefree lifestyle. Kanani Wailea amenities include a heated infinity-edge pool, spa, fitness room, and cabana with full kitchen. Just minutes from Wailea’s world-class beaches, golf, dining, and shopping, this is a rare opportunity to own in one of South Maui’s most coveted communities.

100 Poailani Pl Unit 29, Kihei

Listing courtesy of McEntire Realty.

$2,595,000
4 Beds ⋅ 4 Baths ⋅ 409467 MLS ⋅ Fee Simple Tenure ⋅ Kanani Wailea BLDG.
Also listed as Residential MLS# 409490. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-level residence offers the community’s most desirable floor plan. Located in an exclusive gated enclave of just 38 detached residential condominiums, this beautifully appointed 4-bedroom, 4-bath home blends luxury, privacy, and effortless island living. The 2,129 sq. ft. interior features an open-concept design filled with natural light and quality finishes like Hunter Douglas interior blinds and remote exterior blinds. The recently remodeled kitchen features top-of-the-line appliances like Wolf and Sub-Zero. Modern upgrades include the latest Wi-Fi system, a multi-zone Sonos sound system throughout, and a security system for added convenience and peace of mind. Two true primary suites offer spacious walk-in closets and large double-vanity baths, each remodeled with Toto Washlets. A third bedroom is located in the main living area with a full bath just across the hall, while the fourth bedroom and bath are privately situated off the courtyard—ideal for guests or extended family. Offered fully furnished and turn-key, the home includes a complete inventory of housewares and essentials, making it ready for immediate enjoyment or effortless second-home ownership. Lovely ocean views with dreamy sunsets from your large, private lanai, and the ease of lock-and-leave ownership make this home especially appealing. Association-maintained landscaping enhances the carefree lifestyle. Kanani Wailea amenities include a heated infinity-edge pool, spa, fitness room, and cabana with full kitchen. Just minutes from Wailea’s world-class beaches, golf, dining, and shopping, this is a rare opportunity to own in one of South Maui’s most coveted communities.

100 Poailani Pl Unit 29, Kihei

Listing courtesy of McEntire Realty.

$11,245,000
3 Beds ⋅ 4 Baths ⋅ 409204 MLS ⋅ Fee Simple Tenure ⋅ Andaz Residences BLDG.
Andaz Residences Unit 801 (F2) offers a rare opportunity to own one of the coveted private villas at the Andaz Maui Wailea Resort. Ownership combines the privacy of an oceanfront home with full access to the exceptional amenities of the Andaz Hotel including pools, spa, fitness center, beach service, concierge, and award-winning dining. These exclusive residences rarely come to market. This spacious 3-bedroom, 4-bathroom villa features a thoughtfully designed floor plan with en-suite baths for each bedroom. Stunning ocean and sunset views from the lanai, great room, kitchen, and primary suite. The light-filled great room showcases custom designer furnishings, floor-to-ceiling windows, and sliding glass doors that invite Maui’s signature ocean breezes. The chef’s kitchen with Miele appliances opens seamlessly to the lanai with outdoor grill and dining area, perfect for indoor-outdoor island living. A well-equipped butler’s pantry includes an additional dishwasher, ice maker, wine refrigerator, and generous storage. Each bedroom suite offers a soaking tub, separate shower, and private water closet. Additional features include a powder bath with walk-in shower, laundry room with Miele washer and dryer, lockable owner closet, electric blackout and sheer shades, Apple TV, and zoned Sonos sound. While the unit was not previously in a vacation rental program it’s eligible to participate, this furnished turnkey villa is ready for personal enjoyment and/or guest stays. Owners enjoy a dedicated poolside cabana and two garage parking spaces, Mokapu Beach and the Wailea Beach Path are just steps away. Pet-friendly complex.

3550 Wailea Alanui Dr Unit 801 (F2), Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$4,650,000
3 Beds ⋅ 4 Baths ⋅ 408839 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
E Komo Mai and welcome to Ho'olei 21-4, an elegant 3 bed, 3.5 bath townhome located in the heart of Wailea, Maui. This Hotel Zoned property boasts wonderful ocean views and is offered tastefully furnished, totally turnkey, and is active and successful in the Grand Wailea's exclusive vacation rental program. The Plumeria floor plan enjoys the widest lanai and forward most position of the building, enhancing privacy and extending the living area. This villa has new upgraded flooring in the bedrooms, a chef's kitchen with Wolf and Sub Zero appliances, a built in BBQ and fridge on the lanai, attached garage, private elevator, and so much more. Pocketing Fleetwood glass sliders blend the indoors with the outdoors, making a perfect space for entertaining your family and guests. The Ho'olei property offers a resort style pool and spas, with a state of the art workout facility and saunas. Ho'olei is gated with 24hr security and lush landscaping that gives you a sense of place here in Hawai'i. Owners are eligible for the Kulana Club with the Grand Wailea, allowing them rental management, shuttle service, on-site front desk and concierge, as well as a myriad of discounts and perks. The Wailea Resort offers some of the finest dining, shopping, golf, tennis, beaches, sunny days and views in the world!

21 Kiloa St Unit O-4, Kihei

Listing courtesy of Hawaii Life (W).

$1,599,000
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.

$4,795,000
3 Beds ⋅ 4 Baths ⋅ 408559 MLS ⋅ Fee Simple Tenure
3943 Wailea Ekolu is one of Wailea Golf Estates' most distinctive ocean-view Residences, offering Panoramic Ocean, Outer-Island & Mountain Views, Estate-Scale Living, Timeless Architectural Character, and a Premier Golf-Frontage Setting. Encompassing approximately 4,355 square feet, this expansive residence features 3 bedrooms, an office/den, 4 full bathrooms, a spacious great room, and an additional living room that opens seamlessly to the pool and outdoor entertaining area. Designed with enduring craftsmanship, generous proportions, and a grand sense of arrival, the home showcases architectural details rarely found in today's newer luxury residences. From the moment you enter, arched mahogany-and-glass entry doors accented with African Wenge welcome you into a dramatic curved vestibule, where rounded plaster walls, rich mahogany millwork, and a grand staircase immediately reveal the craftsmanship and architectural character that define this remarkable home. Two en-suite bedrooms located on the ground floor each enjoys its own outdoor space—ideal should you want to have SINGLE FLOOR-PLAN LIVING. Upstairs, a PRIVATE SANCTUARY awaits: the approx. 1,581 sq. ft. primary bedroom suite and den offer exceptional PRIVACY and unparalleled OCEAN AND OUTER ISLAND VIEWS WITH WRAP AROUND LANAIS, along with impressive Haleakala vistas that shift beautifully with the light. The generous kitchen opens to a bright great room with SLIDING WALLS OF GLASS on two sides—inviting lovely cross-ventilation and framing views to the sparkling PACIFIC OCEAN. The formal living room offers a warm focal fireplace, natural cedar ceiling, and a recessed art niche. Expansive sliders from the great room and living room open to an OCEAN VIEW POOL AND SPA with a SPACIOUS TILED SUN DECK, made for sunset lounging and DINING AL FRESCO UNDER THE STARS. The layout is wonderfully open, yet intentionally defined, with sight lines that draw you toward the outdoors and the enchanting views beyond. This home is a LUMINOUS LIGHT-FILLED CANVAS—ready for your vision: an extraordinary opportunity to re-imagine and elevate a residence of substance, scale, & soul. Set within the prestigious gated Wailea Golf Estates, backing to the 11th fairway of the Wailea Blue Course, and moments to Wailea’s world-class beaches, dining, shopping, golf, tennis, water sports, and spas.

3943 Wailea Ekolu Pl, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

$4,999,999
3 Beds ⋅ 4 Baths ⋅ 408222 MLS ⋅ Fee Simple Tenure ⋅ Hoolei BLDG.
Discover luxury resort living in this exceptional ocean-view Villa located within the prestigious gated community of Ho'olei in Wailea. It is ideally positioned near world-class resorts, fine dining, luxury shopping, championship golf courses, and Maui's best beaches. The Villa features 3 bedrooms and 3.5 bathrooms, in a two-story townhome-style, encompassing 2,426 square feet. There is an additional 596 square feet of covered lanais across two levels. Each bedroom includes a private ensuite bath, offering comfort and privacy for owners and guests alike. Thoughtful design elements include a private elevator, an attached garage, a covered carport, and an outdoor storage closet. Floor-to-ceiling sliding glass doors and retractable screens open almost 30 feet onto the expansive lanai, embracing Maui's indoor/outdoor lifestyle. The lanai is ideal for entertaining and is equipped with a Wolf 36" grill, a Sub-Zero under-counter refrigerator, and custom cabinets. The Villa features polished travertine floors, recessed lighting, high tray ceilings, surround sound, a security system, and a 2-zone central air conditioning system. The Chef's kitchen includes premium appliances by Sub-Zero, Wolf, Thermador, and Bosch. A touch of elegance is added with the Snaidero Italian custom cabinetry. You can enjoy ocean views from high above the resort pool. Ho'olei's amenities include a lagoon-style pool with cascading waterfalls and grottos, a sandy beach entry, two hot tubs, a massage cabana, an outdoor kitchen with covered pavilion, and a fully equipped, air-conditioned fitness center with sauna, locker rooms, and showers. Offered fully furnished, the Villa is truly turn-key & has been meticulously maintained. The property is hotel-zoned, allowing use as a short-term vacation rental, private residence, or a combination of both. Successfully operated as a vacation rental since 2007, the Villa has received over 150 five-star reviews. The owner is willing to continue marketing the property or assist with a smooth transition to new management. This remarkable Ho'olei Villa presents a rare opportunity to own a luxury, hotel-zoned home in paradise.

81 Makakehau St Unit Apt H-2, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$5,950,000
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).

$3,000,000
3 Beds ⋅ 4 Baths ⋅ 407659 MLS ⋅ Fee Simple Tenure
This is also Listed as a Condo MLS 407638. **This is a CPR Residential Condo property** A Home That Defines “Custom” First time offered, this Hokulani Golf Villas residence is custom in every sense of the word — designed and built as the owner’s forever home, with no expense spared. From the moment you enter, you’re greeted by a bright, white, and contemporary aesthetic — a clean palette that reflects light and amplifies the home’s open concept design. An abundance of built-in cabinetry provides both function and elegance, complementing the expansive great room that flows seamlessly from kitchen to living to lanai. The home features two master suites and a third ensuite bedroom, providing flexibility for guests or multigenerational living. Every detail has been considered — from the layout to the materials to the feeling of effortless space. A 58-panel photovoltaic system powers the home, a reflection of the thoughtful investment in both sustainability and efficiency. Set gracefully along the par-5 fairway of the Maui Nui Golf Course, this home enjoys a backdrop of lush green views and the serenity unique to the Hokulani Golf Villas community. Seeing is believing — this is a rare opportunity to own one of Hokulani’s most refined, privately crafted homes.

2399 Umeke Cir Unit 68, Kihei

Listing courtesy of Hawaii Life (W).

$3,000,000
3 Beds ⋅ 4 Baths ⋅ 407638 MLS ⋅ Fee Simple Tenure ⋅ Hokulani Golf Villas BLDG.
A Home That Defines “Custom” First time offered, this Hokulani Golf Villas residence is custom in every sense of the word — designed and built as the owner’s forever home, with no expense spared. From the moment you enter, you’re greeted by a bright, white, and contemporary aesthetic — a clean palette that reflects light and amplifies the home’s open concept design. An abundance of built-in cabinetry provides both function and elegance, complementing the expansive great room that flows seamlessly from kitchen to living to lanai. The home features two master suites and a third ensuite bedroom, providing flexibility for guests or multigenerational living. Every detail has been considered — from the layout to the materials to the feeling of effortless space. A 58-panel photovoltaic system powers the home, a reflection of the thoughtful investment in both sustainability and efficiency. Set gracefully along the par-5 fairway of the Maui Nui Golf Course, this home enjoys a backdrop of lush green views and the serenity unique to the Hokulani Golf Villas community. Seeing is believing — this is a rare opportunity to own one of Hokulani’s most refined, privately crafted homes.

2399 Umeke Cir Unit 68, Kihei

Listing courtesy of Hawaii Life (W).

$14,990,000
3 Beds ⋅ 4 Baths ⋅ 407472 MLS ⋅ Fee Simple Tenure ⋅ Wailea Beach Villas BLDG.
THE BEACHFRONT VILLA - A once in a generation oceanfront sanctuary! The sophisticated remodel completed in January 2025 transformed the B-101 front row Villa into one of Wailea’s most exceptional properties rarely available. Fresh, elegant, and contemporary - fully furnished turnkey residence is ready to deliver the ultimate Maui lifestyle by providing breathtaking ocean, sunset and outer island views. Private amenities include a plunge pool, outdoor shower and a one car garage. The renovation encompasses a new kitchen with premium appliances and finishes, wide plank wood flooring, recessed lighting, upgraded electrical fixtures with LED lighting, Nest temperature controls, new interior paint, automated window coverings & blackout shades feature new custom mahogany valances, new dry bar with wine and beverage refrigerators, new RH furnishings, curated wall art and a new juke box. The Beachfront Villa occupies one of the most private and pristine locations in all Wailea Beach Villas. The premier 10 acre resort community is located in the heart of the prestigious Wailea Resort, only steps away are Wailea’s world class beaches, dining, and boutique shopping. An optional 2025 guest rental pro-forma is available. Enjoy the professional photos and cinema!

3800 Wailea Alanui Dr Unit B-101, Kihei

Listing courtesy of Compass-W.

$1,200,000
4 Beds ⋅ 4 Baths ⋅ 407417 MLS ⋅ Fee Simple Tenure
OFFERED BELOW APPRAISED VALUE. Welcome to 206 Oluea Circle, a stunning plantation-style residence in the highly sought-after Kamali‘i Alayna neighborhood of Kihei. This beautifully maintained home perfectly balances spaciousness, elegance, and island comfort offering a luxurious retreat just moments from Maui’s golden sand beaches. Step inside to discover a bright and airy living space with soaring cathedral ceilings that fill the home with natural light. The open-concept layout flows seamlessly from the living area to the kitchen and formal dining room, creating the ideal setting for relaxing, entertaining, and everyday island living. This exceptional home offers two primary bedroom options, one on each level, providing flexibility and comfort for family or guests. The downstairs primary suite opens to a peaceful lanai, perfect for quiet mornings outdoors and features a spa-inspired ensuite with dual vanities, a soaking tub, and a separate shower. Upstairs, you’ll find three additional spacious bedrooms, including an alternate primary suite with its own ensuite bath featuring a walk-in shower and dual vanity. With a total of 3.5 baths, a formal dining room, and a two-car garage, this home provides both comfort and practicality while maintaining its elegant, coastal charm. The kitchen is beautifully maintained with modern appliances and direct access to the backyard and wrap-around deck, creating an effortless indoor-outdoor flow for entertaining or enjoying meals al fresco. Thoughtful updates reflect pride of ownership throughout, including freshly painted lanais and front exterior, new carpeting on the stairs and upstairs bedrooms, and a recently installed air conditioner. Ideally located just minutes from Kihei’s beaches, shopping, dining, and schools, 206 Oluea Circle offers the best of island living - comfort, convenience, and timeless Maui style in one beautifully cared-for home.

206 Oluea Cir, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$4,300,000
3 Beds ⋅ 4 Baths ⋅ 401515 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
OUTSTANDING VALUE for one of Wailea Point's most FABULOUS VIEW UNITS. This is the highly sought after Upper Level D plan, Wailea Point’s second largest standard floor plan located on the top 2 floors of a 4-story building; 2 levels, 3 bedrooms, 4 bathrooms. The location is a “10”, affording spectacular ocean views. The vaulted ceilings are a bonus, and new windows were installed in 2022, including the gorgeous mitered glass bay window that makes the ocean view from the living room simply POP! Facing west, 180-degree ocean views, year-round sunsets, and whales galore! The entire upstairs is a master suite with full bath & soaking tub, and its own private, 144 sq. ft. “crow’s nest" lanai with stunning views. Original condition except for the beautiful new windows. Unfurnished. Wailea Point was built to be the finest residential condominium in all of Hawaii - and many believe it is just that. Built in the late 1980's, it stole the show at the 1986 Parade of Homes, a competition sponsored by the Building Industry Association of Hawaii. It also won a national award from Sunset Magazine for best use of glass - and the sellers have improved on that by replacing windows, and installing the awesome "mitered glass bay window" in the living room. Aside from its World Class location, Wailea Point boasts ultra-high quality design & construction, very low density (just over 4 units per acre), low rise structures in a magnificent, garden environment. 24-hour roving & gated security; 2 elaborate pool pavilions with kitchens & barbecues; 4 pools (including a 2-lane, 25-meter lap pool); 2 whirlpool spas; lighted tennis & pickleball courts; superb fitness gym; extensive fruit & herb gardens; ample parking; and it's golf cart friendly! Enjoy the Four Seasons and Fairmont Kea Lani resorts as immediate neighbors, plus the Grand Wailea a short walk away, and all the 5-star restaurants & other services they offer. Well run AOAO. 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 2502, Kihei

Listing courtesy of Wailea Point Realty, Inc..

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.