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$2,950,000
1 Beds ⋅ 2 Baths ⋅ 409117 MLS ⋅ Fee Simple Tenure ⋅ Wailea Elua I A BLDG.
Welcome to Wailea Elua, an exclusive oceanfront, hotel-zoned vacation rental set atop a lush greenbelt in prestigious Wailea. Spanning 24 acres of tropical paradise, this sought-after community offers an unparalleled blend of luxury, serenity, and income potential in South Maui. This rare second-floor 1-bedroom, 2-bathroom condominium is your gateway to breathtaking sunsets and front-row whale watching from your expansive covered lanai. Thoughtfully designed with high-end finishes, this exquisite retreat features central A/C, stylish tile in the bathrooms, gourmet kitchen with elegant granite countertops, a spacious island, and rich Cherry cabinetry including a paneled refrigerator. The open concept living space is a harmonious blend of comfort and sophistication, offering breathtaking ocean views from your private oasis. Wailea Elua is steps to a scenic oceanfront walking path that places you conveniently to both beachfront and legendary diving and turtle watching point. The complex itself is nestled between the Luxury resorts of Wailea Beach Resort and the Andaz which provides World-Class dining and entertainment experiences. Elevate your lifestyle on property and enjoy Resort-Style amenities such as Pickleball, gym, two pristine swimming pools, including an oceanfront pool and rejuvenating hot tub. Grill down at the expansive entertainment pavilion with barbecues and a fully equipped kitchen. Pool with patio/deck and barbeque area convenient to 2012 as well. This turnkey property is fully furnished, complete with artwork and linens, making it move-in ready for immediate enjoyment or as a top-producing vacation rental. Cherished by its owners and repeat guests for over 28 years, this is a rare opportunity to claim your piece of paradise in one of South Maui's most coveted oceanfront communities. Live the dream-your Maui escape awaits.

3600 Wailea Alanui Dr Unit 2012, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$2,100,000
2 Beds ⋅ 2 Baths ⋅ 408944 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.
Keala O Wailea 5-103 offers panoramic Pacific Ocean views from one of Wailea's premier hillside communities. This single-level 2-bedroom, 2-bathroom residence spans approximately 1,248 square feet and was built in 2018, with updates completed in 2025. Retractable glass doors frame sweeping ocean vistas and create seamless indoor-outdoor living. The open-concept layout positions the living area, kitchen, and primary suite to capture vibrant sunsets and seasonal whale activity. The kitchen features Bosch stainless steel appliances, quality countertops, maple cabinetry, and a functional design ideal for everyday living or entertaining. Engineered hardwood flooring enhances the main living areas, with plush carpet in the bedrooms. The primary suite offers ocean views, a walk-in closet, and an en suite bath with dual vanities. A privately situated second bedroom provides flexibility for guests or office use. The covered lanai delivers a front-row seat to Maui's iconic scenery. Located within the exclusive 70-residence Keala O Wailea enclave, Building 5 enjoys a peaceful setting just minutes from beaches, golf, dining, and shopping. Seller intends to complete a 1031 exchange at no cost or delay to the buyer.

63 Wailea Gateway Pl Unit 5103, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$2,795,000
2 Beds ⋅ 2 Baths ⋅ 408567 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
You Deserve To Own & Experience Your Oceanfront Paradise Today! Unit 3404 is a delightful 2 bedroom, 2 bathroom upper-level, privately located, & meticulously maintained residence, within the highly-coveted, low density, lushly landscaped, & world-class tropical paradise known as Wailea Point. Upon entering the residence, you are transfixed by the lovely pastoral-framed Ocean, Molokini Crater, & Island of Kaho’olawe views. The award-winning construction & design affords vaulted 16-ft Clear Cedar ceilings, perimeter soffits with recessed art lighting, & book-matched Hawaiian Koa doors & accents throughout, which exude a feeling of warmth & elegance. The recent installation of floor-to-ceiling mitered glass bay windows in the great room brings in volumes of natural light, & creates mesmerizing views of the ocean & outer islands, breaching whales, & painterly sunsets. The open & functional design in the kitchen, with glass-on-glass corner windows, allows for scenic views while creating gourmet culinary delights. The spacious primary bedroom, with a Clear Cedar ceiling & recessed lighting, is filled with natural light & offers an en-suite private bathroom, & garden views from its dedicated lanai. The guest suite's wall of glass allows for extra light & tropical garden views. The spacious & tranquil wrap-around lanai offers lovely ocean views, alfresco dining, an upgraded built-in BBQ area, & electronic privacy sunshades. The laundry room features a full-size washer & dryer, ample storage & counter space. There is also a deeded 1 car garage with an electric car charge connection that comes with the residence. Wailea Point is prominently positioned upon 28 prime pastoral oceanfront acres in the world-class Wailea Resort area, adjacent to the Four Seasons Maui & Fairmont Kea Lani. Experience ‘The Best’ that Maui has to offer, as you drive your golf cart or meander through the property, enjoy direct access to two of Maui’s most iconic beaches & the adjacent 1.5-mile oceanfront 'Wailea Walk', & explore fine dining & shopping at The Shops at Wailea or relax in the luxury spas of Maui's finest resorts. World-class golf is conveniently nearby, & tennis & pickleball courts are located onsite. The complex offers guard-gated & 24-hour roving security. Second to none on Maui are the two on-site recreation pavilions; one is family-oriented & includes a lap pool, kids' pool, cold plunge & state of the art gym, while the other is the 'quiet' pool area. Savor the best of Maui, at Wailea Point 3404!

4000 Wailea Alanui Dr Unit 3404, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

$2,500,000
3 Beds ⋅ 3 Baths ⋅ 408470 MLS ⋅ Fee Simple Tenure
Wailea Kai is one of the closest communities to the beach! 3 BR 2.5 BA with a pool and easy walking distance to Keawakapu Beach. This recently updated home offers a unique living style with the master on the main level and 2 bedrooms tucked away separately with a jack & jill bath, all 3 with vaulted ceilings. The master has a large lanai that overlooks the pool and lawn area. A major remodel of the living room and kitchen were completed last year, including all new appliances and furnishings. Relax in the openness of the living room and kitchen, which includes a large island with numerous sitting spaces, all overlooking the pool through numerous windows and sliding doors. Enjoy the large pool and covered lanai's with a very private feel with no road noise, surrounded by beautiful gardens and fruit trees. Split A/C units in the living room and all 3 bedrooms. Capitalize on very low electric bills with 22 owned solar panels under the banked system, and a solar hot water system. 2 car garage. Located at the end of a quiet cul-de-sac.

3142 Waiea Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$2,180,000
4 Beds ⋅ 3 Baths ⋅ 408295 MLS ⋅ Fee Simple Tenure
Up to 3 units total. 3 Bed 2 Bath Main Dwelling + Attached Studio Ohana + 1 Bed 1 Bath Unattached Cottage Ohana with lanais on both buildings. Maui Meadows is renowned for its awe-inspiring ocean views. Prominently situated with a single level on the hillside, you'll discover within this contemporary elegant home, a spacious living-room kitchen area that seamlessly extends to the highlight of the property, an expansive covered lanai with breathtaking views of the ocean and outer islands. Watch the boats race to Molokini in the morning, or view the whales breach while grilling dinner with family and friends. This remarkable half acre property just underwent a complete transformation. Beautifully reimagined and thoughtfully finished, the Main Dwelling provides a large chef’s kitchen with high open beam ceilings, new floors, Quartz countertops, and stainless steel farmhouse sink, perfect for gatherings. From the living-room hallway, you will pass 2 Bedrooms and 1 Bath on your way to the Primary Suite, with large en-suite bath, which provides a perfect space for modern luxury living, complete with a 4 zone mini split AC system for your comfort. For added convenience, this contemporary residence is divided into three distinct living spaces. The Attached Studio Ohana is connected to the main dwelling through a solar service and storage closet, which can be used flexibly as a fourth bedroom with en-suite bath, or as a convenient grandmother's quarter's for rental income. Additionally, the Detached 1-bedroom, 1-bathroom Cottage Ohana with a covered lanai can provide steady rental income to help with island expenses or serve as extra living area for family, with ample locked indoor storage underneath. With 3 freshly updated units, this modern half acre is a great candidate for a future CPR subdivision, a process in which the detached cottage ohana and main dwelling could be sold separately, while a third unit could be possibly designated and another permitted detached ohana dwelling built. With such a large property, the possibilities stack up quickly. Come experience the luxury of island living in this contemporary versatile residence, nestled high in one of South Maui’s most desirable neighborhoods. All this just minutes from the beach, Wailea’s world-class restaurants, golf courses, and everything that South Maui has to provide. Contact your favorite Realtor today to schedule a showing! Digital staging used in some of MLS photos.

614 Kupulau Pl, Kihei

Listing courtesy of Bello Realty Inc.

$2,767,300
408098 MLS ⋅ Fee Simple Tenure
** Sale includes MLS #s 408092, 408093, 408094, 408095, 408096, 408097, 408098, 408099, 408100, 408101, 408143, 408102, 408103, 408104, 408106 & 408107 ** Rare opportunity to acquire a multi-site land portfolio spanning Wailuku, Kihei, and Makawao—three of Maui’s most sought-after and growing regions. The portfolio consists of 16 parcels totaling approximately 272.055 acres, offering significant scale, diverse topography, and strategic locations suitable for investment, master planning, or phased development. Properties are offered for sale exclusively as a single portfolio. Any individual parcel pricing shown is for MLS compliance purposes only and does not reflect standalone availability or value. The portfolio purchase price is $48,000,000.00

1144 S Kihei Rd, Kihei

Listing courtesy of Commercial Prop of Maui LLC.

$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).

$2,998,000
3 Beds ⋅ 2 Baths ⋅ 407495 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
From the moment you enter Wailea Point 1904, the world seems to pause. Before you lies a sea of liquid blue: waves shimmering under the sun, clouds drifting like silk across the West Maui Mountains, and the scent of salt carried on the breeze. It’s not just a view; it’s an experience that reaches into your senses and holds you there, suspended between sea and sky. Polished marble floors guide you through a space defined by craftsmanship and grace. The great room, with soaring 20-foot ceilings and natural clear cedar soffits illuminated by art lighting, opens wide to a 24-foot mitered glass bay window that frames Wailea Point’s lush gardens and the boundless Pacific beyond. Here, light is architecture, and every surface, from the richly grained Hawaiian Koa doors to the glass walls that dissolve the boundary between indoors and out, invites calm and connection. Step through sliding glass doors onto the expansive 339-square-foot wraparound lanai, where the rustle of palm fronds and the fragrance of plumeria accompany every meal. This is the essence of island living: dining alfresco, surrounded by nature’s color and sound. A built-in BBQ and ocean-view kitchen make entertaining effortless, with glass-on-glass corner windows that bring the gardens and horizon into every culinary moment. The primary suite, a sanctuary of quiet refinement, opens to its own private lanai. Sunlight pours through three skylights into the en-suite bath, complete with dual vanities, a radius-tiled shower, and thoughtful design that feels both indulgent and intimate. The guest suite offers its own sense of retreat, with garden vistas that soothe the spirit. Ascend the sculptural steamed-and-bent mahogany spiral staircase to a lofted third bedroom, an airy hideaway with a walk-in closet, perfect for guests or a creative escape. Set across 28 acres of oceanfront paradise, Wailea Point is a world unto itself bordered by two of Maui’s finest beaches and adjacent to the Four Seasons and Fairmont Kea Lani Resorts. A gated enclave offering unmatched privacy and prestige. Enjoy two resort-quality pool pavilions for hosting community gatherings as well as the owners' private use, a fully equipped gym, lighted tennis and pickleball courts, a cold plunge, multiple BBQ areas, and 24-hour roving security. Fine dining & shopping, world-class golf & tennis, plus hiking & diving are all nearby! Wailea Point is Maui’s Finest Condominium and a Legacy Property!

4000 Wailea Alanui Dr Unit 1904, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

$2,549,000
3 Beds ⋅ 3 Baths ⋅ 407284 MLS ⋅ Fee Simple Tenure
Luxury Spanish Villa in Wailea, Maui. Nestled in one of Wailea’s most sought-after neighborhoods, this meticulously upgraded contemporary Spanish villa blends timeless elegance with modern comfort. Situated on over half an acre of prime real estate and boasting over 5,000 square feet of living space under roof, this estate epitomizes luxury island living with single level living, having only the third bedroom upstairs. Recently reimagined, the home has undergone extensive renovations to seamlessly combine classic Spanish architectural elements such as 2' x 4' porcelain tiles and custom Moroccan pendant in kitchen with modern-day amenities.The iconic Spanish tile roof enhances the property’s curb appeal, while the grand entry and courtyard create a stately ambiance, welcoming you to your private sanctuary. Every detail has been thoughtfully upgraded in recent years, from high-end finishes such as European Oak wood floors, Hoppe windows and doors, Thermador appliances, to state-of-the-art systems such as Mitsubishi Air Conditioning and Luxe garage doors, ensuring a home that is both stylish and functional. The expansive outdoor living spaces include a large swimming pool, an inviting pool deck, and a covered lanai—perfect for entertaining or enjoying Maui’s year-round tropical climate. The property’s elevated position at the end of a quiet cul-de-sac provides unparalleled privacy and seclusion, free from through traffic. Inside, new air conditioning systems, premium finishes, and refined touches elevate the living experience. The oversized upper deck is a true showstopper, offering breathtaking ocean views, daily sunsets over the outer islands, and seasonal whale-watching opportunities. This estate is move-in ready and waiting to welcome its next discerning homeowner to indulge in tranquility, beauty, and exclusivity with proximity to Wailea and Makena's best beaches and resorts.

3291 Waileia Pl, Kihei

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$2,400,000
3 Beds ⋅ 3 Baths ⋅ 404328 MLS ⋅ Fee Simple Tenure
Amazing ocean and West Maui Mountain views from this three bedroom, three bath pole house in Maui Meadows on a flag lot. Enjoy the pool and spa together with the spectacular views.

3300 Keha Dr, Kihei

Listing courtesy of Capitol Properties.

$2,399,000
403794 MLS ⋅ Fee Simple Tenure
DEVELOPMENT OPPORTUNITY: 6 vacant lots for sale within a 9-Unit Residential Condominium. This project has six vacant lots allocated for single family residential homes ranging from approximately 4,200 square feet to 4,450 with one smaller ohana unit just shy of 3,400 square feet. Buildable area for each unit has been laid out and will service 1,300 square feet to 1,500 square feet homes and 960 square feet for the ohana unit. Develop? Sell? Rent? Property has 2 county water meters. Do your part to create homes for Maui families! Buyer to do their own due diligence. Also listed with 3 existing homes in MLS Single Family Residential listing #403945.

490 Kaiola Pl, Kihei

Listing courtesy of Hale Anuenue Realty LLC.

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.