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$2,680,000
3 Beds ⋅ 2 Baths ⋅ 410656 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.
Experience front-row ocean views at Keala O Wailea #4-201, a beautifully positioned 3-bedroom, 2-bathroom residence in one of the most sought-after buildings within the complex. Set on the second level, this home delivers sweeping views across the ocean to the West Maui Mountains, neighboring islands, and iconic Molokini — a panorama that rarely comes available. Unlike most properties in Wailea, this unit offers the rare luxury of your own private BBQ on the lanai, perfect for sunset dinners with an ever-changing ocean backdrop. It also comes with a private garage plus a deeded parking stall right in front of the unit — a level of convenience hard to find at this price point. Residents of Keala O Wailea enjoy resort-style amenities, including a pool, spa, outdoor clubhouse with kitchen, and fitness center overlooking the water. The pet-friendly complex sits just steps from Wailea Gateway Center's shopping and dining, and within the renowned Wailea Resort, home to three championship golf courses, tennis, pristine beaches, and world-class hotels — all moments away. Whether a full-time residence or vacation retreat #4-201 offers an unmatched combination of location, views, and lifestyle.

59 Wailea Gateway Pl Unit 4-201, Kihei

Listing courtesy of Hawaii Life (W).

$1,670,000
2 Beds ⋅ 2 Baths ⋅ 410361 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.
Discover one of Wailea's rarest offerings ; a beautifully appointed ground-floor residence that pairs effortless access with exceptional views. This stunning 2-bedroom condominium at Keala O Wailea offers a combination seldom found: the convenience of single-level living, breathtaking ocean views, and the privacy of one of the community's most desirable locations. Thoughtfully positioned in a quiet corner of the complex, this meticulously maintained home enjoys an expansive green lawn just beyond the lanai, making it an ideal retreat for pet owners and those who appreciate seamless indoor-outdoor living. The sense of privacy is remarkable, creating a peaceful sanctuary surrounded by lush tropical landscaping. Inside, every detail reflects quality and care. High-end luxury furnishings, sophisticated finishes, and several custom enhancements elevate the home well beyond the ordinary. The spacious, open-concept floor plan is filled with natural light and captures the beauty of Wailea from the main living areas, creating an inviting atmosphere for both everyday living and entertaining. Keala O Wailea is one of Wailea's premier luxury residential communities, ideally perched above the Wailea Blue Golf Course. This gated enclave offers an exceptional island lifestyle with resort-inspired amenities, including an elegant pool and spa, a beautifully appointed pavilion with an outdoor kitchen, and a spacious fitness center. Just moments away are Wailea's world-renowned beaches, championship golf courses, luxury shopping, acclaimed restaurants, scenic coastal paths, and the unparalleled natural beauty that defines South Maui. Whether you're searching for a full-time residence or an elegant island retreat, this exceptional home embodies the privacy, comfort, and refined island lifestyle that make Wailea one of Hawaii's most coveted places to call home.

67 Wailea Gateway Pl Unit 6-103, Kihei

Listing courtesy of Hawaii Life (W).

$2,895,000
3 Beds ⋅ 2 Baths ⋅ 409559 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.
Welcome to modern Hawaiian luxury at Keala o Wailea Unit 4-101. This rare 3-bedroom, 2-bathroom residence offers effortless single-level living with absolutely no stairs in an exclusive, pet-friendly gated community. Premiere ground floor units in this community rarely come up for sale. Offered fully furnished and turnkey, the home features a soothing, neutral coastal aesthetic. The open-concept living area is highlighted by large retractable glass doors that create seamless indoor/outdoor living. Step onto your spacious covered lanai to soak in massive ocean views spanning Kaho'olawe, Molokini, West Maui and Lanai, all while overlooking the Wailea Blue Golf Course. The gourmet kitchen is equipped with sleek contemporary cabinetry, elegant quartz countertops, and premium Bosch appliances. Every detail is thoughtfully designed for comfort and elevated island living. Due to its location in the center of the complex, the unit is conveniently located near the amenities including a stunning ocean-view pool, spa, fitness room, and clubhouse with BBQ facilities This unit includes two parking spaces, featuring a covered carport with built-in storage, and a second space which is just steps from the front door. There is access to additional storage for your recreational equipment. You are also situated immediately adjacent to the Wailea Gateway Shops, putting exceptional dining, shopping, fitness facilities, doctor's office and a pharmacy just a short stroll from your front door. Experience the pinnacle of quiet, contemporary Wailea living in Unit 4-101, where breathtaking vistas, sophisticated design, and everyday convenience perfectly align.

59 Wailea Gateway Pl Unit 4-101, Kihei

Listing courtesy of Hawaii Life (W).

$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).