Wailea Kai Real Estate

Welcome to Wailea Kai, a hidden gem nestled in the heart of Maui, Hawaii. This enchanting neighborhood is part of the vibrant Kihei community and offers an idyllic blend of luxury living and natural beauty. Known for its stunning ocean views and lush landscapes, Wailea Kai is a paradise for those seeking a serene lifestyle amidst tropical splendor.

As you stroll through the palm-lined streets of Wailea Kai, you'll be captivated by the upscale homes that embody the essence of Hawaiian architecture, seamlessly blending with the surrounding environment. This tightly-knit community boasts a friendly atmosphere, where neighbors become friends and the spirit of aloha is ever-present.

One of the most appealing aspects of Wailea Kai is its proximity to some of Maui’s most pristine beaches. Just moments away, you can sink your toes into the soft, golden sands of Wailea Beach or enjoy a day of snorkeling in the crystal-clear waters of Molokini Crater. For those who appreciate outdoor activities, the nearby Wailea Golf Club offers world-class golfing amidst breathtaking scenery.

Culinary enthusiasts will delight in the array of dining options available, from casual beachside eateries to upscale restaurants featuring farm-to-table cuisine. Additionally, the neighborhood is conveniently located near shopping centers, art galleries, and local markets, ensuring that residents have everything they need within easy reach.

Wailea Kai is not just a place to live; it’s a lifestyle. With its stunning natural beauty, welcoming community, and endless recreational opportunities, this neighborhood truly embodies the spirit of island living. Come discover your slice of paradise in Wailea Kai!

Newest Listings in Wailea Kai

$2,499,000

3 Beds ⋅ 3 Baths ⋅ 410251 MLS ⋅ Fee Simple Tenure

Welcome to 139 Waaula St, a stunning single-family home in the gated Wailea Kai community, just one block from Keawakapu Beach. Set on a large 10,000-square-foot lot, this multi-level residence lives large, with generous indoor and outdoor spaces designed for entertaining, relaxing, & enjoying the Maui lifestyle. Bay windows frame the mature tropical landscaping & fill the open-concept interior with natural light. The formal living room connects seamlessly to the dining area and kitchen, while a separate game room offers vaulted ceilings, a wet bar, built-in cabinetry, & a game table that can double as a second dining space. The spacious primary suite & two additional upstairs bedrooms also feature vaulted ceilings. A charming upper lanai brings a touch of Romeo and Juliet romance while offering a peaceful place to enjoy sunset colors, evening breezes, and star-filled skies. Outside, a large pool & hot tub are surrounded by lush tropical landscaping, creating a private backyard retreat. A convenient half bath opens directly to the pool area, helping keep wet feet out of the main living spaces. Split AC in every room provides year-round comfort, while owned solar panels help keep electric costs low. The two-car garage includes a caretaker’s quarters, adding further value and flexibility for guests, extended family, or additional living needs. Thoughtfully designed throughout, this home offers room to gather, room to unwind, & room to enjoy Wailea living to the fullest.

139 Waaula Way, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$2,395,000

4 Beds ⋅ 3 Baths ⋅ 410122 MLS ⋅ Fee Simple Tenure

Welcome to 3236 Pikai Way, an exceptional single-level residence nestled within the exclusive gated enclave of Wailea Kai, just across the street from the golden sands of world-famous Keawakapu Beach. Situated on a quiet private cul-de-sac in Little Wailea Kai, this beautifully maintained 4-bedroom, 3-bath home offers the perfect blend of luxury, privacy, and effortless island living. Designed with an open-concept floor plan, the home features soaring vaulted ceilings, abundant natural light, and seamless indoor-outdoor living. Expansive sliding glass doors open to your own tropical retreat, where a resort-style in-ground pool is surrounded by lush, mature landscaping—creating a private oasis ideal for relaxing or entertaining family and friends year-round. The spacious kitchen is thoughtfully designed for gathering and entertaining, complete with a large center island, granite countertops, newer appliances, generous walk-in pantry, and an adjacent private laundry room. Split air conditioning throughout the home provides year-round comfort while maintaining the home's bright and airy island ambiance. Wailea Kai is one of South Maui's most sought-after gated communities, prized for its peaceful setting and unmatched convenience. From your front door, enjoy an easy stroll to Keawakapu Beach, consistently ranked among Maui's finest white sand beaches. Just minutes away are Wailea's celebrated championship golf courses, luxury resorts, award-winning restaurants, tennis facilities, scenic oceanfront walking paths, and the upscale boutiques and dining at The Shops at Wailea. Whether you're searching for a primary residence, second home, or luxury island retreat, 3236 Pikai Way presents a rare opportunity to own in one of Wailea's most desirable neighborhoods, where timeless island elegance meets the very best of the Maui lifestyle. Seller discloses to all parties he is a licensed Hawaii real estate broker, owns Kokua Realty, LLC and is a principal in this sale.

3236 Pikai Way, Kihei

Listing courtesy of Kokua Realty LLC.

$1,875,000

4 Beds ⋅ 3 Baths ⋅ 407427 MLS ⋅ Fee Simple Tenure

Motivated Seller — Unbeatable Wailea Value Steps from Keawakapu Beach! The seller is highly motivated, presenting an extraordinary opportunity to secure a beautifully upgraded residence in Wailea Kai, one of South Maui’s most desirable gated communities. This is your chance to capture timeless island luxury with unmatched value in today's market. Designed for effortless comfort, this inviting two-level home perfectly blends a smart, functional layout with modern updates. True single-level living defines the main floor, which hosts the primary bedroom suite, a beautifully renovated kitchen, an airy great room, expansive Ipe decks, a private spa/hot tub, and the garage. Living without daily stairs makes this setup incredibly convenient, while the lower level features three additional bedrooms, offering excellent privacy and flexibility for family or guests. Inside, the open layout shines with soaring vaulted ceilings that flood the living spaces with natural light. The chef's kitchen features granite countertops, high-end appliances, and modern fixtures, while rich bamboo flooring and upgraded lighting add warmth and sophistication throughout. Sliding glass doors seamlessly connect the indoor spaces to a lush, private garden retreat, creating an ideal setting for al fresco dining and tropical relaxation. Located just a short walk to world-famous Keawakapu Beach, this property perfectly balances neighborhood tranquility with ultimate coastal convenience. Residents enjoy secure gated entry and immediate proximity to Wailea’s renowned championship golf courses, five-star resorts, and premier dining and shopping. Whether you’re seeking a full-time residence, a vacation retreat, or a sharp investment, the seller’s motivation makes 53 Waikai the ultimate Wailea opportunity. Act fast and bring your offer today!

53 Waikai St, Kihei

Listing courtesy of Compass-W.

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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.