Wailea, HI Homes for Sale under $2,000,000

This well-maintained 2,700 sq. ft. home offers an exceptional, highly flexible layout. The upper level features the main primary bedroom suite and a beautifully remodeled kitchen that opens to a bright living area and a spacious lanai with a hot tub—perfect for indoor-outdoor entertaining. The lower level offers one bedroom with an attached bath, plus two additional separate bedrooms, a newly

Roger Pleski Coldwell Banker Island Prop(S)

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

Josef Erlemann Compass-W

Set within the prestigious Wailea Pualani Estates, this 3-bedroom, 2.5-bath residence with an additional office/media room offers refined island living with a seamless indoor-outdoor flow. The private backyard is designed for entertaining, featuring a saline heated pool with waterfall features, surrounded by lush, mature landscaping. The ocean-view primary suite includes a private lanai, creating

Jesseca Curry Compass-W

Gorgeous home with a legal attached ohana located on a quiet cul-de-sac just up the hill from Kamaole Beach Park III and Keawakapu Beach. This distinctive property, constructed with beautiful cedar siding on a solid slab foundation, features a 4-bedroom, 2-bath main home on the upper level with open beam vaulted ceilings, dual system air conditioning, and a fully remodeled kitchen. The home also

Travis Speck Redfin Corporation

Welcome to a private gated retreat in Maui Meadows set on 0.7 acres of lush tropical landscaping. With no HOA restrictions and multiple detached structures, this unique property presents an extraordinary opportunity just a short distance from the beach. Enter through the private electric gates and take in the mature fruit trees, exotic palms, and colorful gardens that create a true island

Mark Waite Compass-W

Privately positioned in Maui Meadows, 505 Ho'ohalahala offers exceptional space, flexibility, and privacy. Located just minutes away from resort amenities and resort beaches, this home delivers the Wailea location without the Wailea price tag. This fully fenced and gated estate provides a true sense of privacy with expansive, all usable grounds. Mature landscaping surrounds the property,

Dano Sayles Coldwell Banker Island Prop(S)

Rarely does an opportunity like this come along at Wailea Ekahi. This beautifully positioned downstairs 1-bedroom, 2-bathroom villa enjoys stunning ocean views and sits in one of the community's most desirable green belt locations, offering a peaceful, open setting with lush tropical surroundings. Being sold turnkey, this villa is ready for immediate enjoyment as a full-time residence, second

Alex Abreu Hawaii Life (W)

The Ultimate Ocean View You’ve Been Waiting For at Wailea Ekolu #1706! Enjoy upper floor privacy with absolutely amazing ocean and outer island views from this recently renovated (2025), 2 Bedroom, 2 bath unit! You are immediately drawn to the large, private lanai where stunning views await and are always available from the living, dining, and kitchen areas, as well as the primary bedroom. Your

Jeff Simon Hawaii Life (W)

Located in the highly desirable neighborhood of Maui Meadows, 3248 Akala Drive offers a spacious and well maintained property situated on a beautifully landscaped 1⁄2-acre lot. The thoughtfully updated main residence features a wraparound deck with ocean views, a PV system, and a tile roof. The main home offers a flexible floor plan with the primary suite, additional bedroom, full bathroom,

Melissa Montgomery Coldwell Banker Island Prop(S)

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

Alana Rucynski Hawaii Life (W)

AMAZING VALUE - SINGLE LEVEL LIVING 3 BEDROOM OCEAN VIEW RESIDENCE PLUS GARAGE!!! Where the Ocean Becomes Your Backdrop and Wailea Becomes Your Everyday. Wailea Town Center C-203 is a rare offering, blending the privacy of a boutique residential enclave with the panoramic beauty of the Pacific and the unmatched convenience of Wailea’s vibrant core. From this vantage point above it all, life

Jeannie Kong-Evarts Maui Real Estate Advisors LLC

Wailea Ekolu #1008 offers the pinnacle of Wailea living—an immaculate upstairs 2-bedroom, 2-bathroom condo with panoramic ocean views. This spacious, end-unit residence features vaulted ceilings and comes fully furnished and turnkey, allowing for effortless enjoyment or immediate vacation rental income. Inside, stay comfortable year-round with split AC units in the primary suite and living area,

Sloan Allison Coldwell Banker Island Prop(S)

Welcome to Kai Malu 43B, beautifully remodeled in 2024, this 3-bedroom, 2.5-bathroom home offers unparalleled privacy, a spacious outdoor area and breathtaking views of the ocean and outer islands. Step inside to discover an open-concept kitchen and living room, perfect for both entertaining and everyday living. Wide plank oak flooring graces the upper and lower levels, adding warmth and elegance

Patrick Franta Coldwell Banker Island Prop(S)

Mana Kai magic! Peace and privacy are the hallmarks of this fabulous east-end unit with incredible Ocean, Keawakapu Beach, outer island (Molokini and Kahoolawe), and Upcountry views, with Pu’u Ola’i standing proudly to the south and majestic Haleakala to the east. This 2 bedroom, 2 bath gem in this HOTEL ZONED resort is ideally located to be convenient to everything South Kihei and the Wailea

Jeff Simon Hawaii Life (W)

Hale Hui Kai is a true hidden gem on Keawakapu Beach — a boutique oceanfront complex in an unbeatable location. From the moment you step into its quiet, lush walkways, you’re greeted with the timeless charm of old Hawaiiana. This beautifully remodeled ground floor two bedroom, two-bath residence features a thoughtful, creative design throughout. The spacious lanai offers a pleasant view — not

Mary Kerstulovich Hawaii Life (W)

Exceptional opportunity to own an ocean-view property in one of South Kihei's most desirable neighborhoods. Set on a 1/2 Acre lot, 739 Launa Drive offers breathtaking Pacific Ocean views, spectacular sunsets, and the rare opportunity to create your dream Maui home in Maui Meadows. The property is improved with an existing 1-bedroom, 1-bath cottage, allowing you to enjoy the property while

Todd Hudson Keller Williams Realty Maui-Ki

HOTEL ZONING! Enjoy spectacular ocean views from BOTH sides of this wonderful two bedroom, two bath condominium unit! From the living area, the main bedroom, and the spacious lanai, there are breathtaking ocean, Keawakapu Beach, Molokini, Kahoolawe, and Upcountry views!! The guest bedroom on the north side of the unit offers both spectacular ocean and West Maui mountain views! The positioning of

Jeff Simon Hawaii Life (W)

Aloha and welcome to Mana Kai 514. This beautifully updated 2-bedroom, 2-bath unit features two walk-in showers, two split A/C units, smoothed ceilings, full tile flooring, and stunning ocean views overlooking world-famous Keawakapu Beach. The owners also took advantage of the "walled-off" extra door in the primary bedroom and rotated the bed to capture those incredible ocean views directly from

David McAlear Coldwell Banker Island Prop-Ku

Meticulously maintained 3 bedroom 2.5 bathroom Ocean and Mountain View Kai Malu unit with new plush carpets upstairs, luxury vinyl floors downstairs, beautiful epoxy two car garage floor and new wi-fi garage door opener as well as new hot water heater with timer, new stainless steel refrigerator, and new lanai sunshades. An advantage of this particular unit location is the North facing lanai to

Adam Falb Berkshire Hathaway Maui Prop-W

Wailea Palms #3202 boasts a private location in the complex overlooking meticulously manicured lawn, gardens and putting green where one can enjoy splendid sunsets, perfectly framed with palm trees and lush landscaping. The light-filled living area has west-facing windows which open to a spacious living area and a stunning view of the ocean. Relax and enjoy the ocean view from your lanai, living

Mardi Werner Coldwell Banker Island Prop-Ku

If you’re looking for the ultimate Maui property, this is it! This luxury top-floor condo at the highly sought-after Palms at Wailea puts you just steps from the spectacular resort-style pool, relaxing Jacuzzi, and all the amenities that make this community so desirable. Beautifully maintained and fully air-conditioned, this spacious two-bedroom, two-bath residence offers approximately 1,200

Kento Tanaka-Tamaki Coldwell Banker Island Prop(S)

Welcome to your private tropical oasis in serene Maui Meadows. This remarkable and rare property spans over a 0.52-acre corner lot, offering a true resort-style experience with lush tropical landscaping that provides exceptional privacy and tranquility. This unique estate features three distinct dwellings, making it ideal for multi-generational living, rental income opportunities, or a private

Jordan Smith Island Sotheby's International Realty(W)