Wailuku Real Estate Search

Wailuku Homes with a Pool for Sale

Our website features the best real estate search for homes with a pool properties available in Wailuku and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Wailuku Homes with a Pool for Sale

$4,895,000
4 Beds ⋅ 6 Baths ⋅ 409534 MLS ⋅ Fee Simple Tenure
Located within the coveted acreage community of Wailuku Country Estates, 2150 Kamaile Street offers a rare combination of privacy, scale, and resort-style living across approximately 2.78 acres. The main residence spans approximately 3,175 square feet and is designed to capture the essence of indoor-outdoor island living. Generous living spaces flow effortlessly to the surrounding grounds, creating an inviting setting for both everyday comfort and elevated entertaining. A detached two-bedroom, two-bathroom Ohana of approximately 1,000 square feet enhances the compound feel of the property. Complete with an oversized garage, this separate residence offers privacy and versatility while remaining integrated into the overall estate design. Recent enhancements have transformed the outdoor experience into a private retreat. A newly constructed resort-style pool and spa anchor the property’s recreational amenities, complemented by an expanded pool deck ideal for gatherings. A tranquil water feature and private putting green further elevate the grounds, creating a curated setting designed for relaxation and enjoyment. The detached barn structure has been thoughtfully upgraded and finished, adding substantial flexibility to the estate. Whether utilized as a studio, gym, office, creative space, or extended entertaining area, it contributes meaningful utility and enhances the property’s overall functionality. With nearly three acres of usable land, multiple structures, and newly added resort-level amenities, 2150 Kamaile Street presents a compelling opportunity to own a private lifestyle compound in one of Central Maui’s most desirable estate communities. This is a property designed not only as a residence — but as a destination.

2150 Kamaile St, Wailuku

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$3,595,000
4 Beds ⋅ 6 Baths ⋅ 408673 MLS ⋅ Fee Simple Tenure
Come and see this spacious 7,595 square foot estate home located in the peaceful countryside of Wailuku Country Estates. Just 10 minutes from town, the setting feels quiet and rural while still being conveniently close to everyday amenities. The 2 acre property offers a wonderful sense of openness, with plenty of room to enjoy the outdoors, including putting greens for practicing your golf game. The right side of the home is designed for recreation and fitness, featuring a half court basketball area that leads into an above ground pool room with a jetted swim pool for exercising against the current. A welcoming porte cochere leads into a large entry area with dual staircases that open to an upstairs office and landing. From here, enjoy expansive views of the mountains and ocean, an ideal spot for working from home. Upstairs on the right side are three bedrooms, each with its own bathroom, along with a generous laundry area. The left side of the upper level is dedicated to the main suite, which includes a spacious bedroom, a large dressing room with built-in storage, and a well appointed bathroom. A private staircase connects the main suite to the kitchen, dining, and family gathering areas below. The kitchen sits at the center of the home, designed so the cook remains part of the conversation and activity. Additional features include a three-bay garage with space for vehicles and hobbies, an electric vehicle charging station, and solar panels that help keep energy costs down. A separate single-story cottage offers approximately 1,000 square feet with two bedrooms and two baths, perfect for hosting guests or accommodating extended family. Bright and airy, it features a comfortable living room, a separate dining space, a garage, and a covered lanai where you can enjoy the island breeze. This property is designed for comfortable everyday living. Schedule a private showing with your agent today and come see it for yourself.

2673 Kamaile St, Wailuku

Listing courtesy of Compass-W.

$1,374,000
3 Beds ⋅ 3 Baths ⋅ 408465 MLS ⋅ Fee Simple Tenure
Beautiful home with in-ground pool and spa on spacious corner lot in the highly desirable Kealohilani neighborhood at Kehalani. Incredible views of the North Shore, Haleakala, and West Maui mountains from all throughout the house and pool area. 5 split system A/C units keep the entire 3 bedroom, 2.5 bathroom home comfortable. The photovoltaic system helps keep things affordable. This only seven year old home, just had the exterior professionally painted. Stamped cement walkway and pool deck, over 100' of tight joint rock wall, Privacy fence, and gates create an ideal outdoor sanctuary. 9' ceilings and large windows add to the spacious feeling throughout the home. Conveniently located, near shopping, hospital, airport, Iao Valley, golf, and ocean activities. Please check out the video link above.

100 Lili Lehua St, Wailuku

Listing courtesy of Haleakala Realty, LLC.

$3,849,000
4 Beds ⋅ 6 Baths ⋅ 407886 MLS ⋅ Fee Simple Tenure
Welcome to Hale Ho’omalu, “a place of peace and content” located in the exclusive gated enclave of Maluhia Country Ranches, this extraordinary custom estate exudes opulence, ultimate privacy and a one-of-a-kind ambiance where awe inspiring ocean and North shore coastal views are the theme. This unparalleled offering hosts a spacious, well thought out floorplan to accommodate your entourage in this single level layout with four separate en-suites and 5.5 baths with multiple indoor/outdoor spaces that seamlessly integrate indoor/outdoor living. The expansive master suite with private lanai and integrated personal office space is sure to impress with continuous views, vaulted ceilings and incredible natural light throughout. Be compelled to enjoy the expansive views from the multilevel custom Brazilian hardwood wood deck that adorn the colossal infinity edge saltwater pool with incorporated 10-person hot tub, ideal for the discerning lap swimmer. On the lower pool deck level, the views continue where whale spotting, magnificent sunrises and entertaining with your favorite libations will create lasting memories. Further exploring will lead you to a private wellness area with a full gym and a spacious spa inspired pool bathroom and sauna with relaxation in mind. This incredible estate boasts many additional amenities such as a 49 panel solar array with 4 tesla power wall batteries, fiber optic internet throughout, a proper chef’s kitchen with commercial grade stainless appliances and gas cooking, a spacious 3 car garage and multiple water features/fountains throughout the impeccably manicured grounds. The meticulous nature of the seller and pride of ownership is highly evident. Home is sold fully furnished and turn key with a UTV machine to explore the 2.25 acres with ease. Schedule your private showing today!

39 Lahaole Pl Unit 14, Wailuku

Listing courtesy of Coldwell Banker Island Prop-KP.

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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.