Wailuku Homes with Pool

Welcome to Wailuku, a charming town nestled in the heart of Maui, Hawaii. Known for its rich history, vibrant culture, and stunning natural beauty, Wailuku offers a unique blend of island living and small-town charm. As the county seat of Maui, this quaint town is surrounded by lush landscapes, majestic mountains, and the tranquil waters of the Pacific Ocean, making it an idyllic place to call home.

Wailuku is steeped in Hawaiian heritage, with numerous historical sites and cultural landmarks that tell the story of the island's past. Residents and visitors alike can explore the beautiful Iao Valley State Park, where the iconic Iao Needle rises dramatically from the lush greenery, providing breathtaking views and hiking opportunities. The town's lively downtown area is filled with eclectic shops, delightful eateries, and local art galleries, creating a vibrant atmosphere that celebrates the spirit of Maui.

For those seeking a slice of paradise, Wailuku offers an array of homes with pools, perfect for enjoying the island's warm climate and stunning sunsets. Imagine lounging by your private pool, surrounded by tropical foliage, while the gentle trade winds rustle through the palm trees. These homes not only provide a luxurious retreat but also serve as an ideal space for entertaining friends and family or simply unwinding after a day of exploring the island.

With its perfect blend of natural beauty, cultural richness, and modern amenities, Wailuku is a place where you can truly live the Hawaiian dream. Whether you're looking to buy a home with a pool or simply explore this enchanting town, Wailuku welcomes you with open arms.

Newest Wailuku Homes with Pool

$545,000

2 Beds ⋅ 2 Baths ⋅ 409765 MLS ⋅ Fee Simple Tenure ⋅ Iao Gardens BLDG.

Welcome home to this beautifully upgraded 2-bedroom, 2-bath Corner Unit with Impressive Views of Iao Valley, the West Maui and Waihee Mountains, and Ocean Views from the Lanai and Primary Suite. With 839 SF of thoughtfully designed living space, this inviting floorplan offers both comfort and privacy, featuring a spacious great room that separates the primary suite from the second bedroom and bath. Inside, you’ll find tasteful updates throughout, including luxury vinyl plank flooring, fresh interior paint, refreshed white cabinetry, granite countertops, new bathroom vanities, and a generous walk-in storage closet. The convenience of an in-unit washer and dryer adds to the ease of everyday living. Glass doors from both bedrooms open directly to the lanai, allowing refreshing tradewinds to flow naturally through the home and creating a seamless indoor-outdoor lifestyle. Surrounded by a mature tropical landscape, the lanai features a built-in bar with footrest — the perfect place to enjoy morning coffee, outdoor dining, or simply relax while taking in the scenic ocean and mountain views. This secure and well-maintained building offers an elevator, covered parking, an inground pool, and a barbecue deck area designed for enjoying Maui’s year-round island lifestyle. This Unit includes one assigned parking stall with additional nearby street parking and the Wailuku Parking Structure. Ideally located in the Heart of Historic Wailuku Town, you’ll enjoy easy access to restaurants, shopping, entertainment, medical facilities, schools, parks, banks, churches, and government offices. This property is perfectly suited as a primary residence, second home, or an investment opportunity. Schedule your private showing today and discover a beautiful condo to call home, where gentle tradewinds, lush tropical surroundings, and scenic mountain and ocean views create a peaceful island retreat. As a Bonus, furnishings & housewares are included!

2180 W Vineyard St Unit 106, Wailuku

Listing courtesy of Maui Real Estate Advisors LLC.

$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.

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