Wailuku Homes with Pool

Wailuku Homes with Pool

Welcome to Wailuku, a charming town nestled in the heart of Maui County, Hawaii. This vibrant community is not just the county seat of Maui; it’s a place where rich history meets stunning natural beauty. Surrounded by lush landscapes and breathtaking views of the West Maui Mountains, Wailuku offers an idyllic setting for those seeking a serene lifestyle infused with the spirit of Aloha.

Wailuku is known for its warm, welcoming atmosphere and a strong sense of community. With a blend of historic architecture and modern amenities, residents enjoy easy access to local shops, delightful eateries, and cultural experiences, including the iconic Iao Valley State Park, where the majestic Iao Needle rises dramatically against the sky. Whether you're exploring the quaint streets, attending local festivals, or enjoying the vibrant arts scene, Wailuku has something for everyone.

For those seeking a slice of paradise, Wailuku offers an array of homes with pools, providing the perfect oasis for relaxation and entertainment. Imagine lounging by your private pool, surrounded by tropical gardens, while the gentle Hawaiian breeze whispers through the palm trees. These homes are designed not only for comfort but also to embrace the outdoor lifestyle that is quintessentially Maui.

If you’re looking for a place where every day feels like a vacation, Wailuku is the perfect choice. With its stunning homes featuring pools and the captivating beauty of the island, you’ll find a true sense of belonging in this remarkable town. Come experience the magic of Wailuku, where your dream home awaits!

Newest Wailuku Homes with Pool

$899,000
2 Beds ⋅ 2 Baths ⋅ 410311 MLS ⋅ Leasehold Tenure ⋅ Kanai A Nalu BLDG.
Your front row seat to paradise and oceanfront luxury awaits at Kanai A Nalu #417! This exceptional 4th-floor 2-bedroom, 2-bath residence offers breathtaking panoramic views of the Pacific Ocean, Sugar Beach, Haleakala, and spectacular year-round sunrises. Extensively remodeled with over $200,000 in premium upgrades, this turnkey condominium showcases an open-concept design with a beautifully appointed kitchen, quality cabinetry, stone countertops, stainless steel appliances, luxury flooring, designer lighting, and tastefully remodeled bathrooms. Enjoy year-round comfort with three split-system A/C units serving the living area and both bedrooms. The spacious oceanfront lanai is the perfect place to relax while watching humpback whales (seasonal), sea turtles, and the soothing waves along Maui's shoreline. Kanai A Nalu is a heavily booked short-term vacation rental, making this an outstanding opportunity for both personal enjoyment and investment potential. Ideally located on Maui's longest white sand beach, the complex features a heated oceanfront pool, BBQ area, elevator, lush tropical landscaping, and convenient parking, all just minutes from Ma?alaea Harbor, restaurants, shops, golf, Kahului Airport, Wailea, and West Maui. Offered fully furnished and move-in ready. This is a leasehold property.

250 Hauoli St Unit 417, Wailuku

Listing courtesy of Century 21 Island Homes.

$679,000
2 Beds ⋅ 2 Baths ⋅ 409819 MLS ⋅ Leasehold Tenure ⋅ Maalaea Yacht Marina BLDG.
Best in the complex! Top-corner Penthouse unit featuring a wraparound lanai and stunning ocean views. No expense has been spared in this beautifully maintained condo. Long-term rental only in a fantastic, well-managed complex. The pictures truly tell the story! This is a Leasehold property.

30 Hauoli St Unit 410, Wailuku

Listing courtesy of Coldwell Banker Island Prop-Ku.

$599,000
1 Beds ⋅ 1 Baths ⋅ 409767 MLS ⋅ Fee Simple Tenure ⋅ Island Sands BLDG.
Rarely does a one bedroom residence on Maui's South Shore offer this kind of presence. Positioned on the third floor of Island Sands, this beautifully appointed oceanfront condominium opens to sweeping Pacific views that stretch from the palms framing the lanai all the way to the neighbor islands on the horizon. The interior is warm and well finished throughout, with wood look flooring, white cabinetry, stainless steel appliances, and coastal themed artwork and decor that give the space a genuine sense of place. The generous lanai is oriented to capture unobstructed ocean and palm tree views and serves as the true heart of the home. Offered turn key and move in ready, this unit is currently active in a successful vacation rental program. In-unit washer and dryer, dishwasher, air conditioning, community pool, elevator access, and one deeded parking stall complete this exceptional offering in one of South Maui's most sought after oceanfront communities.

150 Hauoli St Unit 303, Wailuku

Listing courtesy of Sunny Maui Vacations.

$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.

$510,000
2 Beds ⋅ 2 Baths ⋅ 409737 MLS ⋅ Fee Simple Tenure ⋅ Iao Gardens BLDG.
Perched on the top floor as a coveted corner unit, Iao Gardens Unit 302 is a thoughtfully updated 2 bedroom, 2 bathroom residence with 839 square feet of comfortable living space with privacy, views and Central Maui convenience. Vaulted ceilings with upper jalousie windows invite refreshing trade winds and abundant natural airflow, while expansive windows frame beautiful Haleakala views and bring natural light into the home. From the primary bedroom, enjoy ocean views that add to the unit’s unique sense of place. Thoughtfully updated, the residence features honey oak luxury vinyl plank flooring throughout the main living spaces and recently installed carpet in the bedrooms for added comfort. The lanai overlooks Vineyard Street toward Haleakala, creating the perfect setting to enjoy cool breezes year round. Customized storage solutions maximize functionality, while a large loft provides valuable additional storage space. Kitchen and bathroom remodels offer stylish and functional updates to the home. The primary ensuite stands out with honeycomb tile, wallpaper and custom wood accents that add warmth and personality. A custom built Murphy bed in the second bedroom creates exceptional flexibility, allowing the space to easily function as a guest room, office, or creative retreat. Located within a secured elevator building, Iao Gardens is a quiet community with a pool and barbecue area, conveniently positioned near County offices, Wailuku Elementary, the library, Market Street, restaurants, shops, and Wailuku First Fridays. Unit 302 is among the rare few with two deeded parking stalls, plus close proximity to Maui Memorial Hospital, Iao Valley, and North Shore surf. Listing agent is owner.

2180 Vineyard St Unit 302, Wailuku

Listing courtesy of Island Sotheby's International Realty(W).

$550,000
2 Beds ⋅ 2 Baths ⋅ 409736 MLS ⋅ Fee Simple Tenure ⋅ Iao Gardens BLDG.
Located in the heart of Wailuku, Iao Gardens offers convenient Central Maui living close to government buildings, schools, medical facilities, restaurants, shopping, parks, and other local businesses. Nearby Iao Valley State Monument, home to the iconic Iao Needle, is just minutes away. This secured complex features an elevator, one covered parking, swimming pool, BBQ and car wash amenities. The spacious 839 sqft unit enjoys refreshing breezes, views overlooking Happy Valley, and a partial ocean view. The well-maintained interior includes upgraded kitchen and bathroom finishes, creating a clean and comfortable living space in a convenient Wailuku location. The primary shower has a fiberglass molded one piece seated shower on a steel frame.

2180 Vineyard St Unit 204, Wailuku

Listing courtesy of Coldwell Banker Island Prop(S).

$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.

$475,000
2 Beds ⋅ 2 Baths ⋅ 409457 MLS ⋅ Fee Simple Tenure ⋅ Iao Gardens BLDG.
Tucked into the heart of Wailuku, this 2-bedroom, 2-bath, third-floor condo in a secured building offers comfortable living in a highly convenient location. Situated less than a 1 mile radius of local shops, restaurants, lounges, markets, medical facilities, and county buildings. High ceilings create an open, airy feel, while expansive West Maui Mountain views add a natural sense of calm. The layout flows easily between the kitchen and living area, making the space both functional and inviting. Located less than 5 miles from the airport, Central Kahului and North Shore beaches like Kanaha—known for its world-class windsurfing and kiteboarding—this is a central base that supports both daily life and an active island lifestyle. A great opportunity for a buyer looking to make it their own, this unit offers potential to add value over time. Whether you’re searching for a primary residence or an investment, this is a well-located option worth exploring.

2180 Vineyard St Unit 308, Wailuku

Listing courtesy of Keller Williams Realty Maui-Ka.

$975,000
2 Beds ⋅ 2 Baths ⋅ 409309 MLS ⋅ Fee Simple Tenure ⋅ Lauloa BLDG.
Lauloa 209 — oceanfront, fully renovated, and ready to go. Step inside to wide-plank floors, solid wood cabinetry, new countertops, and split A/C throughout. The living area opens to a lanai with unobstructed views across Ma'alaea Bay to Haleakala. Primary suite has an ensuite bath and ocean views. The building sits right on the water with a pool, lawn, and easy access to Ma'alaea Harbor, Sugar Beach, and nearby restaurants. Turnkey condition with proven rental history. Second home, investment, or both — this one checks the boxes.

100 Hauoli St Unit 209, Wailuku

Listing courtesy of Luxe Maui Properties LLC.

$430,000
2 Beds ⋅ 2 Baths ⋅ 409306 MLS ⋅ Leasehold Tenure ⋅ Kanai A Nalu BLDG.
Welcome to Kanai A Nalu 208 a beautifully renovated second-floor unit offering views over the pool and out to the ocean. This inviting 2-bedroom, 2-bathroom condo has been tastefully updated with newer appliances, air conditioning, a decorative wall mural, and stylish furnishings throughout. Whether you’re seeking a primary residence, second home, or a short term rental opportunity, this property checks all the boxes. Kanai A Nalu is just steps from Maui’s longest stretch of sandy shoreline - Sugar Beach. and is centrally located in Ma?alaea with convenient access to all parts of the island. You’re minutes from shopping, restaurants, the Maui Ocean Center, and Maalaea Harbor. Residents and guests enjoy a renovated, solar-heated pool beautifully lit at night for added ambiance and a new BBQ area perfect for outdoor gatherings. This is a leasehold property with one of the longest remaining terms available. Lease rent is fixed at $1,004 /month from 2016–2026 .

250 Hauoli St Unit 208, Wailuku

Listing courtesy of Hawaii Life (W).

$999,000
2 Beds ⋅ 2 Baths ⋅ 409251 MLS ⋅ Fee Simple Tenure ⋅ Maalaea Banyans BLDG.
Welcome to Unit 412 at Maalea Banyans—an inviting 2 Bedroom 2 Bathroom oceanfront retreat nestled in the heart of Maalaea. This well-positioned condo offers breathtaking views of the Pacific, where you can enjoy stunning sunrises, seasonal whale watching, and the soothing sound of waves right from your private lanai. Inside, the unit features a bright and airy layout designed to maximize natural light and coastal breezes. The open-concept living and dining area flows seamlessly, creating a relaxed island atmosphere perfect for both everyday living and entertaining. Large windows and sliding glass doors bring the outdoors in, enhancing the tranquil beachfront experience. Convenience is a standout feature of this location. Maalaea Harbor is just moments away, offering easy access to world-class snorkeling, boating excursions, and waterfront dining. You’re centrally located between Lahaina and Kihei, making it simple to explore all that Maui has to offer—from pristine beaches and golf courses to shopping and local markets. The nearby Maui Ocean Center and quick access to major roadways add to the ease and enjoyment of daily life.Contact us today for your own private tour.

190 Hauoli Rd Unit 412, Wailuku

Listing courtesy of Keller Williams Realty Maui-Ki.

$799,000
2 Beds ⋅ 2 Baths ⋅ 409219 MLS ⋅ Fee Simple Tenure ⋅ Island Sands BLDG.
Highly sought-after oceanfront top-floor condo in one of Maalaea’s most desirable fee simple buildings. Enjoy spectacular ocean and outer island views from your private covered lanai. This upgraded residence features a beautifully remodeled kitchen with granite countertops, an updated bathroom with a modern vanity and walk-in tiled shower, and tile flooring throughout.The spacious primary bedroom has been thoughtfully reconfigured to create an additional flex space - perfect for a dining area, home office, or extra sleeping quarters. Offered fully furnished, this unit includes one assigned parking stall and is ideally located just a short stroll to the beach, Maalaea Harbor, the Maui Ocean Center, shops, and restaurants.Community amenities include an oceanfront swimming pool and barbecue area.

150 Hauoli St Unit 602, Wailuku

Listing courtesy of Hawaii Life (W).

Start Your Search