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$4,500,000
7 Beds ⋅ 5 Baths ⋅ 202611944 MLS ⋅ FS - Fee Simple Tenure
3 structures. Multiple living spaces. ¾ acre. 180-degree panoramic ocean/island views. Above Wailea in Maui Meadows, this pole-style property offers privacy, flexibility, and multiple residences. The MAIN RESIDENCE:5 beds and 4.5 baths across three levels. The 1st level includes a kitchen & living room opening to an ocean-view lanai, primary bed & 2nd bed with Jack-and-Jill bath. The level below offers a 2nd living area, an ensuite bedroom with an adjoining bed, powder room, office, laundry, and another lanai. The 3rd level is a 1-bed apartment with kitchen, living room, and bath. Outside is a pool, tiki bar, sauna, BBQ area, garage, and carport. The 2ND STRUCTURE:2-bed, 1-bath ohana with kitchen, living room, 3-car garage, & office/studio. The 3RD STRUCTURE: 1-bed, 1-bath cabin. Turn-key & fully furnished, the property includes 71 solar panels, smart-home features, tropical landscaping, koi pond, waterfalls, and mango, avocado, Meyer lemon, & banana trees. The kitchen features a Wolf range, Sub-Zero refrigerator/freezer, & Fisher & Paykel appliances. Views include Kaho?olawe and Lana?i. Rarely available combination of acreage, multiple living spaces, & resort amenities.

3264 Keha Drive, Kihei

Listing courtesy of eXp Realty.

$1,950,000
4 Beds ⋅ 2 Baths ⋅ 202526423 MLS ⋅ FS - Fee Simple Tenure
RARE offering, a main residence plus a private detached Ohana on 2.86 acres in Haiku. Discover this truly magical retreat featuring 2 homes. privately positioned on a premium corner lot, this retreat is framed by lush tropical greenery and crowned with the elegance of solid copper roofing, a rare statement of craftsmanship and longevity. A short distance from the main home which is 4 bedrooms 2 Bath and sits a generous detached Ohana, complete with 1 bedroom, 2 baths, and spacious living areas that are ideal for multi-generational living, guests, or income potential. The grounds are truly remarkable. Breezy, peaceful, and full of natural beauty this property embodies the best of Upcountry Maui living.

44 Kaupakalua Road, Haiku

Listing courtesy of Five Star Realty, Inc..

$1,494,000
1 Beds ⋅ 2 Baths ⋅ 202606780 MLS ⋅ FS - Fee Simple Tenure ⋅ Whaler On Kaanapali Beach BLDG.
Welcome to Unit 670 at The Whaler condominium—a rare opportunity to own a slice of paradise, perfectly positioned on the best part of world-famous Kaanapali Beach. Relax on your large ocean view lanai, stroll the beach for year-round breathtaking sunsets, swimming, snorkeling and fun in the sun. The Whaler’s prime location also places you within a short convenient distance to Whalers Village, where you’ll find a vibrant mix of restaurants, shops, and oceanfront dining. A magnificent blend of gorgeous ocean views and heavenly bliss, you’ll love this larger one bedroom and studio combination with 2 full bathrooms ideally located in Tower 2! Loads of closet space abound for all your storage needs and queen size murphy bed that adds versatility to the unit. Whether you’re seeking a full- time residence, vacation home, or income-producing rental, this property is in excellent “as is” condition and delivers on every level. Experience the best of Maui living—sunsets, sand, and everything in between.

2481 Kaanapali Parkway Unit 670, Lahaina

Listing courtesy of Five Star Realty, Inc..

$549,000
3 Beds ⋅ 2 Baths ⋅ 202606068 MLS ⋅ LH - Leasehold Tenure
This is a Department of Hawaiian Home Lands (DHHL) leasehold property. Buyers must be approved and qualified through DHHL to purchase. This Wailuku Hawaiian Homestead property offers a solid opportunity for an eligible Hawaiian beneficiary to purchase in an established homestead community. The home features 3 bedrooms and 2 bathrooms with approximately 1,080 square feet of interior living space. New Solar water heater in 2025, New window screens 2026. The property sits on an 8,455 square foot lot, providing usable outdoor space for gardening, gathering, or other homestead-related uses. Located in Wailuku, the home benefits from a central Maui location with convenient access to schools, shopping, medical facilities, and everyday essentials, while remaining within a residential neighborhood. Call your favorite agent if you have questions.

39 Hoola Hou Street, Wailuku

Listing courtesy of Coldwell Banker Realty.

$449,000
1 Beds ⋅ 1 Baths ⋅ 202613820 MLS ⋅ FS - Fee Simple Tenure ⋅ Sunset BLDG.
1BR/1BA at Kahana Sunset on Keonenui Bay — one of West Maui's most beloved beachfront communities. This 952 SF unit features two large lanais and a primary bedroom with sweeping ocean views of the Pacific, Molokai, and Lanai. Embrace the vintage vibe or reimagine the interior into your dream Maui retreat. In-unit washer/dryer, full kitchen, two storage closets, and covered parking included. Complex amenities include a 60-ft heated pool, wading pool, two oceanfront BBQ areas, and the Keonenui gathering room overlooking the bay. Step directly onto a semi-private sandy beach for swimming, snorkeling, and paddleboarding. Sea turtles frequent the shoreline and humpback whales appear each winter. Short-term vacation rental allowed — not on the Minatoya List. Fee Simple ownership. Located between Kapalua and Kaanapali, minutes to world-class golf, dining, and shopping. If you have been looking for a cozy beachfront vacation property to make your own, this is the opportunity. All comments, data is provided by seller or seller's representatives. Buyer to confirm all & hold all parties harmless from any discrepancy data in the mls and advertising.

4909 Lower Honoapiilani Road Unit E3E, Lahaina

Listing courtesy of Nathalie Mullinix R. U., Inc..

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.