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$4,500,000
7 Beds 5 Baths 202611944 MLS FS - Fee Simple Tenure
E Komo Mai to Your Own Private Paradise Above Wailea. As you pass through the gates, a lush tropical landscape unfolds. Spread across nearly three-quarters of an acre in the heart of Maui Meadows, this private sanctuary welcomes you home. Cascading waterfalls and a tranquil koi pond greet you upon arrival. Perched high above Wailea on the sun-warmed slopes of Haleakala, this estate commands a 180-degree panoramic view, with Kaho'olawe to the left and Lana'i to the right. Mornings begin slowly, coffee in hand, the ocean below. Evenings end with the sky igniting in color, each sunset an original. Rare in scale and versatility, the main residence offers two living rooms, an attached guest suite, a separate two-bedroom rental, and an additional guest suite. Perfect for multi-generational families or investors. Outside, resort-caliber living awaits: a sparkling pool, sauna, steam room, outdoor bar, and poolside television. Over 72 solar panels and smart home technology reduce energy costs. Offered fully furnished and turnkey, including your own electric car and charging station. Bring your suitcase. Everything else is waiting. Resort Living. Island Privacy. Endless Possibilities.

3264 Keha Drive, Kihei

Listing courtesy of eXp Realty.

$45,000,000
8 Beds 8 Baths 409860 MLS Fee Simple Tenure
An exceptionally rare opportunity to acquire two side-by-side oceanfront properties that creates a private coastal compound in one of South Maui’s most coveted enclaves. Positioned approximately 40 feet above a pristine crescent-shaped white sand beach this offering delivers a setting that cannot be duplicated under current coastal regulations. Behind a gated entry, the combined estate offers unmatched scale, privacy, and flexibility ideal as a legacy family retreat, multi-generational compound, or secure oceanfront enclave. Expansive decks from 2 distinct residences project toward the horizon, capturing sweeping panoramic views from Makena to the West Maui Mountains, with year-round sunsets and an ever-changing Pacific backdrop. A gated footpath leads to a secluded stretch of sand known as “Secret Beach,” offering rare, near-private access just steps from your door. Opportunities of this magnitude—two contiguous oceanfront parcels with elevation, privacy, and direct beach access—are extraordinarily limited. Offered together, this is a chance to secure a one-of-one compound in a supply-constrained market where replacement is simply not possible. Minutes from Wailea’s world-class golf, dining, and shopping, yet worlds apart in privacy and setting. Legacy property. Irreplaceable location. Finite opportunity. **Disclosure, some images have been virtually staged**

4640 & 4650 Makena Rd, Kihei

Listing courtesy of Hawaii Life (W).

$26,500,000
6 Beds 6 Baths 409734 MLS Fee Simple Tenure
THE ULTIMATE MAUI DREAM . .The most sophisticated are no longer asking where to live . .They are asking, “Where can we breathe?” Welcome to The Makena Generational Oceanside Retreat offering resort-style living with smart-home technology, unobstructed ocean & sunset views, Haleakala sunrise views situated on a professionally landscaped one-acre gated and walled tropical estate.The fully operational compound is ready for occupancy offering a vast combination of energy efficiency, self-sufficiency and refined comfort featuring the largest residential Tesla Solar Roof in the US installed in 2024. A unique opportunity to own a private Maui sanctuary of this stature where luxury, wellness and sustainability coexist in harmony. The indoor-outdoor lifestyle is designed for multigenerational living, executive retreats and legacy ownership. In a world moving faster than ever, it is intentionally crafted for life to slow down. Extensively upgraded under the current owner with substantial infrastructure, aesthetic and technology enhancements, the property is now offered well below current replacement cost. The Makena community remains one of Maui’s most coveted luxury destinations. The current property manager creates effortless luxury living with lock-and-leave convenience. The luxurious amenities are endless. The privately separated interior living areas offer exceptional craftsmanship, premium wood finishes, floor-to-ceiling bifold glass doors, elevator, gourmet kitchen, exercise area, massage room, sauna, and steam shower. The dramatic custom water features include a puka lava entry waterfall with pond and interior floor-to-ceiling water feature at the base of the floating staircase. The additional luxury oceanside pool home with its oversized heated pool includes its own gourmet kitchen, Italian brick pizza oven and rear projection entertainment system. Combined with many additional features, the estate offers a total of 8b-8b comfortably accommodating up to 16 guests. Parking is a breeze with a 4+car garage and generous additional parking areas.

7505 Makena Rd, Kihei

Listing courtesy of Compass-W.

$1,465,000
6 Beds 2 Baths 408563 MLS Fee Simple Tenure
Unlock the Endless Possibilities at 251 Manini Place, Kihei, Maui Step into the charm of this distinctive property nestled in a serene South Maui neighborhood. Built in 1973 and situated on a spacious 9,478 sqft lot, this unique offering presents a rare opportunity for multi-generational living or savvy investment potential. The main residence features three separate living units, complemented by a detached 2-bedroom, 1-bathroom ohana cottage set in the backyard. Currently configured as four established family rentals, the property has been occupied by the family and well maintained, reflecting pride of ownership and care. Located just moments from South Maui’s breathtaking beaches, excellent schools, and convenient shopping hubs, this home delivers both tranquility and accessibility. With no HOA fees to contend with, the opportunities are as expansive as the lot itself. Whether you’re dreaming of a home for extended family, envisioning an income-generating rental property, or seeking a blend of both, 251 Manini Place is a rare gem waiting to be discovered. Don’t miss out—contact me today to explore the full potential of this extraordinary property!

251 Manini Pl, Kihei

Listing courtesy of Kokua Realty LLC.

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.