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1544 Halama St, Kihei
$7,770,000
4 Beds ⋅ 3 Baths ⋅ 411096 MLS ⋅ Fee Simple Tenure
Situated along one of South Maui’s most coveted oceanfront streets, 1544 Halama Street presents a rare opportunity to create an extraordinary luxury estate, with years of architectural planning, engineering, and permitting already completed. Following approximately five (5) + years of planning and design, this exceptional property offers approved architectural plans, structural engineering, building permits, and Special Management Area (SMA) approval, allowing the next owner to move forward without starting the lengthy entitlement process from scratch. A particularly compelling aspect of this opportunity is the approved renovation’s ability to preserve much of the existing residence’s oceanfront footprint. Given today’s increasingly restrictive shoreline setback requirements and SMA regulations, achieving a comparable design, scale, and proximity to the ocean could be extremely challenging, if not impossible, through a new permitting process. The thoughtfully designed plans envision a spectacular private oceanfront compound featuring expansive indoor-outdoor living spaces, a beautifully reimagined main residence, a swimming pool, and a separate two-story structure with an upstairs ohana and garage parking below. The design emphasizes a seamless connection between the home and the ocean, creating an exceptional setting for entertaining, relaxation, and enjoying the Maui lifestyle. With the architectural vision established and major approvals in place, the next owner can bring this remarkable estate to life while personalizing the interior finishes to reflect their own style and preferences. Opportunities to acquire oceanfront property with this level of planning, design, and permitting are exceptionally limited. At 1544 Halama Street, the value extends well beyond the land itself—it lies in the opportunity to create a legacy oceanfront estate in a location where comparable development potential may no longer be attainable.

1544 Halama St, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

3234 S Kihei Rd, Kihei
$35,000,000
3 Beds ⋅ 5 Baths ⋅ 410926 MLS ⋅ Fee Simple Tenure
Close to an acre on Keawakapu Beach, where South Kihei Road ends and Wailea begins. Roughly 170 feet along the water lets the homes stand far back behind a wide green lawn and a grove of tall coconut palms. Look west and Kaho'olawe and Lanai fill the horizon, with sunsets in the ocean in every season. The primary residence sits under a great thatched roof, framed in Douglas fir and lined in woven bamboo. The great room rises into the trusses and opens fully to a covered stone lanai. Grass comes next, then the sandy beach. The primary suite is tucked under the ridgeline upstairs, where glass panels fold back to a deck over the sand. A second building stands on the far side of the grounds, with guest quarters on its upper floor. This Ohana has a separate entry, two bedrooms each with its own bath, and a lanai and balcony facing the sea. Between the homes, a freeform pool curves through natural rock, hiding a grotto and a slide, with a shallow ledge for lounging and an elevated spa. This bohemian luxury property is truly a unicorn. Oceanfront land like this is uncommon in Maui. Designed by Ike Kligerman Barkley. Offered fully furnished and in excellent condition.

3234 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (L).

12 Nohokai St, Kihei
$1,385,000
3 Beds ⋅ 2 Baths ⋅ 410591 MLS ⋅ Fee Simple Tenure
Aloha and welcome to 12 Nohokai St, a corner lot on the sunny side of South Maui! Multi-living options on a large lot with the potential to expand. The large lot and layout of the property exude a relaxed and spacious feel. The location of the property is well desired as it's across the street from Yee's Orchards, a block away from McDonald's, schools, shopping, dining out, a gym, Kihei Aquatic Center and oh yeah, don't forget the beach! The property has been well taken care of over the years! The main house has 3 bedroom, 2 baths with a large carport. There is a separate laundry room and a storage room off the carport. The main house was remodeled in 2024 with Formica countertops, wood cabinets, newer appliances and luxurious vinyl plank flooring. The detached cottage has 2 bedrooms with 1 bath and was remodeled in 2022. Each dwelling has their own driveways. If you're looking for a place to live and or an investment property, 12 Nohokai St is one to see! Added bonus!! This property is designated Business Community Plan. A relative of the Sellers holds an Active Hawaii Real Estate license. Buyer(s) to participate in Sellers 1031 Exchange at no cost to the Buyer(s). *Attention investors! Sellers are also selling the adjacent lot, 1164 S.Kihei Rd MLS #410589. Combined the two lots total 5 rental units on 23,714 sqft or 0.5444 acres. The property generates great rental income and is designated “Business/Commercial” on the Kihei Community Plan, opening up many possibilities for future development.

12 Nohokai St, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

1164 S Kihei Rd, Kihei
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 410589 MLS ⋅ Fee Simple Tenure
Aloha and welcome to 1164 S.Kihei Rd on the sunny south side of Maui! Multi-living options on a large lot with the potential to expand. The large lot and layout of the property exude a relaxed and spacious feel. Great location of S.Kihei Rd, across the street from Yee's Orchards, a block away from McDonald's, shopping, dining out, schools, a gym, Kihei Aquatic Center and oh yeah, don't forget the beach! The property has been well taken care of over the years! The main house has 3 bedrooms with 2 baths, today it is utilized as 2 bedrooms with 1 bath and a 1 bedroom with 1 bath (size of a studio). The main house was remodeled in 2023 with Quartz countertops, wood cabinets, and luxurious vinyl plank flooring. The detached cottage has 2 bedrooms with 1 bath. The cottage was remodeled in 2022 with granite countertops, wood cabinets and luxurious vinyl plank flooring. The property offers lots of space for parking and each dwelling has their own covered carport. The yard is easy to maintain too! If you're looking for a place to live and or an investment property, 1164 S.Kihei Rd is one to see! Added bonus, his property is designated Business Community Plan. Licensed Hawaii Real Estate agent is part owner. Buyer(s) to participate in Sellers 1031 Exchange at no cost to the Buyer(s). *Attention investors! Sellers are also selling the adjacent lot, 12 Nohokai St. MLS # 410591. Combined the two lots total 5 rental units on 23,714 sqft or 0.5444 acres. The property generates great rental income and is designated “Business/Commercial” on the Kihei Community Plan, opening up many possibilities for future development.

1164 S Kihei Rd, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

3146 S Kihei Rd, Kihei
$20,500,000
3 Beds ⋅ 4 Baths ⋅ 410482 MLS ⋅ Fee Simple Tenure
Welcome to the quintessential Maui oceanfront estate, ideally situated on Keawakapu Beach—widely regarded as one of Maui’s most beautiful stretches of sand. This timeless Hawaiian residence embraces its unrivaled setting with approximately 2,500 square feet of covered outdoor living space, perfectly suited for beachfront lounging and entertaining. Designed with architectural integrity and island sensibility, the home features traditional Dickey rooflines topped with black glazed tiles imported from Japan. A electronic gate opens into a private, walled compound that includes the main residence, a detached two-bedroom guest cottage (Ohana), a two-car garage with workshop, and a beautifully landscaped courtyard with a pool and spa. The single level main home offers soaring 16 foot ceilings in the great room with a working fireplace serving as the centerpiece, complemented by an open-concept kitchen and expansive glass walls that frame breathtaking ocean views while preserving privacy. The main residence includes three bedrooms and four bathrooms, all designed with ease of access and comfort in mind. The detached two-bedroom, one-bath Ohana is finished to the same high standard, ideal for visiting family or guests. Set on 0.8 acres, the estate flows seamlessly from lush lawn to the beach, where a protective lava rock point cradles the property and collects soft white sand along this dramatic, crescent-shaped shoreline—one of the largest and most coveted on the island. A rare opportunity to own a true legacy property on Maui’s finest beachfront. **Disclosure** Some pictures have been Virtually Re-Staged and noted.

3146 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

221 Mahie Pl, Kihei
$1,395,000
3 Beds ⋅ 3 Baths ⋅ 410473 MLS ⋅ Fee Simple Tenure
Highly motivated seller - sale must close by end of this year. House and cottage with current rents totaling $7,400/month. Located along a quiet cul-de-sac at the edge of Wailea, this two-home property is a blend of resort proximity and easygoing island living. Just steps from the white sand of Keawakapu Beach, this south Kihei setting is one of Maui's most coveted stretches of coastline. This 3 bedroom, 3 bathroom residence has high ceilings and a fully detached cottage with its own private yard — a configuration built for extended family, rental income, or simply room to breathe. Step inside the main home and the great room opens up beneath soaring ceilings, where natural light pours across an open floor plan. Thoughtful recent updates include new appliances in the house and cottage. The primary suite indulges with an oversized jacuzzi tub and dual vanities, a quiet retreat after a day at the beach. Outside, life shifts to the lanai — spacious, covered, and made for entertaining, with a built-in barbecue area ready for sunset gatherings. A stately Royal Poinciana tree anchors the beautifully landscaped yard in cooling shade, while the two-car garage keeps boards, bikes, and beach gear neatly out of sight. The detached cottage is its own quiet escape. PV solar keeps energy costs down. The mature landscaping makes one feel connected to nature. Two homes. One address. All of South Maui's best, right outside the door.

221 Mahie Pl, Kihei

Listing courtesy of Hawaii Life (W).

279 Olani Pl, Kihei
$1,225,000
3 Beds ⋅ 2 Baths ⋅ 409196 MLS ⋅ Fee Simple Tenure
TWO HOMES, ONE PROPERTY. 279 Olani Place offers 1,776 total square feet of living space across two attractive dwellings: a 3-bedroom, 2-bath open-plan main house and a 1-bedroom, 1-bath ohana. If you are looking for an excellent investment opportunity, a private family compound, or a home for yourself with solid rental income on the side, this one deserves your attention. This well-maintained property features a 3-bedroom, 2-bath open-plan main house and a 1-bedroom, 1-bath ohana, located just two blocks from the longest stretch of sandy beach on Maui. Situated on a quiet cul-de-sac on a private flag lot set back from the street, the property offers a fully enclosed, low-maintenance compound in one of the island’s most convenient locations, close to so much of what Maui has to offer. In 2018, the main house kitchen and bathrooms were renovated and new roofing was installed. In 2024, new luxury plank flooring was installed throughout the interior, and both generous decks were replaced, including stainless steel railings and an outdoor shower on the back deck—perfect after a trip to the beach. Also in 2024, a new split AC system was installed. The neighboring ohana is fully self-contained with its own electric meter, brand-new split AC system, and solar water heater. Its kitchen and bathroom were renovated in 2018. Next to the ohana is an outdoor shower and a truly therapeutic, high-end hot tub, ready to soothe your aching muscles any time of day or night. Currently, the house and ohana together would generate approximately $6,700 in monthly rental income, offering an excellent opportunity for investors. The property also works beautifully for a family that wants to live close to the beach while having extended family nearby—or potentially renting the ohana for additional income. This property offers tremendous flexibility and is ready for you to move in, so you can just enjoy being in this special place.

279 Olani Pl, Kihei

Listing courtesy of Real Broker.

3060 S Kihei Rd, Kihei
$24,500,000
4 Beds ⋅ 6 Baths ⋅ 408751 MLS ⋅ Fee Simple Tenure
One-of-a-Kind Keawakapu Beachfront Estate in one of Maui’s most coveted oceanfront settings, offering an extraordinary blend of irreplaceable beach proximity, modern structural integrity, and timeless refined island design. The residence was completely rebuilt from the foundation up, completed in 2013—retaining only the original pool and foundation to preserve its rare, grandfathered beachfront setback. The result is a fully reimagined wood-framed home enhanced with structural steel beams, allowing for expansive open spans and a modern layout. The estate includes a spacious main residence, separate guest home, and three-car garage, creating a private compound ideal for multigenerational living or luxury hosting. Designed for unforgettable gatherings, multiple indoor and outdoor living spaces flow effortlessly to a spectacular resort-style pool with slide, hot tub, waterfalls, and dramatic rock grotto. A distinctive basement level serves as the ultimate retreat, featuring a game room with custom Koa wood bar, in-home gym, craft room, and additional guest suite with full bath. Lush tropical landscaping, sauna, and multiple outdoor showers enhance the resort-caliber experience. The chef’s kitchen and dining area showcases Sepalle wood detailing and striking Labradorite granite countertops, blending warmth with sophistication. The primary suite is a sanctuary, complete with a spa-inspired bath featuring a floating tub, private sundeck, and panoramic Haleakala views. Throughout the property, incredible details and textures create a custom, curated feel. Meticulously rebuilt in 2013 to combine modern structural capability with an irreplaceable oceanfront location, this legacy beachfront estate represents a rare and irreplaceable offering on Maui.

3060 S Kihei Rd, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

1011 S Kihei Rd Unit B, Kihei
$1,599,000
5 Beds ⋅ 4 Baths ⋅ 408728 MLS ⋅ Fee Simple Tenure
Experience the essence of Maui coastal living and investment potential all in one. Located directly across from the beach on S. Kihei Road, this versatile property offers four separately rentable units for maximum income and flexibility. The main home is thoughtfully configured into three distinct living spaces—an upstairs 3-bedroom / 1.5-bath, and two separate 1-bedroom / 1-bath units downstairs. A detached 2-bedroom / 1-bath cottage provides additional income or ohana living options. Each dwelling enjoys its own yard space, beautifully landscaped with tropical flowers and fruit trees, and fully fenced for privacy. The main house includes a shared coin-operated laundry, while the cottage enjoys its own private laundry. With ample parking, no HOA or maintenance fees, and shared ownership of the access drive lot included in the sale, this property represents one of the best ROI opportunities in Kihei. Perfect for multi-generational living or as a fully occupied investment, this property is just minutes from Kihei’s charming town center, boutique shops, parks, and world-class ocean activities. Discover the rare combination of lifestyle, location, and long-term value—right here in the heart of South Maui. Photos have been virtually staged.

1011 S Kihei Rd Unit B, Kihei

Listing courtesy of Compass-W.

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