Maui Real Estate - Ask Josh

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Maui Real Estate - Ask Josh

Josh Jerman, RB-19728, Hawaii Life. Realtor-Broker of the Year for the Realtors Association of Maui (2019). Top 100 Realtor in Hawaii 2013-2025

I am a top producing broker with Hawaii Real Estate Brokers. In my spare time, I serve on the Realtors Association of Maui (RAM) Board of Directors, RAM Education Committee and the Hawai‘i Association of Realtors’ State Finance Committee. I am also the founder of the Josh Jerman Foundation, the Josh Jerman Maui Nui Scholarship Fund, and an avid supporter of a number of nonprofit organizations and charities here on the Valley Isle.

05/07/2026

Just listed in Kihei

This 3-bedroom, 3-bath home offers 2,130 square feet of interior space and is priced at $1,665,000. Built in 1997, it sits on nearly 9,400 square feet of lushly landscaped grounds in South Kihei, moments from beaches, golf courses, and the food trucks at South Maui Gardens, with Wailea just a short drive away. The open-concept layout features soaring ceilings and flows seamlessly to a wraparound covered lanai with sweeping views of Haleakala and the Pacific Ocean. A pool, hot tub, and award-winning tropical landscaping including mango, starfruit, banana varieties, and dragonfruit make the outdoor space as impressive as the interior. The lower level includes a second kitchen and additional bedroom, ideal for guests or extended family. Additional highlights include an owned 28-panel photovoltaic system with two Tesla Powerwalls, solar hot water, split-system AC, and a two-car garage.

Message me for more details or to schedule a private showing.

https://www.hawaiilife.com/listings/19-hoolalei-way-kihei-hi-96753-2

04/28/2026

Just listed in Paia

This 3-bedroom, 2.5-bath home offers 1,257 square feet of interior space and is priced at $1,250,000. Built in 2003, it’s ideally located in the heart of Paia, just a short walk from local restaurants, boutique shops, and everyday essentials. The layout is bright and functional, with a seamless connection to over 300 square feet of covered outdoor lanai, perfect for enjoying Maui’s indoor-outdoor lifestyle. The private front and backyard are surrounded by mature tropical landscaping, giving the home a peaceful, tucked-away feel while still being minutes from everything. A one-car garage adds convenience, and the overall setting captures the relaxed, walkable lifestyle Paia is known for.

Message me for more details or to schedule a private showing.

https://www.hawaiilife.com/listings/23-hoku-pl-paia-hi-96779

04/20/2026

Ground-floor living in one of South Maui’s most sought-after communities.

This beautifully renovated 1-bedroom, 2-bath condo at Maui Kamaole offers the kind of layout you rarely find, with two full bathrooms and a seamless indoor-outdoor flow.

Enjoy private lanais on both sides that open to lush tropical landscaping, just steps from the pool and BBQ area. Inside, the open-concept design, updated kitchen, split AC, and new furnishings make it easy to settle in or start generating rental income right away.

Located directly across from Kamaole Beach Park III and minutes from Wailea’s dining, shopping, and golf.

View details and more photos here: https://www.hawaiilife.com/listings/2777-s-kihei-rd-l-109-kihei-hi-96753-3

Message me for a private showing.

04/16/2026

This top floor 2-bed, 2-bath condo in Maui Vista offers vaulted ceilings and a bright, open feel. Enjoy your morning coffee on the lanai with ocean views and unwind in the evening with beautiful sunsets. The kitchen features granite countertops, and the unit sits in a prime South Maui location right across from Charley Young Beach. Residents and guests can enjoy three pools, designated grilling areas, and a relaxed island lifestyle. Whether you are looking for a personal getaway or an investment property, this one is worth a look. Offered at $850,000.

Message me for details or a private showing.

https://www.hawaiilife.com/listings/2191-s-kihei-rd-2419-kihei-hi-96753-2

04/14/2026

This 4 bed, 3 bath condo in the Cottages at Kulamalu offers the best of Upcountry living with cool breezes, clean air, and beautiful ocean and mountain views. The layout is both practical and flexible, with one bedroom and full bath on the first floor and the rest upstairs. Enjoy a covered entry porch, central AC, and a two car garage, plus a beautifully maintained fenced backyard with a covered lanai that is perfect for relaxing or entertaining. Located just minutes from Foodland, Pukalani Community Center, local restaurants, and everyday essentials, with the airport and Costco about 15 minutes away.

Offered at $999,000.

Message me for details or a private showing.

https://www.hawaiilife.com/listings/46-kuinehe-pl-18-pukalani-hi-96768-2

04/10/2026

7700 Kula Hwy offers 58 acres across 8 lots with real infrastructure already in place. This is not just land. It’s a working property with income potential from day one.

The property includes multiple ag buildings, two fully automated greenhouses, and an off-grid solar system powering the operation. There’s also an office and shop space, making it functional for both business and day-to-day use.

Roughly 40 acres have already been cleared, with additional site work completed to support access and long-term use. Existing leases add immediate income, while the layout allows for future expansion or new uses.

If you’ve been looking for a large-scale property in Upcountry Maui with flexibility and built-in value, this one is worth a closer look.

Message me for details or a private tour.

https://www.hawaiilife.com/listings/7700-kula-hwy-kula-hi-96790-1

04/02/2026

This private 3 bed, 4 bath estate offers 3,136 sqft of living on over 4 acres of lush, tropical grounds with mature fruit trees, peaceful walking paths, and a separate upgraded cottage perfect for guests or extended living. Originally designed by Maui architect Harry Rice and reimagined as a mid-century modern retreat, the home features light-filled interiors, expansive lanais, and a seamless indoor outdoor flow.

The gourmet kitchen is equipped with high end appliances and custom cabinetry, while each bedroom includes its own ensuite bath for comfort and privacy. A spa style outdoor bath with a soaking tub, a treehouse overlooking the forested gulch, and handcrafted details throughout create a true North Shore escape.

Tucked at the end of a quiet country road, this property offers a rare blend of privacy, design, and everyday island living.

https://www.hawaiilife.com/listings/965-hog-back-rd-haiku-hi-96708-2

Video tour: https://player.vimeo.com/video/1178423573?amp;loop=1

02/24/2026

Immaculate 2-bedroom, 2-bath residence at Wailea Town Center offering streamlined island living in a prime Wailea location. This second-story condo, with elevator access, enjoys sweeping ocean views stretching from Kahoolawe to the West Maui Mountains and fronts the Wailea Tennis Club. The open living and kitchen area is bright and spacious, enhanced by extra side windows and nine-foot ceilings, and flows seamlessly to a large covered lanai with a built-in grill - your ideal spot for outdoor dining and seasonal whale watching. The kitchen features a 5-burner gas cooktop, wine refrigerator, granite peninsula with generous workspace and bar seating, and quality finishes throughout. Mahogany and travertine floors, cherry shaker-style cabinetry, custom window treatments, and a built-in sound system reflect the home’s pristine condition. The primary suite offers a spa-like bath with soaking tub, walk-in shower, dual granite vanity, and a custom walk-in closet. The en-suite guest bedroom provides privacy, ample space, and striking Haleakala views. Additional highlights include a separate one-car enclosed garage with storage, an additional reserved parking space, and access to a private pool and spa. Conveniently located near Wailea’s beaches, golf, tennis, shopping, and dining, this residence combines comfort, quality, and an exceptional setting.

02/18/2026

Set across sixteen acres of fully fenced acreage, this Haiku estate is a world unto itself. Private, expansive, and rich with possibility. Thoughtfully positioned structures create a harmonious compound designed for inspired living, hosting, and creativity. Whether envisioned as an exclusive mountain residence, an artist’s enclave, or a destination wellness retreat, the setting effortlessly supports a life well-lived. At the heart of the property, the main home captures the essence of refined rural living. An impressive primary suite is wrapped in glass windows and doors, inviting natural light and lush views from nearly every angle. A warm fireplace lounge in the living area sets the tone for intimate evenings, while a concealed projection screen transforms the space into a private cinema. The screened lanai area offers flexibility for gatherings or hosting events of any kind. Throughout the grounds, there are additional dwellings and versatile spaces, including a two-room cottage currently utilized as an office, an upper guest cottage with its own outdoor shower house, and a two-story building tucked privately toward the rear of the acreage. Each structure enhances the estate’s ability to accommodate guests or creative pursuits. The outdoor experience is equally compelling. Pass by the courtyard area and enjoy the sounds of the cascading waterfall and koi fish pond, and head out to meandering trails that wind through the landscape. A commercial-grade kitchen with an adjacent screened-in gathering space, along with dedicated men’s and women’s bathhouses, reflects the property’s history as a curated retreat destination. Leisure and restoration take center stage with a resort-style pool complete with a water slide, waterfall, an accompanying pool house, and a tranquil massage pavilion. This is more than acreage; it is a legacy estate with the capacity to evolve alongside your vision, all within a setting that feels worlds away.

https://www.hawaiilife.com/listings/1055-kaupakalua-rd-haiku-hi-96708-1

02/12/2026

Welcome to 572 Liholiho Street, where sweeping ocean views pair beautifully with the majestic backdrop of Haleakala. This centrally located residence offers versatile living spaces designed to capture the scenery from multiple vantage points. The living room opens to a lanai—an inviting spot to relax or enjoy the ocean panorama with your favorite beverage. The primary bedroom also features ocean views and an ensuite bath, alongside three additional bedrooms. Further options include a lock-off with a one-bedroom, one-bathroom suite with its own ocean view. The home features a leased photovoltaic system, ample parking, and a covered carport for two vehicles. Downstairs, a private two bedrooms and one bathroom provides flexibility for extended family and guests. Set on a larger R-3 zoned lot, this property presents potential for renovation and expansion—offering the opportunity to remodel and create a home that reflects your personal style and vision. Conveniently located near schools, hospitals, grocery stores, restaurants, Keopuolani Park, shopping centers, golf courses, the YMCA, War Memorial Stadium, Maui Arts & Cultural Center, medical and dental offices, Coach Sakamoto Pool, and Kahului Pool, this home combines inspiring views, flexibility, and everyday convenience.

https://www.hawaiilife.com/listings/572-liholiho-st-wailuku-hi-96793

Address

Hawaii Life Real Estate Brokers, 3750 Wailea Alanui Drive , Suite B-16
Wailea, HI
96753

Website

http://www.joshjerman.com/, http://www.joshjermanfoundation.org/

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