Kaanapali Hillside Homes with Fee Simple Land tenure

Kaanapali Hillside Homes with Fee Simple Land tenure

Welcome to Kaanapali Hillside, a stunning subdivision nestled in the breathtaking landscape of Lahaina, Maui. This picturesque community is renowned for its lush surroundings, panoramic ocean views, and the tranquil ambiance that characterizes life in Hawaii. Kaanapali Hillside offers a unique blend of luxury and comfort, making it an ideal choice for those seeking a serene yet vibrant lifestyle.

The homes in Kaanapali Hillside are designed with elegance and functionality in mind, featuring spacious layouts that cater to both relaxation and entertaining. Many residences boast modern amenities, private pools, and beautifully landscaped gardens, allowing residents to enjoy the quintessential Hawaiian lifestyle right at home. With fee simple land tenure, homeowners can take pride in owning their slice of paradise, ensuring both stability and investment value.

Kaanapali Hillside is conveniently located near some of Maui's most iconic attractions, including world-class beaches, golf courses, and gourmet dining options. Residents can indulge in outdoor activities such as snorkeling, hiking, and surfing, all just moments from their doorstep. The community is also known for its friendly atmosphere, where neighbors become friends and create a close-knit environment.

Whether you’re looking for a permanent residence, a vacation getaway, or an investment opportunity, Kaanapali Hillside offers the perfect blend of luxury, comfort, and natural beauty. Discover the charm of this exceptional subdivision and embrace the Hawaiian lifestyle that awaits you. Your dream home in paradise is just a visit away!

Newest Kaanapali Hillside Homes with Fee Simple Land tenure

4 Beds ⋅ 4 Baths ⋅ 409052 MLS ⋅ Fee Simple Tenure

Fabulous Maui ocean, island & resort views await YOU from YOUR home at 196 Hakui Loop! Built in 1995 and extensively renovated in 2014, this two-level home offers 4BD, 3.5BA spread across 3,240 living sq. ft., plus YOUR own private pool! Enjoy dramatic sunrise/sunset ocean views from the large-picture windows of the great room and lanais off the kitchen/great room and YOUR primary bedroom – a NEW Painting Every Day! The extensive 2014 renovation included the installation of wood-look, diagonal-placed Italian porcelain tile floors (easy to maintain) and a complete redesign of the kitchen and all bathrooms. Major recent improvements included attention to home efficiency, safety & performance: 44 photovoltaic panels / 2 Telsa batteries (2020), Starlink satellite system (2023), ramp on the exterior downstairs lanai, additional hand rails at front entrance, pool, and stairwell, and shower grab bars; a new garage door opener (2022 - complete with external touchpad opener); vinyl side fencing on west side and pool entrance provide additional privacy; installation of new water heater (2024) & water descaling system (2025). The exteriors were painted in 2018. The parcel is rich with established plantings, including dwarf tropical fruit trees including lemon, lime, finger-lime, papaya, calamansi, and avocado. In 2021 the pool was remodeled resulting in wide stairs with a Baja Bench & table with port for umbrella, new plaster and new tile. Throughout, strong luxury appliance & home improvement brands exist including Sub-Zero refrigeration systems, Samsung induction range top, 2 Bosch dishwashers, KitchenAid microwave/oven combo, Jacuzzi jet-tub, Minka Aire/Regency Ceiling Fans, Lutron wall controls, two Lennox AC systems, GE, Maytag, Domus hardware & Kohler sink/toilet systems. The home is located in a quiet, less-traveled, private area of the exclusively resort community known as the Kaanapali Hillside. Kaanapali Hillside is a residential community consisting of 158 residential homes or vacant parcels (phase 1 and 2). Community amenities include a sprawling park/swing area. Monthly homeowner association dues are an incredibly reasonable $137.15 (paid quarterly). Hillside owners are minutes away from the world famous North Kaanapali beach (aka "Airport" beach) where great swimming, snorkeling and lounging is experienced! The Hillside is centrally located to downtown Lahaina and the resort community of Kapalua, plus the West Side’s public & private schools including: Kamehameha III Elementary, Hawaii Technology Academy (HTA), Sacred Hearts, and Maui Preparatory Academy—all within a 10-minute drive. Golf-carting to restaurants, work, the park, your neighbors' homes and to Kaanapali Resort is a lifestyle that most people dream about. Sold furnished with EXCEPTION. YOUR Time Is Now.

196 Hakui Pl, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

3 Beds ⋅ 3 Baths ⋅ 408922 MLS ⋅ Fee Simple Tenure

Nestled in the coveted Kaanapali Hillside subdivision, this single-story contemporary residence blends classic architectural character with timeless island living. Built in 1984 and crowned by an elegant copper roof, the home reflects enduring craftsmanship and a distinctive design rarely found in today’s construction. Featuring three bedrooms and three bathrooms, the floor plan offers effortless flow and comfortable separation of living spaces, ideal for both everyday living and hosting guests. The single-level layout enhances accessibility and indoor-outdoor connectivity, while the contemporary lines complement the home’s original architectural integrity. A private pool with a beautifully designed surrounding deck creates an inviting outdoor retreat—perfect for relaxing, entertaining, or enjoying Maui’s year-round sunshine. The outdoor living space enhances the home’s resort-style feel while maintaining privacy and comfort. Located just above the world-renowned Kaanapali Resort, Kaanapali Hillside is prized for its quiet streets, upscale homes, and proximity to beaches, golf, dining, and resort amenities—all while maintaining a peaceful residential feel. This is a rare opportunity to own a well-designed home in one of West Maui’s most sought-after neighborhoods. Perfect as a full-time residence or island retreat, this property offers the ideal blend of location, style, and enduring value in the heart of Kaanapali.

9 Puu Hale St, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

407012 MLS ⋅ Fee Simple Tenure

Front-Row Opportunity in Ka'anapali Hillside Design and build your dream estate on this expansive 10,011 sq. ft. homesite, one of the very last available parcels along the prestigious front line of Ka’anapali Hillside. Perched at the end of a quiet cul-de-sac, the property showcases sweeping, unobstructed ocean and multi-island views, where vibrant sunsets and seasonal whale watching can be enjoyed right from your future lanai. Ka’anapali Hillside is a highly sought-after neighborhood, offering both elegant second homes and full-time residences. Owners enjoy a serene two-acre private park, low association dues of under $400 per quarter, and the exclusivity of a community designed for privacy and luxury. From this vantage point, you are within close proximity—whether by a short drive or leisurely walk—to Ka’anapali’s world-famous white sand beaches. The golf-cart-friendly community allows for convenient street-legal golf cart use, making it easy to access the beach or resort amenities in true island style. Within minutes, you’ll find two championship golf courses, the Ka’anapali Tennis Club, and world-class shopping and dining at Whalers Village, creating a seamless connection between home and resort living. Convenience is another hallmark of the location. Lahaina Town’s shops, art galleries, and restaurants are just a short drive away, while Maui Preparatory Academy (K–12) is only five minutes up the road—an ideal advantage for families seeking both lifestyle and accessibility. This is a once-in-a-generation opportunity to secure a premier build site in one of West Maui’s most coveted communities. Whether envisioned as a primary residence, vacation retreat, or legacy estate, this property offers the foundation for a lifestyle of elegance, recreation, and natural beauty.

152 Eke Pl, Lahaina

Listing courtesy of Berkshire Hathaway Maui Prop-L.

406548 MLS ⋅ Fee Simple Tenure

YOUR WAIT IS OVER if you wish to build YOUR home in Paradise. The 10,767 sq. ft. parcel is located in the exclusively resort community known as the Hillside of Kaanapali. Kaanapali Hillside is a residential community consisting of 158 residential homes or vacant parcels (phase 1 and 2). Community amenities include a park and playground area. Monthly homeowner association dues are $127.66 (paid quarterly). Hillside owners are minutes away from the world famous North Kaanapali beach (aka "Airport" beach) where great swimming, snorkeling and lounging is experienced! The Hillside is centrally located to downtown Lahaina and the resort community of Kapalua as well as the public & private schools based in Napili & Kahana. Golf-carting to restaurants, work, the park, your neighbors' homes and to Kaanapali Resort is a lifestyle that most people dream about.

51 Pihaa St Unit 48, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

Start Your Search

Debbie Rasar Fitts

My feet first touched Maui soil in June 1999. I had never been to Hawaiʻi before. Fresh out of college (Go Cougs!), I was invited to Maui by my uncle, Monte—a trip that would change the course of my life. After hours jetting across the vast Pacific and leaving the bustle of Honolulu behind, we boarded a small prop plane bound for Maui. As we crossed the channel, waterfalls cascaded down the sea cliffs of Molokaʻi, and the island unfolded beneath us. We floated above pineapple fields and waving sugarcane before touching down at Kapalua Airport. My skin met the warm island air as my uncle placed a tuberose lei around my neck. To this day, the smell of tuberose transports me back to that very moment —the beginning of my Maui story. After college, I built a life in San Francisco, living and working at The Presidio, another place that captured my heart. But when the opportunity arose to move to Maui in 2003, I didn't hesitate. It remains one of the best decisions I've ever made. Over the past two decades, my appreciation for this island has only deepened. Through countless adventures, meaningful friendships, and the privilege of working alongside some of the finest people in Hawaiʻi, Maui has become far more than a place I live—it has become part of who I am. Today, I love helping others discover the Maui that I know and cherish. Maui is more than leis, shave ice, and mai tais. Those experiences are wonderful, but the island's true magic lies deeper—in its people, culture, history, landscapes, and spirit of aloha. When you slow down, explore beyond the obvious, and immerse yourself in all that Maui has to offer, you'll create memories that stay with you long after you've returned home. Because once Maui finds its way into your heart, it never really leaves. There's no place like Maui.

Learn More

Browse Kaanapali Hillside Homes by View