Kaanapali Hillside Real Estate

Kaanapali Hillside Real Estate

Welcome to the prestigious subdivision of Kaanapali Hillside, nestled in the breathtaking city of Lahaina on the island of Maui, Hawaii. This exclusive community offers a luxurious lifestyle with stunning ocean views and access to world-class amenities.

Kaanapali Hillside is a sought-after neighborhood in Lahaina, known for its upscale homes and well-manicured streets. Residents here enjoy the perfect blend of tranquility and convenience, with easy access to pristine beaches, championship golf courses, and upscale shopping and dining options.

Living in Kaanapali Hillside means waking up to the sound of waves crashing against the shore and enjoying spectacular sunsets over the Pacific Ocean. Whether you're looking for a primary residence or a vacation home, this subdivision offers the perfect setting for those seeking a slice of paradise.

With its prime location in Lahaina, residents of Kaanapali Hillside have access to top-rated schools, medical facilities, and outdoor recreational activities. Whether you prefer lounging on the beach, hiking in the mountains, or exploring the vibrant local culture, there is something for everyone in this vibrant community.

Come experience the beauty and serenity of Kaanapali Hillside and discover why this neighborhood is one of the most desirable places to live in Maui. Live the luxury lifestyle you deserve in this exclusive enclave in Lahaina, Hawaii.

Newest Listings in Kaanapali Hillside

6 Beds ⋅ 6 Baths ⋅ 410430 MLS ⋅ Fee Simple Tenure

Kaanapali Hillside's Crown Jewel! Few homes on Maui are built to this scale, and fewer still are built to run this efficiently. Nearly 6,100 square feet on the highest street in Kaaanapali Hillside, West Maui, with an owned 41-panel PV system, solar water heating, 3-zone central AC, and HOA dues under $500 per quarter. The kitchen was fully remodeled in 2024 — Wolf throughout, with a 48" dual-fuel range, steam oven, warming drawer, and coffee station with cup warmer, plus Sub-Zero refrigeration — opening to a bay-windowed dine-in area. Ocean views from an expansive upper-level sun deck above the blue-tiled private pool, in Kaanapali's famously perfect year-round climate. A double-height reception hall opens the home at proportions rarely built on Maui: formal living room, wood-paneled office, dining room, and an expansive family room built for graceful entertaining with a custom bar and French doors to the lanai. Backlit stained glass in the kitchen, skylights and bay windows and custom built-ins throughout. Six bedrooms, 5 full and 2 half baths — four en suite, including two primary suites; one bedroom is currently a media room. Indoor sauna, and generous closets. Manicured, irrigated grounds on a fenced 11,000+ sf lot. Minutes to beaches, golf, and dining.

54 Hakui Loop, 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

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.

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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.

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