Ryan MacLaughlin RB-21325, Realtor® (B), Owner, Broker-In-Charge

Ryan MacLaughlin RB-21325

Realtor® (B), Owner, Broker-In-Charge

A third-generation real estate professional, Ryan MacLaughlin is one of Maui’s most trusted and respected agents, specializing in luxury homes, oceanfront estates, and investment properties. Since 2003, Ryan has built a reputation for his deep market expertise, strong negotiation skills, and unwavering commitment to his clients.

Born and raised on Maui, Ryan blends local knowledge with a global perspective, offering clients an unmatched understanding of the island’s premier real estate opportunities. His background in Travel Industry Management from the University of Hawaii, combined with his extensive worldwide travels, gives him a unique ability to connect with buyers and sellers from all walks of life.

Ryan’s expertise in Hawaii’s luxury market has earned him features in The Wall Street Journal, The New York Times, The Financial Times, Mansion Global, and Hawaii Business Magazine, among others. His insights are frequently sought after by leading real estate publications, and his properties have been showcased in prestigious media outlets, reinforcing his status as a leader in high-end real estate.

His approach to real estate is guided by Kuleana, Pono, Aloha—a deep sense of responsibility, integrity, and genuine care for his clients. Whether working with longtime island residents or those discovering Maui for the first time, Ryan is known for creating a seamless, stress-free experience that consistently exceeds expectations.

Beyond real estate, Ryan is actively involved in the community, serving as a director for the Seabury Hall Alumni Association and supporting organizations like the Maui Native Hawaiian Chamber of Commerce. When he’s not helping clients find their dream homes, you’ll find him in the ocean—surfing, fishing, diving—or on the golf course, embracing the island lifestyle he loves.

Whether you’re buying or selling in Hawaii, Ryan delivers exceptional service with a deep-rooted passion for the islands, ensuring every client feels at home in paradise.

Contact Ryan

Cell Phone 808-283-7965
Office Phone 808-572-8600
Ryan's Listings
7505 Makena Rd, Wailea/Makena

7505 Makena Rd

$33,000,000
  • Residential
  • 7 Beds
  • 8 Baths
  • 10,500 SqFt
Welcome to one of the most extraordinary private estates in the world — an iconic expression of coastal luxury at 7505 Makena Road. Set on a full acre of lush, meticulously curated grounds with protected ocean view corridors along Maui’s most covete...
400 Mehana Rd, Haiku

400 Mehana Rd

$11,900,000
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 5,403 SqFt
Above a quarter mile of untouched North Shore coastline rises a rare opportunity to own one of Maui’s most extraordinary oceanfront estates. 400 Mehana Road commands sweeping 180 degree views of the Pacific from its elevated perch 275 feet above the ...
454 Wailau Pl, Lahaina

454 Wailau Pl

$11,000,000
  • Residential
  • 4 Beds
  • 5 Baths
  • 6,640 SqFt
An iconic gated estate in Lahaina where refined architecture, rare craftsmanship, and Maui’s natural beauty come together in extraordinary fashion. Set across 52.775 acres spanning two TMKs, this 6,640 square foot single-level residence enjoys comman...
4584 Makena Rd, Wailea/Makena

4584 Makena Rd

$9,000,000
  • Residential
  • 2 Beds
  • 3.5 Baths
  • 2,760 SqFt
Over an acre of direct beachfront in Makena is an exceptional rarity — and 4584 Makena Road stands as one of the most compelling value opportunities along Maui's coastline. Positioned on Poolenalena Beach, the property offers expansive grounds, excep...
533 Luawai St, Olowalu

533 Luawai St

$7,950,000 ↓ $1,300,000
  • Residential
  • 4 Beds
  • 5 Baths
  • 4,417 SqFt
A modern architectural masterpiece set on over 5.8 acres, this Maui estate captures unobstructed ocean vistas and dramatic mountain backdrops from one of Olowalu’s most desirable settings. Completed in 2020, the residence is the result of exceptional...
3857 Waakaula Pl, Wailea/Makena

3857 Waakaula Pl

$5,995,000
  • Residential
  • 4 Beds
  • 4 Baths
  • 4,292 SqFt
Experience the pinnacle of luxury island living at 3857 Waakaula Place. Nestled within the prestigious gated subdivision of Wailea Golf Estates and bordered by the iconic Wailea Blue Golf Course, this elegant 4,292 sq. ft. residence boasts sweeping o...
20 Kapuaimilia Pl, Haiku

20 Kapuaimilia Pl

$3,350,000 ↓ $300,000 In Escrow
  • Residential
  • 4 Beds
  • 3.5 Baths
  • 3,879 SqFt
Proudly presented for sale is a stunning single-level estate that masterfully blends contemporary design, privacy, and seamless indoor / outdoor living, all in one of the North Shore’s most sought-after neighborhoods. Set on an immaculately landscape...
1821 Halama St, Kihei

1821 Halama St

$3,200,000
  • Residential
  • 4 Beds
  • 3 Baths
  • 2,783 SqFt
Set at the end of a quiet cul-de-sac, 1821 Halama Street enjoys a truly special position overlooking the expansive 36 acre Kalama Park, offering sweeping ocean views, whale watching in season, and unforgettable sunsets. The sense of openness created ...
384 Pualoa Nani Pl, Wailea/Makena

384 Pualoa Nani Pl

$2,490,000 ↓ $160,000
  • Residential
  • 3 Beds
  • 2 Baths
  • 2,078 SqFt
Within the gated community of Wailea Pualani, 384 Pualoa Nani Place is a design forward residence that blends privacy, craftsmanship, and modern comfort in a truly special setting. This 3 bedroom, 2 bathroom home with a large dedicated office spans 2...
Recent Sales by Ryan
18 Ualei Pl, Wailea/Makena

18 Ualei Pl

$14,470,000
  • Residential
  • 5 Beds
  • 4.5 Baths
  • 7,356 SqFt
Sold Before Listed...
1 Bay Dr 3501, Kapalua

1 Bay Dr 3501

$5,250,000
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,065 SqFt
Introducing a rare offering in one of Hawaii’s most acclaimed resorts: Montage Residences Kapalua Bay 3501. The awe-inspiring 3 bedroom / 3.5 bathroom luxury unit is a corner unit on the top level (no unit above it), enhancing its privacy and view co...
110 Mehana Rd, Haiku

110 Mehana Rd

$4,500,000
  • Residential
  • 5 Beds
  • 4 Baths
  • 3,567 SqFt
North Shore Luxury Living Redefined. The epitome of upscale living amidst Maui’s famed North Shore, 110 Mehana Road offers spectacular ocean views, incredibly landscaped grounds, and the level of privacy most want yet few attain. With over twelve acr...
36 Kai Malu #202 Dr 5-D, Wailea/Makena

36 Kai Malu #202 Dr 5-D

$3,900,000
  • Residential
  • 3 Beds
  • 3 Baths
  • 1,742 SqFt
Introducing one of the best values in the Hawaii luxury market: La'i Loa 5-D. This highly coveted 3-bedroom condominium boasts unrivaled craftsmanship, a modern design, and one of the best locations within the heart of the Wailea master-planned commu...
175 W Ikea Moku Pl, Wailea/Makena

175 W Ikea Moku Pl

$3,599,000
  • Residential
  • 2 Beds
  • 2 Baths
  • 3,105 SqFt
Perched quietly above a cul de sac in Wailea’s esteemed Kialoa community, 175 W Ikea Moku feels less like a residence and more like a private sanctuary. The home opens to a sweeping panorama of the Pacific and neighboring islands and was thoughtfully...
206 Heleuma Pl, Wailea/Makena

206 Heleuma Pl

$3,500,000
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 3,169 SqFt
Ideally positioned near the top of an exclusive cul-de-sac in one of Wailea’s most desirable gated communities, 206 Heleuma Place captures the essence of refined Hawaiian island living. Gentle trade winds drift through open, airy interiors where ocea...
1185 Nanihoku Pl, Haiku

1185 Nanihoku Pl

$2,700,000
  • Residential
  • 3 Beds
  • 3 Baths
  • 2,045 SqFt
Step into this secluded retreat in the Heart of Haiku to explore a world apart. Discover unparalleled privacy and serenity in this exceptional 3-bedroom, 3-bathroom meticulously maintained home with a detached Ohana, nestled at the end of a quiet cu...
44 Kai Malu Pl 7-A, Wailea/Makena

44 Kai Malu Pl 7-A

$2,450,000
  • Residential
  • 2 Beds
  • 2 Baths
  • 1,374 SqFt
Introducing a rare opportunity at Lai Loa, Wailea's newest development. A serene never-lived in 2 bedroom / 2 bathroom retreat embracing casual Hawaiian island elegance and seamless indoor/outdoor living. Nestled within a tranquil island escape, this...
1032 S Kihei Rd B-323, Kihei

1032 S Kihei Rd B-323

$2,170,000
  • Residential
  • 3 Beds
  • 3 Baths
  • 1,392 SqFt
Welcome to the epitome of Hawaii island living at Maui Sunset B-323, one of the most perfectly located condominiums in Kihei. This exquisite third-floor condo offers three bedrooms and three bathrooms, encompassing nearly 1,400 square feet of luxurio...
66 Puu Hale St, Kaanapali

66 Puu Hale St

$1,985,000
  • Residential
  • 4 Beds
  • 2.5 Baths
  • 3,089 SqFt
Aloha and welcome to 66 Puu Hale, an exclusive residence nestled upon Kaanapali Hillside, only a few minutes by golf cart to the world-famous Kaanapali Golf Course, Whalers Village Mall, and Beach next to Black Rock in West Maui. Here, you may partak...
10 Wailea Ekolu Pl 909, Wailea/Makena

10 Wailea Ekolu Pl 909

$1,800,000
  • Residential
  • 2 Beds
  • 2 Baths
  • 1,071 SqFt
Wailea Ekolu Village presents a rare opportunity to obtain a Hawaiian legacy unit of your very own for the enjoyment of ohana, friends, or guests alike. Arrive at the easily accessible ground floor unit and you are immediately met with blue panoramic...
10 Wailea Ekolu Pl 1305, Wailea/Makena

10 Wailea Ekolu Pl 1305

$1,795,000
  • Residential
  • 2 Beds
  • 2 Baths
  • 1,071 SqFt
Welcome to Wailea Ekolu 1305, a newly renovated 2-bedroom, 2-bathroom haven that captures lovely ocean views and embodies Hawaiian-style luxury. This meticulously maintained ground-floor condo features upscale touches and stylish décor throughout. En...
1699 Kaupakalua Rd, Haiku

1699 Kaupakalua Rd

$1,749,000
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 2,566 SqFt
Experience the charm of country living in this beautifully updated single-level custom home, set on 2 usable acres of lush, gated property. Boasting 2,566 sq. ft. of living space, this 3-bedroom, 3.5-bathroom residence offers new luxury vinyl plank (...
3200 Wailea Alanui Dr 1001, Wailea/Makena

3200 Wailea Alanui Dr 1001

$1,595,000
  • Residential
  • 2 Beds
  • 2 Baths
  • 1,242 SqFt
Discover the perfect blend of luxury, privacy, and island charm in this ground-floor, 2-bedroom, 2-bath condo in the highly sought-after Building 10. Nestled alongside the greenbelt, this beautifully, painstakingly maintained unit offers beautiful oc...
3075 Alaneo Pl, Wailuku

3075 Alaneo Pl

$1,595,000
  • Residential
  • 2 Beds
  • 3 Baths
  • 1,673 SqFt
3075 Alaneo Place — a dream home in Old Wailuku Heights offering unmatched privacy, breathtaking ocean views of Maui’s North Shore and Haleakala. This 2 bedroom, 3 bathroom residence with an additional flex room spans 1,673 sq. ft. and sits at the en...
Mehana Rd Lot 7 Partition Hui Kuai, Haiku

Mehana Rd Lot 7 Partition Hui Kuai

$1,450,000
  • Land
  • 0 Beds
  • 0 Baths
  • 0 SqFt
Sold prior to listing...

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