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
3060 S Kihei Rd, Kihei

3060 S Kihei Rd

$27,500,000 ↓ $5,000,000
  • Residential
  • 4 Beds
  • 5.5 Baths
  • 5,435 SqFt
An exclusive opportunity awaits to own a legacy property nestled upon the pristine sands of Keawakapu Beach. Spread on over 5,000 square feet of interior living space, this trophy estate offers unrivaled panoramic views of year-round sunsets, gentle ...
4850 Makena Alanui Rd, Unit A-103, Wailea/Makena

4850 Makena Alanui Rd, Unit A-103

$15,500,000
  • Residential
  • 3 Beds
  • 3.5 Baths
  • 3,415 SqFt
Introducing one of the most rare offerings in the Hawaii luxury real estate market: Makena Surf A-103. Built as the largest Makena Surf unit at a substantial 3,415 square feet of interior living space seamlessly expanded with over 900 square feet of ...
454 Wailau Pl, Lahaina

454 Wailau Pl

$11,500,000
  • Residential
  • 4 Beds
  • 5 Baths
  • 6,640 SqFt
An iconic gated estate in Lahaina where refined architecture, rare craftsmanship, and natural beauty converge. Set on 52.775 acres across two TMKs, this 6,640 sq. ft. single-level residence offers commanding ocean views with the West Maui Mountains a...
3857 Waakaula Pl, Wailea/Makena

3857 Waakaula Pl

$6,500,000
  • 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...
206 Heleuma Pl, Wailea/Makena

206 Heleuma Pl

$4,775,000
  • Residential
  • 2 Beds
  • 2.5 Baths
  • 3,169 SqFt
Situated at the end of a quiet cul-de-sac within one of South Maui’s premier gated communities, 206 Heleuma Place offers a serene island lifestyle with ocean views and thoughtfully designed indoor-outdoor living. This warm and inviting single level h...
965 Hog Back Rd, Unit 1, Haiku

965 Hog Back Rd, Unit 1

$3,995,000
  • Residential
  • 3 Beds
  • 4 Baths
  • 3,136 SqFt
Rarely do the stars align as they have here – the character and beauty of a light-filled mid-century modern home custom designed by renowned Maui architect Harry Rice, has been thoughtfully and meticulously upgraded into a modern and luxurious, turn-...
36 Kai Malu #202 Dr, Unit 5-D, Wailea/Makena

36 Kai Malu #202 Dr, Unit 5-D

$3,900,000 In Escrow
  • 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...
5171 Makena Rd, Wailea/Makena

5171 Makena Rd

$3,499,000 ↓ $251,000
  • Land
  • 0 Beds
  • 0 Baths
  • 0 SqFt
Picture-perfect Lot 7 in Papaanui Makena offers an exceptional opportunity to create a dream home on 0.472 acres in one of Maui’s most peaceful and picturesque locations. Overlooking the historic Makena Landing, this lot boasts expansive, south-facin...
270 Umeke St, Unit Apt 41, Kihei

270 Umeke St, Unit Apt 41

$2,200,000 ↓ $100,000
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,450 SqFt
Also listed as a Condominium (MLS#405192). Step into this beautifully crafted 3-bedroom, 2.5-bathroom two story home offering 2,450 sq. ft. of elegant living space. Tiger wood floors add warmth and sophistication, complemented with tile throughout th...
270 Umeke St, Unit 41, Kihei

270 Umeke St, Unit 41

$2,200,000 ↓ $100,000
  • Residential
  • 3 Beds
  • 2.5 Baths
  • 2,450 SqFt
Also listed as Single Family Residential (MLS#405191). Step into this beautifully crafted 3-bedroom, 2.5-bathroom two story home offering 2,450 sq. ft. of elegant living space. Tiger wood floors add warmth and sophistication, complemented with tile t...
130 Kai Malina Pkwy, Unit NR332, Kaanapali

130 Kai Malina Pkwy, Unit NR332

$1,859,000 ↓ $136,000
  • Residential
  • 2 Beds
  • 2 Baths
  • 1,080 SqFt
Look no further for your island paradise than this exceptional two-bedroom, two-bath property, priced under $2 million. Experience the ultimate in luxury living with 1,080 square feet of thoughtfully designed space, Hotel-zoned to continue as a succe...
1699 Kaupakalua Rd, Haiku

1699 Kaupakalua Rd

$1,749,000 ↓ $136,000 In Escrow
  • 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, Unit 1001, Wailea/Makena

3200 Wailea Alanui Dr, Unit 1001

$1,595,000 ↓ $105,000 In Escrow
  • 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...
44 Kanani Rd, Unit I-303, Kihei

44 Kanani Rd, Unit I-303

$920,000 ↓ $30,000 In Escrow
  • Residential
  • 2 Beds
  • 2 Baths
  • 890 SqFt
Welcome to Hale Kanani, a desirable condominium complex perfectly situated in the heart of Kihei, just steps from Cove Park and Kamaole Beach Park. This meticulously maintained 2 bedroom, 2 bathroom unit offers 890 sq. ft. of bright, airy living spac...
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...
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...
1032 S Kihei Rd, Unit B-323, Kihei

1032 S Kihei Rd, Unit B-323

$2,170,000 ↓ $330,000
  • 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...
10 Wailea Ekolu Pl, Unit 1305, Wailea/Makena

10 Wailea Ekolu Pl, Unit 1305

$1,795,000 ↓ $55,000
  • 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...
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...
389 Kualono Pl, Wailea/Makena

389 Kualono Pl

$695,000 ↓ $55,000
  • Land
  • 0 Beds
  • 0 Baths
  • 0 SqFt
Offering a rare opportunity to own vacant land in one of Wailea’s premier subdivisions: Wailea Pualani. The gated subdivision is within a convenient distance to some of the island’s best beaches, finest restaurants, renowned spas, world class shoppin...

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