Shore to Shore Realty, Inc. | Real Estate Sales & Property Management, Wailuku Maui

Two doors, one office

Most people arrive here for one of two reasons: they own a property on Maui, or they are ready to buy or sell one. Pick the door you came through and we will show you exactly what happens on the other side of it.

Full Service Property Management Services

Own a condo, home, or investment property on Maui? Let Shore to Shore Realty manage it for you. With decades of experience serving local and out-of-state owners, we make renting your property easy and stress-free, giving you peace of mind every step of the way.

We manage properties in compliance with Hawaii landlord-tenant codes
We take care of all property advertising and marketing
Applicants are screened thoroughly to improve residency length and to protect your property
We handle lease preparation, execution, and follow through
Professional and timely rent collections
Maintenance and repair coordination
Move-in and move-out property inspections
Biannual inspections and reports
Annual accounting service including creating IRS 1099 forms
Creation of an annual expense statement

Where we manage

Our management portfolio spans from Upcountry and Haʻikū to Wailuku, Kahului, Kīhei, and Lahaina. We offer a variety of rental options, including single-family homes, apartments, duplexes, and condominiums.

Upcountry
Haʻikū
Wailuku
Kahului
Kīhei
Lahaina

Owner Portal

Monitor your property’s performance anytime with our secure Owner Portal and enjoy fast electronic fund transfers. Shore to Shore Realty, Inc. offers a full-service team with quick response times and hassle-free property management.

Talk to us about managing your property Call (808) 244-7142

Buy, Sell, Invest

Whether you’re ready to buy, sell, rent, or invest, our experienced team is here to make the process smooth and stress-free. Let’s connect and turn your Maui real estate goals into reality.

Buying on Maui, guided by a brokerage that has worked this island since 1980
Selling, listing and marketing your Maui property
Investment strategies, including 1031 exchanges
Residential and commercial investment experience, held first-hand by our Principal Broker
Mentoring for aspiring investors, so local residents can become successful owners
Buying an investment property and having it managed by the same office from day one
Renting now, buying later: as brokers in Hawaii we can assist you should you become ready to transition from renting to becoming a property owner

1031 exchanges

Van Waki has been an active Maui investor since 1989, with holdings in both residential and commercial property, and brings decades of hands-on experience in investment strategies, including 1031 exchanges.

Why the sales desk sits beside the management desk

The same office that helps you buy the property can take over running it. One client described exactly that: found the property, assisted with the loan, placed the tenant, and has managed it ever since.

Ready to buy, sell, or invest? Let’s connect Call (808) 244-7142

Since 1980

Established in 1980, we have a long-standing presence in Maui’s real estate community. Here is how the firm passed from hand to hand, told in its own words.

1980
Founded by respected Realtor and educator Nobu Agena, with a foundation of integrity, dedication, and aloha.
2001
Van Waki and Al Imamura took the helm, continuing the company’s strong reputation for honest, prompt, and personalized service.
Today
Leadership is in the hands of a father and daughter duo, Van Waki as Principal Broker and Alyssa Waki as Broker-in-Charge, combining decades of family experience with fresh energy, modern systems, and a full support team.

Our mission is simple: provide unmatched service with excellence, integrity, and the spirit of aloha.

Who you will be working with

As a family-owned local business, we proudly serve the Maui community by connecting people with homes and investment opportunities, offering property owners and tenants exceptional, hassle-free service, and protecting the value of every property we manage.

Principal Broker

Van Waki, PB

License RB-18191

Van graduated from the University of Hawaiʻi at Mānoa Shidler College of Business in 1986 with a Bachelor’s degree in Business Administration. He began his real estate career in 1989 and is an active investor with holdings in both residential and commercial properties on Maui. Van brings decades of hands-on experience in property management, real estate sales, and investment strategies, including 1031 exchanges, to his work with clients.

Passionate about the Maui community, Van’s goal is to help local residents become successful investors and to support keeping Hawaiʻi’s local people at home. He mentors aspiring investors and works to create opportunities for long-term wealth while preserving the unique culture and spirit of the islands.

Broker-in-Charge

Alyssa Waki, BIC

License RB-24132

Alyssa Waki graduated from the University of Hawaiʻi at Mānoa’s Shidler College of Business with a double major in Entrepreneurship and Marketing. She is a driven and proactive professional who brings energy, creativity, and local expertise to every transaction at Shore to Shore Realty, Inc.

With hands-on experience in property management and real estate sales, she is dedicated to providing the best service and practical guidance to help clients confidently buy, sell, or invest in Hawaii properties. Passionate about her community, Alyssa serves as founder of the Holo Holo Hiking Club and loves to travel and explore new experiences.

Property Manager

Chad Saki, R(S)

License RS-59830

Serving as our Property Manager, Chad oversees all of our inspections and showings. He has also been known to assist with sales on occasion. Should you wish to have Shore to Shore Realty manage your property, feel free to contact Chad for assistance. When not working, Chad loves to spend time with his family and friends.

Office

Aileen Waki, R(S)

License RS-63506

Aileen joined the office staff in 2010. She is one of the friendly voices you hear when calling our office for rental information. In her spare time she loves to shop and spend time with her family and friends.

Also on the office team: Kamery Lee.

Our licensed sales bench

Nine licensed Hawaii salespeople work the sales track alongside the principals. Reach any of them through the office.

Sharon Kuwae, R(S)RS-35086
Zane Mukai, R(S)RS-23316
Chavi Downing, R(S)RS-82784
Colleen Okazaki, R(S)RS-61786
Emmett Rodrigues, R(S)RS-59736
Helene A. Yoshizawa, R(S)RS-28365
Sandy Shimabukuro, R(S)RS-64044
Ione Tokishi, R(S)RS-64848
Troy Waki, R(S)RS-84327

See what our customers have to say

Every quote below is published on Shore to Shore Realty’s own testimonials page, word for word.

4.1 Google rating from 30 reviews

When my husband & I decided to invest in a condominium, we contacted Shore to Shore Realty. Van Waki was our realtor and he walked us through the whole process from finding the real estate property, to assisting with the loan, and even getting a tenant into our condo. They have been our property management company since the beginning and we are very happy with their service.

Rhonda Kurohara

I have used the services of Shore to Shore Realty as my condo rental agent for over 20 years, starting from its inception when it consisted solely of Nobu Agena and his assistant. Through these many years and the growth that Shore to Shore has experienced, I have received nothing short of honest, prompt and courteous service from every member of their staff. I cannot recommend them highly enough.

Ronald Baxter

In the month of May, our rental income was less than our expenses. Instead of not giving us a check for that month, they dispersed the expenses over a 3 month period so we could continue receiving an income check. By contract, they didn’t have to do that. But these are some of the things they do that we are very appreciative of.
When they got the place ‘rent ready’, they found an outstanding tenant in less than 2 weeks.

Charles & Mitch Araki

We recommend Shore to Shore Realty and Management for all of your real estate needs. After using two other real estate firms in the past with no success we were pleased when Shore to Shore Realty had our house listed, viewed and sold within a couple of weeks!

Ford & Susan Kawamoto

Chad is da bomb. When it comes to taking care of our rental he is always on it. That makes for happy tenants and our peace of mind.

The Kalaiwaa’s

If there’s a broken water heater at 2:00 in the morning, they get the call.

Hana Kraker

It’s been a pleasure to deal with Shore to Shore Realty through the years. The expertise and professionalism is top notch! We don’t have to worry about anything because they have it under control.

Wendy & Alan Isbell

Owners and tenants, kept separate

Two different jobs, two different logins. Neither one should ever make you hunt for the other.

Property owners

For property owners, whether they live on island, on the mainland, or even internationally, we deliver peace of mind by minimizing hassles and maximizing return on investment.

Owner Portal log in Ask about management

Tenants and renters

We encourage our residents to quickly activate their Tenant Portal. This portal allows you to schedule, pay, and track your rent payments securely online. If you encounter a routine property maintenance issue during your stay, please let us know about it through our online system.

Pay rent / Tenant Portal Maintenance request Search rentals

Ready to buy, sell, rent, or invest?

Contact us at Shore to Shore Realty, Inc. and let’s discuss your goals. Mahalo.

Office: 331 Hookahi St #202
Wailuku, HI 96793
Phone: (808) 244-7142
Email: info@shoretoshorerealtyinc.net
Hours: Monday to Friday, 9:00am to 4:00pm
Saturday and Sunday, closed
Find us: Open in Google Maps