Shore to Shore Realty, Inc.
Wailuku, Maui · Established 1980

Local since 1980. Both sides of the door.

A family-owned Maui real estate sales and property management company, guiding clients every step of the way. Buy, sell, rent, or invest: the same team handles all of it.

4.1 Google rating from 30 reviews

1980 established in Wailuku

2 desks, one office

Aerial view across the green central Maui isthmus with the West Maui mountains rising on one side and the ocean on both
Maui scenery, shown to set the place. Not a listing or a managed property.

Shore to shore is the coverage, not the slogan

The name has been on the door since 1980, and it describes where the work actually happens. The management portfolio spans from Upcountry and Haʻikū to Wailuku, Kahului, Kīhei, and Lahaina.

Established
1980, Wailuku
Ownership
Local and family owned
Leadership today
A father and daughter
Under one roof
Sales and management

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

What we do

Two tracks, one office. Most clients end up using both, which is the whole point of keeping them together.

Property management

Own a condo, home, or investment property on Maui? With decades of experience serving local and out-of-state owners, we make renting your property easy and stress-free.

  • Managed in compliance with Hawaii landlord-tenant codes
  • All property advertising and marketing handled
  • Applicants screened thoroughly, to improve residency length and protect your property
  • 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 IRS 1099 forms
  • Creation of an annual expense statement
Talk to us

Buying on Maui

Guided by a brokerage that has worked this island since 1980, with a team that knows the ground because it manages property on it every day.

  • Buyer representation across the island
  • Buy an investment property and have the same office manage it from day one
  • As brokers in Hawaii we can help you move from renting to owning
Start a search

Selling your property

Listing and marketing your Maui property, handled by the principals rather than passed down a chain.

  • Listing, marketing and sale of residential property
  • Sellers who are also owners keep the same point of contact throughout
Ask what it is worth

Investment and 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. His stated goal is to help local residents become successful investors, and to support keeping Hawaiʻi’s local people at home.

  • Residential and commercial investment experience, held first-hand
  • Mentoring for aspiring investors
  • 1031 exchange strategy
Talk strategy

Three sets of hands, one firm

Established in 1980, with a long-standing presence in Maui’s real estate community. Here is how the firm passed from hand to hand.

  • 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.

Who you will be working with

A family-owned local business serving the Maui community by connecting people with homes and investment opportunities, 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.

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 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. She is also the founder of the Holo Holo Hiking Club.

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

One client, both desks

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

“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.

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.

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 Search rentals

Answers, before you call

The questions the office fields most often, answered here so nobody has to wait until Monday at nine to find out.

Which parts of Maui do you manage property in?

The management portfolio spans from Upcountry and Haʻikū to Wailuku, Kahului, Kīhei, and Lahaina. The office itself has been on Hookahi Street in Wailuku for decades, so owners, tenants and buyers all reach the same team at the same desk.

What kinds of property do you manage?

Rental options across the portfolio include single-family homes, apartments, duplexes, and condominiums.

What does full-service management actually cover?

Advertising and marketing the property, thorough applicant screening, lease preparation and execution, rent collection, maintenance and repair coordination, move-in and move-out inspections, and biannual inspections with reports. All of it managed in compliance with Hawaii landlord-tenant codes.

How do I get paid, and what do I get at tax time?

Through the secure Owner Portal, with fast electronic fund transfers and the ability to monitor your property’s performance anytime. At year end you get annual accounting service, including creation of IRS 1099 forms, plus an annual expense statement.

How do tenants pay rent or report a maintenance issue?

Through the Tenant Portal, which lets residents schedule, pay, and track rent payments securely online, with a choice of payment options. Routine maintenance issues are reported through the same online system and scheduled for prompt resolution.

For a serious property emergency, where property or tenant safety is at risk, call the emergency contact number immediately rather than using the portal.

I am renting from you now. Can you help me buy?

Yes. As real estate brokers in Hawaii, we can assist you should you become ready to transition from renting to becoming a property owner. It is the same office either way.

Do you work on investment property and 1031 exchanges?

Yes. 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. He also mentors aspiring investors, with the goal of helping local residents become successful owners.

Who am I actually dealing with?

A local, family-owned firm, established in Wailuku in 1980 and now led by a father and daughter: Van Waki as Principal Broker, license RB-18191, and Alyssa Waki as Broker-in-Charge, license RB-24132, with a full support team behind them.

Ready to buy, sell, rent, or invest?

Contact us at Shore to Shore Realty, Inc. and let us 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

This is a concept demonstration. The form is not connected to anything and will not send. To reach the office today, call (808) 244-7142.