WHY WINDERMERE SAN JUAN ISLANDS

Local Expertise.
Island Perspective.

Real estate on the islands is different. It requires local knowledge, thoughtful strategy, and a deep understanding of the rhythms that shape life here. We combine decades of experience with Windermere’s trusted reputation to guide every client with clarity, professionalism, and care.

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OUR ROOTS. OUR COMMITMENT

Experience You Can Rely On

Local Smarts. As long-standing members of the Islands' communities, we understand what makes this market unique. From waterfront estates and legacy properties to investment opportunities and year-round residences, we provide steady guidance backed by insight and integrity.

We are proud to be part of the Windermere network — a brand built on relationships, professionalism, and service. That foundation allows us to offer both hyperlocal expertise and the strength of a respected regional presence.

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PROVEN EXPERIENCE

A Legacy of Local Leadership

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years of combined experience
0
Average Price
0
of local real estate transactions - That's Windermere!

Total Value Over$155 M Record-Breaking Sales Year After Year

HOW WE SUPPORT YOU

Every Step of the Way

From your first questions to the final signature, we provide thoughtful guidance, strategic insight, and steady communication. Whether buying, selling, or investing, our role is to simplify the process and protect your interests.

LOCAL
PROPERTY SEARCH

Access current listings with real-time market insight and accurate island data.

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STRATEGIC
SELLING

Thoughtful preparation, smart pricing, and targeted exposure for today’s market.

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MARKET
ANALYSIS

A detailed evaluation based on current island trends and comparable sales.

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OUR BROKERS

All In... For You

Our team brings together diverse experience, deep island knowledge, and a shared commitment to serving our community with integrity.
Every broker at Windermere San Juan Islands is dedicated to guiding clients with care, clarity, and professionalism.

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Annette Schaffer

Annette Schaffer

Managing Broker and Realtor
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Bette Cantrell

Bette Cantrell

Broker and Realtor
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Dick Sandmeyer

Dick Sandmeyer

Broker and Realtor
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Ellen Johnson

Ellen Johnson

Broker and Realtor
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Greg King

Greg King

Broker and Realtor
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Jordan Heath

Jordan Heath

Broker and Realtor
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Linda McMahon

Linda McMahon

Broker and Realtor
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Mary Jane Anderson

Mary Jane Anderson

Broker and Realtor
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Rebecca Hughes

Rebecca Hughes

Broker and Realtor
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CLIENT EXPERIENCES

What Our Clients Say

"Greg and Sybil are a great team and their market knowledge and service levels are superior!"
John Kretchmer
"Thanks Sam!"
Samantha Bryner
"Bette found us a property which far exceeded our expectations. The property had some inherent challenges and Bette led the charge so all questions were answered and all issues reso… Read MoreRead Less
Trevor and Cathy Hilpert
"Bette is an excellent agent… she is an absolute treasure to work with! Highly recommend her!"
Craig and Dianne Andrus
"I didn't realize how much a dedicated realtor could do for you until we worked with Betty Cantrell. Months before listing the property she helped us find gardeners and other trades… Read MoreRead Less
Carole Dagg
"I don't know how I would have sold my house without Bette. She was always willing to go the extra mile with a smile too. When I was at a loss to find a tradesman to complete my "… Read MoreRead Less
Pamela Arnold
"Bette listened very well and knew really well what appealed to us."
Peter and Martha Woodman
"We are deeply appreciative and fortunate to have had Tamara by our side in purchasing our new home on Brown Island. Tamara is extremely knowledgeable professional and kind. The ent… Read MoreRead Less
Harvey
"We enjoyed working with Debbie so much for the sale of our cabin and purchase of our home so much that she has become a dear friend. Debbie is knowledgeable about the industry and… Read MoreRead Less
Raquel Lackey
"Rebecca Hughes has been very professional and helpful in my search for a home. She worked closely with me to figure out all the details that I needed to make a decision and then f… Read MoreRead Less
Jim Steele
"My property had an unusual amount of needs to get it ready to sell and Linda was able to put me together with the correct contractors and get the property ready for the best value … Read MoreRead Less
Kurt Johnson
"Linda has excellent marketing skills and her efforts got results. She helped coordinate repairs to the property and additional landscaping work that was well received by buyers. Sh… Read MoreRead Less
Angus Walker
"We recently purchased a condominium with Susan's help in Friday harbor. It has been something we have dreamed about doing for 30 years and we couldn't be more grateful for her assi… Read MoreRead Less
Larry
"Annette is tops in her profession. We couldn't have had a better experience or nicer outcome"
Elaine and Miles Frazel
"Annette is a pro - realistic capable experienced and resourceful. I've referred her to friends and everyone agrees that she is a fabulous broker!Linda H"
Linda Hume
"It was a pleasure working with Tamara. I would happily recommend her to my friends & family. Windermere San Juan is lucky to have such a thoughtful and kind human on their team. Th… Read MoreRead Less
Brawner
"Vail McClure is the best real estate agent I have ever worked with. She knows her business and she takes care of all of the details so that the client doesn't have to do any more t… Read MoreRead Less
Kyle
"Annette Schaffer is an amazingly knowledgeable realtor. I highly recommend if you are interested in real estate services you make Annette your first consideration."
Constantine Costakes
"We have used Rebecca for 3 transactions and would never use anyone else!Martin and Carolyn"
Carolyn Eberhard
"We loved working with Vail! She helped us look at several properties before we found the one!"
Elizabeth Jackson

Let’s Make Your

Next Move Count

If you’re considering buying or selling on the San Juan Islands, we’re here to provide clear guidance and a steady hand throughout the process.

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