San Juan Islands Real Estate

Where Island Living
Becomes Your Everyday

Deep Smarts. Big Hearts. Remarkable Results.

Buy With Us
Sell With Us
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ROOTED IN THE SAN JUAN ISLANDS

Deep Smarts

We are proud to serve San Juan Islands with a deep understanding of the communities, landscapes, and lifestyles that make this place extraordinary. Real estate here is more than a transaction — it’s a transition into a new chapter of island living.

With decades of combined experience, strong market insight, and a commitment to doing what’s right, we guide buyers and sellers with clarity, professionalism, and care. As part of Windermere Real Estate, we combine trusted local expertise with the strength of a respected regional brand — ensuring every client receives thoughtful strategy and exceptional service.

Why Choose Us
Meet The Team
0
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

EXPLORE THE ISLANDS

Explore by Area

Each island community offers its own character and pace. Click below to view homes, local insights, and current market activity.

HOW WE SERVE

Rooted in the San Juan Islands.
Focused on you.

Whether buying, selling, or simply exploring your options, we provide clear guidance tailored to island living.

For Buyers

Find Your Place
in the Islands

From waterfront retreats to quiet wooded acreage, we help island properties find their people.

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For Sellers

Positioned for the
Right Results

With strategic pricing, thoughtful preparation, and targeted exposure, we present your property with care and purpose.

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Know Your Worth

Understand Your
Home’s Market Position

Receive a detailed analysis grounded in current island market trends — not automated estimates.

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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!"
"Thanks Sam!"
"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 resoRead MoreRead Less
"Bette is an excellent agent… she is an absolute treasure to work with! Highly recommend her!"
"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 tradesRead MoreRead Less
"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
"Bette listened very well and knew really well what appealed to us."
"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 entRead MoreRead Less
"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 andRead MoreRead Less
"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 fRead MoreRead Less
"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
"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. ShRead MoreRead Less
"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 assiRead MoreRead Less
"Annette is tops in her profession. We couldn't have had a better experience or nicer outcome"
"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"
"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. ThRead MoreRead Less
"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 tRead MoreRead Less
"Annette Schaffer is an amazingly knowledgeable realtor. I highly recommend if you are interested in real estate services you make Annette your first consideration."
"We have used Rebecca for 3 transactions and would never use anyone else!Martin and Carolyn"
"We loved working with Vail! She helped us look at several properties before we found the one!"

Featured Homes

Featured Island Properties

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Ready to

Make Your Move?

Whether you’re buying, selling, or simply exploring your options on the San Juan Islands, we’re here to provide clarity, strategy, and trusted local guidance every step of the way.

Connect With Us