Available Listings

$3,950,000 (USD)
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Friday Harbor Area Residential

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571 Golf Course Road Friday Harbor, WA 98250

3 Bed
5 Baths
4120 sqft
MLS# 2501315
Virtual Tour
Perched on a rare and private point of San Juan Island, this architecturally significant waterfront estate offers an exceptional blend of design, scale, and lifestyle. Encompassing 3 parcels and 640± feet of shoreline, the property captures sweeping waterviews framed by Mt. Baker, with walls of glass that bring the ever-changing seascape into every living space and a setting surrounded by water on three sides. The 4,120± sf main home is thoughtfully designed with a refined yet livable layout, offering 3 bed/4 baths and multiple flex spaces for office, media, or guest use. The primary suite is a serene retreat, evoking the feeling of being on a boat with expansive waterviews, a walk-in closet, and spa-inspired 5-piece bath. Medium bank waterfront with accessible shoreline invites paddleboarding and kayaking, while low tide reveals a beach ideal for exploring, with crabs under rocks and a hidden cave. A permitted mooring buoy accommodates up to a 45' boat. Includes an additional waterfront lot for future development or privacy. A detached 3-car garage is complemented by an 864± sf ADU studio, ideal for guests or income potential. Walking distance to the San Juan Golf & CC and a short bike ride to town, with a compliant vacation rental permit for added flexibility and investment appeal. A truly rare waterfront legacy property!
Listing Courtesy of Northwest MLS as distributed by MLS GRID / Windermere Real Estate San Juan Island / Greg King
$3,500,000 (USD)
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Estate Living On Henry

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1 & 2 Driftwood Shores Henry Island, WA 98250

3 Bed
4 Baths
3559 sqft
MLS# 2502876
Virtual Tour
Gracefully designed with classic symmetry, stately columns & refined architectural detail, this home evokes the charm of a bygone era while offering modern luxury in a breathtaking island setting on 2 lots. Gourmet kitchen blends form & function, high-end appliances, a monolithic island, abundance of cabinets, a walk-in pantry & sleek stone. Seamless flow into formal & casual gathering areas. Primary suite is a true sanctuary framed by tranquil views, a luxe bath, banks of closets & direct access to the wraparound porches. Every element of this remarkable retreat reflects thoughtful design & uncompromising quality. An ensuite retreat offers comfort/privacy with its own private lanai, while a charming finished attic provides extra space for guests. Also, beautifully restored 1920s cottage serves as a delightful guest haven with its own kitchen, bed/bath + an artist’s studio; perfect space for creativity, crafts, games & gathering. Lots 1 & 2 share a private dock located on Lot 1, offering easy waterfront access, Lot 2 provides ample space for the potential development of an additional residence. The estate unfolds into beautiful, lush grounds, covered verandas and sun-drenched terraces invite you to relax & take in the peaceful surroundings of the San Juan Islands, this rare offering combines New Orleans grace with PNW splendor—just a short boat ride or drive to the charm, marina & dining of Roche Harbor. A truly exceptional opportunity to own a one-of-a-kind legacy property.
Listing Courtesy of Northwest MLS as distributed by MLS GRID / Windermere Real Estate San Juan Island / Richard Sandmeyer
$1,598,000 (USD)
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Deep Water Dock On Henry Is

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5 Smugglers Rowe Henry Island, WA 98250

2 Bed
1 Baths
1504 sqft
MLS# 2478563
Virtual Tour
Perched along the coveted shores of Henry Island, this exceptional waterfront retreat captures sweeping views across sparkling waters to Roche Harbor and beyond. A rare offering, the property features a deep-water, shared dock, providing effortless access for boating, crabbing, fishing, and spontaneous sunset cruises.The home is thoughtfully positioned to embrace its breathtaking surroundings, with expansive windows that frame ever-changing marine vistas—boats gliding by, seabirds soaring, and the harbor lights twinkling at dusk. Two bedrooms on the main plus a sleeping- play loft above. The kitchen has beach-cottage cabinetry, a breakfast bar and a spacious dining area. The great room gets cozy with ambiance of the wood burning fireplace plus there’s another wood stove in the primary suite for a relaxing Winters night. Open-concept living spaces flow seamlessly to a generous outdoor deck, creating the perfect setting for summer gatherings or quiet mornings with coffee and sea air. Designed for both comfort and convenience, the property offers cabin chic finishes, inviting gathering spaces, and private retreats for guests and family alike. Whether you envision a full-time island lifestyle or a legacy getaway, this property delivers the ultimate San Juan Islands experience—privacy, protected moorage, and postcard-worthy views just minutes from Roche Harbor Resort. A rare opportunity to own premier waterfront in one of the San Juans’ most sought-after locations. Book your tour!
Listing Courtesy of Northwest MLS as distributed by MLS GRID / Windermere Real Estate Hlc / Jill Sjolin