A true island sanctuary, this architecturally striking estate spans 47 acres with 440 feet of pristine waterfront, offering commanding views across San Juan Channel to Mt. Baker. Designed renowned firm Hoedemaker Pfeiffer, the 5022 sf main residence is a masterwork of craftsmanship—featuring 3 bedrooms, 3.5 baths, and interiors that gracefully fuse refined comfort with the surrounding natural beauty. A charming 2460 sf guesthouse with 4 bedrooms and 2 baths provides ample space for hosting or extended stays. The grounds are equally compelling with a detached garage, a barn with loft, sport court, and a flourishing orchard. A rare opportunity to own a generational property where design, privacy, and the essence of island living converge.
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$8,495,000
Roche Harbor Area Residential
Pending
51 Claramar Drive San Juan Island, WA 98250
3 Bed
4 Baths
6879 sqft
MLS# 2231170
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$4,299,000
Town Area Residential
Active
560 Warbass Way Friday Harbor, WA 98250
3 Bed
4 Baths
5130 sqft
MLS# 2354144
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$3,700,000
San Juan Island Area Residential
Active
148 Yarrow Road Friday Harbor, WA 98250
6 Bed
5 Baths
6276 sqft
MLS# 2380721
A masterpiece of craftsmanship and design, this custom homebuilder's personal residence offers luxury living at its finest. Set on 5 private acres, this 6276 sf Craftsman estate showcases stunning seasonal and waterviews of San Juan Valley, Mt. Baker, San Juan Channel, and Haro Strait. Impeccably maintained, the home features main-level living designed for entertaining, with elegant living, dining, and family rooms, a chef's kitchen, and cozy breakfast nook. Upstairs offers 4 bedrooms, including a view primary suite with a spa-inspired bath. The lower level includes a guest or MIL suite with private entrance, great room, 2 bedrooms, and bath. Enjoy patio surrounded by mature landscaping, 2-car garage, and generator. Relaxing island life!
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$3,645,000
West Area Residential
Active
2000 2001 Mount Dallas Road Friday Harbor, WA 98250
3 Bed
4 Baths
4131 sqft
MLS# 2388190
Commanding 360° views from its 22-acre perch atop Mt. Dallas, this extraordinary property spans 2 parcels and captures sweeping vistas from Haro Strait to Mt. Baker. The luxurious, tigerwood-clad main home features a grand living room with stone fireplace, chef’s kitchen with artisan cabinetry and high-end appliances, and 2 elegant water-view suites with spa-like baths. A separate guest suite with kitchen, woodstove, and steam shower offers ideal flexibility. A charming off-grid cabin adds rustic appeal with solar power, wood cook stove, and multi-level decks for dining, stargazing, or tent camping. With water storage, heat pump with AC, high-speed internet, and 2-car garage, this private, versatile retreat is the pinnacle of island living.
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$3,495,000
San Juan Island Area Residential
Active
311 Madrona Drive Friday Harbor, WA 98250
4 Bed
3 Baths
2840 sqft
MLS# 2359878
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$3,470,000
San Juan Island Area Residential
Active
128 Twin Oaks Drive San Juan Island, WA 98250
2 Bed
4 Baths
3176 sqft
MLS# 2344703
Discover an extraordinary equestrian estate on 49+/- dividable acres surrounded by 885+/- acres of National Park land featuring incredible horseback, mountain biking, and walking trails. The property offers breathtaking views of the Straits and the Olympics and includes a beautifully remodeled 3,176 sf, 2 bedroom, 3 bath home with bonus rooms offering natural textures and serene spaces. Enjoy a 2-car garage, tennis court with cabana, tranquil pond, 3-stall horse barn with arena, tack room, granary, multiple pastures, 3,360 sq. ft. barn with shop, RV hook-up, and a charming chicken coop. A true equestrian paradise!
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$2,850,000
San Juan Island Area Residential
Active
3528 Beaverton Valley Road Friday Harbor, WA 98250
4 Bed
3 Baths
3667 sqft
MLS# 2378841
Embrace the island lifestyle on this sun-drenched 21-acre log home estate. Thoughtfully maintained, this 3,667 sf retreat offers 4 bedrooms, 3 baths, a main-level primary suite, and a cozy river rock fireplace. Cook and gather in the chef's kitchen, explore gardens and fruit trees, or unwind by the pond with a dock. Multiple barns support your hobbies, horses, or weekend toys. Radiant heat, tile roof, and a 2-car detached garage add comfort and ease. Arrive via a picturesque paved drive and soak in the peaceful blend of open space and wooded privacy - your dream escape awaits.
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$2,800,000
Lopez Island Area Residential
Active
268 Rum Runner Road Lopez Island, WA 98261
3 Bed
4 Baths
3200 sqft
MLS# 2367260
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$2,750,000
West Area Residential
Active
2000 Mount Dallas Road Friday Harbor, WA 98250
3 Bed
4 Baths
4131 sqft
MLS# 2389584
Perched above Haro Strait with panoramic views of Vancouver Island, the Olympics and unforgettable sunsets, this luxurious island retreat blends timeless design with modern comfort. Wrapped in tigerwood decking and siding, the home features a stunning living room with gas fireplace and stone surround, plus a chef's kitchen with high end appliances and artisan cabinetry. 2 elegant waterview primary suites offer spa-like baths with steam showers, soaking tubs, and radiant heat. An office, walk-in pantry, and a separate guest suite with kitchen, woodstove, and steam shower add flexibility and ease. Equipped with a heat pump and AC, water storage, high speed internet, metal roof, 2-car garage, and more. Refined, private, and impeccably crafted!
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$1,375,000
San Juan Island Area Residential
Pending
722 Prohaska Road Friday Harbor, WA 98250
3 Bed
4 Baths
3648 sqft
MLS# 2368430
Once a cherished writers’ retreat where several books were written, this magical dividable 18-acre San Juan Island property is a haven of creativity and tranquility. The 3,648 sf home is designed with versatility in mind, offering essentially two complete living spaces—each with its own kitchen, bedroom, bathroom, and living room—ideal for multi-generational living or guest accommodations. A separate 320 sf guest cottage with bath adds even more flexibility. Thoughtful updates include laminate flooring, refreshed bathrooms, newer heating system, expansive decking, and a saltwater hot tub. The grounds are equally magical, with fruit trees, ponds, mature landscaping, a 2 stall horse paddock, an artist’s shop, and a mystical forest to explore.
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$895,000
West Area Land
Active
2001 Mount Dallas Road Friday Harbor, WA 98250
Bed
0 Baths
sqft
MLS# 2389070
Perched atop Mt. Dallas on 17 acres of natural splendor, this off-grid retreat captures breathtaking views of San Juan Channel, Mt. Baker, and the vibrant valleys below - where each season paints a new masterpiece. Gaze out to glimpses of Haro Strait from your own multi-level tigerwood deck, perfect for dining, gathering around the firepit, or pitching a tent under the stars. The charming, solar-powered cabin offers warm hardwood floors, a wood cook stove, propane refrigerator, copper-accented sink, and a composting toilet - simple luxury in harmony with nature. With two access driveways and a completed soil test, this property invites you to enjoy weekends away or envision your future dream home in the sky.
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$890,000
North Area Residential
Pending
182 Kittiwake Lane San Juan Island, WA 98250
3 Bed
3 Baths
2512 sqft
MLS# 2382319
Island Living at Its Best! Embrace the quiet charm of San Juan Island on this open and sunny .5-acre retreat just steps from the water. The main home offers over 2157 sf of cozy living with 3 bedrooms, 2 updated baths, and multiple spaces to relax or gather—upstairs features hardwood oak floors, a propane stove, and a kitchen with Kenmore appliances; downstairs, a wood-burning stove, media space, and gym area add comfort and function. A detached garage includes a full bath and shop, while a separate 355 sf studio boasts a cedar sauna, outdoor shower, and kitchenette—perfect for guests or your creative space. Garden, unwind, and soak in peekaboo views of San Juan Channel.
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$299,000
Blakely Island Area Land
Active
155 Driftwood Drive Blakely Island, WA 98222
Bed
0 Baths
sqft
MLS# 2257697
Breathtaking land opportunity on Blakely Island! Discover the perfect island escape with this stunning ½+ acre lot, offering captivating views of Mt. Baker and Peavine Pass. Enjoy the serene beauty of the San Juan Islands with easy access via a paved road and a short walk to 1,000+ feet of low-bank community waterfront. This prime location is just moments from sought-after community amenities, including a private airstrip, peaceful ponds, a marina, and a seasonal store. Whether you arrive by boat or plane, getting here is effortless. Embrace the tranquility of island living and build your dream retreat in this unparalleled setting!
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King
$255,000
Town Area Land
Active
365 Marguerite Place S Friday Harbor, WA 98250
Bed
0 Baths
sqft
MLS# 2361397
Versatile .26-acre multifamily lot in town on San Juan Island with utilities - water, sewer, and electricity - already in place. Zoned for up to 4 units (buyer to verify), it's perfect for a single-family home, duplex, or triplex. Potential second-story water views and a convenient location near all the amenities of Friday Harbor.
Listing Courtesy of Northwest MLS / Windermere Real Estate/San Juan Island / Greg King