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$1,800,000
4 Beds ⋅ 3 Baths ⋅ 2514538 MLS ⋅ ACTIVE Status
This property has been in the owner's family for close to a hundred years. Owner's Grandparents built the home on the most desirable location on their property in 1937. The most compelling aspect of this property is the view, lot size (1.5), and its safety from storms/flooding. Extraordinary views, with majestic Mt Baker to the east. Spring, summer, and fall provide a beautiful morning sunrise with the mountain glowing in the pre-dawn twilight. Watch the ferries come and go, splendid luxury yachts, and commercial and recreational fishing vessels go about their business of whale watching, wildlife viewing, and salmon, crab, and shrimp fishing. Watch eagles, seals, hawks, ravens, seabirds, right from the living room, bedrooms, kitchen, and deck. You can throw a rock and hit the water it's so close. The property is unique in that it comprises a lot and a half. This feature insures you could build a huge house, with plenty of room on either side. The property is sheltered from the prevailing SE,S, and westerly winds. It can blow 50 mph and you're sheltered from its fury. It's close to town (half mile). There is a studio apartment in the basement that the Seller rents out for $800 per month! This is a very special property! Property sold as-is.

460 Harrison Street, Friday Harbor

Listing courtesy of List4FlatFee.com, LLC.

$929,000
3 Beds ⋅ 2 Baths ⋅ 2513768 MLS ⋅ ACTIVE Status
Perched in the heart of Deer Harbor Hamlet with views of the estuary and open water, this two-bedroom, two-bath home combines natural beauty with everyday functionality. Nearly three-quarters of an acre of private grounds frame the ever-changing tidal landscape, while an attached garage offers secure storage and workspace — a genuine asset on island. Light-filled interiors, two full baths, and a setting steps from the charm of one of Orcas Island's most treasured communities make this an exceptional opportunity whether you're seeking a full-time residence, seasonal retreat, or long-term investment in the Pacific Northwest.

4622 Deer Harbor Road, Orcas Island

Listing courtesy of COMPASS.

$1,075,000
3 Beds ⋅ 3 Baths ⋅ 2505360 MLS ⋅ ACTIVE Status
Immaculate and spacious, this inviting home offers the perfect blend of comfort, privacy, and partial views of the Straits, sun-washed valleys, and glowing sunrises. Designed for both everyday living and entertaining, the updated kitchen features a propane cooktop, stainless steel appliances, and generous storage—ideal for gatherings large and small. The thoughtfully designed 3-bedroom, 3-bath layout supports easy main-floor living, while the lower level provides flexible space with an additional bedroom, bath, and large great room—perfect for guests, hobbies, or media room potential. Sun-drenched decks extend the living space outdoors, creating the perfect setting for morning coffee, evening dinners, or unwinding in the hot tub. Set on 1.7 acres, the property includes a fenced garden area, fruit trees, raised beds, firepit, and a charming historic bunkhouse that adds character and versatility. This is a home where you can relax, entertain, and fully embrace the island lifestyle. By appt.

222 Oak Hill Drive, Friday Harbor

Listing courtesy of Coldwell Banker San Juan Is..

$1,150,000
2 Beds ⋅ 2 Baths ⋅ 2509390 MLS ⋅ ACTIVE Status
This one-of-a-kind timber frame home with sweeping views, rises above the treetops like a modern forest lookout. Totally private with all-day sun and a beautiful natural setting. Reclaimed beams, history-rich fir floors, soapstone counters, and hand-crafted stonework all show examples of the superior craftsmanship in this home. Wraparound windows and a dramatic opening glass wall erase the boundary between indoors and out. The second-floor primary suite feels like a private hideaway, with windows in every direction and a partially covered wraparound deck perfect for sunlit mornings. A solar array powers the boiler that feeds the main-floor radiators and heated floor, while a European wood stove adds warmth and atmosphere, keeping the home comfortable year-round. Every detail reflects thoughtful design and enduring quality. The guest cabin is equally enchanting—a serene retreat with a spa-like bath with custom finish work and clawfoot tub. Guests will never want to leave. Both dwellings include generous window seats that double as storage and additional sleeping space. Perched on a sunny south-facing hillside and bordered by 30 acres of shared forestland. Owners enjoy access to the Decatur Shores deep-water dock, private airstrip, and waterfront park, all just a quick 20-minute boat ride from Anacortes. Mooring buoy negotiable.

123 South Ridge Road, Decatur Island

Listing courtesy of Windermere RE Anacortes Prop..

$1,450,000
2 Beds ⋅ 2 Baths ⋅ 2503343 MLS ⋅ ACTIVE Status
Exquisitely crafted private estate on 12 acres of serene, secluded land. This exceptional Craftsman-inspired home combines refined craftsmanship, advanced infrastructure, tranquil privacy. Fully fenced yard designed for pets while excluding wildlife. A second building site w/utilities offers outstanding future potential/water views. Artisan details showcased throughout, including timber frame accents, custom solid-wood interior doors, natural wood trim, slate switch plates, subtle LED lighting. A Hearthstone freestanding wood stove anchors the living space, while architectural eave lighting enhances exterior. The kitchen blends elegance/functionality with cherry cabinetry, quartz countertops, stainless farmhouse sink, touchless faucet, under-cabinet lighting, pull-out waste/recycling. The main bathroom features quartz counter, ceramic basins, tiled tub surrounds. Bedrooms utilize built-in closet organizers. Built with ICF lower level, SIP upper walls, exceptional efficiency, Andersen double-pane windows, heat recovery ventilation, hydronic radiant floor heating. Durable fiber-cement siding, metal roof provide longevity. Outdoor living includes a TimberTech deck, lighted stairs, integrated planters, propane connections, molded concrete paver patio. Infrastructure: 2 wells, dual septic tanks, permitted 5 bed drainfield, backup generator, buried propane tank, heated insulated shop, RV parking w/utilities. A rare offering where craftsmanship, comfort and infrastructure converge.

424 Logan's Run Road, Orcas Island

Listing courtesy of TWilliams Realty.

$3,250,000
2 Beds ⋅ 2 Baths ⋅ 2508508 MLS ⋅ ACTIVE Status
Stunning waterfront estate spanning two sun-filled parcels with 44’ deepwater dock in extremely desirable West sound. Expansive south-facing views look over Salish Sea, outer islands and Olympic Mountains in the distance. Property includes a shared dock and a mooring buoy. The approximately 1200 square-foot luxury home on the first lot is finished with high-end materials, hydro floor heating throughout, steam shower, gas fireplaces in living room and bedroom, Hubbardton Forge fixtures, ironwood deck, solar panels, hot tub, outdoor shower, and an EV outlet. The property offers the flexibility to reside in the existing home and build a new residence on the upper lot, which already has a three-bedroom septic drain-field and on-site utilities.

1022 & 1024 Deer Harbor Road, Orcas Island

Listing courtesy of COMPASS.

$2,500,000
3 Beds ⋅ 3 Baths ⋅ 2508583 MLS ⋅ ACTIVE Status
A rare chance to own a true stretch of Orcas Island shoreline, this north shore property offers 412 feet of walk-out waterfront—a scale and presence that is increasingly hard to find. Adjacent to public land, the setting feels both expansive and private, with panoramic views across the Salish Sea to the city of Vancouver and a tapestry of surrounding islands. Set on 2.8 acres, the property encompasses nearly 5,810 square feet of living space across three separate residences with six bedrooms, offering exceptional flexibility for multi-generational living, guests, or income. The 3,707-square-foot midcentury 2 bedroom main home captures sweeping water views and invites a thoughtful refresh. A 1,442-square-foot 3 bedroom guest house, complete with an active vacation rental permit, provides immediate income potential, while the detached 660-square-foot 1 bedroom bungalow adds even more versatility. A spacious indoor swimming pool extends the property's year-round recreational appeal. With two mooring buoys and direct beach access, the waterfront lifestyle is effortless—launch a kayak, set a crab pot, beach-comb along your own shoreline, or simply enjoy the ever-changing marine activity and sunsets over the water. Priced substantially below assessed value, this is a compelling opportunity to secure a legacy waterfront estate with remarkable scale, income potential, and room to shape it into something extraordinary over time.

664 Tidewinds Lane, Orcas Island

Listing courtesy of Orcas Island Realty.

$4,900,000
3 Beds ⋅ 4 Baths ⋅ 2502025 MLS ⋅ ACTIVE Status
LOPEZ ISLAND LUXURY---A rare blend of privacy, distinction & breathtaking views. This custom NW Craftsman sits on 27 waterfront acres overlooking MacKaye Harbor & Vancouver Is across the Straits to the OLympic Mtns. Designed for the southern vistas, the 3 bedroom/3.5 bath home features madrona floors, banks of windows, clear fir cabinetry with many built-ins & fine finishes. The Great Room centers on a stone fireplace flanked by built-ins & roomy view daybed. The chef's kitchen, which is the heart of the home, offers slate counters, double ovens, Wolf cooktop & spacious breakfast nook. Two ensuite primary bedrooms with walk-in closets, one with a covered deck. French doors open to sunny stone patio perfect for entertaining or watching eagles soar. Detached garage with studio above allowing plenty of privacy for guests. Seasonal creek winds thru mature woods & pasture past the pond. Large shop/garage, fenced garden with raised beds, fruit trees, beautiful chicken house & more. Everything you need for island living plus the house is wired for a generator.

481 Grimes Riker Lane, Lopez Island

Listing courtesy of Windermere RE/Lopez Island.

$640,000
2 Beds ⋅ 1 Baths ⋅ 2506312 MLS ⋅ ACTIVE Status
Rustic and rooted in island culture, this sweet little property sits on half an acre of peaceful land on Lopez Island's south end. Originally built as a hunting cabin, the main building has evolved into an inviting and cozy home with an open living/kitchen area warmed by an enormous wood stove, two bedrooms, a full bathroom, an attached greenhouse, and a laundry room. Retreat into the hand-built studio, aka "the coop," to work or just idle the time away in the quiet, light-filled space tucked amongst towering Douglas firs. Soak up the afternoon sun and the solace of nature in the meditation hut, which looks out over irrigated garden beds and a lovely pond. The sunny clearing by the pond has been the site of many joyful gatherings, and you will never be short of birds and woodland visitors who also appreciate this half-wild, half-cultivated haven. Completely private and enclosed on the north/street side by hand-hewn clapboards made from salvaged, island grown cedar and fir logs, and fully fenced along the boundary shared with the neighboring farm. Cold plunge alcove, composting toilet situated in an outbuilding near the coop studio, sheltered sitting and storage areas, large fire pit, buried erratic boulder near pond, older growth trees, and more. Conveniently located near Watmough Bay beach, many hiking trails, and Islandale Grocery and Restaurant. Two bedroom septic, private well, propane heating/cooling unit in main house in addition to wood stove, no HOA.

4160 Mud Bay Road, Lopez Island

Listing courtesy of Windermere RE/Lopez Island.

$3,800,000
3 Beds ⋅ 5 Baths ⋅ 2491041 MLS ⋅ ACTIVE Status
Tucked at the end of a quiet lane in sought-after West Sound, this timeless Northwest Colonial captures a refined island lifestyle framed by the calm waters of White Beach Bay, evergreens, and open sky. Set behind a gated drive, the property offers exceptional privacy across two tax parcels totaling 1.35 acres, with stairs leading to a fully accessible waterfront—an increasingly rare and coveted feature. Built in 1990, the 3,800+ sq. ft. residence blends classic architecture with warm, inviting interiors. Expansive gathering spaces, a thoughtfully designed kitchen, and quality craftsmanship throughout create a home that lives as comfortably as it entertains. Three bedrooms, including two ensuites, two bonus rooms and 4.5 baths provide flexibility and privacy for both residents and guests. Outdoor living is equally compelling, with two spacious decks and a hot tub positioned to take in the setting. A striking water-filled quarry forms a dramatic natural backdrop, framed by rugged stone and evergreens, and serves as a non-potable water source for landscape irrigation. An attached two-car garage adds convenience, while the surrounding grounds offer a true sense of seclusion. Located just moments from West Sound Marina, the West Sound Community Club, Orcas Island Yacht Club, and waterfront dining, this property delivers a rare balance of timeless design, functional amenities, and effortless connection to the island’s coastal lifestyle.

117 Martha Lane, Orcas Island

Listing courtesy of The Agency Seattle/Eastside.

$1,599,000
3 Beds ⋅ 2 Baths ⋅ 2503458 MLS ⋅ ACTIVE Status
Experience the boating lifestyle of waterfront living at this exceptional Lopez Island retreat. Set along the protected waters of Fisherman Bay, this home includes a private tidal dock and mooring buoy, creating effortless access to endless days of cruising, crabbing, kayaking, and island hopping right out your back door. Lovingly held by the same family for more than 35 years, the home reflects a legacy of comfort, connection, and unforgettable waterfront memories. A substantial update in 2000 enhanced both form and function, introducing warm hardwood floors, expanded living areas, and an inviting layout that embraces the home’s stunning southeasterly water and territorial views. With 3 beds, 1.75 baths and a desirable main-level primary suite, the residence offers a comfortable and flexible floor plan ideal for quiet retreat or effortless hosting. Whether envisioned as a full-time residence, refined island getaway, or legacy waterfront property, this is a rare opportunity to enjoy the very best of Lopez Island living—where elegance meets ease, and every day begins with the rhythm of the tide.

1794 Bayshore Road, Lopez Island

Listing courtesy of COMPASS.

$2,785,000
3 Beds ⋅ 3 Baths ⋅ 2503378 MLS ⋅ ACTIVE Status
This is where the noise stops. Perched on the west side with over 180 degrees of open water views, this custom-built estate occupies one of the most sought-after positions in the archipelago. Sheltered by the lee of Henry Island, the orientation delivers dramatic sunsets and calm, unhurried water for your boat — a rare combination on the islands. The main residence has been meticulously maintained and recently transformed: new carpet, heat pump system, and a massive rebuilt wraparound deck, ready for years of enjoyment. Walls of windows pull the water into every room. A private staircase leads down to your tidelands, and 251 feet of deeded shoreline and 2.5 legal parcels convey with the sale. Your mooring buoy is already in the water. There’s even a hidden room in the basement — the kind of detail that makes a house a home. The guest house earns its keep with views that rival the main residence, fully self-contained and privately situated. A dedicated detached office and two garages round out the compound, giving you the infrastructure to actually live here full time. Orca sightings, tall ships at sunset, deeded waterfront and room to expand. All yours.

1501 Yacht Haven Road, Friday Harbor

Listing courtesy of eXp Realty.

$3,950,000
3 Beds ⋅ 5 Baths ⋅ 2501315 MLS ⋅ ACTIVE Status
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!

571 Golf Course Road, Friday Harbor

Listing courtesy of Windermere RE San Juan Islands.

$3,450,000
2 Beds ⋅ 2 Baths ⋅ 2493318 MLS ⋅ ACTIVE Status
Experience the pinnacle of island living in the extraordinary waterfront retreat, crafted by Edward Carr and built by Sound Construction. Nestled to capture sweeping vistas of Eastsound Village, Buck Mountain, Mt Constitution and the East Sound Bay, (historically known as Fishing Bay) this unique home offers an idyllic waterfront lifestyle. Spanning 1.5 acres across two parcels, the 2520 square foot main home embodies timeless Northwest design. Enjoy two bedrooms, walk-in closet, office/hobby room and 1.5 baths, all adorned with custom cabinetry, a gourmet kitchen, Brazillian cherry floors, radiant heat and vaulted ceilings. With historical lime kiln, pocket beaches and ownership of the tidelands, this property also features a 748 square foot guest house full of natural light, a bedroom and ¾ bath. The detached garage offers ample space for vehicles and gear, plus a covered area for all your outdoor equipment. Dive into the Salish Sea for crabbing, kayaking or beach combing, whale watching and seasonal birding/wildlife activity ie seals, ducks, eagles, king fisher, osprey, surf scoters and spawning herring. Just minutes from Eastsound Village and Crescent Beach. Your adventure begins right at your doorstep.

69 Myer's, Orcas Island

Listing courtesy of TWilliams Realty.

$6,650,000
3 Beds ⋅ 3 Baths ⋅ 2497499 MLS ⋅ ACTIVE Status
Newly constructed modern waterfront residence with unparalleled panoramic 180° views of the Salish Sea. Situated on a rare low bank 0.53 acre lot this is the last home permitted to be built within the 30 foot ordinary, high water mark in San Juan County. Secluded beach, mooring buoy and rare boat launch. 16’ soaring VG fir ceilings, gourmet chefs kitchen, and spa like primary suite with a steam shower. Fossilized limestone, travertine, and European wide plank oak flooring. Granite stone exterior with Roman paver driveway and patio. Tucked at the end of Davison Head and minutes to Roche Harbor, this ultra secluded half acre is a rare and refined haven. Whether boating, or watching wildlife, this is modern waterfront living.

477 Davison Head Drive, Friday Harbor

Listing courtesy of List4FlatFee.com, LLC.

$1,068,000
3 Beds ⋅ 3 Baths ⋅ 2500030 MLS ⋅ ACTIVE Status
Designed for both comfort & connection to its surroundings, this 2,262sf Northwest home offers a thoughtful balance of function, warmth, & flexibility. A welcoming entry opens easily to the main living spaces & attached garage, creating a natural flow for everyday island living. The kitchen is both inviting & practical, with an eating bar & a charming breakfast nook framed by windows overlooking a quiet forest floor blanketed in green moss. From here, the home unfolds into the dining area & a sun-filled sitting room, all oriented toward the fenced garden. Upstairs, three bedrooms & two full baths are thoughtfully arranged. The primary suite enjoys a private balcony with distant views of Strait of Juan de Fuca & Olympic Mtns, dual closets including a walk-in & a soaking tub. Vaulted ceilings & expansive windows fill the main living area with natural light, while over 700 sq ft of decking & a covered front porch extend the living space outdoors. The wooded landscape offers a sense of privacy with minimal maintenance beyond the fenced garden. A greenhouse is nestled among mossy rock outcroppings & mature fir trees, offering a peaceful space for growing. A standout feature is the 1,008 sf detached barn with studio space, offering a full bath, loft, spacious open ground level & additional storage or workshop areas—well suited for a wide range of creative & practical uses. A distinctive San Juan Island property offering space to live, create & settle into the rhythm of island life.

391 Little Mountain Road, Friday Harbor

Listing courtesy of Windermere RE San Juan Islands.

$2,100,000
3 Beds ⋅ 5 Baths ⋅ 2483494 MLS ⋅ ACTIVE Status
Southwest-facing waterfront home with private dock on Brown Island, offering 3,527 sq ft of beautifully designed living with 3 bedrooms, 2 offices, and 5 baths. This remodeled NW Craftsman 1-story home with basement blends classic style with modern comfort, featuring an atrium entry, open floor plan, and spacious chef’s kitchen. Most rooms including the main-level primary suite with deck access, capture stunning harbor and sunset views. The lower level offers a bedroom and bath with separate entry, ideal for guests or extended living. Outdoor living shines with expansive main-level decks, a sunny waterfront bulkhead patio with steps to the beach, and a private dock on 107 feet of accessible shoreline. A detached golf cart garage/shop, hot tub, and bocce court complete this exceptional setting. Brown Island amenities include community moorage, pool, clubhouse with fitness room, caretaker boat service, and easy access to Friday Harbor by boat. From your decks, enjoy ferries, boats, seaplanes, and the glow of town lights at night. With golf cart parking and boat launch, this island blends secluded island privacy with easy access to the vibrant town, marina, shopping, and dining of Friday Harbor. An extraordinary Brown Island residence offering spectacular sunsets, premier waterfront living, and an unmatched island lifestyle.

3 Brown Island, Friday Harbor

Listing courtesy of Coldwell Banker San Juan Is..

$1,850,000
4 Beds ⋅ 4 Baths ⋅ 2498455 MLS ⋅ ACTIVE Status
Stunning 4 bedroom, 3.5 bath home in premium location with protected Roche Harbor Marina views. Designed for both comfort and entertaining the spacious layout features an open-concept living area, expansive windows, 7-speaker surround system, 10-ft ceilings throughout the main floor, a propane fireplace, and a 3-car garage. The gourmet kitchen anchors the heart of the home featuring granite counters, a farmhouse sink, and custom cabinetry. The primary suite offers a soaking tub, 3-person steam room, and deck access to the hot tub overlooking the marina. Short walk to airstrip and resort amenities, plus from your yard you can access a popular foot path that leads directly to the resort. Make this your private front-row seat to all the activities Roche Harbor has to offer, including July 4th fireworks.

247 Afterglow Drive, Friday Harbor

Listing courtesy of Coldwell Banker San Juan Is..

$3,485,000
5 Beds ⋅ 5 Baths ⋅ 2496208 MLS ⋅ ACTIVE Status
Exceptional craftsmanship and timeless design define this custom homebuilder's own residence, thoughtfully created for both elegant living and everyday comfort. Privately set on 5 acres, this 5,800 sq ft Craftsman estate captures sweeping seasonal and water views of San Juan Valley, Mt. Baker, San Juan Channel, and Haro Strait. Impeccably maintained, the home offers spacious main-level living ideal for gathering and entertaining, featuring inviting living, dining, and family rooms, a chef's kitchen, and a sunny breakfast nook. Upstairs you'll find four bedrooms, including a stunning primary suite with panoramic views and a spa-inspired bath designed for relaxation. The lower level provides wonderful flexibility with a guest or MIL suite, private entrance, great room, bedroom, and bath – perfect for extended stays, multigenerational living, or hosting visitors. Step outside to a beautiful patio framed by mature landscaping, offering space to unwind and enjoy the peaceful island setting. Complete with a two-car garage and generator, this remarkable home blends comfort, quality, and the best of island living.

148 Yarrow Road, Friday Harbor

Listing courtesy of Windermere RE San Juan Islands.

$12,900,000
3 Beds ⋅ 3 Baths ⋅ 2493253 MLS ⋅ ACTIVE Status
Absolutely stunning 28-acre waterfront estate on picturesque Orcas Island. This luxury property combines complete privacy & incredible natural beauty across two waterfront tax parcels with a beautiful main home, separate guesthouse, your own 65-foot protected deepwater dock, two private beaches and a brilliant waterfront pavilion with kitchen, wet bar & fireplace. The masterfully designed main residence features 2 bds & 2 baths and a massive deck all directly on the Salish Sea. Tucked near one of your beaches find the 1-bed, 1-bath guesthouse with full kitchen & fireplace. A large garage & bunkhouse sit above main home while the park-like grounds include a fenced garden, greenhouse and meandering trails along the shoreline.

Orcas Island

Listing courtesy of COMPASS.

$795,000
2 Beds ⋅ 1 Baths ⋅ 2495781 MLS ⋅ ACTIVE Status
Wanting a home at the beach? This island retreat sits less than 50 yards from the water, with sweeping views toward Thatcher Pass and the surrounding islands. It’s a great getaway from Seattle and a second home in the islands doesn’t have to mean long ferry lines or complicated logistics. A private passenger ferry can bring you to Decatur Island from Anacortes in about 30 minutes and you'll find just what you've been looking for. Inside, the home is warm, bright, and easy to settle into: wood floors, vaulted ceilings, a cozy propane stove, and sunlight pouring through generous windows. The kitchen features stainless steel appliances, including a new induction range and Bosch refrigerator, and looks out over a gently sloping green hillside where sheep often wander. The open "Great Room" keeps cooking, dining, and relaxing connected. A main-floor primary bedroom and ¾ bath add convenience, while upstairs offers another bedroom plus a spacious bonus room perfect for guests, movie nights, or a dedicated home office. Beds, dresser and Eames-style chair can stay. Also includes 2020 Yamaha golf cart. Decatur Northwest spans 600 acres of forest, meadow, and shoreline, with two sandy beaches, a deep-water dock, regularly scheduled private passenger ferry, Skyline parking space, tennis courts, community gardens, and miles of trails. Whether you’re into kayaking, beachcombing, hiking, or simply unwinding in nature, this island home at Sylvan Cove offers it all.

68 Sylvan Cove West, Decatur Island

Listing courtesy of Windermere RE Anacortes Prop..

$7,950,000
3 Beds ⋅ 4 Baths ⋅ 2493364 MLS ⋅ ACTIVE Status
Poised above the shores of Haro Strait on San Juan Island's coveted west side, this exceptional waterfront estate is a rare fusion of architectural significance and natural beauty. Designed by acclaimed firm Bohlin Cywinski Jackson (BCJ), the residence is privately sited on 6 acres spanning 4 tax parcels with 400’ of pristine shoreline. Nearly 6,500 sf of thoughtfully designed living space showcases timeless contemporary architecture, seamlessly connecting dramatic island landscapes, expansive water views, and refined luxury living. Expansive walls of glass, soaring ceilings, and warm natural materials frame sweeping views of Haro Strait, the Olympic Mountains, spectacular sunsets, and passing whales. Designed for entertaining and everyday comfort, the home features a chef's kitchen, elegant great room, tranquil primary suite, guest accommodations, wine cellar, and flexible hobby or fitness space. Complementing the residence is a detached garage and workshop with a private studio apartment and full kitchen—ideal for guests, extended stays, or creative pursuits. A fully equipped greenhouse, fenced gardens, and open space enhance the property's connection to the land. A rare offering on San Juan Island's most sought-after shoreline, this legacy property delivers exceptional privacy, architectural significance, and an unparalleled waterfront lifestyle.

4415 West Side Road, Friday Harbor

Listing courtesy of Windermere RE San Juan Islands.

$2,375,000
2 Beds ⋅ 2 Baths ⋅ 2493374 MLS ⋅ ACTIVE Status
Isthmus House is a rare opportunity to acquire style and a totally unique location, positioned to provide breathtaking views East to Harney Channel and Orcas Island and West to Wasp Passage and Bell Island.With 250 feet of waterfront on the East and the West side of the home, and a mooring buoy in the East bay, Isthmus House is not just a home but a lifestyle to be cherished for a lifetime. Open plan with vaulted ceilings in every room. Built in 1969, addition added in `1989. Extensive removations and updating. Kitchen and bathrooms and have been completely renovated. Expansive decks on east and west side of home create a seamless transition from indoors to outdoors. Perfect blend of modern comfort and classic mid-century modern charm. FULLY FURNISHED (some art work not included) and ready for your Shaw Island adventure!

512 Broken Point Road, Shaw Island

Listing courtesy of COMPASS.

$1,995,000
3 Beds ⋅ 4 Baths ⋅ 2492919 MLS ⋅ ACTIVE Status
Stunning 3-bedroom, 2.5-bath Pacific Northwest home on 7 serene acres w/guest house, pond-side studio, finished 2-car garage, tranquil hot tub pavilion & flagstone fire pit patio. Circular drive & beautifully landscaped grounds complete the setting. Ross Chapin Architect designed main house features a 14-ft Great Room w/reclaimed Columbia River beams, bamboo floors, fir cabinetry & custom stone fireplace w/log lighter. Ground-floor primary suite includes steam shower, walk-in closet & reading nook. Light-filled laundry & workspace w/folding island, built-in desk & ample storage. Radiant in-floor heat throughout. Floating ipe decks connect to guest house w/full bath. A peaceful intentional retreat where timeless design meets modern comfort.

72 Thunderbird Trail, Orcas Island

Listing courtesy of Orcas Island Realty.

$4,950,000
3 Beds ⋅ 5 Baths ⋅ 2492904 MLS ⋅ CONTINGENT Status
Awe-inspiring elegant and peaceful waterfront home and shared dock with views of Obstruction Pass offers pristine low bank beach & rocky promontory, bringing in nature from nearly everywhere on the gently sloping 2.28 acre site. This thoughtfully renovated home has soaring ceilings, luminous light & an open floorpan with space for everyday living & celebrations of any size. Formal living & dining, lofted den, 3 bedrooms, 4.5 baths, bonus rooms for added guests & many flexible spaces for relaxing, socializing & fun. Fabulous design blends indoor & outdoor living areas. Amazing party room opens to a stone patio with dining table for seafood dinners! Move-in ready w/most of the furnishings, art & decorations included. Features list available.

202 Avilion Place, Orcas Island

Listing courtesy of Orcas Island Realty.

$899,000
3 Beds ⋅ 2 Baths ⋅ 2491866 MLS ⋅ ACTIVE Status
Island oasis on 2.5 private acres w/vacation rental permit—a rare find on Orcas! This immaculate 3-bed, 2-bath +bonus rooms home sits at the end of a quiet road, just 2 miles from Eastsound. Surrounded by mature landscaping, privacy fencing, serene ponds, & a gazebo w/fire pit beside a cascading waterfall feature, it’s a peaceful, retreat-ready property w/no HOA/CCRs. Spacious kitchen for entertaining, newer roof, fresh paint, on-demand hot water, soaking tubs, large pantry, walk-in closets, generator hookup, RV/boat parking w/power, large shed w/porch (12x24), tool shed (8x8), sunny garden space, & lower pasture area. Enjoy birds, sunrise/sunset views through expansive windows. Walk to golf course!

168 Jackson Road, Orcas Island

Listing courtesy of True North Realty.

$3,200,000
4 Beds ⋅ 5 Baths ⋅ 2491777 MLS ⋅ ACTIVE Status
STUNNING NORTH SHORE WATERFRONT, A RARE ORCAS ISLAND SANCTUARY Reached by a meandering drive through a reserve of majestic old-growth cedar forest, this extraordinary waterfront retreat sits perched along the shores of the Salish Sea in one of Orcas Island's most magical locations. Sweeping 180° views unfold across the water to Mt. Baker, the Canadian Coast Mountains, and the surrounding San Juan Islands including Sucia, Patos, and Lummi. Ever-changing marine light, dramatic sunsets, and endless coastal scenery create a breathtaking backdrop. Wildlife is abundant and ever-present. Bald eagles nest in the towering cedars, raising their young overhead, while orcas pass through nearby waters, herons wade the shoreline, and harbor seals bask on sun-warmed rocks. Stone steps, crafted by local artisan Zack Leck, descend to 169 feet of accessible beachfront, tidepools teeming with sea life, and calm waters perfect for kayaking. The 4,014 sq ft residence features soaring ceilings, hardwood and stone floors, four fireplaces, a gourmet kitchen, sunroom, and a great room framing the water like a living painting. An attached 2-bedroom guest suite offers full kitchen, bath, and living room. Landscaped grounds include manicured lawns, a fenced garden with raised beds, and an orchard of plum, apple, and cherry trees. Minutes to Eastsound yet worlds away.

285 Raptor Road, Orcas Island

Listing courtesy of Orcas Island Realty.

$1,795,000
3 Beds ⋅ 3 Baths ⋅ 2474873 MLS ⋅ ACTIVE Status
SPECTACULAR MARINE VIEW, Victorian Estate with glorious Westerly facing views over East Sound, Turtleback and beyond to Canada. Enjoy the 7.5 park-like, private acres with beautifully landscaped, walled garden, ponds, waterfalls, a gazebo and a greenhouse and walking paths. Should you wish to explore further, you will find easy access to miles of hiking trails and lakes in Moran State Park. This superb, quality home was built by renowned Pearson Construction and features antique light fixtures, hand-painted wall paper, stained glass doors and 1800’s mantels. Modern updates include HVAC, solar panels, full irrigation system and Wolf & Sub-Zero appliances. Walled gardens, covered porches, and a fire pit perfect for outdoor living in the summer, while a Vermont Castings wood stove keeps winter cozy! Minutes from Eastsound amenities yet a world away.

1656 Eagle Ridge Road, Orcas Island

Listing courtesy of True North Realty.

$999,000
2 Beds ⋅ 1 Baths ⋅ 2489159 MLS ⋅ ACTIVE Status
Paradise Found at Fox Glove Cottage! Turn-key, active vacation rental with bookings throughout the summer! Walk right into an income generating property! Waterfront, two bedroom, one bath beach cottage in Deer Harbor overlooking the Deer Harbor marina. Enjoy the best of both worlds with a charming and lovingly updated beach cottage and coveted outdoor oasis. Watch the comings and goings of the boats at the Deer Harbor and Cayou Quay marinas from the spacious deck. Grassy yard with picnic table and benches leads to easy steps to your private beach and tidelands. Many updates within the last year, including new paint, new flooring, gorgeous new fireplace, ductless heat pump/mini-split. The home is a highly sought after and a successful vacation rental with a current vacation rental permit and rental history. Property comes turn-key, furnished and ready to rent or enjoy. Charming, breakfast bar, countertop dining, spacious deck with views of the channel and the Deer Harbor marina. Walk to marina and amenities of Deer Harbor community including, post-office, dining options, marina market and more. High speed internet/Rock Island Fiber, Deer Harbor Marina Water and Sewer.

5244 Deer Harbor Road, Orcas Island

Listing courtesy of True North Realty.

$375,000
2 Beds ⋅ 1 Baths ⋅ 2487574 MLS ⋅ ACTIVE Status
BOAT or FLY In & escape to the quiet charm of Stuart Island & experience cabin life the way it was meant to be! Nestled among proud evergreens, this cozy island retreat offers the perfect place to unplug & enjoy the beauty of the outer San Juans. Spend your days exploring nearby beaches, crabbing & fishing in surrounding waters, or hiking to the iconic Turn Point Lighthouse. Inside, the warm & inviting cabin captures the spirit of classic PNW getaways. A 1 owner abode, with a cozy great room with a wood burning fireplace, an efficient & quaint kitchen plus you’ll love the main floor bedroom & bath. The sleeping loft overlooks the main living area—complete with a firefighter pole for a quick & playful slide down to the great room below. True to its rustic roots, the property also includes a traditional outhouse, adding to the authentic off-grid island experience. A large shed for your tools/toys & the cabin comes furnished. A short boat ride from the vibrant marina, shops & dining at Roche Harbor, this peaceful retreat offers privacy, nature & the rare chance to own a slice of the San Juan Islands’ most beloved outer-island lifestyle. Whether you’re seeking a weekend escape, summer basecamp, or a place to reconnect with nature, this cabin is ready to welcome you. Stuart Island Airway Park (7WA5) is a well maintained, private, grass airstrip that provides the primary transportation option for many of the property owners too. Only a short walk from the airport to the cabin!

436 Marine Lane, Stuart Island

Listing courtesy of Windermere Real Estate/HLC.

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