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$2,795,000
5 Beds ⋅ 4 Baths ⋅ 2496322 MLS ⋅ ACTIVE Status
Set on two tax parcels at the end of a private lane, this exceptional 5-bed 4 bath 15 acre estate offers the perfect balance of peaceful seclusion and close-to-town convenience. Beautiful valley views are showcased throughout the home, creating a warm and inviting backdrop from nearly every room. Thoughtful updates and timeless finishes include butcher block countertops, recently refinished hardwood floors, and spaces designed for both comfortable everyday living and effortless entertaining. The property features a stunning swimming pool, a serene pond, and an expansive 1664 sf 2 bath barn with bonus spaces ideal for guests and entertaining. Protected view easement helps preserve the primary residence’s stunning outlooks while still allowing for multiple potential building sites positioned to capture exceptional southern exposure, valley vistas, and Mountain views. With end-of-road privacy, versatile amenities, and a setting that captures the beauty of the surrounding landscape, this is a rare opportunity to own a truly distinctive property just minutes from town.

164 Songbird Lane, Friday Harbor

Listing courtesy of COMPASS.

$35,000,000
11 Beds ⋅ 13 Baths ⋅ 2495846 MLS ⋅ ACTIVE Status
Presenting Halftide Farms. A gated 90± acre waterfront estate on San Juan Island, with 650± feet of pristine low-bank beachfront & commanding panoramic views across open water to Mount Baker. Curated over three decades and built by Schultz Miller, the estate spans approx, 19,000± SF across six structures, including three primary residences, The Beach House, The Farm House, and The Field House — each with its own guest cottage, a bunkhouse, game house, & caretaker’s residence. Resort-level amenities include two pools with cabana, tennis & pickleball courts, a 3-hole golf course, four ponds, a greenhouse, & two mooring buoys. Anchored by Friday Harbor & the iconic Roche Harbor Resort, San Juan Island offers world-class yachting, dining, coastal charm, hiking, biking, fishing, crabbing, whale watching, paddleboarding, kayaking, boating, exceptional culinary experiences, & access to quality healthcare. Ranked by Travel + Leisure among the top islands in the continental U.S. for five consecutive years, the San Juan Islands have long captured global attention. What the world couldn’t access until now is this: an estate without equal. Arrive by seaplane from Seattle in approx. 45 minutes, private jet via Friday Harbor Airport or nearby Bellingham Airport, private vessel to your shoreline, or ferry through the San Juan archipelago. Vancouver, BC lies just 60 miles to the north. A rare Washington legacy acquisition for a buyer who thinks in generations.

Friday Harbor

Listing courtesy of The Agency Seattle/Eastside.

$2,395,000
8 Beds ⋅ 10 Baths ⋅ 2504992 MLS ⋅ ACTIVE Status
Tucked into a peaceful pastoral setting just outside Friday Harbor, Trumpeter Inn offers a rare opportunity to step into a life shaped by connection, hospitality & place. Named for trumpeter swans that winter nearby, the inn has welcomed guests since 1989 & has grown into one of the area’s top-rated boutique accommodations, known for its warm, personalized experience & loyal repeat clientele. Set on approximately five pristine acres with views of the Olympic Mtns., the property blends the charm of a boutique retreat with the privacy & scale of an island estate. The 3,414 sq ft inn features well-appointed guest suites and inviting common spaces, complemented by a separate 1,232 sq ft owner’s cottage for private living. A proven income-producing property, the inn generates over $300,000 annually, creating immediate income potential with opportunities for growth. A 1,200 sq ft accessory building, currently leased at market rate, offers supplemental income or flexible use as a studio, workshop, or expanded guest amenity. The grounds include open lawns, mature trees, and an orchard, creating a peaceful setting just minutes from the ferry and town. With its thoughtful layout & generous acreage, the property offers exceptional versatility—suited for continued inn operation, a retreat or event-based business, multi-generational living, or small-scale farming or equestrian use.Seller is a licensed real estate broker in the State of WA & has an ownership interest in the selling entity.

318 Trumpeter Way, Friday Harbor

Listing courtesy of Windermere RE San Juan Islands.

$995,000
2 Beds ⋅ 2 Baths ⋅ 2502988 MLS ⋅ ACTIVE Status
Nestled on a sun-drenched southern-facing hillside, this inviting Rosario view home offers a peaceful retreat overlooking Cascade Bay, with Blakely gracing the horizon. Set on .64 acres, the thoughtfully positioned residence blends comfort, warmth and natural beauty in a truly special setting. The two bedroom, two bath home features a beautifully remodeled kitchen with new appliances, updated windows and efficient heating and cooling. Tall ceilings and rich wood floors create an airy, cozy interior, while large windows invite in abundant natural light and tranquil water views. Roomy dining area with added space for lounging and relaxing. Outdoors, the fully fenced terraced yard is both private and picturesque, anchored by a pair of mature maples that lend character and shade. The view deck is an ideal place to unwind, complete with a hot tub! Attached two-car garage & standby 22kw propane generator add convenience and peace of mind. Ideally located, the home is just a short stroll from Moran State Park’s Cascade Way loop trail, as well as picnic and beach areas. Enjoy easy access to Rosario’s marina and nearby waterfront, making this property a wonderful blend of serene seclusion and close proximity to outdoor recreation and coastal amenities.

263 Cascade Way, Orcas Island

Listing courtesy of Orcas Island Realty.

$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..

$2,195,000
5 Beds ⋅ 5 Baths ⋅ 2507008 MLS ⋅ ACTIVE Status
Updated 1,902 sq. ft. home in 2016 located in heart of Friday Harbor with a 618 sq. ft. converted garage offering excellent flex-space potential. Fully remodeled with new windows, insulation, kitchen, bathrooms, plumbing, electrical, flooring, exterior wood, decks, and more. The home features 4 bedrooms, including a main-level primary suite, and a functional layout suited for full-time living. Convenient in-town location close to schools, shops, and the ferry. A turnkey opportunity with strong long-term upside. TWO TAX PARCELS; 351151115000 & 351151116000 being sold together, zoned as Light Industrial. The Yoga business is not included in this sale.

326 Carter Street, San Juan Island

Listing courtesy of Windermere RE San Juan Islands.

$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.

$595,000
1 Beds ⋅ 1 Baths ⋅ 2507420 MLS ⋅ ACTIVE Status
Beautifully crafted carriage house on 2.5 sunny acres with distant water views and a peaceful, private setting. Built for low-maintenance living with cement plank siding and a metal roof, the home feels bright and welcoming inside with bamboo floors, high ceilings, and large windows that frame trees to the north and water to the south.The kitchen is efficient and thoughtfully designed with granite counters, a propane range, stainless appliances, an eating counter, and generous storage. A 2.5' X 14' bench spans the south-facing windows, creating a perfect spot for reading, relaxing, or offering extra sleeping space for guests. Quality shows throughout, including the bathroom with floor-to-ceiling tile and the many finished storage closets. There's even one large enough to serve as a small sleeping nook.A wood stove and wall heater keep the upper-level cozy in cooler months. The 728-sf main level is insulated, painted, and finished with custom wood windows and carriage doors. It’s ready for your vision—convert it to additional living space, create a golf cart garage, enclose laundry area, or design a studio or workshop.The property includes an approved 3-bedroom septic and private well. A large clearing offers great garden potential, and 30 acres of unspoiled common area provide lasting privacy. Owners enjoy access to a deep-water dock, 2,500' airstrip, and expansive beaches. Decatur Island is just a quick 30-minute water taxi ride from Skyline Marina in Anacortes.

186 South Ridge Road, Decatur Island

Listing courtesy of Windermere RE Anacortes Prop..

$1,150,000
5 Beds ⋅ 5 Baths ⋅ 2502026 MLS ⋅ ACTIVE Status
The Sand Dollar is a rare 5-bedroom, 5-bath home or bed & breakfast overlooking serene Buck Bay, with easy access to Olga Village shops and restaurants, local trails, and Moran State Park. The current owners have lovingly restored the property to its former glory with refinished island fir floors, fresh interior and exterior paint, new appliances, and thoughtful landscaping improvements. Major capital projects are behind you: new roof, foundation repairs, septic work, new stormwater drainage, water heaters, thermostats, updated heating system with new boiler, basement cleanup, and new vapor barrier. Three bedrooms may operate as guest rooms when an owner or manager is on site, with a breakfast-only food service. On the main level, the south-facing living room, dining room, and sunroom enjoy views of the sound and a mature garden. Upstairs are two bedrooms with ensuite baths, a third bedroom and full bath, and an office niche. The backyard features a vintage garage, shop, or studio building on a slab, with gorgeous original multi-pane windows. Mature landscaping, ample parking, and a forested buffer to the north complete the picture. Sold fully furnished — this turnkey business opportunity and move-in-ready home is not to be missed.

445 Point Lawrence Road, Orcas Island

Listing courtesy of Orcas Island Realty.

$2,400,000
2 Beds ⋅ 3 Baths ⋅ 2484568 MLS ⋅ ACTIVE Status
Nearly ten acres of terraced shoreline and mature landscaping, just a short stroll from the Lopez Ferry Landing. The centerpiece is a rare deep-water private dock with a 35-foot float, solid depth, power, and vehicle access for easy boat loading — a genuine rarity in the San Juans. (The float is currently stored off site.) The 1962 main house offers sweeping views of open water, mountains, and ferry traffic from 2,410 sf across two levels. A 600 sf waterfront cottage adds flexible space for guests, a studio, or a home office. Rounding out the property: a 960 sf detached garage and shop, two-car carport, chicken coop, fenced garden, dog run, and additional storage sheds. Two tax parcels, two wells, catchment with storage for irrigation, pocket beaches, a 20KW backup generator, and excellent privacy make this a self-sufficient retreat. Community Hilltop water and Rock Island fiber are available on the property but not yet connected — easy upgrades for the next owner.

208 Tide's End Road, Lopez Island

Listing courtesy of Orcas Island Realty.

$3,295,000
4 Beds ⋅ 5 Baths ⋅ 2506381 MLS ⋅ ACTIVE Status
Experience the ultimate in coastal living in this stunning Craftsman-style home set on rare no-bank waterfront in the coveted community of Cape San Juan. This architectural masterpiece is beautifully crafted with timeless, high-end finishes throughout. Impeccably maintained, the residence feels brand new and offers an unparalleled standard of island luxury. Enjoy dramatic western exposure that provides a front-row seat to the Salish Sea’s most unforgettable sunsets each evening. The heart of the home is a gourmet chef’s kitchen that opens seamlessly to a heated, covered patio, creating a perfect environment for year-round dining and sophisticated entertaining. The thoughtful floor plan features two spacious primary suites, one on each level, to provide comfort and flexibility. Two additional bedrooms and den/office space are strategically placed within the home to ensure privacy. Unwind by the cozy fireplace or step outside to launch your kayak or paddleboard directly from your own pebbled beach. Enjoy the convenience of your own private mooring buoy for your boat. Offering a unique connection to nature where you can enjoy watching abundant wildlife. As part of the coveted Cape San Juan community, you will also have access to top-tier amenities including a seasonal swimming pool, a private marina, a sandy beach, and miles of expansive scenic walking trails. This is a rare waterfront retreat designed for creating a lifetime of memories in a setting of unmatched natural beauty.

745 Cape Drive, Friday Harbor

Listing courtesy of Coldwell Banker Bain.

$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.

$2,995,000
3 Beds ⋅ 4 Baths ⋅ 2502876 MLS ⋅ ACTIVE Status
Exceptional site, just a short boat ride the historic charm of ROCHE HARBOR & adjacent to the Seattle Yacht Club outpost! 2 WATERFRONT lots, 2 HOMES & a private dock! 1-of-a-kind legacy estate in the heart of the San Juan's. Elegance while delivering modern luxury. An unparalleled blend of privacy, beauty & future potential. The gourmet kitchen is both stunning & functional featuring premium appliances, a dramatic monolithic island, abundant custom cabinetry, a walk-in pantry & sleek stone surfaces. Formal & casual living spaces flow seamlessly together, creating inviting settings for entertaining & everyday living. The primary is framed by tranquil views & complemented by a spa-inspired bath, extensive closet space & direct access to wraparound verandas. An elegant ensuite guest retreat offers exceptional comfort and privacy with its own secluded lanai, while the charming finished attic provides additional accommodations for family and friends. Adding to the estate's unique appeal is a beautifully restored 1920s cottage, complete with its own kitchen, bdrm & bath. An adjacent artist's studio offers space for creativity, hobbies, or games. Lots 1 & 2 share a private dock located on Lot 1. Lot 2 offers ample room for potential development of an additional residence, creating a rare opportunity for expansion or a future legacy compound.The estate unfolds across beautifully landscaped grounds where covered porches & sun-drenched terraces invite quiet mornings, sunset gatherings.

1 & 2 Driftwood Shores, Henry Island

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.

$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.

$768,500
3 Beds ⋅ 2 Baths ⋅ 2496316 MLS ⋅ ACTIVE Status
Nestled beneath towering old-growth trees, this inviting log home offers peaceful seclusion just minutes from some of the area’s best walking trails. A gentle stream winds through the backyard, its soft murmur greeting you in the morning and creating a tranquil backdrop throughout the day, while the rustle of wind through the trees lulls you to sleep at night. Inside, the warm, woodsy character of the home shines in the open-concept living, dining, and kitchen area, where natural wood finishes and a cozy wood stove create a welcoming gathering space. The lower level provides additional flexibility with its own kitchenette and ¾ bath—ideal for guests, hobbies, or extended stays. A newer detached garage/shop offers excellent space for projects, storage, or creative pursuits. More than just a home, this property invites you to settle into an island lifestyle of quiet moments, fresh air, and a slower, more peaceful pace of living.

60 Miller Road, 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..

$2,799,000
4 Beds ⋅ 2 Baths ⋅ 2492969 MLS ⋅ ACTIVE Status
Panorama Point lives up to its name, perched on a southeast-facing point with an exceptional connection to the surrounding waters & natural beauty of Orcas Island. Expansive windows & soaring ceilings in the great room capture stunning waterfront views & fill the home with natural light throughout the day, creating an inviting & uplifting living space. A beautiful stone fireplace with a wood-burning insert provides warmth & ambiance, making the great room an ideal place to gather on cozy island evenings while enjoying the ever-changing scenery beyond. Thoughtfully designed to embrace both privacy & setting, and completely renovated in 2000, the home sits on nearly five acres of peaceful waterfront property. As you wind down the drive through the wooded landscape, the property offers a wonderful sense of arrival and seclusion. The generous acreage & installed 5 BD septic system provide room to further enhance the property and create a truly remarkable island estate. The home features four bedrooms (one in the loft with dramatic views), two full bathrooms, a loft, and a den, offering comfortable accommodations for owners and guests alike. Whether enjoyed as a private retreat or shared with visitors, the home is perfectly suited to island living. With an active vacation rental permit and a long-standing history of strong rental income, Panorama Point presents a rare opportunity to own a beautiful waterfront home on Orcas Island that also serves as a proven investment property.

122 Lohman Lane, Orcas Island

Listing courtesy of True North Realty.

$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.

$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.

$449,000
3 Beds ⋅ 3 Baths ⋅ 2484143 MLS ⋅ ACTIVE Status
Large Farmhouse. Includes spacious 2nd story studio apt w Airbnb VR permit. Charming 1 bed cabin also sits quietly in the back. Private island in the San Juan islands 20 min from Anacortes. Use as an equestrian farm, full time residence or vacation home. Several outbuildings including a barn, bunkhouse and greenhouse. Centrally located. Short walk to the K-8th grade school. 1/2 mile walk to the beach. Live, work remotely on this large 2.64 acre lot. Partly wooded. Fiber for internet. Daily water taxi from Anacortes. 90 min drive from Seattle.

641 Decatur Head Drive, Decatur Island

Listing courtesy of KW Greater Seattle.

$695,000
2 Beds ⋅ 3 Baths ⋅ 2480319 MLS ⋅ ACTIVE Status
Quintessential island bungalow living in the heart of Friday Harbor. Ideally located directly across from the San Juan Island Fairgrounds and just a short stroll to downtown shops, restaurants, schools, and the ferry, this well-maintained 2 bed, 3 bath home offers the rare combination of charm, convenience, and everyday ease. Inside, approximately 2,300 sqft of thoughtfully designed living space has been refreshed with a beautifully remodeled kitchen and main living area, along with an updated upstairs bathroom creating a clean, move-in-ready feel while preserving its classic island character. The flexible floor plan offers generous living areas, ideal for both relaxed daily living and hosting guests. A spacious walk-in pantry complete with an additional refrigerator and freezer adds a level of functionality rarely found in homes this close to town. This is island life as it’s meant to be: simple, connected, and effortlessly close to everything.

847 Argyle Avenue, Friday Harbor

Listing courtesy of COMPASS.

$19,800,000
6 Beds ⋅ 6 Baths ⋅ 2483787 MLS ⋅ ACTIVE Status
Experience the pinnacle of luxury island living with end-of-road privacy on 63± acres across and 515± feet of coveted low-bank waterfront. Panoramic views sweep over the San Juan Channel to Mount Baker and the North Cascades, offering a breathtaking natural backdrop year-round. The 8,674± sf two-level residence presents 6 bedrooms and 6 baths, thoughtfully designed with refined finishes, rich textures, and seamless indoor-outdoor flow for elevated entertaining and serene everyday living. Expansive terraces overlook orchards, gardens, and tranquil pond, creating a private retreat of rare beauty. Premier amenities include indoor pool, private gym, multiple garages, a historic barn, and a FAA-certified 2,400± ft airstrip with helipad - providing exceptional convenience and exclusivity. A distinguished legacy estate - commanding in presence, yet warmly inviting.

735 Rosler Road, San Juan Island

Listing courtesy of Windermere RE San Juan Islands.

$2,800,000
3 Beds ⋅ 5 Baths ⋅ 2455427 MLS ⋅ ACTIVE Status
Perched above Deer Harbor, this Roy Lundgren–designed high-bank waterfront home offers a front-row seat to the marine activity of Deer Harbor Marina, with sweeping views of Pole Pass, ferries, sea planes, whale-watching boats, and lively boat traffic. Built in 1994 by skilled local craftsmen and impeccably maintained, this 3,500+ sq ft residence features three ensuite bedrooms plus a bonus room, all filled with abundant south-facing light and vaulted ceilings. An attached two-car garage adds convenience, and two nearby marinas provide excellent access to island recreation. Kenmore Air float planes depart just minutes away, offering fast, direct travel to Seattle for appointments or sporting events. Furnishings are available with sale. Deeded shoreline shared access via neighborhood common area. Limited dock use for loading and unloading.

573 Harborview Lane, Orcas Island

Listing courtesy of Orcas Island Realty.

$1,299,000
2 Beds ⋅ 4 Baths ⋅ 2454692 MLS ⋅ ACTIVE Status
Welcome to nearly 9 private acres overlooking the Sound, where a European-inspired estate offers over 5,000 SF of secluded living. The main home offers a peaceful sense of space, quiet places to unwind, and a generous primary bedroom that feels like its own haven. From French floor tiles to the Alabaster fireplace in the primary suite, to the custom Eckbank seating with Judd Bay views, this is truly a one of a kind retreat. The detached guest house includes a bedroom, 2 baths, full kitchen and bonus room with a view. The shop and detached garage provide plenty of storage. Surrounded by forest, it feels a world away, yet Eastsound and the ferry are just down the road. Come see where the island life meets the soul of the Pacific Northwest.

223 Blanc Road, Orcas Island

Listing courtesy of simpliHOM Residential.

$349,500
2 Beds ⋅ 1 Baths ⋅ 2449235 MLS ⋅ ACTIVE Status
Stuart Island Retreat! Tucked among lush greenery on a private 0.56-acre lot on Stuart Island, this 3-bed, 1-bath home offers 1,038 sq ft of inviting living space that feels like a cozy tree house. Multiple wood decks create indoor-outdoor living with open interior. A 128 sq ft garage provides extra convenience, and an almost-new 2024 4-wheeler is included (used only to access property). Also included is a 3,484.80 sq ft special-use hangar lot just off the main airstrip, offering added ease and flexibility for travel to and from the island. The community features a beach, airstrip, and boat launching area, with a desirable south-facing orientation overlooking historic Roche Harbor. This tranquil escape blends comfort and coastal beauty.

156 Vista Place, Friday Harbor

Listing courtesy of COMPASS.

$775,000
1 Beds ⋅ 2 Baths ⋅ 2441540 MLS ⋅ ACTIVE Status
PRIME DEER HARBOR ACREAGE WITH CARRIAGE HOUSE Private, mostly level 3.38± acre parcel in the desirable Suncrest neighborhood offering an exceptional opportunity to build a larger home while enjoying the sweet carriage house. With selective tree trimming, a future residence could capture views toward Turtleback Mountain. Infrastructure is already in place, including a 3-bedroom septic system, fiber optic internet, driveway, and utilities, making this an ideal build-ready site. A well-maintained Craftsman-style carriage house allows for comfortable living during construction, featuring 506± sq ft upper-level open living space with full bath, covered deck, and attic storage. The lower level includes radiant-heated finished space with half bath and a 552± sq ft area currently used as living space that can easily be restored to a true 2-car garage. Recent upgrades in upper level include: flooring and trim, closet and built-in bedroom dresser, kitchen, bathroom vanity. Downstairs upgrades include: bathroom vanity, floor paint, new washer/dryer. New interior/exterior paint throughout. Lightly treed grounds offer garden space and multiple potential building areas. Conveniently located near Deer Harbor and Cayou Quay marinas.

87 Levon Lane, Orcas Island

Listing courtesy of Orcas Island Realty.

$2,395,000
3 Beds ⋅ 3 Baths ⋅ 2423666 MLS ⋅ ACTIVE Status
Welcome to 90 Montgomery Lane, a waterfront custom home located just outside Eastsound Village. This exceptional west facing property boasts 2 private bedrooms, a ship-like bunkroom for guests, encompassing 3223 square feet of finely crafted architecture, all with East Sound views and sunsets! An expansive, warm textured great room and dining area highlight the use of wood with indirect lighting on the main floor. Comfortable conversation area boasts marine views plus a library section for enjoying your favorite best seller. Local artisans executed exemplary built-in cabinets throughout. Rough hewn, wide plank fir flooring from the property is secured by old-school smooth nails. Prolific use of copper detail adds to durability and longevity. A well-designed, bright custom chef's kitchen is perfect for entertaining, including high-end appliances, substantial professional grade vent hood and convenient island with storage. An expansive primary suite encompasses the entire 2nd floor with a lavish bathroom, including a walk-in tiled shower, workout space, separate private vanities plus a deep soaking tub. Custom built-in cabinets & dressers extend from the primary to the den/hobby/work area with large custom desk and W/D utility room with sink. An oversized detached 2 car garage with shop space is wired for a high-end kiln and has a 2nd floor finished loft, ideal for a additional workspace, office, hobby area or storage. Ready to move in!

90 Montgomery Lane, Orcas Island

Listing courtesy of COMPASS.

$719,000
2 Beds ⋅ 2 Baths ⋅ 2421415 MLS ⋅ ACTIVE Status
Tucked beneath towering evergreens just minutes from Eastsound, this beautifully rebuilt island retreat offers exceptional craftsmanship, modern efficiency, and an unbeatable location. Walk to restaurants, shops, the marina, and waterfront, with the Orcas Island Airport just minutes away. Rebuilt from the ground up on a new foundation, nearly every major component is new, including the standing seam metal roof, windows, insulation, siding, mechanical systems, and stylish interior. Vaulted ceilings, warm wood accents, abundant natural light, and an open floor plan create a bright, inviting living space. The flexible floor plan features two bedrooms, two full baths, and a spacious loft for guests, an office, or extra sleeping space. Relax on the private deck surrounded by evergreens after a day exploring Moran State Park, kayaking, boating, or hiking. Pre-wired for a future sauna, the home offers an easy opportunity to create your own private spa retreat. Offered fully furnished, this turnkey property is ideal as a full-time residence, vacation home, or weekend getaway.

311 Enchanted Forest Road, Orcas Island

Listing courtesy of COMPASS.

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