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$7,690,000
3 Beds 5 Baths 2557051 MLS ACTIVE Status
First time ever offered, this extraordinary waterfront estate represents the pinnacle of San Juan Island living. Perfectly positioned at the end of Yacht Haven, this private 1.76± acre legacy property offers 389 feet of shoreline, owned tidelands, a mooring buoy, and an exceptional private year-round deep-water dock with approximately 64 feet of outside moorage and 58 feet inside the floats— the perfect setting to host unforgettable waterfront gatherings with friends. The 4,638 SF residence was thoughtfully designed to embrace the beauty of its surroundings, featuring soaring ceilings, open-concept one-level living, expansive entertaining spaces, an office/flex room, and walls of glass framing captivating bay views. Beautifully landscaped grounds blend seamlessly with the natural setting, while a detached outbuilding offers versatile space for vessel storage, recreational equipment, a workshop, and additional storage. An attached three-car garage and automatic whole-house generator provide exceptional comfort and peace of mind. A second parcel includes a charming 980 SF guest cottage with two bedrooms, 1.5 baths, a full kitchen, and a private view deck. Located just inside Garrison Bay with quick, protected access to open water, enjoy world-class salmon fishing, crabbing, whale watching, island cruising, and kayaking from your private dock. Whether departing by yacht or arriving by floatplane, every arrival feels like a getaway and every day is lived on the water.

28 Fir Lane, Friday Harbor

Listing courtesy of Coldwell Banker Bain.

$1,990,000
4 Beds 4 Baths 2535522 MLS ACTIVE Status
Sanctuary found. From the forever views across islands and sea to the Cascade Mountains, to the 15 peaceful acres of forest, field and year-round pond that’s a magnet for birds and other wildlife, this Orcas Island oasis invites you to relax and connect. An alluring drive leads to the heart of the property, a 3814 sq.ft. home built by Con Russell that combines enduring craftsmanship with a warm and welcoming feel. The cozy library and gathering spaces draw you in with Brazilian cherry floors, wood ceilings, built-ins, a striking brick fireplace and windows all around to capture light and views. You'll appreciate cooking in the well-arranged kitchen designed by Bonnie Ward which comes fully equipped with Viking 6-burner cooktop, pot filler, prep sink, 2 ovens and walk-in pantry. Wake to sunrise views from the main-level primary suite or upper-level suite, each with private balcony, perfect for morning coffee & moonlit nights. Lower level offers 1247 sq.ft. flex space for work, exercise, hobbies & guests, plus a heated workshop with access to the 696 sq.ft. garage. Other amenities include extensive lighting, radiant heat throughout, fiber internet, 8 kW generator, central vac and commercial fire suppression for peace of mind & lower insurance rates. Includes 2 additional tax parcels + water memberships, offering bonus investment value, max control of privacy/view & the option to create a multi-home retreat. Near Doe Bay Café/Resort for dining, spa & beach access. Come see!

206 Upper Cow Hill Road, Orcas Island

Listing courtesy of TWilliams Realty.

$2,495,000
3 Beds 5 Baths 2524982 MLS ACTIVE Status
Generational Living At It's Best with 2 houses on 440+ feet of waterfront with deep water dock share & private buoy + 2 additional separate tax parcels for future building. Everything you need for a family compound. The main home has vaulted ceilings with skylighted entry, clear fir trim, oak floors, tons of built-ins & storage, 2 woodstoves & flexible spaces. The kitchen overlooks the Great Room and boasts double ovens, separate Thermador cooktop, SubZero refrigerator, oak cabinets and walk-in pantry. The snooker table room with wood stove and deck door is as versatile as your imagination. Lower level spacious, ensuite primary bedroom incl separate closets with built-in dressers & office/exercise area. Extra 3/4 bath off the laundry room with exterior door to scrub down after a day on the boat. Both houses have view decks with enviable panoramas to wile away an afternoon. Second home (1044 sqft) built in 1982 has 2 bedrooms & 2 baths with wood stove, built-in dressers & laundry. Adjacent to the circle driveway is a detached 2 car garage with separate shop & wood storage carport. A very natural and private 17+ acres incl terraced waterfront, rocky outcrops, mature woods & sunny pasture. Close to Lopez Hill trails. Listed below assessed value.

470 Bonanza Drive, Lopez Island

Listing courtesy of Windermere RE/Lopez Island.

$4,750,000
3 Beds 6 Baths 2515849 MLS ACTIVE Status
Extraordinary custom-built home with views of the Salish Sea & Olympic Mountains with whales so close you can literally hear them breathe. Designed to entertain multiple generations on one breathtaking property, the home features high-end craftsmanship, premium systems and beautiful guest house. Main residence, completed in 2019, offers expansive open-concept with chef’s kitchen, dining room, hickory floors and 8’ tall windows and doors throughout. Two primary suites and multiple bathrooms provide ideal space and flexibility on the main floor while the upstairs apartment features soaring 10-foot ceilings, marble countertops, spacious primary suite, office/reading nook, and additional living space. The downstairs light-filled entertainment area has custom wood bar and additional opportunities. The detached 1-bedroom guest house includes custom kitchen, living area, gas fireplace and private deck. Extensive hardwood decks and outdoor dining spaces wrap the front of main residence creating seamless indoor-outdoor living looking over the Sea and wildlife. Finally, enjoy your own vegetables and flowers from Property and infrastructure are also impressive with a one of a kind fully fenced raised concrete-bed garden area with impressive gardening shed, 3-car garage/shop, Tesla battery backup, 500-gallon propane tank, a shared community well and a separate private well, whole-house filtration, UV purification, rain catchment system, and multiple 2,000-gallon storage tanks.

115 Clipper Way, Friday Harbor

Listing courtesy of COMPASS.

$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.

$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.

$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.

$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.

$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.

$1,150,000
2 Beds 3 Baths 2426289 MLS ACTIVE Status
Roche Harbor Retreat. Nestled on a .57-acre bordering iconic Roche Harbor Resort, this inviting south-facing gem offers the perfect blend of privacy & proximity, with direct access to one of the San Juans most beloved destinations. The home welcomes you with a light-filled great room, main floor bedroom & bath, upper primary ensuite with balcony, cedar-lined closets. Daylight lower level with wood stove adds warmth & flexibility for guests, hobbies or entertainment. Step outside to a peaceful deck with filtered water views of the resort, relax and soak in the island atmosphere. Easy access to pool, pickleball, marina, dining & more. 2-car garage, deer-fenced garden. Fully furnished for your vacation home or full-time residence.

309 Afterglow Drive, Friday Harbor

Listing courtesy of Coldwell Banker San Juan Is..

$3,799,900
4 Beds 5 Baths 2409167 MLS ACTIVE Status
The iconic contemporary home everyone has been asking about on San Juan Island. Overlooking the Seattle Yacht Club Marina & harbor with spectacular views of Mount Baker. This unique-designed estate was created by architect Anna Howden and sustainably built with striking Cor-Ten steel siding composed of nickel, copper & steel with clear cedar accents on exteriors. Rustic-Modern would be the best description of this multi building estate, designed by a family architect that has a footprint history of island properties designed. The 3,555 SF main residence features an open gourmet kitchen flowing to the living room with views of Mount Baker and marine life. Use of a free-flowing floating staircase or use elevator access to the lower level. Primary suite with full bath, large walk-in closet on main level & half bath. Guest bedroom, a Flex room may be a possible 3rd bedroom, 1 full bath, 3/4 bath on lower level. Detached 1-bedroom apartment building includes a full kitchen, full bath & office/bedroom w/3/4 bath. Apartment ideal for guests with full studio to work-from-home. Two separate attached single-car garages, an On-demand generator for both buildings. Radiant heated floors in both buildings. Zoned Multi-Family for investment income rentals. Guest apartment building currently rented to 12/31/2026 @ $5000/month. Become inspired with the water, marina & mountain views from every room. Additional photos & video tour available. A personal tour will dazzle your imagination.

630 Harrison Street, Friday Harbor

Listing courtesy of Better Properties of San Juan.

$11,000,000
3 Beds 4 Baths 2255472 MLS ACTIVE Status
Perched at the water’s edge on the coveted southwest shores of San Juan Island. Showcasing exquisite craftsmanship throughout. The great room, with a soaring ceiling and floor to ceiling river rock fireplace, flows to a stone patio overlooking Haro Strait and the Olympic Mountains. The main floor primary suite affords spectacular water and mountain views. The lower level features a home theater, water view guest suite, workshop with stainless steel countertops, and a large laundry room with a dog wash station. 1165 sf guest cottage, two 3-car garages, a 4-bay service garage, and landscaping serviced with a smart water system. State-of-the-art D-Salinization water system. 3.2 acres and 368 ft of shoreline. Being sold Turn-key!

535 MacGinitie Road, Friday Harbor

Listing courtesy of Coldwell Banker San Juan Is..

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