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505 Linder Street, Friday Harbor
$800,000
2 Beds ⋅ 1 Baths ⋅ 2591633 MLS ⋅ ACTIVE Status
A great opportunity in Friday Harbor! This versatile multi-family property offers two distinct homes, each with its own private space, creating a wonderful setup for multi-generational living, rental income, guest accommodations, or simply having room for friends. The character-filled main home, built in 1948, offers the charm and personality of an older island home. Including 2 bedrooms, a nicely sized living room and an office space on the upper level. The lower level is a full size basement that can be used as it fits ones needs. The second residence, built in 1997, provides a sweet space with thoughtful finishing touches. The homes are thoughtfully positioned on the property allowing each home to enjoy its own sense of privacy and independence. The basement level of the main home could potentially be converted to another rental/income producer. There’s more to dream about—the property offers potential for further development, providing options for those looking to expand, create additional living space, or maximize the property’s long-term possibilities. Whether you envision a compound, investment property, or a place where everyone can have their own space while staying close, this unique Friday Harbor property offers flexibility, character, and opportunity.

505 Linder Street, Friday Harbor

Listing Broker: Coldwell Banker San Juan Is.; Michele Mayer; 360-317-5683; michele@sanjuanislands.com

782 Nash Street, San Juan Island
$685,000
3 Beds ⋅ 2 Baths ⋅ 2588054 MLS ⋅ ACTIVE Status
Walk to absolutely everything in Friday Harbor from this inviting, centrally located 3-bedroom, 2-bath, 1,792 sq ft home. This pristine one-level gem features a casual great room floor plan with a spacious open kitchen, large pantry, informal eating area, and dedicated laundry room—perfect for keeping the cook part of the party. The primary suite offers a private retreat, complemented by two additional bedrooms and a full bath. 400 sqft of bonus space, offering exceptional long-term rental potential, a private home office, or guest quarters. Sunny garden space perfect for your green thumb. This income potential property is a rare find just steps away from downtown shops, schools, senior center, grocery stores, and the ferry landing.

782 Nash Street, San Juan Island

Listing Broker: Coldwell Banker Bain; Stephanie L Buffum; 360-472-0404; sbuffum4@gmail.com

164 Bramblewood Lane, Friday Harbor
$1,795,000
4 Beds ⋅ 4 Baths ⋅ 2564603 MLS ⋅ ACTIVE Status
Experience the best of San Juan Island living in this exceptional waterview home, where privacy, craftsmanship, and timeless design come together on 2.5 peaceful acres. Located only three miles from town, this property is thoughtfully positioned to capture the unforgettable scenery and views. Custom designed with contemporary elegance, offering a warm light-filled interior with striking windows surrounding the high ceilings, rich hardwood flooring, fine wood craftsmanship, and an open layout. The spacious primary suite is its own scenic retreat, while two additional bedrooms, a dedicated family room and inviting living spaces provide room for every lifestyle. One of the property's most valuable features is the attached Mother-in-Law Suite, complete with a private entrance, full kitchen, living room, bedroom, full bath, and patio. Perfectly suited for extended guests or offers the opportunity to use as a long-term rental, adding flexibility and value without sacrificing privacy. Outside, both natural and landscape design create a serene setting to relax, entertain, garden or simply enjoy the peaceful surroundings. An oversized garage with workshop space provides room for hobbies and storage. Just down the street, a community beach invites you to experience everything island life has to offer. You must see in person to fully appreciate this thoughtfully designed and well maintained residence. This rare offering delivers an exceptional lifestyle in one remarkable package.

164 Bramblewood Lane, Friday Harbor

Listing Broker: Island Grp Sotheby's Int Rlty; Terese Prescott; 360-298-0824; terese@sanjuans.com

421 Scott Hill Drive, Orcas Island
$3,195,000
6 Beds ⋅ 4 Baths ⋅ 2557481 MLS ⋅ ACTIVE Status
Remarkable 180-degree southern views of the sunrise and sunset over the Salish Sea from one incredible private island estate! This nearly 10-acre sun-filled generational retreat encompasses the entire top of Scott Hill on Orcas Island. With 6 bedrooms and 5 bathrooms between the main house and guesthouse, a massive deck and acres of lawn and park-like grounds for enjoying the summer and an indoor pool or bowling alley (you choose), this hilltop sanctuary offer multiple generations an ideal island escape. Enjoy deer-fenced meadows, wildflowers, fruit trees, forests, gardens, ponds & infinite privacy in your own peaceful Orcas Oasis.

421 Scott Hill Drive, Orcas Island

Listing Broker: COMPASS; Kevin Ranker; 360-472-1850; kevin.ranker@compass.com

750 Shaner Armstrong Road, Orcas Island
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 2550846 MLS ⋅ ACTIVE Status
Discover the ultimate private estate combining luxury living, income potential and unmatech utility. Nestled on 6 serene, private acres this meticulously maintained property has 3 bedroom, 2 bath main residence, a premium detached shop with office and studio plus fully self contained 1 bedroom accessory dwelling. Entry into the main residence is beautifully landscaped and fenced . The home features a gourmet kitchen with porcelain tile floors, custom cabinetry and quartzite countertops. The living room with floor to ceiling windows is bathed in natural light. Majestic stone accent wall and granite hearth around the Xtrordinair fireplace complete the room. Primary suite with spa-bath boasts massive walk-in shower, custom vanity, countertops and radiant floor heat. Attached garage has been converted into family room living space with kitchenette and ample room for pool table. Premium 36 x 36 Texmo building with vaulted ceilings, concrete slab and separate office space. Above the shop is studio space with 3/4 bath and kitchen. Modern 2020 Park Model tiny home is 600 sq ft of independent living perfect for multi-generational living, guest house or rental income. Adjoining gazebo with stone patio and firepit for quiet outdoor evenings. Property is served by 2 wells with 4 - 2500 gallon storage tanks. Rain catchment off the shop roof. New roof in main home in July of 2026.

750 Shaner Armstrong Road, Orcas Island

Listing Broker: COMPASS; Deborah Hansen; 360-622-7009; D.hansen@compass.com

259 Willbrook Lane, Lopez Island
$1,990,000
3 Beds ⋅ 3 Baths ⋅ 2551797 MLS ⋅ ACTIVE Status
Discover the extraordinary Island Lifestyle you've been dreaming of! This stunning NW contemporary home on Lopez Island is an estate on 7 private acres with breathtaking panoramic views of Puget Sound, San Juan Islands, passing ferries, and Cascade mountains. Custom designed to embrace its spectacular setting, this 3,917-square-foot residence showcases soaring vaulted ceilings, exposed timber beams, impressive 8-foot doors, radiant heated floors and walls of glass bring the outdoors in! The gourmet chef's kitchen features custom cabinetry, granite counters, double ovens, and generous gathering spaces for entertaining. Three gas fireplaces create a warm ambiance, while expansive view decks provide unforgettable sunsets and ever-changing marine vistas. A loft retreat offers the perfect office and reading sanctuary. The versatile lower level offers a beautifully finished living suite for guests, multigenerational living, or rental income, plus a light-filled artist's studio. Outside, unwind in the spa, rinse off in the outdoor shower after a day at the beach, or enjoy the greenhouse, fenced gardens, mature fruit trees, and peaceful surroundings. The heated garage doubles as a dream woodworking shop and exercise studio. Home is wired for a generator. Most furnishings included! Just a short walk to the beach and minutes from the Village, ferry terminal, and Odlin Park, this exceptional estate offers the perfect blend of luxury, privacy, and the timeless beauty of island living.

259 Willbrook Lane, Lopez Island

Listing Broker: John L. Scott, Inc.; Shirley Kimmel; 425-941-1466; SKimmel@johnlscott.com

450 Eagle Bay Road, Blakely Island
$7,900,000
4 Beds ⋅ 7 Baths ⋅ 2543410 MLS ⋅ ACTIVE Status
Extraordinary generational Blakely Island beachfront estate with remarkable sun-drenched southern exposure. This exceptional private estate offers a rare blend of luxury and serene island living. Designed as a private retreat, four distinct coastal structures and the accompanying airport hangar balance comfort, entertainment, natural beauty for multiple generations with convenient access. The main house showcases refined craftsmanship with custom inlaid hardwood floors, a sun-filled living area with pool table and full bar, two ensuite bedrooms, kitchen, dining area, steam room, and an expansive deck with sweeping views. Steps from the hundreds of feet of private shoreline, the beach house delivers an immersive coastal experience: open-concept living and dining, a marble bar, state-of-the-art sound and lighting, and nano doors opening to a wraparound deck where the rhythm of the sea becomes part of everyday life. A large hangar at the neighboring airstrip rounds out the estate—ready to house your aircraft, boat, or an impressive collection of toys and recreational gear. This south-facing retreat is more than a property—it's a legacy estate in the San Juan Islands.

450 Eagle Bay Road, Blakely Island

Listing Broker: COMPASS; Kevin Ranker; 360-472-1850; kevin.ranker@compass.com

18 Fishing Aly, Orcas Island
$2,500,000
5 Beds ⋅ 4 Baths ⋅ 2537507 MLS ⋅ ACTIVE Status
Provide your guests with the ultimate experience of Pacific Northwest living in this stunning, custom-built contemporary vacation rental property with beautiful southerly views over East Sound and just one block from the village of Eastsound. Crafted in 2012 by renowned builder Con Russell, this meticulously maintained 3,439 sq ft property with a new roof in 2026 balances architectural elegance with modern luxury. Comprised of 3 separate residential units totaling 5 spacious bedrooms and 4 baths, it is a premier investment opportunity with a short-term rental permit. The property showcases a beautiful blend of stone and wood both inside and out opening to a bright, expansive two story layout featuring vaulted ceilings and a warm welcoming ambiance. High-end details throughout the building. Furnishings included in sale. The Admiral's Suite on the top floor features a expansive great room, primary bedroom with full bath, second bedroom with 3/4 bath and 3rd room ideal for additional guests or office. Wrap around deck with fireplace completes the suite. The Captain's Suite on the main floor offers separate living and dining, 2 bedrooms and full bathroom. The Lieutenant's Suite, also on the main floor, has charming great room with vaulted ceilings, loft bedroom and 3/4 bath. All units have washer and dryers. Admiral's Suite rents for $412 to $580 per night, Captain's Suite rents for $317 to $510 per night and the Lieutenant's Suite rents for $303 to $486 per night.

18 Fishing Aly, Orcas Island

Listing Broker: COMPASS; Deborah Hansen; 360-622-7009; D.hansen@compass.com

177 Blakely Drive, Blakely Island
$825,000
2 Beds ⋅ 3 Baths ⋅ 2536611 MLS ⋅ ACTIVE Status
Two homes for the price of one—and opportunities like this don't come along often. We're proud to offer an incredible, truly turnkey property on coveted Blakely Island, the "Martha's Vineyard of the San Juans." Everything stays, from the bedding and dishes to the silverware, washer, and dryer. Just arrive by plane or boat and start living. The island stays peaceful, private, and refreshingly uncrowded. Built in 1980, the 1,920 sq ft main home offers 2 bedrooms and 2.5 baths, while a thoughtfully situated 480 sq ft detached guest house adds a private 1 bed, 1 bath retreat for visitors. A 224 sq ft garage rounds out the package with room for island gear and toys. Unwind on the large covered patio, where windows frame sweeping bay and ocean views. Positioned right on the runway, you'll have a front-row seat to planes gliding in and out—with the marina just a short walk away. Beyond your door: sandy beaches, scenic trails, stocked lakes, and full marina access. This is more than a home—it's an invitation to a rare and refined island lifestyle. Discover Blakely living at its finest. Schedule your private viewing today.

177 Blakely Drive, Blakely Island

Listing Broker: Bellwether Real Estate; Donnie Rubenack; 360-815-1168; donnie@bellwetherrealestate.com

105 Windfall Lane, Orcas Island
$1,075,000
3 Beds ⋅ 3 Baths ⋅ 2533487 MLS ⋅ ACTIVE Status
Perched on a hillside and tucked into the trees, this comfortable 3-bedroom, 3-bath Orcas Island home opens to a sweeping 180-degree northern water view. From this private setting, the view stretches across the sound to Mt. Baker, the Canadian coastal mountains, distant Vancouver city lights, and surrounding islands, with boats and marine life moving through the water below. The main level is warm and inviting, with vaulted ceilings, solid hickory floors, an open great-room layout, and a walk-in pantry. The daylight lower level is where the property’s upside really comes into focus. With a separate entrance, three bonus rooms, a partial kitchen, and plumbing already in place, it offers room to expand how the home lives. Finish work is still needed, including some drywall, paint, flooring, and bathroom fixtures, but the potential is significant, nearly doubling the finished living area and creating flexible space for guests, multigenerational living, studio use, or possible income. Set at the end of the road in private Raccoon Point, the property includes a detached garage, attached carport, and a pleasant, level front yard with room for gardening. Deeded community waterfront access provides a large beach with room for small boats and kayaks. Peaceful, private, and only about 10 minutes from Eastsound, this is a special Orcas Island setting with room to make it your own.

105 Windfall Lane, Orcas Island

Listing Broker: Orcas Island Realty; Deborah J. Jones; 360-298-4558; dhjoneshomes@gmail.com

398 Hannah Road, Friday Harbor
$3,990,000
5 Beds ⋅ 6 Baths ⋅ 2532527 MLS ⋅ ACTIVE Status
Encompassing 18 scenic acres across 3 parcels, this exceptional estate offers a rare opportunity for multi-generational living, future development, and flexible use. Featuring multiple residences, event spaces, specialty buildings, and room to expand, the property is ideal for creating a private compound or legacy retreat. The main residence includes 2 spacious living suites, a chef’s kitchen, and expansive decks with sweeping Olympic Mountain views. All Ipe wood decking! A separate guest house with its own deck provides comfortable accommodations for extended living or visitors, while the additional home on Bullfrog Road captures beautiful ocean and mountain views with a large backyard and recreation space. Additional structures include a versatile multi-use building for living space, studio, gallery, or events, a peaceful meditation cabin, and a flexible fitness house suited for wellness, hobbies, or creative pursuits. The greenhouse and fully fenced raised-bed gardens support productive year-round growing. Maintenance shop stores tools, supplies, vehicles, and service crew bathroom. A large garage and workshop building offers excellent storage, office, bathroom, or vehicle collection potential. Multiple gated entrances provide added privacy and convenience. This unique property combines existing infrastructure, development potential, and endless possibilities in an extraordinary setting. Come tour this rare opportunity!

398 Hannah Road, Friday Harbor

Listing Broker: American Dream R. E. Services; Forbes Hansen; 360-507-5175; forbesahansen@gmail.com

189 Calle Aguila, Lopez Island
$2,250,000
4 Beds ⋅ 3 Baths ⋅ 2526760 MLS ⋅ ACTIVE Status
Once-in-a-lifetime legacy estate. Properties like this come around very rarely – set on the edge of a bluff with 180 degrees of southwest exposure and 1,651’ of waterfront, the large home enjoys a footprint that cannot be replicated. Remodel the house or use the valuable footprint to take advantage of the panoramic views stretching across the sparkling blue water of the Straits all the way to the Olympics. Includes two sunny and private cove beaches – the larger of the two is a rare sandy oasis while the other still holds the remains of a beach shed with power and water. Two tax parcels totaling 8.07 aces, a large, detached garage and shop with metal roof and original orchard. Both properties have a conservation easement. Adjacent to county property and close to county boat launch and dock. Property is being sold as is, septic system has all required upgrades, well pump was replaced in 2024.

189 Calle Aguila, Lopez Island

Listing Broker: Windermere RE/Lopez Island; Alan Roberson; 360-468-3344; lopezislandalan@gmail.com

285 Raptor Road, Orcas Island
$2,976,000
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 Broker: Orcas Island Realty; Marcela Barrientos; 206-234-6354; marcela@somelabdesign.com

178 Fossil Bay Drive, Orcas Island
$1,990,000
17 Beds ⋅ 17 Baths ⋅ 2475226 MLS ⋅ ACTIVE Status
Bartwood Lodge presents a rare Orcas Island waterfront opportunity with sweeping panoramic views and exceptional development potential. Located on the quiet North Shore in the residential Bartwood neighborhood, this unique property offers flexibility for a single or multi-family estate, condo remodel for resale, apartment renovation for long-term income, or immediate use as employee housing. The property features two separate buildings. The main three-story lodge includes 15 guest rooms with private baths, plus a top-floor one-bedroom apartment with kitchen. A second building provides a spacious common living and dining area with large kitchen—ideal for gatherings or shared use. Installed Rock Island Fiber-Optic internet. Enjoy 180° vistas stretching north to the Canadian Coastal Range, east to Mount Baker, and west to stunning summer sunsets. A large waterfront deck leads to the community dock, beach, and boat ramp. Additional amenities include parking for 40+ vehicles and access to a HOA tennis, pickleball, and basketball court. Centrally located near the Orcas Island Airport, marina, and Eastsound Village shops and dining, Bartwood Lodge offers an exceptional combination of waterfront living, convenience, and income or redevelopment potential.

178 Fossil Bay Drive, Orcas Island

Listing Broker: The Agency Seattle; Christopher Peacock; 360-317-6076; Christopher.Peacock@theagencyre.com

1189 Tomihi Drive, Orcas Island
$2,600,000
4 Beds ⋅ 4 Baths ⋅ 2451928 MLS ⋅ ACTIVE Status
Island Living at its finest! Experience this private, end of the road, Orcas Island home with sweeping water, mountain and village views. This is a high bank waterfront property where you control your views across East Sound and beyond. Ideally located, offering easy access to Moran State Park, Mt Constitution, lakes, public beaches and shopping in Eastsound. Main floor living offers chef’s kitchen as focal point, with oversized island, top tier appliances; elevated dining area; primary suite that captures views from every angle, modern spa bath, walk-in closets, sitting area-gas/propane fireplace; bonus room, large 2 car garage. Lower level showcases 1 bed/1 bath studio apartment. Upper level includes 2 bed/1 bath and flex space. Custom cabinetry throughout, attention to detail. Enjoy NW year-round with covered outdoor bbq/picnic area, fire pit and patio area located on second tax parcel. This home is as functional as it is beautiful.

1189 Tomihi Drive, Orcas Island

Listing Broker: TWilliams Realty; Teri Williams; 360-319-6256; teri@twilliamsrealty.com

630 Harrison Street, Friday Harbor
$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 Broker: Better Properties of San Juan; James M. Carroll; 360-298-5034; SanJuanIsland@aol.com

Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
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