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$1,598,000
2 Beds ⋅ 1 Baths ⋅ 2478563 MLS ⋅ ACTIVE Status
Watch Roche Harbor fireworks from your dock! Perched along the coveted shores of Henry Is, this exceptional waterfront retreat captures sweeping views across sparkling waters to Roche Harbor & beyond. A rare offering, the property features a deep-water, shared dock, providing effortless access for boating, crabbing, fishing, and spontaneous sunset cruises.The home is thoughtfully positioned to embrace its breathtaking surroundings, with expansive windows that frame ever-changing marine vistas—boats gliding by, seabirds soaring, and the harbor lights twinkling at dusk. Two bedrooms on the main plus a sleeping- play loft above. The kitchen has beach-cottage cabinetry, a breakfast bar & a spacious dining area. The great room gets cozy with ambiance of the wood burning fireplace plus there’s another wd stove in the primary suite for a relaxing Winters night. Open-concept living spaces flow seamlessly to a generous outdoor deck, creating the perfect setting for summer gatherings or quiet mornings with coffee and sea air. Designed for both comfort and convenience, the property offers cabin chic finishes, inviting gathering spaces, and private retreats for guests. Whether you envision a full-time island lifestyle or a legacy getaway, this property delivers the ultimate San Juan Islands experience—privacy, protected moorage & postcard-worthy views just minutes from Roche Harbor Resort. A rare opportunity to own premier waterfront in one of the San Juans’ most sought-after locations.

5 Smugglers Rowe, Henry Island

Listing courtesy of Windermere Real Estate/HLC.

$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 courtesy of The Agency Seattle.

$2,829,000
5 Beds ⋅ 4 Baths ⋅ 2459755 MLS ⋅ ACTIVE Status
Perched above the sparkling waters of Orcas Village, this reimagined coastal retreat captures the essence of endless island summers. With 345± feet of shoreline and panoramic views stretching across Cayou Channel, every day begins with sun dancing on the water and ends with breathtaking sunsets over the sea. Inside, walls of glass frame the ever-changing marine landscape, creating the feeling of living right on the water's edge. The 3,411± sf home is designed for both relaxed getaways and unforgettable gatherings, featuring dual primary suites, spa-inspired baths, inviting wood-burning fireplaces, and beautifully updated spaces that blend modern comfort with timeless coastal charm. Spend your days launching kayaks from the shoreline, strolling to the nearby village for coffee or dinner, catching the ferry for an island adventure, or simply unwinding on the deck as boats drift by. Whether it's a summer escape, a weekend retreat, or a place to create lasting memories with friends, this exceptional waterfront home offers the very best of island living—where every day feels like vacation.

8256 Orcas Road, Orcas Island

Listing courtesy of Windermere RE San Juan Islands.

$599,000
2467648 MLS ⋅ ACTIVE Status
Discover the tranquility of island living on this 1.6-acre Henry Island homesite, located just minutes from the charm and amenities of Roche Harbor Resort. Enjoy sweeping views and peaceful privacy, perched above a huge limestone bluff. This special parcel offers wonderful seascapes of the Harbor, endless boat traffic, plus it's bathed in natural light. This build-ready parcel has community water, power, septic, and access to a deep-water dock. This is community waterfront and a private bouy conveys to the new buyer. Explore the nearby Preservation Trust hiking trails, where abundant wildlife and breathtaking views over Open Bay create an immersive island lifestyle. All this and much more. Call for your private boat ride and tour it today!

7 Roche Harbor Shores, 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.

$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 courtesy of TWilliams Realty.

$1,695,000
2 Beds ⋅ 2 Baths ⋅ 2453010 MLS ⋅ ACTIVE Status
WEST-FACING WATERFRONT HOME IN ROSARIO Designed by Vandervort Architects and built by Burke Thomas of Woodsong. This contemporary 2,367± sq ft home blends simple elegance with quality craftsmanship. Exquisite lighting highlights clean architectural lines, while sunlight and serene water views fill the open-concept living area, creating a seamless connection to nature. A striking handcrafted wood-and-steel staircase leads to a lofted office/guest retreat. The lower level offers two bedrooms, a spacious bath with jetted tub, and a laundry/utility room. Conveniently located near Rosario Resort, Moran State Park, and minutes from Eastsound, this turnkey home is offered fully furnished (with a few exclusions) for an effortless island lifestyle.

599 Shore Drive, Orcas Island

Listing courtesy of Orcas Island Realty.

$295,000
2446457 MLS ⋅ ACTIVE Status
A rare opportunity to own waterfront property with a private dinghy dock on beautiful Henry Island. Take in sweeping western views across the protected waters of Nelson Bay, with 100 feet of private beach and included tidelands. Surrounded by nature, the property offers access to scenic hiking trails that connect to conserved land, ideal for outdoor enthusiasts. Just a quick ten-minute boat ride from Roche Harbor, this peaceful retreat combines seclusion with convenience. Utilities are available at the road; water and septic systems will need to be developed, making it a perfect canvas to build your island dream.

Lot 25 Henry Island, Henry Island

Listing courtesy of Coldwell Banker San Juan Is..

$1,985,000
2 Beds ⋅ 2 Baths ⋅ 2393309 MLS ⋅ ACTIVE Status
Offered is a West Sound 5.45 acre old island waterfront homestead with accessible private cove, and sandy beach, just off Skull Island State Park. The sunny property, an orchard farm in years gone by, is divided by the county road. On the north side of the road is a single floor, charming 1910 two bed two bath home that has been remodeled and updated and currently used as a summer retreat. A spectacular, level and spacious south facing waterfront building site overlooking Massacre Bay is on the south side. The cove/beach has shellfish, wildlife and privacy just a few steps down a gentle path from the waterfront building site*. The property has a very good well, power, a three bedroom septic system recently inspected, and plenty of usable land for outbuildings. Bearing pear, plum and apple trees, some 100+ years old, and a bounty of summer blackberries, evoke the history of this property plus a seasonal creek returns rain to the sea. The neighboring waterfront property is listed (NWMLS #2460007, Vacant Land, old WF cabin on .53 acres). Buy both and create opportunities for boundary line modifications and shared utilities. *Permits to build on the waterfront side of the county road may require modifications to the existing home.

3388 Deer Harbor Road, Orcas Island

Listing courtesy of COMPASS.

$295,000
2362715 MLS ⋅ ACTIVE Status
Ready to trade traffic for tide charts? This serene 1.67-acre slice of paradise on Raccoon Point is perched on the peaceful north shore of Orcas Island where the only thing louder than the quiet is the view. With a level building site, community water, & a brand-new 2-bedroom septic design, this property is basically saying, “Let’s build something amazing. Enjoy jaw-dropping views of the Strait of Georgia, Matia Island, & on a clear day—the ever-so-dramatic Canadian Coastal Range. It’s like having front row seats to Mother Nature’s highlight reel. The land? A dreamy mix of towering firs, sun-dappled meadows, & freshly enhanced views. Just a quick drive from Eastsound, where you can stock up on island essentials. Island life is calling.

Matia View Short Plat Unit #Lot 2, Orcas Island

Listing courtesy of COMPASS.

$998,000
3 Beds ⋅ 4 Baths ⋅ 2293493 MLS ⋅ ACTIVE Status
This end unit townhome has southwest exposure and a vacation rental permit. Enjoy life in the heart of Eastsound in new construction 3 bedrms/3.5 bath at the corner of Fern & Madrona near schools, beaches and the amenities of the Village. Five units in the complex each with separate entries. Contemporary design features wood exterior, quartz & butcher block counters, stainless appliances and white walls. Main floor can be a locked off studio space with 3/4 bath or integrated into the unit. Second floor features an open concept living, dining & kitchen space w/ 1/2 bath. The upper floor has 2 bedrooms both w/ ensuite 3/4 baths. One dedicated parking space plus plenty of street parking. Eastsound water and sewer with power metered separately.

231 Madrona Street Unit #5, Orcas Island

Listing courtesy of Orcas Island Realty.

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