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269 Main Street, Orcas Island
$2,850,000
3 Beds ⋅ 6 Baths ⋅ 2579007 MLS ⋅ ACTIVE Status
A rare opportunity in the heart of Eastsound, this exceptional mixed-use property combines island living with multiple income streams, steps from restaurants, shops, galleries and the waterfront. Overlooking the Salish Sea, the property holds a prominent location on the village's Main Street, just steps from restaurants, shops, galleries and the waterfront. The second level features two beautifully furnished water-view residential units: a spacious 2-bedroom, 2-bath residence and a 1-bedroom, 1-bath residence, currently operating as highly rated vacation rentals. Enjoy one as your own island home or family retreat while generating income from the other - or continue using both as successful rentals. View vacation rentals on line. The ground level features two established, street-facing retail spaces in a high-traffic location, plus a rear office, providing fully leased income streams. Rooftop solar provides both environmental and economic benefits. A 4,000 sqft private parking lot at the rear of the building provides additional income from leased spaces. This Orcas Island property offers a fantastic blend of residential living, vacation rental flexibility and established commercial income.

269 Main Street, Orcas Island

Listing Broker: COMPASS; Wally Gudgell; 360-507-5443; wally@compass.com

Friday Harbor
$28,000,000
9 Beds ⋅ 11 Baths ⋅ 2530572 MLS ⋅ ACTIVE Status
Perched high above the active waters of the Haro Strait with commanding westerly views to Victoria, this once-in-a-generation San Juan Island estate is the definition of a legacy holding. Encompassing nearly 23 acres, this gated property offers extraordinary privacy, resort-caliber amenities, and an uncompromising connection to the sea and sky. Designed as a passion project for hosting on a grand scale, the nearly 12,000 square foot residence lives entirely under one roof, where every bedroom suite opens to its own deck and captures breathtaking water views. Immaculately maintained and updated to 2026 technology standards, the estate features two wells, formal cutting gardens, a sports court, separate maintenance facilities, fully irrigated and curated grounds, and nearly a mile of private trails with serene viewpoints throughout. The dedicated whale watching room is unforgettable yet overshadowed by the setting itself. Secure, timeless, and built for generations to gather, celebrate, and retreat above it all. A World-class destination available for the first time.

Friday Harbor

Listing Broker: Real Residential; Shawn Filer; 206-919-5388; shawn@realresidential.com

Friday Harbor
$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 Broker: The Agency Seattle/Eastside; Jen Cameron; 425-305-9400; jen.cameron@theagencyre.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

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