Refine Search
Map
Sort by
$2,200,000
5 Beds ⋅ 3 Baths ⋅ 2553674 MLS ⋅ ACTIVE Status
Exceptional single-level island property just minutes from Eastsound, privately situated on 21.72 acres with sweeping southeast views down East Sound and across Crow Valley. The 3,226 sq. ft. home offers 5 bedrooms and 2.5 baths, with flexibility for guests, multi-generational living, offices, hobbies, or a home-based business. The entire home was cosmetically remodeled in 2025, including an updated kitchen and baths, wood flooring, new decking, fresh exterior paint, and a clean tiled roof. The sunken living room features panoramic windows, while the primary suite is thoughtfully arranged with an office and bath positioned to maximize the views, including a soaking tub overlooking the landscape, with the sleeping area tucked into the darker side of the room for a gentler start at sunrise. Just up the hill, a spectacular rocky bald feels like the top of the world, with phenomenal views stretching from the Canadian Coast Mountains across Eastsound to Massacre Bay. Trails wind throughout the acreage, and the main landscaped and usable area is fully deer-fenced with multiple gates, creating privacy around the home, pond, fruit trees, and garden. A 1,320 sq. ft. garage/shop and 750 sq. ft. detached Texmo building provide abundant storage and workspace, and an athletic court offers space for basketball or tennis. A wood shed is on a second driveway. Grid-tied solar helps reduce utility costs, and high-speed internet is available through an existing Orcas Online arrangement.

404 Lookout Loop, Orcas Island

Listing courtesy of Orcas Island Realty.

$2,695,000
4 Beds ⋅ 3 Baths ⋅ 2569539 MLS ⋅ ACTIVE Status
A rare opportunity to own one of the San Juan Islands’ most beautiful private estates. Set on 23+ acres of rolling pasture, mature woods, orchard, and gardens, this custom Craftsman offers exceptional privacy, southern protected valley views, and direct county road access. Designed and built by Island Shelter Construction, the 3,226 sq ft, 4-bedroom, 3-bath home showcases meticulous craftsmanship and timeless finishes. Clear cedar coffered ceilings, beautiful millwork, and warm details create a relaxed country-luxury atmosphere. The spacious great room is anchored by a dramatic fieldstone wood-burning fireplace, creating an inviting gathering space with views of the surrounding landscape. Outside, enjoy a mature irrigated orchard, sunny fenced garden, sports court, hot tub, woodshed, and charming treehouse. A gracious winding drive through the woods leads to the residence and an impressive 2,136 sq ft shop with separate studio and office spaces. A 1,252 sq ft equipment shed provides additional storage and workspace.With its extraordinary setting, thoughtful design, abundant amenities, and complete sense of seclusion, this exceptional San Juan Islands property offers a rare combination of natural beauty, craftsmanship, and versatility.

14 Fieldstone Road, Friday Harbor

Listing courtesy of Coldwell Banker San Juan Is..

$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 over 22 acres, the 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 courtesy of Real Residential.

$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.

$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.

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.
IDX information is provided exclusively for consumers’ personal noncommercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.