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$2,700,000
5 Beds 3 Baths 2423450 MLS ACTIVE Status
Traverse over a mile of pristine State Park land above Pearrygin Lake to arrive at Hilltop; a 3600+ sf Prentiss-Balance-Wickline Architects masterpiece offering forever views, rare privacy, and a front row seat to nature’s majesty. Chef’s kitchen, expansive living spaces, two offices, primary suite on its own level, and an attached apartment are among the spaces to discover. Large sliding doors and a screened sitting area with hot tub just outside encourage indoor-outdoor living, and views of the lake far below. Custom details such as a built-in yoga wall, artistic metal shade screens, abundant water storage and a massive 35 kilovolt autostart generator blend practicality with luxury. Architecture and setting in perfect harmony.

99 Hilltop Drive, Winthrop

Listing courtesy of CB Cascade RE - Winthrop.

$495,000
2 Beds 1 Baths 2431937 MLS SOLD Status
BEAUTIFULLY UPDATED ARTISAN CABIN – Charming 2bd/1ba home w/ an efficient, comfortable layout & timeless custom touches. Designed for easy living inside & out, this cabin blends style w/ practicality. Interior highlights include colored concrete floors, maple cabinets topped w/ elegant Soapstone counters, custom tile tub, blue pine custom doors, & a newly installed mini-split system for year-round comfort. Recent upgrades feature a new architectural shingle composite roof. Enjoy the private covered front porch framed by mature landscaping, or take advantage of the built-in insulated storage shed—complete w/ power & lighting—for all your outdoor gear. Ideally situated just minutes from the Nordic trailhead, the Meadowlark Trail, & downtown.

816 Castle Avenue, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Mountain to River Realty LLC.

$471,500
2 Beds 1 Baths 2410441 MLS SOLD Status
Winthrop Handcrafted Charmer – Energy-efficient and semi-earthbermed, this thoughtfully designed 2-bedroom, 1-bath home offers a warm, light-filled interior with smart window placement and a comfortable, open layout. Custom finishes throughout include colored concrete floors, blue pine interior doors, and a new architectural shingle composite roof. A mini-split system provides efficient heating and cooling year-round.Low-maintenance living continues outside with mature landscaping, a serene covered front porch perfect for relaxing, and a built-in storage shed for outdoor gear. Just minutes from downtown Winthrop, the Nordic trailhead, and the scenic Meadowlark Trail, this inviting home blends style, efficiency, and location.

812 Castle Avenue, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Blue Sky Real Estate, LLC.

$1,000,000
3 Beds 3 Baths 2378862 MLS SOLD Status
Beautiful 9.97-acre mountain retreat with forest, meadow, and mountain views. Backs to National Forest and is just steps from community trails. The 2,200 sq ft home features 3BD, 2BA, a spacious upstairs primary ensuite with balcony, and a versatile bonus room. The great room offers vaulted ceilings, skylights, and a wall of windows nestled in aspen trees with views of dramatic rock walls. Enjoy all-new appliances, wood floors, and a cozy propane stove. Outdoor living includes a large deck, screened porch, hot tub, and fenced backyard. The insulated garage offers a workshop, bathroom, kitchenette, and upper-level studio. A thoughtfully designed retreat with a peaceful, private setting and direct access to year-round recreation.

18306 Highway 20, Winthrop

Listing courtesy of Windermere RE/Methow Valley. Selling Office: Blue Sky Real Estate, LLC.

$499,500
1 Beds 1 Baths 2380294 MLS SOLD Status
Charming Edelweiss Cabin w/ Custom Details –This inviting 1-bd, 1-bath cabin features an open floor plan w/ generous space for cooking, entertaining, & relaxing. Upstairs enclosed loft room sleeps 2 & adds additional space for guests. Beautifully crafted w/ wood accents & custom cabinetry throughout. Enjoy year-round outdoor living from the deck off the great room or unwind on your private patio. A seasonal creek borders the property, adding a peaceful, natural soundtrack to your surroundings. A charming stand-alone heated shed offers extra storage & includes a dedicated waxing bench. Ideally located on Homestead Rd, minutes from National Forest access, 5 trailheads within 5 miles, community trail system & community summer pool.

98 Homestead Road, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Mountain to River Realty LLC.

$475,000
2 Beds 1 Baths 2379840 MLS SOLD Status
Cozy & comfortable year-round with a mini-split system, propane stove, & furnace for warmth in winter, plus air conditioning to keep things cool in the summer. Enjoy forever-unobstructed, breathtaking upvalley views through large picture windows. This inviting home features 2 bedrooms, 1 full bath & a spacious loft area—perfect for extra living or guest space. A covered porch & low-maintenance landscaping offer more time for outdoor adventures, whether skiing nearby trails, hiking, biking, or simply exploring this 3+ acre sunflower-filled property. Just minutes from downtown Winthrop for shopping & social events. As part of the Sun Mountain Ranch Club, enjoy community amenities including a pool, BBQ area, sport courts, picnic area.

11 Appaloosa Road, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Mountain to River Realty LLC.

$525,000
3 Beds 2 Baths 2376367 MLS SOLD Status
WINTHROP/CASCADE CONDOS: Super clean and well maintained, this one-owner turnkey condo is perfect for full or part-time Methow Valley living. Coveted 1,517 sq ft, 3-bedroom, 2-bath floorplan features a spacious main-floor primary suite and an inviting great room with vaulted ceilings and a river-rock propane fireplace for warmth and ambiance. Decorated in a timeless ski-lodge style, the home comes fully furnished with high-quality pieces. Tucked away at the quiet end of a cul-de-sac, you’ll enjoy peekaboo mountain views and added privacy. The well-appointed kitchen offers custom quarter-sawn oak cabinetry, upgraded appliances, and an ideal layout for entertaining. An attached one-car garage includes dedicated ski storage and a waxing station—perfect for outdoor enthusiasts. Additional upgrades include extra insulation and soundproofing for enhanced comfort. With exterior and yard maintenance handled by the Cascade Condos HOA, this is truly easy-care living. Ideally located close to hiking, biking, and ski trails, as well as all the shops, dining, and entertainment downtown Winthrop has to offer. Nightly rentals are allowed, and this unit has a well-established rental history as the aptly name “Alpen Trails” condo, currently managed by Methow Reservations. A fantastic opportunity for a year-round retreat, part-time getaway, or income producing property!

302 Cascadian Court Unit #18, Winthrop

Listing courtesy of Windermere RE/Methow Valley. Selling Office: Blue Sky Real Estate, LLC.

$889,900
3 Beds 3 Baths 2373179 MLS SOLD Status
Stunning single-level 3 bed, 2.5 bath home on 5 level, irrigated acres. Features a spacious open kitchen with brick accents, cathedral ceilings, and a cozy double fireplace. Enjoy big mountain views from the living areas, a covered patio for year-round outdoor living, and a deck perfect for relaxing or entertaining. The manicured grounds include fruit trees, vibrant flowers, and lush landscaping that invite peaceful outdoor living. Ideal for horse lovers with a deluxe barn, fenced pastures, large storage shed, and detached garage. Inside and out, this property blends comfort, function, and natural beauty—perfect for those seeking a serene country lifestyle just minutes from town conveniences. Don’t miss out!

28 Wandling Road, Winthrop

Listing courtesy of Windermere RE/Methow Valley. Selling Office: Windermere RE/Methow Valley.

$590,000
2 Beds 1 Baths 2369208 MLS SOLD Status
Sun-lit spotless 768 sf cabin is just right, near the Old West Town of Winthrop. 1 story level has 2 Bed/1 Bath. Full Kitchen. Real wood cabinets & includes appliances. Interior shines. Gleaming pine-wood ceilings & white tile floors. Kitchen, dining and living room has Mountain views. Covered decks. Natural landscape with gravel driveway. Heirloom Apple trees. Abundant Wildlife seen here. Small shop outbuilding/storage area. Individual well & installed on-site septic system. Lots of parking for friends and guests. Fun outdoor patio w/ firepit for gathering. Unfinished walk-out Daylight basement is yours to finish as you like. Utility room spacious.(2) Deeded walking easements to River. Take a swim & splash your feet in the Chewuch River!

3 Northcott Road, Winthrop

Listing courtesy of North Cascade Land & Home Co.. Selling Office: CB Cascade - Winthrop.

$460,000
2 Beds 1 Baths 2368238 MLS SOLD Status
WINTHROP ARTISAN CABIN - Perfectly laid out smaller 2bd/1 bath home with comfortable floorplan, custom aesthetic finishes & low maintenance requirements inside & out. Colored concrete floors, maple & wood slab counters, newly installed mini-splits for heating and cooling, new architectural shingle composite roof & blue pine custom doors are just a few of the features in this efficient &bright home. The private covered front and back porches, & mature landscaping create a serene outdoor living space to unwind. Built-in storage shed for outdoor gear & toys. Enjoy the convenience of being close to everything—only minutes to the Nordic trailhead, the Meadowlark Trail & downtown Winthrop.

811 Filer Avenue, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Blue Sky Real Estate, LLC.

$920,000
4 Beds 3 Baths 2364054 MLS SOLD Status
Easy-living 4-br home suited for full or part-time use. Located on quiet cul-de-sac at the edge of town w/quick access to ski trails, shopping, cinema & more! Great floor plan has lots of storage & large rec room. Well maintained w/many upgrades. Largest bedrooms both w/en suite bathrooms, one with radiant floor heating! Finishes are classy & understated. Outdoor features include propane plumbing to both back patio & breezeway for year-round grilling, covered front & side porch, irrigation, city open space next door for extra privacy & elevated screened summer house for dining/sleeping! EV hookup in garage, with 200 Amp capacity for 2nd EV and/or shop! Previously a very popular monthly vacation rental managed by Methow Reservations.

175 Saddleback Road, Winthrop

Listing courtesy of CB Cascade - Winthrop. Selling Office: Blue Sky Real Estate, LLC.

$285,000
2364357 MLS SOLD Status
Winthrop phenomenon! Perched on the edge of town with massive protected views, year-round access, and a large level building site—water and power on site. This property hasn't been on market for almost 30 years. One of the last parcels within city limits heading west toward Mazama. This 1.5-acre gem is primed for your home and ADU. Access Vista Ct via a paved, county-maintained road, then follow the gentle driveway to your expansive, flat building platform. Enjoy stunning west and northwest-facing views—elevated terrain ensures your view corridor stays unobstructed. City water and power are already in place. Walk or bike into downtown Winthrop for shopping, dining, entertainment, and outdoor fun.

2 Vista Court, Winthrop

Listing courtesy of Blue Sky Real Estate, LLC. Selling Office: Blue Sky Real Estate, LLC.

$1,010,414
2 Beds 2 Baths 2354760 MLS SOLD Status
Relax to the sounds of the river from this South-facing home. Expansive river & mountain views! Enjoy your morning coffee on the inviting covered deck. Property consists of 5.25 acres w/ walking trail down to 200-feet of level low bank Chewuch River frontage w/ a great fishing hole. 2 tax parcels w/trails. Classic Methow designed home w/ board & batt siding, pine cathedral ceilings, wood stove on river rock hearth, updated granite counters, bathrooms &appliances, pine-slab kitchen eating bar. Other features include a spacious mudroom with a large sink, newer mini-splits for heating & cooling, irrigation water rights, fenced garden, partially fenced, oversized 2-car garage for outdoor gear & dog kennel, minutes from Winthrop & valley trails.

2 Northcott Road, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Windermere RE/Methow Valley.

$850,000
3 Beds 2 Baths 2355248 MLS SOLD Status
Beautiful 20 acre property boasting a lovely 3 bedroom, 2 bath home. Property also features a deluxe shop and storage area. The second story is roughed in living space ready for your custom finishing touches. Breathtaking views that will leave you speechless. Surrounded by towering aspens and majestic pines, this is the perfect mountain oasis for those seeking tranquility and peace away from the hustle and bustle of city life. With its spacious interior, modern amenities, and countless outdoor recreational activities nearby, this property is truly a dream come true. Don't wait, schedule a tour today and see for yourself what this amazing property has to offer!

143 Harrier Hill Road, Winthrop

Listing courtesy of Windermere RE/Methow Valley. Selling Office: Windermere RE/Methow Valley.

$901,000
3 Beds 2 Baths 2296776 MLS SOLD Status
You thought you wanted Mazama, think again! Highly desirable, mountain modern home adjacent protected Conservancy property in Winthrop. Super private only minutes to town. Enjoy the ease of trailside access with landowner ski passes in a rare & secluded location! Single level, open floor plan, low maintenance home & landscaping are timeless features for easy mountain living. Large windows for natural light with calming forested & mountain views. Elegant simplicity pairing modern lines w warm wood features. Pleasing outdoor living spaces. Primary bedroom w ensuite bath & walk-in closet. 2 more bedrooms w ample storage. Flex room as family/media rm. Mudroom & carport for an active mountain lifestyle. Special one of a kind location!

13 Shooting Star Rd, Winthrop

Listing courtesy of Blue Sky Real Estate, LLC. Selling Office: North Cascade Land & Home Co..

$506,750
3 Beds 2 Baths 2292211 MLS SOLD Status
Classic storybook cabin with 3 bedrooms and 2 bathrooms, great trail access and a perfect location for maximum recreation! This cabin was extensively updated including new roof, bathrooms, & kitchen featuring custom cabinets, granite counters, & all new appliances. Invite your friends to come stay with new RV parking with 50AMP service. The home was recently fire wised and professionally terraced to maximize the usable outdoor space and recently seeded with a native seed blend from Methow Natives. The large deck is perfect for relaxing while overlooking the profuse aspen grove below. Delight in a sunny location, peering through the trees from this private cabin close to Winthrop with some of the best trail access in the Methow.

56 Sugar Pine, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Windermere RE/Methow Valley.

$1,000,000
2 Beds 2 Baths 2284766 MLS SOLD Status
Modern Farmhouse in Wolf Creek! Beautifully finished 2,038 sf home bordering world class Ski Trail in Winthrop! Stunning Sunrise & Sunsets to be savored from this 2 plus Acre location in Cottonwood Meadows. Kitchen w/stainless steel appliances. Hardwood floors. Gather in Kitchen gallery, Dining & Living rooms warm glo of fireplace, Entertainment Bonus room! Spacious 2,400 sf Garage/Shop 4 car capacity, finished professional Gym over garage. Stay in top shape to Hike, Ski, Bike, & Run to outdoor adventures. Covered entry walkway from Garage/Workout room to Home. Stay comfortable with electric A/C mini-splits, FS Propane fireplace, Forced air, electric B.B. heat systems. (2) Lifetime Annual Ski passes! Built/1999. Garage/Built 2021.

28 Cottonwood Drive, Winthrop

Listing courtesy of North Cascade Land & Home Co.. Selling Office: Mountain to River Realty LLC.

$970,000
2 Beds 3 Baths 2276090 MLS SOLD Status
Expansive, wide-open mountain & lake views from this stunning location with waterfront on both Big and Little Twin Lakes! Lake views from every window in this turn-key, thoughtfully designed and lovingly cared for modern home. Gorgeous open beam ceiling on main floor & primary bedroom with ensuite bathroom. The kitchen features granite counter tops, wine fridge & upgraded appliances. Lake view pergola & outdoor jacuzzi. Spacious, light filled lower level with family/media room & bar with sink & custom wine storage. Second bedroom/office with queen murphy bed. Private, natural, expansive shoreline on both lakes. Not part of Sun Mt Ranch- No HOA. Birdwatch, swim, paddle from your home! Close to trailheads for skiing, hiking and biking!

43 Twin Lakes Access RD, Winthrop

Listing courtesy of Blue Sky Real Estate, LLC. Selling Office: Windermere RE/Methow Valley.

$1,260,000
3 Beds 3 Baths 2245814 MLS SOLD Status
Stunning 360-degree views, artistry, and craftsmanship in this 3 bdrm, 2.5 bth house on 11.8 irrigated acres. Hard wood / slate tile floors, walnut doors, built-ins, bay window and much more. Covered deck off great room with Cascade mountain vistas. 1 BR apartment adds 2nd kitchen. Mudroom/entry, 2 bonus rooms, office, high speed internet and loft. Custom outdoor living area, pergola, gardens, sauna, and hot tub. 4 horse stalls / paddocks, garage/shop/barn with heated ski waxing/tack room, 3 bay hay/vehicle storage, portable horse stall, and wood shed. Riding arena, private trails, fencing/cross fencing and irrigation system. Premier location, close to Winthrop with maximum privacy and panoramic beauty. Endless possibilities. Rare offering

275 Eastside Chewuch Road, Winthrop

Listing courtesy of Windermere RE/Methow Valley. Selling Office: Blue Sky Real Estate, LLC.

$1,723,055
3 Beds 2 Baths 2245491 MLS SOLD Status
Mazama Mountain Modern. Highly desirable, private home adjacent National Forest & Goat Creek. Quiet location filled w the sound of Goat Creek! Trail access within a few hundred yards! Low pitch roof, open floor plan & low maintenance landscaping are timeless features for easy mountain living. Lg windows for natural light w calming forested & mountain views. Elegant simplicity by pairing modern lines w warm wood features. Pleasing mix of native plants & trees surround outdoor living spaces. Primary bedroom w ensuite bath & walk-in closets. 2nd bedroom & full bathroom appointed for quiet comfort. Den/3rd bedroom provides office & guest space. Insulated 2 car garage & spacious mudroom for an active mountain lifestyle. Zoned for nightly rental.

11 Spring Creek Lane, Winthrop

Listing courtesy of Blue Sky Real Estate, LLC. Selling Office: Windermere RE/Methow Valley.

$440,000
3 Beds 1 Baths 2240481 MLS SOLD Status
Dramatic homesite in the forest at the base of Lucky Jim Bluff, this nearly 5.5-acre property near Mazama is private and peaceful, adjacent to public land with end-of-road location. Minimal select tree removal will open up views from the homesite across the valley to Grizzly Mountain and Fawn Peak. Three bedroom Timberland home with pleasing forest views is well maintained and move-in ready! Two small bunk-houses and an outdoor shower-house to accommodate extra guests. Numerous outbuildings for storage. A great getaway or well-suited for full time living. Conveniently located between Winthrop and Mazama for access to the amenities of town and all the recreation opportunities the upper valley has to offer.

20 McKinney Road, Winthrop

Listing courtesy of CB Cascade - Winthrop. Selling Office: Blue Sky Real Estate, LLC.

$640,000
2 Beds 2 Baths 2224168 MLS SOLD Status
Edelweiss: Private quiet siting, stylish 2 bds 1.75 baths one story. Radiant floor heating in baths/great room w free-standing Jotul propane stove, baseboard heat in bedrooms. Custom accents throughout. High ceilings, high speed Internet, highly energy efficient. All house water filtration system protects plumbing. Firewise. Earth bermed. Most furniture/furnishings included, live in ready. Outdoor patio and shower. Covered entryway, deck with seating . Forests, abundant wild flowers, and tranquil mountain scenes w year-round easy access. Adjacent to common area, trails. Community features pool, riverfront, and trails that weave into Methow Trails and Okanogan National Forest all surrounding magical Mazama. Unique find first time on market.

11 Mustard Mountain Road, Winthrop

Listing courtesy of Windermere RE/Methow Valley. Selling Office: Windermere RE/Methow Valley.

$617,000
2 Beds 2 Baths 2223140 MLS SOLD Status
Great combination of indoor/outdoor space in this 3 level lakefront (about. 130 ft lake frontage) home w/gorgeous views of Big Twin Lake, Patterson Mt. & surrounding mountains. Large deck wraps around the main level creating wonderful outdoor space on every side. Features: wood wrapped windows, custom hickory cabinets throughout, bamboo flooring, open floorplan, fam room, & tall ceilings. Mature landscaping screens out neighbors. Bonus room on lower level. Fenced garden & yard, small shop & lots of storage for toys. This home would work great for either full time or part time living. Close proximity to the Methow Valley School District, downtown Winthrop, & summer/winter trail systems. Community pool, club house, trash/recycle & playground.

212 Twin Lakes Drive, Winthrop

Listing courtesy of Mountain to River Realty LLC. Selling Office: Blue Sky Real Estate, LLC.

$799,950
2 Beds 2 Baths 2215832 MLS SOLD Status
LUSH private aspen grove and meadow setting with this shy 7 acre property minutes from downtown Winthrop. Architectural artistry and attention to detail through out this energy efficient 2 bed, 2 bath one story home. Vaulted ceilings, exposed log beams, fireplace in living room and master bedroom. Chef's kitchen with quartz countertops & walk in pantry. Mica slate entry, wood and stone detailing sourced from the property itself. River rock & mosaic inlays create a bathing experience in your radiant heated master bath. Covered gazebo gives you a three season outdoor living space. Walk from your bedroom straight onto your hot tub deck. 110sf detached studio space & 750sf two car garage provide hobby space. Not just a house-habitable art.

19 Wright Road, Winthrop

Listing courtesy of Blue Sky Real Estate, LLC. Selling Office: Mountain to River Realty LLC.

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