Newest Homes for Sale in Winston, OR

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  /26

  $135,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  134 NW Anne Ave, Winston, OR 97496

  Well maintained 1296 sf manufactured home with a very functional floor plan. This home has 3 bedrooms, 2 bathrooms, a spacious living room and kitchen with plenty of storage including a walk-in pantry, separate dining room and laundry room. The home is located on a nice size lot that has fully fenced front and back yards, a large storage shed, and carport. Enjoy low space rent of $450/month in

  Debra Moore Currieco Real Estate

  

  134 NW Anne Ave, Winston, OR 97496
• Explore Winston

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  /48

  $634,900

  • 4 Beds
  • 3.5 Baths
  • 3,072 Sq Ft

  635 Wil Way, Winston, OR 97496

  Panoramic valley views, over 20 acres of RM-zoned land, and a location bordering Wildlife Safari make this 4-bedroom, 3.5-bath, 3,072 SF property one of Southern Oregon’s most unique offerings. Positioned at the end of the road, it enjoys exceptional privacy while overlooking Abacela Vineyards, rolling valleys, and Wildlife Safari, with potential for 360-degree views. RM zoning adds rare

  Anthony Beckham Different Better Real Estate

  

  635 Wil Way, Winston, OR 97496
• 

  

  /2

  $249,000

  • Land
  • 27.31 Acres
  • $9,118 per Acre

  0 E Willis Creek Rd, Winston, OR 97496

  27.31 acres offering the opportunity to build your dream home either atop the property with expansive views or tucked into the peaceful valley below. City water is available, and additional utilities are accessible via a recorded easement. Boundary lines shown in photos are approximate; buyers to perform their own due diligence regarding property lines, buildability, utilities, and intended use.

  Tim Rist DORE

  

  0 E Willis Creek Rd, Winston, OR 97496
• 

  

  

  /46

  $509,999

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 2,091 Sq Ft

  330 Wil Way, Winston, OR 97496

  Custom-built in 2014 and thoughtfully designed by the owner, this 2,091 SF ranch style home offers 4 bedrooms and 2 full bathrooms on a spacious corner lot. The inviting great room showcases vaulted ceilings, abundant natural light, and a stunning floor-to-ceiling stone fireplace that serves as the centerpiece of the home. The open-concept kitchen features stainless steel appliances, including a

  Shea Martin United Real Estate Properties

  

  330 Wil Way, Winston, OR 97496
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  /32

  $280,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  509 NW Elwood Dr, Winston, OR 97496

  This adorable 3-bedroom, 1-bathroom home is the perfect starter home or an excellent addition to your investment portfolio. The kitchen was remodeled earlier this year. Conveniently located close to an elementary school, shopping, and everyday amenities, this home combines comfort with convenience. Whether you’re a first-time homebuyer, looking to downsize, or searching for a rental property,

  Jada Whited Oregon Life Homes

  

  509 NW Elwood Dr, Winston, OR 97496
• 

  

  /10

  $235,000

  • Land
  • 42,253 Sq Ft
  • $242,268 per Acre

  740 Ireland Rd, Winston, OR 97496

  Peaceful Country Escape with Endless Potential! Just minutes from Winston, about 75 miles to the coast and close to Ben Irving Reservoir Area. Embrace the quiet country lifestyle on this beautiful 0.97-acre parcel, offering the perfect blend of rural tranquility and functional utility. Framed by gorgeous, views of the surrounding woods and mountains, this property is a blank canvas ready for your

  Cynthia Beach The Neil Company Real Estate

  

  740 Ireland Rd, Winston, OR 97496
• 

  

  /31

  $98,000

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft

  190 Twin Oaks Loop, Winston, OR 97496

  Welcome to this cozy 3-bedroom, 2-bathroom home located in the sought-after Twin Oaks Mobile Park Estates. Situated in a quiet and well-maintained 55+ community in Winston, Oregon, this charming property offers the perfect blend of comfort and conveniences. This home features a spacious, functional open floor plan. The living room flows seamlessly into a modern kitchen, which comes complete with

  Kimberley Ferguson eXp Realty, LLC

  

  190 Twin Oaks Loop, Winston, OR 97496
• 

  

  /23

  $389,000

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  10 SW Peach Ln, Winston, OR 97496

  Welcome to 10 SW Peach Ln, where every day feels like a peaceful retreat and every corner invites you to slow down and savor the moment. This special property blends warmth, character, and an unforgettable backyard oasis designed to elevate your everyday living.Step outside and imagine hosting summer gatherings on the resort-style brick patio, unwinding beside the soothing sounds of your private

  Kimberly Krebs Stellar Realty Northwest

  

  10 SW Peach Ln, Winston, OR 97496
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  /41

  $169,900

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  600 SE Edgewood St, Winston, OR 97496

  WOW! Affordable 2-bedroom 1-bath home set on nearly half an acre in the heart of Winston. With 0.43 acres of usable ground, a fully fenced yard, mature shade trees, and room for RVs, trailers, boats, equipment, gardens, and outdoor projects, or possible future development, there's plenty of flexibility here! Inside features an open living area with updated laminate flooring, abundant natural

  Anthony Beckham Different Better Real Estate

  

  600 SE Edgewood St, Winston, OR 97496
• 

  

  /35

  $160,000

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  105 Stephanie Ct, Winston, OR 97496

  Welcome home to this well-maintained single-level home offering comfort, convenience, and an inviting open-concept design. The spacious living area flows seamlessly into a beautifully appointed kitchen featuring abundant cabinet storage, a pantry, stainless steel appliances, and a large island perfect for meal prep, casual dining, or gathering with family and friends.Luxury vinyl plank flooring

  Tammi Ellison eXp Realty, LLC

  

  105 Stephanie Ct, Winston, OR 97496
• 

  

  /48

  $409,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft

  265 SE Logan St, Winston, OR 97496

  Welcome to Rolling Meadows Estates, Winston's newest neighborhood community where quality craftsmanship, modern design, and Southern Oregon lifestyle come together. Surrounded by attractive newer homes and a growing sense of community, this is an opportunity to enjoy the benefits of new construction in one of Winston's most exciting new developments.Built by Premier Home Construction, a respected

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  265 SE Logan St, Winston, OR 97496
• 

  

  /6

  $485,000

  • 3 Beds
  • 3 Baths

  51 SW Brantley Dr, Winston, OR 97496

  INVESTMENT PROPERTY OPPORTUNITY! Well-maintained 4-unit apartment building located in a quiet, centrally located neighborhood. This property features a desirable unit mix with two spacious 2-bedroom, 2-bath units and two comfortable 1-bedroom, 1-bath units, offering strong rental appeal for a variety of tenants. Conveniently situated close to schools, shopping, dining, and local amenities, with

  Vera-Anne Wallace Vera-Anne International Real Estate

  

  51 SW Brantley Dr, Winston, OR 97496
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  /39

  $190,000

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft

  0 Rice Creek Rd, Winston, OR 97496

  Escape to your own off-grid retreat on a 20-acre shared property in a gated community with coded access. This is a unique property on jointly owned lot, in an off grid community. Seller is selling 50% share in 20 acre lot. Land use agreement in place. This beautifully crafted 1,000 SF cabin showcases exceptional handcrafted woodwork and rustic charm throughout. Features include 1 bedroom plus a

  Starlight Turner Starlight Realty

  

  0 Rice Creek Rd, Winston, OR 97496
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  /27

  $249,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 939 Sq Ft

  71 SE Ronald St, Winston, OR 97496

  Charming remodeled cottage-style home situated on a large quarter acre lot offering comfortable single-level living. This updated residence features new interior paint, newer roof and siding, and thoughtful modern upgrades throughout. The kitchen includes stainless steel appliances, adding a sleek and functional touch to the heart of the home. Enjoy a bright and inviting layout with practical

  Joshua Glaspie ICON Real Estate Group

  

  71 SE Ronald St, Winston, OR 97496
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  /30

  $205,000

  • 2 Beds
  • 1 Bath
  • 1,323 Sq Ft

  381 SE Gregory Dr, Winston, OR 97496

  Incredible and rare opportunity in Winston, Oregon! Developers, investors, and visionaries take notice. This charming 1940s 2-bedroom, 1-bath home is full of character and ready for its next chapter. With a little vision and elbow grease, this property offers endless possibilities.Situated on a spacious, level lot with mature greenery, the property presents potential for future development,

  Shae Ellison Platinum Realty

  

  381 SE Gregory Dr, Winston, OR 97496
• 

  

  /4

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  0 Berry Creek Rd, Winston, OR 97496

  This private, level 4-acre parcel offers convenient access to Ben Irving Reservoir and is the perfect setting for recreation, relaxation, or a future getaway retreat. The property features a large natural meadow surrounded by 20-year-old Douglas fir reprod, creating a peaceful and secluded atmosphere. Adjacent to BLM land, it provides direct access to endless outdoor opportunities. Improvements

  Ryan Fox Berkshire Hathaway HomeServices Real Estate Professionals

  

  0 Berry Creek Rd, Winston, OR 97496
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  /30

  $259,000

  $1K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,070 Sq Ft

  3707 Willis Creek Rd, Winston, OR 97496

  Rare rural opportunity priced at land and utility value — for the investor, builder, or country-living dreamer ready to create something truly their own in the hills of Douglas County, Oregon. Utilities are already in place — a significant head start on any rural build. The property is served by Pacific Power electric and Winston City Water (public water), with an on-site septic system. Septic

  Michelle Kohlhoff Sundance Realty LLC

  

  3707 Willis Creek Rd, Winston, OR 97496
• 

  

  /48

  $699,000

  $26K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,362 Sq Ft

  1068 Rice Creek Rd, Winston, OR 97496

  Security gated 8.52-acre property! This beautiful ranch-style home features, updates, paved driveway, newer roof, interior & exterior paint, gourmet kitchen, double ovens, large walk-in pantry, lots of outdoor light, large living room with a cozy fireplace, great views, huge primary bedroom with a walk-in closet and bathroom with 2-headed shower, 4th bedroom could easily be used as an office, new

  Joan Smith The Neil Company Real Estate

  

  1068 Rice Creek Rd, Winston, OR 97496
• 

  

  /44

  $499,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  2581 NW Brockway Rd, Winston, OR 97496

  Open House 5/30 2-5pm New listing! This beautifully crafted new construction home offers 2,576 square feet with 3 bedrooms and 2.5 bathrooms, thoughtfully designed with quality finishes and modern comfort throughout.The open-concept floor plan features vaulted ceilings, abundant natural light, and recessed lighting, creating a bright and inviting living space. The kitchen is designed for both

  

  Tyler Head

  Turning Point Realty Group

  

  2581 NW Brockway Rd, Winston, OR 97496
• 

  

  /21

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  572 Dillard Gardens Rd, Winston, OR 97496

  Charming farmhouse on the South Umpqua River. Features a 1,440 sf home on 6.9 acres. The 2 bedroom 2 bathroom interior has wood floors, good natural light, a cozy living room, an open kitchen and dining area, a large primary bedroom with an attached bath and walk in closet. Multi-use laundry room. Covered deck opens to the patio and yard filled with flowers and shade trees. New septic system

  Mike Nichols MORE Realty, Inc.

  

  572 Dillard Gardens Rd, Winston, OR 97496
• 

  

  /83

  $735,000

  $50K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,722 Sq Ft

  9114 Old Highway 99 S, Winston, OR 97496

  Escape to the peace and beauty of rural Oregon with this beautifully remodeled country retreat set on 5.4 usable acres of fenced pastureland. Offering the perfect blend of modern comfort and small-acreage functionality, this stunning single-level home features 2,722 sq. ft. with 3 bedrooms, 3 full baths, and a versatile flex space ideal for a home office or hobby room. Each bedroom includes its

  

  Kristina Scott

  Umpqua Legacy Realty LLC

  9114 Old Highway 99 S, Winston, OR 97496
• 

  

  /19

  $24,999

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,022 Sq Ft

  228 Estate Loop, Winston, OR 97496

  2 bed, 1 bath home in a desirable 55+ park featuring spacious living areas and a well-appointed kitchen with breakfast bar. Attached dining area includes built-ins for added storage and charm. Separate laundry room, plus a bathroom with walk-in shower for convenience. Outside features include covered porch, carport with attached storage area. Located close to shopping, dining, and other amenities.

  Jason Mann J Mann Realty

  

  228 Estate Loop, Winston, OR 97496
• 

  

  /48

  $375,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft

  186 Woodduck St, Winston, OR 97496

  Well-maintained home in a quiet neighborhood in the heart of Winston. Move-in ready with brand new floors recently installed. Minimal outdoor maintenance. Garden shed and room to park a 5th wheel. Don’t miss your opportunity to own a solid, easy-living home in a great location.

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  186 Woodduck St, Winston, OR 97496
• 

  

  /36

  $459,000

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  311 SE Grape Ave, Winston, OR 97496

  Great investment opportunity on a spacious 0.74-acre lot! This property features a 3-bedroom, 1-bath single-level home with approximately 1,250 sq ft of living space, plus a duplex on the same lot—offering excellent potential for rental income or multi-generational living. The main home includes a full basement, forced air heating, and public utilities. Situated on a level to gently sloped lot

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  311 SE Grape Ave, Winston, OR 97496
• 

  

  /22

  $315,000

  • 3 Beds
  • 1 Bath
  • 1,348 Sq Ft

  101 SW Peach Ln, Winston, OR 97496

  This single-level home features 3 bedrooms and 1 bathroom, offering comfortable and convenient living. Step outside to a spacious, fully fenced backyard perfect for pets, play or entertaining. Garden enthusiasts will appreciate the dedicated garden area, while multiple tool sheds provide ample storage for tools, equipment and hobbies. A large covered real patio creates an ideal space for

  Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

  

  101 SW Peach Ln, Winston, OR 97496
• 

  

  /48

  $439,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,629 Sq Ft

  260 SE Logan St, Winston, OR 97496

  *** BUILDER INCENTIVE *** Lower Payments Available on this House! Seller offering flexible buyer incentives with acceptable offer, including potential rate buy down, closing cost assistance, or improvement credits. Attractive opportunity for both financed and cash buyers.*** There’s something special about stepping into a home that’s never been lived in—where everything is fresh, thoughtfully

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  260 SE Logan St, Winston, OR 97496
• 

  

  /25

  $318,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  340 SE Darrell Ave, Winston, OR 97496

  Solid 3-bedroom, single-level home with a functional layout, attached garage, and fully fenced yard with covered patio, and front porch.The home features a ductless heat pump for efficient heating and cooling, along with comfortable interior living spaces. Roof replaced within the last few years. Primary bedroom includes a walk-in closet and crown molding. The terraced backyard includes fruit

  Aaron Stansbury Keller Williams Realty Eugene and Springfield

  

  340 SE Darrell Ave, Winston, OR 97496
• 

  /2

  $220,000

  • Land
  • 40 Acres
  • $5,500 per Acre

  0 Willis Creek Rd Unit 124013990, Winston, OR 97496

  Exceptional Farm Forest–zoned timber property offers both natural beauty and strong investment potential. A recent professional timber cruise, inventory, and valuation completed by Resource Management Services highlights the value of this well-managed stand. Timber prices fluctuate but as of March, the net timber value is estimated at $174,749, consisting primarily of healthy, marketable Doug

  Craig Warmouth Berkshire Hathaway HomeServices Real Estate Professionals

  

  0 Willis Creek Rd Unit 124013990, Winston, OR 97496
• 

  

  /35

  $22,500

  • Land
  • 6,098 Sq Ft
  • $160,714 per Acre

  111 SE Lebleu Ln, Winston, OR 97496

  Developable residential lot zoned R1, offering a gentle slope and utilities available including electricity, sewer, and water. Enjoy a pleasant view overlooking nearby vineyards in the valley, providing a peaceful setting for your future home. Conveniently located within driving distance to the Umpqua River and Wildlife Safari, offering access to outdoor recreation and local attractions. Great

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  111 SE Lebleu Ln, Winston, OR 97496
• 

  

  /48

  $1,199,900

  • 3 Beds
  • 2.5 Baths
  • 2,856 Sq Ft

  1349 Willis Creek Rd, Winston, OR 97496

  Quiet country living on private acreage! Offered for the first time ever, this exceptional estate presents a rare opportunity to own a truly special piece of the Pacific Northwest. Featuring two separate residences, this property is perfectly suited for multi-generational living, guest accommodations, or potential rental income. The primary home offers over 2,800 square feet of inviting living

  Jordan Anderson The Anderson Agency

  

  1349 Willis Creek Rd, Winston, OR 97496
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  /34

  $355,000

  $4K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,710 Sq Ft

  380 NW Cary St, Winston, OR 97496

  Schedule your private tour today of this adorable 4bd 2ba open floor plan home, located on a generous lot, with an extra deep garage and additional off-street parking for your RV or Boat. Just a 15-minute drive to Roseburg, close to local schools and just down the street from the Wildlife Safari.

  Willow Pearson Oregon Life Homes

  

  380 NW Cary St, Winston, OR 97496
• 

  

  /46

  $1,100,000

  $100K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,720 Sq Ft

  6700 Upper Olalla Rd, Winston, OR 97496

  Stunning custom cedar home on 5 level acres offering the perfect blend of luxury, functionality, and country living. This Lindal-style home features a spacious 2,400 sq ft shop with a full bath, dual garage doors, and enough space for a 40-foot motorhome. Property also includes 3 RV hookups with power, water, and RV dump access, ideal for guests, multi-use living, or recreational storage.The

  Dan Gandee Real Broker

  

  6700 Upper Olalla Rd, Winston, OR 97496
• 

  

  /11

  $179,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  1580 Winston Section Rd, Winston, OR 97496

  This 3-bedroom, 2-bathroom "fixer upper" sits on a peaceful 0.18-acre corner lot, offering a quiet atmosphere and beautiful mountain views right from your doorstep. While the home is ready for interior renovation, the floor plan features three bedrooms, two bathrooms, laundry room, large kitchen, creating a cozy feeling once restored. A standout is the 576 sqft detached garage/shop, where half

  Cynthia Beach The Neil Company Real Estate

  

  1580 Winston Section Rd, Winston, OR 97496
• 

  

  /15

  $165,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 784 Sq Ft

  101 NE Darrell Ave, Winston, OR 97496

  Charming affordable singlewide manufacture home on .18 of an acre, located on a corner lot. This 2 bedroom, 1 bath home has a covered front porch and back deck with a chain link fenced yard. Storage shed and off street parking.

  Nancy Wood Oregon Life Homes

  

  101 NE Darrell Ave, Winston, OR 97496
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  /47

  $489,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  263 Wil Way, Winston, OR 97496

  Welcome to Your Like-New Custom Home in Winston, Oregon!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality craftsmanship and thoughtful design are evident in every detail. The open-concept floor plan features soaring vaulted ceilings, beautiful flooring, and a warm, inviting layout that flows effortlessly for both everyday living and entertaining.At the

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  263 Wil Way, Winston, OR 97496
• 

  

  /42

  $499,000

  $150K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,431 Sq Ft

  605 Deerwood Ct, Winston, OR 97496

  This custom-built Passive Solar home, constructed in 1979, offers a rare blend of timeless beauty, retro charm, and thoughtful modern updates. This Passive Solar home is thoughtfully designed to work with the sun and climate, providing comfort, efficiency, and sustainability without relying heavily on mechanical systems. Ideally located near local river recreation and just a short drive to the

  Lisa Ollivant RE/MAX Integrity

  

  605 Deerwood Ct, Winston, OR 97496
• 

  

  /48

  $495,000

  $130K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,782 Sq Ft

  624 Willis Creek Rd, Winston, OR 97496

  This rare riverfront horse property on the South Umpqua River is not to be missed! The home features a brand new 600 sq. ft. deck overlooking the property and river, new roof,a centrally located wood stove that heats the entire house, and is tucked away off the road for privacy. Horse facilities include an arena, barn, multiple stalls, and pasture. Additional amenities include an orchard,

  Nancy Kruger Keller Williams Southern Oregon-Umpqua Valley

  

  624 Willis Creek Rd, Winston, OR 97496
• 

  

  /44

  $685,000

  $34K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  411 Woodland Dr, Roseburg, OR 97471

  What if your favorite getaway was home?Set above Lookingglass Creek with stunning views of Abacela Vineyard, this property offers the kind of lifestyle that's getting harder to find. Spend summer afternoons at your own swimming hole, grow fresh produce in the fenced garden and greenhouse, and enjoy the satisfaction of having water rights, irrigation, a K-line system, and pump already in place.The

  Nataly Mattox RE/MAX Integrity

  

  411 Woodland Dr, Roseburg, OR 97471
• 

  

  /15

  $215,000

  $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  90 SE Darrell Ave, Winston, OR 97496

  This charming 2-bedroom, 2-bathroom manufactured home in Winston, Oregon offers comfortable, modern living in a convenient location close to shopping, dining and other local amenities. Nestled on its own land, this home combines privacy with easy access to town.Inside, you’ll love the open-design floor plan that creates a bright, spacious feel throughout the living room, dining area and

  Rebekah Sexauer eXp Realty, LLC

  

  90 SE Darrell Ave, Winston, OR 97496
• 

  

  /41

  $499,900

  New Construction $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,089 Sq Ft

  160 Wil Way, Winston, OR 97496

  New Home by JW Construction Inc. This beautiful one-level home offers just over 2,000 square feet with three bedrooms and two and a half bathrooms. The open great room features vaulted ceilings, luxury vinyl plank flooring, recessed lighting, and a gas fireplace. A large sliding door opens to an expansive deck, perfect for entertaining or relaxing. The kitchen is designed for both style and

  

  Tyler Head

  Turning Point Realty Group

  

  160 Wil Way, Winston, OR 97496

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