Newest Homes for Sale in Winston, OR

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  /41

  $329,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft

  76 SE Darrell Ave, Winston, OR 97496

  Welcome to this brand-new, single-level contemporary home offering 3 bedrooms and 2 bathrooms with a comfortable, open-concept floor plan. The stylish kitchen features quartz countertops and stainless steel appliances, opening to the dining and living areas for easy everyday living and entertaining. The dining room provides convenient slider access to the fenced backyard.The primary suite

  Jennifer Kramer RE/MAX Integrity

  

  76 SE Darrell Ave, Winston, OR 97496
• Explore Winston

• 

  

  

  /10

  $439,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,564 Sq Ft

  158 Collins Ct, Winston, OR 97496

  Nestled in the highly desired Lookingglass Creek Estates Subdivision in Winston. This brand-new home provides exceptional design and craftsmanship, with a popular floor plan that ensures comfort and style. The heart of this home, the kitchen, is adorned with quartz countertops & custom cabinets that extend to the bathrooms, adding elegance and durability. The property comes with the added

  Jacob Gilman The Neil Company Real Estate

  

  158 Collins Ct, Winston, OR 97496
• 

  

  

  /23

  $469,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  161 Collins Rd, Winston, OR 97496

  Brand-new construction in the desirable Lookingglass Creek Estates subdivision! This functionally designed home features an open floor plan with high-end finishes throughout. Offering 3 bedrooms, 2 bathrooms, & 1770 sqft. The kitchen offers beautiful custom soft-close cabinets, quartz countertops, pantry, and waterproof luxury vinyl plank flooring. The spacious primary suite offers a walk-in

  Jacob Gilman The Neil Company Real Estate

  

  161 Collins Rd, Winston, OR 97496
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  /48

  $487,000

  Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  104 Kenya Ct, Winston, OR 97496

  This remarkable home showcases incredible attention to detail throughout, offering a spacious and unique floor plan designed for both comfort and functionality. The large kitchen features an eating bar, granite countertops, new appliances, abundant cabinet storage, overhead and can lighting, and walk-in pantry. The dining room offers beautiful built-in storage, adding both character and

  Shae Ellison Platinum Realty

  

  104 Kenya Ct, Winston, OR 97496
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  /38

  $409,900

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  623 SE Garden Way Dr, Winston, OR 97496

  Welcome to 623 SE Garden Way Dr, Winston, OR, where modern style, comfort, and convenience come together in one beautifully maintained single-level home. Built in 2019, this 3-bedroom, 2-bath residence offers an inviting open-concept layout with soaring vaulted ceilings and durable luxury vinyl flooring throughout, creating a bright, stylish, and low-maintenance living space. The well-appointed

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  623 SE Garden Way Dr, Winston, OR 97496
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  /16

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  261 SE Darrell Ave, Winston, OR 97496

  Wonderful little cottage for the first time home buyer or the investor needing one more rental in there portfolio. This home is located on a double lot. Per city of Winston, lot is dividable. Build an additional house on its own lot, or leave it as-is and build an ADU or shop in your backyard. Come check this out and make your appointment today.

  Angel Smith Trueblood Real Estate

  

  261 SE Darrell Ave, Winston, OR 97496
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  /48

  $439,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft

  535 SE Parkway Dr, Winston, OR 97496

  Must see to believe!! Get inside this beautiful home! Enjoy your own Fourth of July fireworks show from the comfort of your rear deck with front-row views of the surrounding area! Meticulously maintained single-level home located in the highly desirable Parkway Subdivision. Offering 1,442 square feet of comfortable living space, this home features 3 bedrooms and 2 bathrooms and is situated on a

  Lisa Ollivant RE/MAX Integrity

  

  535 SE Parkway Dr, Winston, OR 97496
• 

  

  /10

  $350,000

  • Land
  • 50 Acres
  • $7,000 per Acre

  0 Lookingglass Rd Unit TL 203, Winston, OR 97496

  50 acres in the Umpqua Valley AVA. Great location by Abacela vineyard with incredible views of the countryside. Zoned Residential Medium Density. Potential for a custom home and residential development. Do not access this property without authorization.

  Mike Nichols MORE Realty, Inc.

  

  0 Lookingglass Rd Unit TL 203, Winston, OR 97496
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  /28

  $309,900

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  351 SE Darrell Ave, Winston, OR 97496

  JUST REDUCED!! This 3 Bedroom/1 Bath, family home on over 1/3-acre has been completely updated for your enjoyment. There are many new items, including roof, mini split system, LVP flooring throughout, interior and exterior paint, plumbing and outside waterline. The bathroom/laundry room has been completely renovated. The yards are fully fenced, and there is a nice large deck on the back

  Debra Moore Currieco Real Estate

  

  351 SE Darrell Ave, Winston, OR 97496
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  /30

  $399,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft

  675 SE Brush Ct, Winston, OR 97496

  This beautifully maintained home is tucked away in a cul-de-sac in the heart of Winston, offering both privacy and convenience. With three comfortable bedrooms and two well-appointed bathrooms, the open-concept layout creates a welcoming atmosphere that’s ideal for hosting gatherings. The kitchen features a spacious island, perfect for preparing meals and entertaining guests. Vaulted ceilings in

  Christina Esterbrook J Mann Realty

  

  675 SE Brush Ct, Winston, OR 97496
• 

  

  /17

  $335,000

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,257 Sq Ft

  185 SE Lebleu Ln, Winston, OR 97496

  Picture enjoying your morning coffee on the back deck looking out over a peach orchard! This very tidy and well-maintained 3 bedroom, 2 bath house is situated in a quiet neighborhood and borders Brosi Orchards. Step inside to the living room with vaulted ceilings and gas fireplace, perfect for relaxing after a long day. Smartly designed layout with private master suite on one end of the home.

  Sandra Hart The Neil Company Real Estate

  

  185 SE Lebleu Ln, Winston, OR 97496
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  /33

  $439,900

  • 3 Beds
  • 2 Baths
  • 1,832 Sq Ft

  128 Watusi Ct, Winston, OR 97496

  Welcome home to this spacious single level home in one of Winston's nicest neighborhoods! With great curb appeal, a sprawling tastefully landscaped yard, and no HOA, this property stands out in many ways. The open kitchen with abundant cabinetry is highlighted by beautiful Quartzite countertops, an island with eating bar, pullout shelves, a pantry, and all appliances are included. There is a gas

  Rich Raynor Heritage Real Estate

  

  128 Watusi Ct, Winston, OR 97496
• 

  

  /17

  $305,000

  $10K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  340 NW Elizabeth Ave, Winston, OR 97496

  This 3-bedroom, 2-bath home offers a functional layout with plenty of potential for its next owner. A few minor repairs will help unlock its full charm, making it an excellent opportunity for buyers looking to personalize a home without taking on a major renovation. Conveniently located in Winston near everyday amenities, this property is ready for its next chapter.

  Tiffanie Frasier Keller Williams Southern Oregon-Umpqua Valley

  

  340 NW Elizabeth Ave, Winston, OR 97496
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  /43

  $99,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  180 Twin Oaks Loop, Winston, OR 97496

  WOW! Enjoy affordable living in the sought-after 55+ Twin Oaks community! This spacious 3-bedroom, 2-bath double-wide offers 1404 square feet of comfortable living space with a thoughtful split-bedroom floor plan and vaulted ceilings. The oversized living room flows into the dining area, where a built-in hutch adds both charm and extra storage. The kitchen features granite tile countertops,

  Anthony Beckham Different Better Real Estate

  

  180 Twin Oaks Loop, Winston, OR 97496
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  /45

  $775,000

  • 4 Beds
  • 5 Baths
  • 3,000 Sq Ft

  375 Porter Creek Rd, Winston, OR 97496

  Significant priced improvement! Discover the perfect blend of vineyard lifestyle and modern comfort in this recently updated 41-acre estate, nestled in the heart of Oregon's Umpqua Valley AVA. Surrounded by timber, a year-round creek, and a seasonal pond, this scenic retreat offers privacy, natural beauty, and endless potential. A spacious 3,000 sq ft home featuring four large bedrooms, large

  Lorrie Normann Triple Oaks Realty LLC

  375 Porter Creek Rd, Winston, OR 97496
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  /45

  $499,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 4,024 Sq Ft

  2620 Brockway Rd, Winston, OR 97496

  Beautiful Craftsman-style home with fantastic curb appeal and a slate-tile covered front porch. This spacious 3-bedroom plus office home offers 1,752 square feet of finished living space, along with a full 2,272-square-foot unfinished walkout basement.The main level features a large open kitchen with gas cooking, an island, granite countertops, pantry, stainless steel appliances, and a hammered

  

  Tyler Head

  Turning Point Realty Group

  

  2620 Brockway Rd, Winston, OR 97496
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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, carport, and an additional carport. This home is

  Debra Moore Currieco Real Estate

  

  134 NW Anne Ave, Winston, OR 97496
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  /48

  $619,900

  $15K PRICE DROP

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

  635 Wil Way, Winston, OR 97496

  WOW! 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 home 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
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  /32

  $259,000

  $21K PRICE DROP

  • 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

  $199,000

  $36K PRICE DROP

  • Land
  • 42,253 Sq Ft
  • $205,155 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

  $364,900

  $24K PRICE DROP

  • 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
• 

  /2

  $409,900

  • Land
  • 7,405 Sq Ft
  • $2,411,176 per Acre

  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

  Mary Gilbert Keller Williams Realty Southern Oregon

  265 SE Logan 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
• 

  

  /20

  $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
• 

  

  /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
• 

  

  /30

  $195,000

  $10K PRICE DROP

  • 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
• 

  

  /30

  $255,000

  $5K 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
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  /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

  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 function and style with a large

  

  Tyler Head

  Turning Point Realty Group

  

  2581 NW Brockway Rd, Winston, OR 97496
• 

  

  /22

  $498,000

  $52K PRICE DROP

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

  572 Dillard Gardens Rd, Winston, OR 97496

  Charming farmhouse on the South Umpqua River. Set on 6.9 acres with prime farmland, water rights and an established cherry orchard. The home features wood floors, good natural light, a cozy living room, open kitchen and dining area. Large primary bedroom with a full bathroom and walk in closet. 2nd bedroom is utilized as an office. Laundry room and detached garage. Back yard filled with flowers

  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

  $18,499

  $11K 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

  $366,000

  $19K 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

  $299,000

  $16K PRICE DROP

  • 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
• 

  

  /26

  $270,000

  $48K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  340 SE Darrell Ave, Winston, OR 97496

  ***JUST LOWEREDD PRICE BY $48,000!!!*** 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.

  Aaron Stansbury Keller Williams Realty Eugene and Springfield

  

  340 SE Darrell Ave, Winston, OR 97496
• 

  /2

  $209,900

  $10K PRICE DROP

  • Land
  • 40 Acres
  • $5,248 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

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