Winston Homes for Sale

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  /2

  $387,500

  • 3 Beds
  • 2 Baths
  • 1,426 Sq Ft

  117 NW Romayo Ct, Winston, OR 97496

  Welcome to this well-maintained single-level home nestled on a quiet cul-de-sac in Winston! Built in 2000, this 3-bedroom, 2-bath home offers 1,426 square feet of comfortable living space on a generous .23-acre lot. Conveniently located near schools, restaurants, and shopping, it combines a peaceful setting with everyday convenience.The open-concept great room, dining area, and kitchen feature

  Jennifer Kramer RE/MAX Integrity

  

  117 NW Romayo Ct, 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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  /40

  $459,990

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

  535 SE Parkway Dr, Winston, OR 97496

  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 generously sized lot with beautiful views of the

  Lisa Ollivant RE/MAX Integrity

  

  535 SE Parkway Dr, Winston, OR 97496
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  /10

  $350,000

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

  0 Lookingglass Rd Unit TL 203, Winston, OR 97496

  Peaceful and secluded 50 acres in the Umpqua Valley wine country. Wonderful location by Abacela Vineyard with incredible views of the countryside. Zoned Residential Medium Density. 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

  $320,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  351 SE Darrell Ave, Winston, OR 97496

  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 overlooking the large

  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
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  /17

  $339,000

  • 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
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  /17

  $315,000

  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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  /19

  $69,000

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

  235 Twin Oaks Loop, Winston, OR 97496

  This spacious double-wide manufactured home is waiting for its new owner! A great find, located in Winston's 55+ Twin Oaks Mobile Estates community! This home has plenty of features, including its spacious primary bedroom with bath, 2nd bedroom, a converted office/hobby room, living room, dining area, kitchen, laundry room, and a carport with shed. Space rent fee includes water, sewer, and

  Kimberly Krebs Stellar Realty Northwest

  

  235 Twin Oaks Loop, 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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  /48

  $634,900

  • 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
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  /32

  $268,000

  $12K 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
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  /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
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  /23

  $365,000

  $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
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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
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  /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
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  /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
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  /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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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /34

  $350,000

  $9K 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
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  /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
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  /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

  Nataly Mattox RE/MAX Integrity

  

  411 Woodland Dr, Roseburg, OR 97471
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  /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
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  /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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  /40

  $499,900

  New Construction $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,999 Sq Ft

  150 Wil Way, Winston, OR 97496

  Open House 5/30 2-5 pm New Home by JW Construction Inc. This beautifully crafted 2,143 sq ft home offers 3 bedrooms and 2 1/2 bathrooms with a thoughtful layout and excellent separation of space. Set on a low-maintenance lot with views of trees and the surrounding mountains, 140 Wil Way combines modern design with comfort and convenience. The open-concept main level features high ceilings,

  

  Tyler Head

  Turning Point Realty Group

  

  150 Wil Way, Winston, OR 97496
• 

  

  /23

  $70,000

  $30K PRICE DROP

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

  124 Country Side Ln, Winston, OR 97496

  Welcome home to this charming home located in a beautifully maintained 55+ community! With 3 bedrooms, 2 baths, and 1,296 sq. ft. of inviting living space, this home features vaulted ceilings, a bright open layout, and a manicured corner lot. The walk-through kitchen includes a breakfast bar, built-in microwave, stove, refrigerator, and a brand-new dishwasher. The spacious primary suite offers

  Jason Mann J Mann Realty

  

  124 Country Side Ln, Winston, OR 97496
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  /15

  $185,000

  $90K PRICE DROP

  • Land
  • 4.26 Acres
  • $43,427 per Acre

  0 Wil Way Unit 24292479, Winston, OR 97496

  Unique investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

  

  Ashton Faas

  Faas Realty

  

  0 Wil Way Unit 24292479, Winston, OR 97496
• 

  

  /28

  $350,000

  $150K PRICE DROP

  • Land
  • 7.4 Acres
  • $47,297 per Acre

  0 Wil Way Unit 24094727, Winston, OR 97496

  Rare investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Property has already been approved to be partitioned as either 2 larger parcels or a 28 lot subdivision! Currently no HOA or CC&Rs! Utilities conveniently are available nearby ready to be connected. The 2 parcels are also listed separately. Make an offer today before one or all

  

  Ashton Faas

  Faas Realty

  

  0 Wil Way Unit 24094727, Winston, OR 97496
• 

  

  /15

  $185,000

  $90K PRICE DROP

  • Land
  • 3.14 Acres
  • $58,917 per Acre

  0 Wil Way Unit 24278136, Winston, OR 97496

  Great investment opportunity! This property features astounding views of Abacela Vineyards and the surrounding valleys. Currently no HOA or CC&Rs! Property has already been approved to be partitioned as a larger parcel or a over a dozen lot subdivision! Utilities conveniently are available nearby ready to be connected. The other parcel is also listed separately. Or both properties are available

  

  Ashton Faas

  Faas Realty

  

  0 Wil Way Unit 24278136, Winston, OR 97496
• 

  

  /8

  $590,000

  • Land
  • 4.77 Acres
  • $123,690 per Acre

  350 View Point Terrace, Winston, OR 97496

  Excellent investment opportunity! 31 platted lots prime for development in the growth seeking city of Winston! This early 1980's subdivision is prominently located next to a newer construction community to strengthen the potential development value. Pacific Power just confirmed power is available! Call Winston city manager with all your building/development questions as he will accommodate all

  Michael Fischer Oregon Life Homes

  

  350 View Point Terrace, Winston, OR 97496

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