Winston, OR Homes for Sale

• 

  

  

  /15

  $200,000

  • Land
  • 4.26 Acres
  • $46,948 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

  Different Better Real Estate

  (458) 217-1693

  

  0 Wil Way Unit 24292479, Winston, OR 97496
• 

  

  

  /15

  $200,000

  • Land
  • 3.14 Acres
  • $63,694 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

  Different Better Real Estate

  (458) 224-5797

  

  0 Wil Way Unit 24278136, Winston, OR 97496
• 

  

  

  /28

  $375,000

  • Land
  • 7.4 Acres
  • $50,676 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

  Different Better Real Estate

  (458) 310-3411

  

  0 Wil Way Unit 24094727, Winston, OR 97496
• 

  

  

  /45

  $715,000

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

  635 Wil Way, Winston, OR 97496

  One of a kind property that is a true gem. Panoramic views of the Abacela Vineyards, the Wildlife Safari, the beautiful city, and the stunning valleys. While being tucked away at the end of the road for extra privacy. Nestled on over 20 acres, this parcel adjoins the Wildlife Safari. Imagine watching exotic animals from your back yard! The home is a gorgeous 2019 build featuing many high quality

  

  Ashton Faas

  Different Better Real Estate

  (458) 232-3589

  

  635 Wil Way, Winston, OR 97496
• 

  

  

  /47

  $489,900

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

  263 Wil Way, Winston, OR 97496

  Welcome to Your Like-New Custom Home in Winston, OR!Step inside this beautifully crafted home by Shelby & Miguelena Construction, where quality and thoughtful design shine through every detail. The open concept floor plan boasts soaring vaulted ceilings, stunning floors, and an inviting layout that flows seamlessly for both everyday living and entertaining. At the heart of the home, the gourmet

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  263 Wil Way, Winston, OR 97496
• 

  

  /47

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  621 SE Rose Ridge Dr, Winston, OR 97496

  Welcome to 621 SE Rose Ridge Dr in Winston’s desirable Orchard View neighborhood—a beautifully maintained single-level home built in 2020. This 3-bedroom, 2-bath home offers approximately 1,620 sq ft of thoughtfully designed living space on a landscaped 6,534 sq ft lot. The open-concept great room features vaulted ceilings, while the gourmet kitchen includes solid surface countertops, a stainless

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  621 SE Rose Ridge Dr, Winston, OR 97496
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  /37

  $390,000

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  360 NE Rose Ridge Dr, Winston, OR 97496

  Beautiful 3BD/2BTH home in Winston’s sought-after Rolling Meadows neighborhood! Built by Avery Homes in 2021, this one-level residence feels "like new" and is completely move-in ready. Enjoy an open-concept layout with durable LVP flooring, quartz countertops, and a bright, spacious living area perfect for everyday activities and entertaining. Energy-efficient solar panels installed in July 2024

  Aaron Cherry Oregon Life Homes

  

  360 NE Rose Ridge Dr, Winston, OR 97496
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  /48

  $469,900 New Construction

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

  109 Citation Ct, Winston, OR 97496

  Welcome to 109 Citation Ct, a brand-new single-level home nestled in the highly sought-after Lookingglass Creek Estates subdivision in Winston, Oregon. This contemporary ranch-style residence offers 3 bedrooms, 2 bathrooms, and 1,770 sq. ft. of beautifully designed living space on a .20-acre lot with RV parking behind a private gate. Step inside to find luxury vinyl plank flooring, vaulted

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  109 Citation Ct, Winston, OR 97496
• 

  

  /42

  $375,000 Open Sat 1:30PM - 5:30PM

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

  700 SE Tokay St, Winston, OR 97496

  Welcome to this inviting 3-bedroom, 2-bathroom home offering comfort, convenience, and modern touches throughout. The bright and open kitchen features stainless steel appliances and granite countertops, making meal prep a joy. Enjoy the ease of single-level living with a functional floor plan, perfect for both everyday life and entertaining. The fenced backyard provides a safe space for pets,

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  700 SE Tokay St, Winston, OR 97496
• 

  

  /27

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  631 SE Rose Ridge Dr, Winston, OR 97496

  This is a gem! Single-level upgraded home built in 2020. This custom property combines quality construction with modern finishes throughout. Step inside to an open and inviting floor plan featuring vaulted living room and 9 foot ceilings, recessed lighting, ceiling fans, and a perfect blend of rich wood and stylish tile flooring in the main living areas and bathrooms. The entertainment center in

  Jacob Gilman The Neil Company Real Estate

  

  631 SE Rose Ridge Dr, Winston, OR 97496
• 

  

  /43

  $734,000

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

  1068 Rice Creek Rd, Winston, OR 97496

  This gated, 8.52-acre property is fenced and cross-fenced, offering plenty of country living space. This beautiful ranch-style home features updates, a newer roof, and recent interior and exterior paint. The gourmet kitchen includes double ovens and a walk-in pantry. The large living room features a fireplace.The huge primary bedroom includes a walk-in closet and a two-headed shower. One of the

  Joan Smith G. Stiles Realty

  

  1068 Rice Creek Rd, Winston, OR 97496
• 

  

  /35

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  800 Byron Creek Rd, Winston, OR 97496

  Welcome to this charming country home set on over 5 acres of flat, usable land with Firewise Certification for peace of mind. The well maintained 3 bedroom with 1.5 bathrooms. Home is move-in ready, some of the furniture can be included with the right offer. House has a heat pump, pellet stove, generator, flooring- all done in last 4 years. The propane 22k generator automatically powers the home

  Rebekah Sexauer eXp Realty, LLC

  

  800 Byron Creek Rd, Winston, OR 97496
• 

  

  /35

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  364 NW Teal St, Winston, OR 97496

  Welcome to this move-in ready, well-maintained one-level home in a highly desirable subdivision on the outskirts of Winston. Featuring 3 bedrooms, 2 bathrooms and dedicated home office. This property offers both comfort and convenience. Open floorplan with master suite privately positioned at the opposite end of the house for added tranquility. 3-car attached garage provides ample storage and

  Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

  

  364 NW Teal St, Winston, OR 97496
• 

  

  /20

  $575,000

  • 3 Beds
  • 1.5 Baths
  • 2,026 Sq Ft

  308 Helweg Rd, Winston, OR 97496

  Prime 12.91-acre agricultural property zoned (FC) Exclusive Farm Use-Cropland with 10 acres of primary pond and supplemental river irrigation rights (priority date 1983). This land is perfectly positioned for a profitable homestead, organic farm, or u-pick business. Previously used for hay production and livestock, the soil and water offer a solid foundation for success. The existing home and

  Aaron Cherry Oregon Life Homes

  

  308 Helweg Rd, Winston, OR 97496
• 

  

  /46

  $479,900

  • 4 Beds
  • 2 Baths
  • 2,534 Sq Ft

  13224 Lookingglass Rd, Winston, OR 97496

  Experience the unique allure of this beautifully updated, original homestead farmhouse nestled in Safari Estates. Thoughtful remodel and tasteful updates have modernized this 1900-built farmhouse, preserving its character while enhancing comfort. With 2,516 sq ft of living space, four bedrooms, and two full baths, this home blends historic charm with modern comfort. The kitchen has been remodeled

  Deleta Dickson eXp Realty, LLC

  

  13224 Lookingglass Rd, Winston, OR 97496
• 

  

  /48

  $454,000

  • 2 Beds
  • 1 Bath
  • 2,056 Sq Ft

  0 Rice Creek Rd, Winston, OR 97496

  100% off-grid living on your own 20-acre slice of paradise! Located within "The Ranch" - a close-knit homesteading community of like-minded landowners who each steward their own property while embracing a shared off-grid lifestyle. Just 25 minutes southwest of Winston, Oregon, this property is accessed via a gated 4-mile gravel road through BLM and private timberlands. The resilient home features

  Aaron Cherry Oregon Life Homes

  

  0 Rice Creek Rd, Winston, OR 97496
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  /32

  $585,000

  • 4 Beds
  • 3 Baths
  • 2,660 Sq Ft

  102 Sarah Bear Ln, Winston, OR 97496

  Stately quality 4 br 3 bath home, real wood floors, 2 gas fireplaces, central vac, top quality custom elegant crown molding. Formal dining, gourmet kitchen, over sized gazebo/pergola, colored stamped concrete, sprinkler system, fenced manicured private backyard with raised beds. Has new astro turf for low maintenance, covered patio. The gourmet kitchen has granite, pantry, new gas appliances,

  Valynn Currie Currieco Real Estate

  

  102 Sarah Bear Ln, Winston, OR 97496
• 

  

  /23

  $100,000

  • 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
• 

  

  /6

  $137,000

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

  180 Twin Oaks Loop, Winston, OR 97496

  Please check with listing agent or your agent for application and park requirements, thank you Property Listing: 180 Twin Oaks Loop, Winston, ORRenovated 3-Bedroom, 2-Bathroom Double Wide in 55+ CommunityWelcome to this beautifully renovated 3-bedroom, 2-bathroom home located in the sought-after Twin Oaks Mobile Park Estates, a quiet and well-maintained 55+ community in Winston, OR. This

  Raymond Coburn eXp Realty, LLC

  

  180 Twin Oaks Loop, Winston, OR 97496
• 

  

  /20

  $89,000

  • Land
  • 0.12 Acre
  • $741,667 per Acre

  271 SE Robinson St, Winston, OR 97496

  Build Your Dream Home on This Prime Lot!Nice Lot – Prime Location – All Utilities – Investment Opportunity!Discover the perfect canvas for your future home. This spacious lot comes with full utilities—water, electricity, and sewer—ready for you to build. Nestled in a good location, it’s ideal for families, investors, or anyone looking to live in town. Don’t miss out on this incredible

  Kayla Wehe Lamonte Real Estate Professionals

  

  271 SE Robinson St, Winston, OR 97496
• 

  

  /18

  $239,000

  • Land
  • 0.97 Acre
  • $246,392 per Acre

  740 Ireland Rd, Winston, OR 97496

  Country living at its finest! Septic, well, power installed and ready for use. Property also includes a 30x40 carport/RV cover with an enclosed 16x30 shop area and a partially finished 13x32 shed that could be finished into living area! Large pump house with roll up door for extra storage and plenty of room for a garden or a new home!

  Adrienne Fotopoulos North County Realty

  

  740 Ireland Rd, Winston, OR 97496
• 

  

  /18

  $95,000

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

  241 Twin Oaks Loop, Winston, OR 97496

  NICE GOLDEN WEST MANUFACTURED HOME IN A 55+ PARK. HOME BUILT IN 1998. THREE BR, 2 BATH, WITH A CARPORT, STORAGE SHED/SHOP AND A RAMP FOR EASY ACCESS TO HOME. APPLIANCES IN HOME ARE INCLUDED. SPACE RENT OF $620/MO INCLUDES WATER, GARBAGE, & SEWER.COME SEE AND MAKE THIS YOUR NEW HOME.

  Roger Snyder Berkshire Hathaway HomeServices Real Estate Professionals

  

  241 Twin Oaks Loop, Winston, OR 97496
• 

  /2

  Call for Price

  • Land
  • 160 Acres

  0 Diamond Rock Rd Unit 727456026, Winston, OR 97496

  160± acre Diamond Rock Road Recreation and Timber Tract is located within Umpqua National Forest, six miles south of South Umpqua River community of Tiller, and two miles from Drew at County Road 1. Diamond Rock Road (FS3201 Road) provides access to Drew, and continues through the Tract south, to both private and USFS lands. The entire Tract was impacted by 2015 Stouts Fire, and was replanted

  John Rosenthal Realty Marketing / Northwest

  

  0 Diamond Rock Rd Unit 727456026, Winston, OR 97496
• 

  

  /39

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  617 Poison Oak Dr, Winston, OR 97496

  Escape to the country with this rustic home nestled on nearly 14 beautiful acres. Perfect for those dreaming of a mini-farm or simply wanting space for animals, and rural lifestyle. This property offers usable acreage mixed with stands of timber, seasonal creeks and endless potential. Surround yourself with sweeping mountain views and the serenity of nature, all while enjoying the freedom that

  Bob Lamonte Lamonte Real Estate Professionals

  

  617 Poison Oak Dr, Winston, OR 97496
• 

  

  /45

  $319,900

  • 4 Beds
  • 2 Baths
  • 1,769 Sq Ft

  310 NW Lost Ln, Winston, OR 97496

  Freshly updated and move-in ready, this Winston home combines comfort, convenience, and charm in a desirable location. Featuring 4 bedrooms, 2 baths, and 1,769 sq ft of living space, this property sits on a corner lot along a tucked-away road, just a short stroll to Wildlife Safari and all the amenities Winston has to offer.Step inside to find a freshly painted interior, new carpeting, tile and

  Tammi Ellison eXp Realty, LLC

  

  310 NW Lost Ln, Winston, OR 97496
• 

  

  /8

  $199,000

  • 2 Beds
  • 1 Bath
  • 550 Sq Ft

  9643 Old Highway 99 S, Winston, OR 97496

  Commercial/Residential 1.04 Acre, 550 sq ft block house, 2 septic's, 2 20'x 40' concrete slabs, city water, Corner lot, price reflex condition. bring hammer and nails. used for storage. new upgraded power box on pole for easy connect Bring your 5th wheel while you restore or build new. Flat easy in and out, backs up to Umpqua River (200 ft frontage) with deeded water rights. great possibilities

  Beverly Walters Gold Standard Realty

  

  9643 Old Highway 99 S, Winston, OR 97496
• 

  

  /10

  $249,500

  • Land
  • 0.45 Acre
  • $554,444 per Acre

  0 SW Main St, Winston, OR 97496

  Looking for a retail, office or hospitality location in Winston? This lot is strategically located near the intersection of Hwy 42 & Hwy 99 with easy access to I-5 and on the route to Oregon's coastal destinations! This lot is the best that Winston has to offer...

  Jody Tatone RE/MAX Integrity

  

  0 SW Main St, Winston, OR 97496
• 

  /2

  $62,500

  • Land
  • 0.36 Acre
  • $173,611 per Acre

  320 5th St, Winston, OR 97496

  The perfect large, level lot to build your home or place a manufactured home on. Just outside of Winston in Dillard. This .36 lot is all flat and usable. Currently there's a MFH which is of 'no value' on property. This is an Estate sale, so it is being sold "As is". Buyer to due do own due diligence. Estate will do no repairs. Bring us an offer.

  Beverly Beier G. Stiles Realty

  

  320 5th St, Winston, OR 97496
• 

  

  /8

  $2,125,000

  • Land
  • 15.05 Acres
  • $141,196 per Acre

  215 Parkinson Rd, Winston, OR 97496

  Lovely acreage on South Umpqua River. Zoned agriculture. Water rights from 1953. 44x60 barn has been partially renovated. Running water at barn. Use your imagination on the uses for this wonderful acreage on the river. Buyer to do all due diligence regarding every aspect of the property. Seller makes no disclosures.

  Nick Knight Knight Realty Group LLC

  

  215 Parkinson Rd, Winston, OR 97496
• 

  

  /27

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,421 Sq Ft

  120 SE Edwards Ave, Winston, OR 97496

  Welcome to this 3-bedroom, 2-bath single-level custom home. Thoughtfully designed with comfort and functionality in mind, this 1,421 sq ft residence offers a spacious open-concept layout, vaulted ceilings, and abundant natural light throughout. The kitchen features wood cabinetry, stainless steel appliances, and a breakfast bar perfect for casual meals or entertaining guests. The primary suite

  Jerry Norman Oregon Life Homes

  

  120 SE Edwards Ave, Winston, OR 97496
• 

  

  /34

  $264,100

  • 3 Beds
  • 1 Bath
  • 1,085 Sq Ft

  224 5th St, Winston, OR 97496

  MOTIVATED SELLER!! Charming 3-Bedroom Home on Oversized Lot – Perfect for Entertaining! Discover comfort and charm in this updated 3-bedroom, 1-bath home situated on an expansive .36-acre lot with a spacious backyard designed for entertaining, you’ll love spending time outdoors under the beautiful custom built covered porch—perfect for enjoying your morning coffee or relaxing in the evening. Step

  Terri LeVasseur J Mann Realty

  

  224 5th St, Winston, OR 97496
• 

  

  /17

  $339,000

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

  185 Lebleu Ln, Winston, OR 97496

  Price Improved! Solid home in Winston with a newer roof. Welcome home to this well maintained single-story home with a modern floorplan, featuring an inviting open-concept layout designed for both comfort and privacy. The spacious primary bedroom includes an attached bathroom, offering a private retreat. The living room features a gas fireplace, perfect for relaxing evenings. Step outside to

  Kurt Delahooke Keller Williams Realty Eugene and Springfield

  

  185 Lebleu Ln, Winston, OR 97496
• 

  

  /25

  $695,000

  • 3 Beds
  • 2 Baths
  • 2,167 Sq Ft

  1090 E Willis Creek Rd, Winston, OR 97496

  Secluded private 2167 sq ft 3 br 2 bath contemporary home on 9.81 acres. Has open beam ceilings, wood stove, barn, wood shop, 2 gar garage. Garden area, city water, creek. Mostly level property. Charming kitchen with large pantry and skylight, ample dining room overlooking the garden and yard. Living room has bay window and room to entertain. Covered parking for boat or RV.

  Valynn Currie Currieco Real Estate

  

  1090 E Willis Creek Rd, Winston, OR 97496
• 

  

  /47

  $367,500

  • 3 Beds
  • 1 Bath
  • 1,434 Sq Ft

  10 SE Kegler Ave, Winston, OR 97496

  Set on a full acre at the edge of town, this property blends flexibility, functionality, and a 1,200 sq ft shop that’s hard to ignore! The 3-bedroom, 1-bath home includes an oversized living room with exposed wood accents and rustic-style posts that bring a bit of texture and charm. Heating and cooling are handled with ductless systems, and there’s a gas fireplace to keep things cozy. The kitchen

  Anthony Beckham Different Better Real Estate

  

  10 SE Kegler Ave, Winston, OR 97496
• 

  

  /28

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  140 Teresa Ln, Winston, OR 97496

  This modern, beautiful home is located in the highly sought-after Winston neighborhood. The home has been recently remodeled down to the studs and includes brand new HVAC, new appliances, and new roof. Step inside to find luxury vinyl plank flooring, recessed lighting, and soaring vaulted ceilings, and an abundance of windows that create a spacious and inviting atmosphere. The open-concept

  Jason Mann J Mann Realty

  

  140 Teresa Ln, Winston, OR 97496
• 

  

  /5

  $150,000

  • Land
  • 0.64 Acre
  • $234,375 per Acre

  873 SE Edgewood St, Winston, OR 97496

  0.64 Acre Buildable Lot zoned RR. Out of flood plain. At the end of a quiet dead St. Buyer to do all due diligence to verify buildability. Has not been septic approved.

  Nick Knight Knight Realty Group LLC

  

  873 SE Edgewood St, Winston, OR 97496
• 

  

  /47

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,374 Sq Ft

  231 NE Darrell Ave, Winston, OR 97496

  Great location with a custom built one level home located on .39 of an acre at the end of the road in Winston with City Services! Home built in 1981 with approximately 1,374 square feet, 3 bedrooms and 2 full bathrooms, primary bedroom and bathroom has a walk-in closet and slider door to deck, nice Kitchen with oodles of oak cabinets, lots of counter space, plus a pantry, Living room has

  Cynthia Johnson Johnson Group Real Estate, LLC

  

  231 NE Darrell Ave, Winston, OR 97496
• 

  

  /41

  $830,000

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

  375 Porter Creek Rd, Winston, OR 97496

  Discover the perfect blend of vineyard lifestyle and modern comfort in this beautifully 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.At the heart of the property is a spacious 3,000 sq ft home featuring four large bedrooms and

  Lorrie Normann Triple Oaks Realty LLC

  

  375 Porter Creek Rd, Winston, OR 97496
• 

  

  /21

  $150,000

  • Land
  • 10.56 Acres
  • $14,205 per Acre

  3541 Willis Creek Rd, Winston, OR 97496

  10.56 Acres Bordering Public Land Nestled at 3541 Willis Creek Rd, this 10.56-acre property offers a rare chance to own a slice of Oregon's natural beauty. With a newly cut-in road leading to a potential home site, you'll enjoy a stunning view of the valley-a perfect backdrop for your future home. The essentials are already in place: Community water with a meter installed near the south end

  Cliff Farley Mossy Oak Properties Oregon Field and Stream Realty

  3541 Willis Creek Rd, Winston, OR 97496
• 

  

  /39

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,835 Sq Ft

  151 Sherry St, Winston, OR 97496

  Step into this charming 1965 Ranch-style home, nestled in a peaceful neighborhood on a generous double lot in the heart of Winston, Oregon. With 3 bedrooms, 1.5 bathrooms, and a large, fully fenced corner lot, this property offers both privacy and convenience. This home boasts ample storage space throughout, with built-in shelving and closets to keep your living areas tidy. The cozy and airy

  RaNae Sams Oregon Life Homes

  

  151 Sherry St, Winston, OR 97496

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