Winston, OR Homes for Sale

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  /41

  $670,000

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft

  1260 Ireland Rd, Winston, OR 97496

  Country Retreat on 10.02 acres. The Perfect blend of luxury and privacy in southern Oregon. This custom built 2600 square ft. home offers 3 bedrooms and 2 bathrooms. Step inside to an inviting open floor plan featuring vaulted ceilings and elegant finishes. The gourmet kitchen is a chef's dream, complete with premium appliances, custom cabinets and s spacious island perfect for hosting. The

  

  Daniel Siler

  Engel & Volkers West Portland

  (458) 232-4863

  

  1260 Ireland Rd, Winston, OR 97496
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  /7

  $325,000

  • Land
  • 33 Acres
  • $9,927 per Acre

  0 Ireland Rd, Winston, OR 97496

  Fantastic opportunity to create your own private oasis. This private property is situated up in the hills of Winston with great views of the valley. 2 potential building sites for you to choose from. Additionally, there is marketable timber as well. You don't want to miss out on this great opportunity!

  

  Daniel Siler

  Engel & Volkers West Portland

  (458) 218-8471

  

  0 Ireland Rd, Winston, OR 97496
• 

  

  

  /48

  $995,000

  • 3 Beds
  • 2 Baths
  • 2,600 Sq Ft

  1260 Ireland Rd Unit A, Winston, OR 97496

  Luxury Countryside Retreat on 42.76 AcresDiscover the perfect blend of luxury, privacy, and natural beauty in Winston, OR. Nestled on 42.76 acres of pristine land, this 3-bedroom, 2-bathroom, 2,600 sq. ft. estate offers a rare opportunity to own a sprawling country retreat with breathtaking panoramic views.Step inside to an inviting, open-concept floor plan featuring vaulted ceilings, expansive

  

  Daniel Siler

  Engel & Volkers West Portland

  (458) 310-2741

  

  1260 Ireland Rd Unit A, Winston, OR 97496
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  /35

  $18,500

  • Land
  • 0.14 Acre
  • $132,143 per Acre

  111 SE Lebleu Ln, Winston, OR 97496

  Opportunity awaits at 111 Lebleu, a beautiful lot with breathtaking views! This property offers a unique setting for building your dream home with panoramic vistas. The gentle slope provides the perfect canvas for a custom-designed home that maximizes both the views and the natural landscape.US Bank is offering both lot and construction loans, making this an excellent option for those ready to

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  111 SE Lebleu Ln, Winston, OR 97496
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  /32

  $59,000

  • Land
  • 0.18 Acre
  • $327,778 per Acre

  105 Lebleu Ln, Winston, OR 97496

  Seller willing to owner carry. US Bank offers both lot and constructions loan. Discover the perfect canvas for your dream home at 105 SE Lebleu, a buildable lot nestled on the fringe of a blossoming neighborhood. Embrace the opportunity to create a bespoke living space surrounded by the tranquil beauty of orchards, farms, and the majestic mountains beyond. Don't miss the chance to claim this

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  105 Lebleu Ln, Winston, OR 97496
• 

  

  /35

  $465,000

  • 3 Beds
  • 3 Baths
  • 1,636 Sq Ft

  13130 Lookingglass Rd, Winston, OR 97496

  Check back for open house time this weekend. Single level home built in 2022 on .76 acre. 3 bedroom, 3 full bath and 1636 SF. Kitchen features large island w/ breakfast bar, stainless appliances and panty. Living room has wood burning stove with tile hearth surround. Laminate wood floors throughout. Forced air gas heat and central AC. Covered front porch, back patio and 10x20 tool shed. 2 car

  Sarah Sherman Sarah Sherman Real Estate

  

  13130 Lookingglass Rd, Winston, OR 97496
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  /27

  $609,000 Open Sun 1PM - 3PM

  • 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. In the gourmet kitchen is granite, pantry, new gas appliances,

  Valynn Currie Currieco Real Estate

  

  102 Sarah Bear Ln, Winston, OR 97496
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  /47

  $649,900

  • 4 Beds
  • 2.5 Baths
  • 2,144 Sq Ft

  490 Dawson Dr, Winston, OR 97496

  Escape to the privacy of Byron Creek Estates, where this beautiful 4-bedroom, 2.5-bath home sits on 5 serene acres just outside Winston! Thoughtfully designed with vaulted ceilings and abundant natural light, the home has a fresh interior, featuring new laminate flooring in the main living area, shampooed carpets, and new paint. The spacious master suite with vaulted ceilings upstairs is a

  Anthony Beckham Different Better Real Estate

  

  490 Dawson Dr, Winston, OR 97496
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  /48

  $625,000

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

  7941 Upper Olalla Rd, Winston, OR 97496

  Beautiful 5.01 acre property with 2007 rebuilt home! Lots of flat ground for vegetable/flower garden. Fenced and cross fenced. Good well and 2 - 1200 gallon holding tanks. Ultra violet filter and new water softener. Year-round creek. Large drive-thru shop with 3 - 12ft doors, 3 stall barn, and spring fed holding tanks plumbed to barn. Huge metal building for many uses. Plus, 2 sheds and 1 fort.

  Carol Williams The Neil Company Real Estate

  

  7941 Upper Olalla Rd, Winston, OR 97496
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  /32

  $530,000

  • 3 Beds
  • 2 Baths
  • 2,186 Sq Ft

  240 Wil Way, Winston, OR 97496

  Welcome to the highly desirable neighborhood of Safari Estates. This custom built 3-bedroom, 2 bath home offers stunning views of the rolling forested hills and is in the heart of wine country. The expansive living room is flooded with natural light, showcasing the breathtaking views through large windows that seamlessly connect the indoors to the outdoor patio space. The open-concept with

  Jacob Sanchez Next Generation Real Estate LLC

  

  240 Wil Way, Winston, OR 97496
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  /38

  $774,900

  • 3 Beds
  • 2.5 Baths
  • 1,845 Sq Ft

  1470 E Willis Creek Rd, Winston, OR 97496

  Nestled on 90 acres of private land, this stunning 3-bedroom, 2.5-bath log home offers the perfect retreat for those seeking tranquility and connection with nature. The main home is a masterpiece of rustic craftsmanship, featuring soaring vaulted ceilings, and large windows that bathe the living spaces in natural light. A cozy wood stove anchors the open concept living and dining area, creating

  Rhonda Marshall Knipe Realty ERA Powered

  

  1470 E Willis Creek Rd, Winston, OR 97496
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  /39

  $449,500

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft

  127 NW Teal St, Winston, OR 97496

  *Welcome to Your Dream Home!*Nestled in the heart of Winston, Oregon, this stunning 4-bedroom, 2-bathroom single-family home offers breathtaking mountain views, serene natural surroundings, and unparalleled comfort. With over 1,800 sqft of living space, this beautifully crafted residence boasts:*Interior Features*- Vaulted ceilings and recessed lighting throughout- Split floor plan for optimal

  Zach Field Keller Williams Southern Oregon-Umpqua Valley

  

  127 NW Teal St, Winston, OR 97496
• 

  

  /30

  $469,000

  • 4 Beds
  • 2 Baths
  • 1,994 Sq Ft

  197 Wil Way, Winston, OR 97496

  Beautifully Maintained Custom one level home with 4 bedrooms and 2 baths in Safari Estates. Vaulted ceilings in living room and beautiful mountain east views. Floor plan is open with plenty of natural light. Gas fireplace for those cozy days in the living room. Laminate flooring through out living space with carpet in bedrooms for warmth. Tile flooring in bathrooms with tile shower surrounds and

  Nancy Wood Oregon Life Homes

  

  197 Wil Way, Winston, OR 97496
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  /5

  $120,000

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  234 Reston Ave, Winston, OR 97496

  2 bedroom, 1 bath on 0.19 acre with a nice fenced yard, front and back covered decks, outbuildings, and metal roof.

  John McVeigh The Neil Company Real Estate

  

  234 Reston Ave, Winston, OR 97496
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  /45

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,005 Sq Ft

  400 NW Susan Ave, Winston, OR 97496

  Charming and remodeled, this cozy 3-bedroom, 2-bath home offers comfortable single-level living on a quiet corner lot. Enjoy updates throughout, including a composition roof, ductless heat pump, and updated flooring—all installed in 2020. The open and functional layout is complemented by an attached 1-car garage for convenience. Step outside to a fully fenced backyard featuring a storage shed,

  Shane Mast Oregon Life Homes

  

  400 NW Susan Ave, Winston, OR 97496
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  /43

  $185,000

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  600 SE Edgewood St, Winston, OR 97496

  This 1970 manufactured home sits on a spacious 0.43-acre lot, offering plenty of room to enjoy the outdoors. Featuring a durable metal roof, covered porches, and a carport with an attached tool shed, this property is well-equipped for both convenience and functionality. Additional highlights include a parking pad, multiple outbuildings, and fruit trees, all within a fully fenced yard for added

  Elisa Doudna Pacific Properties

  

  600 SE Edgewood St, Winston, OR 97496
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  /41

  $870,000

  • 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 towering 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

  Lorrie Normann Triple Oaks Realty LLC

  

  375 Porter Creek Rd, Winston, OR 97496
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  /6

  $359,000

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

  185 Lebleu Ln, Winston, OR 97496

  Welcome to this beautifully maintained single-story home, 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 enjoy breathtaking views from the backyard, complete with a deck ideal for a

  Kurt Delahooke Keller Williams Realty Eugene and Springfield

  

  185 Lebleu Ln, Winston, OR 97496
• 

  

  /19

  $1,200,000

  • 7,486 Sq Ft

  240 NW Civil Bend Ave, Winston, OR 97496

  High quality investment opportunity with excellent rental history and upside potential. 9 units total consisting of 2 duplexes built in approximately 1994, 2 updated duplexes built in 1966, a renovated large home built in 1953, and additional land to build at least another duplex. Recently asphalted driveway and ample off-street parking. Interior photos are from 2018 before tenants moved in to

  Jeff Boyter The Neil Company Real Estate

  

  240 NW Civil Bend Ave, Winston, OR 97496
• 

  

  /40

  $349,900

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

  401 Sunnyside Dr, Winston, OR 97496

  Step into this charming 3-bedroom, 2-bathroom home, built in 2004, and perfectly situated on a quiet dead-end street on the outskirts of Winston—just moments from fresh fruits and vegetables at Brosi Sugartree Farms! This well-maintained, move-in-ready home boasts vaulted ceilings, warm laminate floors, and large windows that fill the living and dining areas with natural light and scenic views.

  Anthony Beckham Different Better Real Estate

  

  401 Sunnyside Dr, Winston, OR 97496
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  /21

  $150,000

  • Land
  • 11 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
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  /39

  $350,000

  • 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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  /30

  $289,500

  • 3 Beds
  • 1 Bath
  • 1,005 Sq Ft

  520 SE Dawna Ct, Winston, OR 97496

  Conveniently located just a few blocks from Winston Middle School, this home offers 3 bedrooms, 1 bathroom and updates including laminate flooring throughout and a recent heating and air conditioning system. Outside offers an attached garage, fully fenced back yard as well as side parking. Ready for its new owners, call for an appointment to view!

  Ashley Oberman Oregon Life Homes

  

  520 SE Dawna Ct, Winston, OR 97496
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  /15

  $240,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  751 SE Meadowood Dr, Winston, OR 97496

  1995 Double-wide manufactured home on a good sized lot in Winston. Not perfect but a lot of home for the money. Central heat and air conditioning, carport and lots of room for a garden. A great home for the money. Affordable living, close to park and community center.

  Timothy A Smith RE/MAX Integrity

  

  751 SE Meadowood Dr, Winston, OR 97496
• 

  

  /35

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  401 SE Park St, Winston, OR 97496

  Charming Home with Modern Updates & Great Outdoor Space! Discover this clean and inviting move-in ready home featuring a classic dining room, an engaging living room with beautiful laminate flooring, and an updated kitchen equipped with hickory cabinets, Corian countertops, and built-in appliances. The home also comes with a washer & dryer, plus a gas tankless water heater for energy efficiency.

  Anthony Beckham Different Better Real Estate

  

  401 SE Park St, Winston, OR 97496
• 

  

  /9

  $179,000

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft

  250 SW Ford Ave, Winston, OR 97496

  Newer Roof nice sized lot in an established neighborhood in Winston, OR. This Home is looking for a craftsman to turn it into its better self. The house is very Livable but non-permitted work has been done. "NOT FINACEABLE" with traditional terms, maybe a hard money loan. Call today for an appointment to visit with your investor or contractor.

  Dawn Trapalis Harcourts Integrity Team Real Estate Services, LLC.

  

  250 SW Ford Ave, Winston, OR 97496
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  /36

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,468 Sq Ft

  765 SE Lanola St, Winston, OR 97496

  Home Tour Video: https://vimeo.com/1047621686?share=copy. Stunning one-level home in a tidy & newly established neighborhood on a desirable corner lot with views of the valley & surrounding mountains! Within a mile of the well known & beloved Brosi Sugartree Farms where you can savor fresh delicious produce, partake in seasonal festivities, & so much more! Featuring low maintenance landscaping &

  Shuray Bagley Oregon Life Homes

  

  765 SE Lanola St, Winston, OR 97496
• 

  

  /14

  $199,999

  • 2 Beds
  • 1 Bath
  • 735 Sq Ft

  110 SE Darrell Ave, Winston, OR 97496

  YOU WON'T WANT TO MISS THIS OPPORTUNITY. Cute updated 2 bedroom home with small utility room. Kitchen with appliances. Updated hot water heater, flooring, interior and exterior paint. Living room offers gas heater and a front bonus area. Partially fenced yard with garden shed in back. Nice corner lot with driveway. Call for your showing today!

  Lacey Williams Trueblood Real Estate

  

  110 SE Darrell Ave, Winston, OR 97496
• 

  

  /4

  $265,000

  • Land
  • 0.71 Acre
  • $373,239 per Acre

  0 SE Gregory Dr, Winston, OR 97496

  Ready to go multifamily with construction plans. See attached plans for 3 triplex buildings. Utilities are to property line. Water & sewer available. Great opportunity for a hard to find multifamily property. CLA for more information

  Larry KW Alberts Keller Williams Realty Eugene and Springfield

  

  0 SE Gregory Dr, Winston, OR 97496
• 

  

  /16

  $1,250,000

  • Land
  • 38 Acres
  • $33,016 per Acre

  0 Danielle Dr Unit 122251646, Winston, OR 97496

  Prime development opportunity in Winston, Oregon! This expansive 38-acre property has potential for 90 buildable residential lots, perfect for a new housing community. Situated in a peaceful location with easy access to local amenities, this land offers a great investment potential for developers. Ideal for those looking to create a vibrant neighborhood in a growing area. Don’t miss out on this

  Jeremy Parmenter TLC Realty

  

  0 Danielle Dr Unit 122251646, Winston, OR 97496
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  /28

  $285,000

  • Land
  • 16 Acres
  • $17,812 per Acre

  0 Wil Way Unit 131979738, Winston, OR 97496

  One of a kind property bordering Wild life Safari! Imagine having zebras and other exotic animals right in your back yard! This property offers more than 16 acres that has already been approved for a subdivision. Lookout investors, great investment opportunity right here! 3 phase power available at the top of the hill along with connections to water and sewer. Best of all, no HOA or CC&Rs! To top

  Ashton Faas Different Better Real Estate

  

  0 Wil Way Unit 131979738, Winston, OR 97496
• 

  

  /15

  $250,000

  • Land
  • 4.26 Acres
  • $58,685 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

  

  0 Wil Way Unit 24292479, Winston, OR 97496
• 

  

  /15

  $250,000

  • Land
  • 3.14 Acres
  • $79,618 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

  

  0 Wil Way Unit 24278136, Winston, OR 97496
• 

  

  /28

  $475,000

  • Land
  • 7 Acres
  • $64,189 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

  

  0 Wil Way Unit 24094727, Winston, OR 97496
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  /26

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,279 Sq Ft

  181 Lost Ln, Winston, OR 97496

  Your Dream Home Awaits in Winston, OR! Step right into comfort, style, and privacy with this stunning 2017 Fleetwood manufactured home that’s practically brand-new inside and out! Sitting on an expansive .46 acre lot with mature trees and timed irrigation, this gem offers the kind of peace and seclusion you’ll love—fully fenced with a 6ft. fence for true privacy and tucked away like your own

  Rachel Ball Triple Oaks Realty LLC

  

  181 Lost Ln, Winston, OR 97496
• 

  

  /31

  $369,500

  • 4 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  40 NW Cary St, Winston, OR 97496

  Completely updated Ranch style home entirely fenced corner lot in City limits of Winston. Entire property is landscaped with automatic sprinklers and drip systems. Certified Insert and 2010 Carrier HVAC. Oversize garage, Small shop, 50' RV parking with hookups, Dog run with privacy fence from neighbors. Bonus room/office can be be approved for 4th bedroom. Seller is a licensed Real Estate Broker

  Beverly Heyer Safari Village Real Estate

  

  40 NW Cary St, Winston, OR 97496
• 

  

  /39

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,980 Sq Ft

  2651 NW Brockway Rd, Winston, OR 97496

  This lovely home offers breathtaking views of the mountains, valley, and Abacela Vineyard, creating an atmosphere of natural beauty. The gourmet kitchen is a chef's dream featuring stainless steel appliances, including built-in dishwasher, disposal, free-standing gas range, range hood, and a free-standing refrigerator. With tile countertops, a spacious pantry, and plenty of workspace, it's

  Jacob Gilman The Neil Company Real Estate

  

  2651 NW Brockway Rd, Winston, OR 97496
• 

  

  /22

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  139 Teresa Ln, Winston, OR 97496

  Come take a look at your beautiful new forever home in this established neighborhood. Newer build in 2017 with many amenities. Kitchen boasting all stainless-steel appliances with a wonderful gas stove for the cook in the family, down to the granite countertop and eat in island great for entertaining with its open concept. Spacious master bedroom with a walk-in closet and granite vanity in the

  Angel Smith Trueblood Real Estate

  

  139 Teresa Ln, Winston, OR 97496
• 

  

  /48

  $885,000

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  1800 E Willis Creek Rd, Winston, OR 97496

  Discover your dream retreat on 274 acres of land with this charming 2-bedroom, 1-bath home, offering privacy and tranquility. The large country kitchen is perfect for creating lasting memories with family and friends. Step outside onto the covered deck, where you can relax and enjoy breathtaking views of the surrounding landscape and wildlife. Inside, the cozy living spaces are filled with

  Rhonda Marshall Knipe Realty ERA Powered

  

  1800 E Willis Creek Rd, Winston, OR 97496
• 

  

  /47

  $349,900

  • 3 Beds
  • 2.5 Baths
  • 1,250 Sq Ft

  149 Teresa Ln, Winston, OR 97496

  Adorable newer home situated on a quiet street in Winston with mountain views. This home features laminate flooring flowing throughout the main living area, energy efficient mini splits, and an open floor plan. The kitchen includes stainless steel appliances, granite counter tops, and a large island. The primary suite has plush carpet, full bathroom with walk-in shower and granite counter tops.

  Jennifer Kramer RE/MAX Integrity

  

  149 Teresa Ln, Winston, OR 97496

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