Winston, OR Homes

• 

  

  

  /30

  $399,333 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  145 SE Lebleu Ln, Winston, OR 97496

  Beautifully designed contemporary home in the sought-after Plum Ridge neighborhood! Light and bright with soaring ceilings, this home features gorgeous vinyl flooring throughout, creating a cohesive and modern feel. The chef’s kitchen is complete with sleek granite countertops, stainless steel gas appliances, and a spacious island perfect for meal prep and entertaining. The adjacent dining area

  

  Nick Shivers

  KELLER WILLIAMS PORTLAND CENTRAL

  (458) 455-0940

  

  145 SE Lebleu Ln, Winston, OR 97496
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  Learn More
• 

  

  

  /7

  $876 per month

  • 1 Bed
  • 1 Bath
  • Apartment for Rent

  189 NW Glenhart Ave, Winston, OR 97496

  Rick Rivera Rental Housing Deals

  189 NW Glenhart Ave, Winston, OR 97496
• 

  

  

  /23

  $467,000 Sold Apr 25, 2025

  • 2,037 Sq Ft
  • $229/SF
  • 27 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2017

  295 Wil Way, Winston, OR 97496

  A beautiful home currently available in Safari Estates. This custom-built home, constructed by Shelby & Miguelena Construction, offers an open-concept living space with 2025 square feet, 4 generous bedrooms, and 2 luxurious baths. The expansive great room features LVP flooring, and the 2-car garage includes a convenient RV space next to it. The kitchen and baths showcase elegant granite counters,

  Shahalie Evans Assist 2 Sell-Buyers & Sellers

  

  295 Wil Way, Winston, OR 97496
• 

  

  

  /32

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  125 SE Estate Loop, Winston, OR 97496

  

  125 SE Estate Loop, Winston, OR 97496
• 

  

  

  /41

  $675,000

  • 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
• 

  

  /29

  $338,000 Sold Apr 24, 2025

  • 1,250 Sq Ft
  • $270/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2015

  750 SE Tokay St, Winston, OR 97496

  This modern starter home or investment property is the perfect blend of style, function, and low-maintenance living. Recently rented at $1900 per month, it’s a great opportunity for first-time buyers or investors looking for a hassle-free addition to their portfolio. The home features a sleek kitchen with granite countertops, stainless steel appliances, and a contemporary mix of carpet and dark

  Nataly Mattox RE/MAX Integrity

  

  750 SE Tokay St, Winston, OR 97496
• 

  

  /17

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft

  123 Twin Oaks Loop, Winston, OR 97496

  

  123 Twin Oaks Loop, Winston, OR 97496
• 

  

  /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
• 

  

  /20

  $125,000 Sold Apr 23, 2025

  • 924 Sq Ft
  • $135/SF
  • 17 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1988

  870 SE Thompson Ave, Winston, OR 97496

  Charming single-level home on a .17-acre lot, located in the quiet town of Winston! Enjoy 2 nice size bedrooms and an updated bathroom. Living area is light and bright with huge windows. Efficient kitchen features tons of storage and a new range and hood fan. Large driveway is great for guests and RV parking. Property includes a large storage room, and a separate storage shed. The backyard is

  JENNIFER COOK Berkshire Hathaway HomeServices NW Real Estate

  

  870 SE Thompson Ave, Winston, OR 97496
• 

  

  /24

  Est $443,891 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft

  405 Serengeti Dr, Winston, OR 97496

  

  405 Serengeti Dr, Winston, OR 97496
• 

  

  /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
• 

  

  /15

  $180,000 Sold Apr 22, 2025

  • 972 Sq Ft
  • $185/SF
  • 142 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1982

  315 Degnath Gateway Ln, Winston, OR 97496

  Serene and picturesque 6.6 acre parcel with stunning panoramic views of the mountains and valley! Brand NEW 225' WELL with a pump that produces 8 GPM!! Septic in place. PLUS a NEW 200 Amp electric service. Your own private oasis just outside Winston. Enjoy the SEASONAL CREEK and the peaceful abundance of privacy and wildlife. Close to hunting, fishing, hiking and Ben Irving Reservoir.

  Amy Dean Amy Dean Real Estate, Inc.

  

  315 Degnath Gateway Ln, Winston, OR 97496
• 

  

  /32

  Est $356,201 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,586 Sq Ft

  220 NE Rose Ridge Dr, Winston, OR 97496

  

  220 NE Rose Ridge Dr, Winston, OR 97496
• 

  

  /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

  $289,000 Sold Apr 17, 2025

  • 1,395 Sq Ft
  • $207/SF
  • 22 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1977

  250 NW Glenhart Ave, Winston, OR 97496

  Darling home in very good condition. Kitchen is bright and open with granite counters, and a newer sink and faucet. The range and fridge are included in sale. The dining room features a glass sliding door to access the back yard. The living room is roomys a big picture window. Three bedrooms and a Jack n Jill bath with door to hall and master bedroom. Everything is very nicely maintained and

  Marilyn Kittelman Cutting Edge Real Estate

  

  250 NW Glenhart Ave, Winston, OR 97496
• 

  

  /28

  Est $407,630 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft

  118 Watusi Ct, Winston, OR 97496

  

  118 Watusi Ct, Winston, OR 97496
• 

  

  /48

  $464,000

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft

  7950 Upper Olalla Rd, Winston, OR 97496

  Escape to your own private slice of country paradise! Nestled on 3.3 acres with creek frontage with water rights. This well-cared-for 3-bedroom, 2-bath home is ready for your animals, garden, and more. Enjoy peaceful mornings on the covered deck, where the Main bedroom offers sliding-door access and tranquil views of the creek.This property has it all — a barn, detached garage, paved looped

  Rachel Sturdevant eXp Realty, LLC

  

  7950 Upper Olalla Rd, Winston, OR 97496
• 

  

  /48

  $469,900 Sold Apr 16, 2025

  • 1,679 Sq Ft
  • $280/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  117 Citation Ct, Winston, OR 97496

  Brand-new construction in the desirable Lookingglass Creek Estates subdivision! This thoughtfully designed home features an open floor plan with high-end finishes throughout. The kitchen boasts beautiful soft-close cabinets, quartz countertops, a pantry, and waterproof luxury vinyl plank flooring. The spacious primary suite offers a walk-in closet, double sinks, and an ensuite with a step-in

  Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

  

  117 Citation Ct, Winston, OR 97496
• 

  

  /32

  Est $871,000 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,052 Sq Ft

  350 Woodland Dr, Winston, OR 97496

  

  350 Woodland Dr, 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
• 

  

  /29

  $309,000 Sold Apr 11, 2025

  • 1,728 Sq Ft
  • $179/SF
  • 104 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1997

  241 Timothy Ave, Winston, OR 97496

  Looking for a home that combines space, functionality, and convenience? This generously sized manufactured home is the perfect blend of comfort and practicality. Featuring both a living room and a family room, the great room concept creates a seamless flow for entertaining or relaxing. The kitchen stands out with its central island, ideal for meal prep, casual dining, or gathering with loved

  Nataly Mattox RE/MAX Integrity

  

  241 Timothy Ave, Winston, OR 97496
• 

  

  /39

  Est $340,722 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,466 Sq Ft

  213 NE Plum Ridge Dr, Winston, OR 97496

  

  213 NE Plum Ridge Dr, Winston, OR 97496
• 

  

  /32

  $609,000

  • 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
• 

  

  /27

  $259,900 Sold Apr 01, 2025

  • 1,088 Sq Ft
  • $239/SF
  • 6 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1994

  415 NW Apollo Ct, Winston, OR 97496

  Great home ready for a little TLC for a lot of sweat equity! This sweet little 3 bed/1bath house on a quiet cut-de-sac is perfect for your personal touch and upgrades. Backyard and deck offer lovely views of the valley. The 2 car garage in addition to the double deep driveway provides ample parking. Don’t miss this diamond in the rough with so much potential!

  Bob Lamonte Lamonte Real Estate Professionals

  

  415 NW Apollo Ct, Winston, OR 97496
• 

  

  /25

  Not Listed For Sale

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

  124 NW Bree Dr, Winston, OR 97496

  

  124 NW Bree Dr, Winston, OR 97496
• 

  

  /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
• 

  

  /15

  $185,000 Sold Apr 01, 2025

  • 1,180 Sq Ft
  • $157/SF
  • 33 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1953

  260 SW Ford Ave, Winston, OR 97496

  Great investment property! 3 Bedroom/1 Bath with family room, mini-split ductless HVAC system, newer roof on home, large fenced front and back yards, and double-pane vinyl windows. This home has been mostly painted inside and outside but needs some touch-up. New carpet is in home but installation needs to be completed. Some additional work is needed to make this a perfect starter home.

  Debra Moore Currieco Real Estate

  

  260 SW Ford Ave, Winston, OR 97496
• 

  

  /47

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  258 NW Bree Dr, Winston, OR 97496

  

  258 NW Bree Dr, Winston, OR 97496
• 

  

  /32

  $499,500

  • 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
• 

  

  /22

  $112,000 Sold Apr 01, 2025

  • 1,300 Sq Ft
  • $86/SF
  • 32 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1999

  338 NW Broc Dr, Winston, OR 97496

  Discover the perfect blend of style and comfort in this tastefully remodeled home, situated in an all-age community park with affordable rent! This three-bedroom, two-bathroom home has been meticulously updated by a retired custom home designer and builder, showcasing custom standards throughout.The residence features new waterproof engineered wood flooring across most areas, with plush carpeting

  Rachel Sturdevant eXp Realty, LLC

  

  338 NW Broc Dr, Winston, OR 97496
• 

  

  /32

  Not Listed For Sale

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

  Unlisted Address

  

  Unlisted Address
• 

  

  /36

  $389,000

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

  765 SE Lanola St, Winston, OR 97496

  Home Tour Video: . Back on Market at NO fault to home-buyers financing fell through**. 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

  Shuray Bagley Oregon Life Homes

  

  765 SE Lanola St, Winston, OR 97496
• 

  

  /14

  $222,000 Sold Mar 21, 2025

  • 752 Sq Ft
  • $295/SF
  • 7 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1952

  111 SE Grape Ave, Winston, OR 97496

  Cute bungalow on a HUGE lot has been completely updated and is ready for a new owner. Thoughtful updates make this house live larger than its size. Vaulted ceilings, LVT flooring, new kitchen, and new fixtures throughout make this a low maintenance, turn-key home for your buyers. There is enough room on this lot to possibly build an ADU or a second home and make this the ADU. Buyer to do due

  Stephen Erving Premiere Property Group, LLC

  

  111 SE Grape Ave, Winston, OR 97496
• 

  

  /32

  Est $358,924 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  165 Teresa Ct, Winston, OR 97496

  

  165 Teresa Ct, 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
• 

  

  /48

  $355,000 Sold Mar 21, 2025

  • 1,808 Sq Ft
  • $196/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1993

  660 Byron Creek Rd, Winston, OR 97496

  Discover nature's privacy tucked away on your very own 5 acres! Step inside and you'll be greeted with a dedicated family & living room with vaulted ceilings and cozy wood burning fireplace. Dining room connects to a large insulated sun porch with exterior entry. Kitchen adorned with tile countertops and complimented with a stone tile backsplash. There is no scarcity when it comes to cabinet

  Felicia Mondragon Keller Williams Realty Eugene and Springfield

  

  660 Byron Creek Rd, Winston, OR 97496
• 

  

  /45

  Est $419,188 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft

  291 SE Kara St, Winston, OR 97496

  

  291 SE Kara St, Winston, OR 97496
• 

  

  /39

  $434,500

  • 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
• 

  

  /5

  $295,000 Sold Mar 19, 2025

  • 1,608 Sq Ft
  • $183/SF
  • 150 Days On Market

  • Built 1978

  53 SE Darrell Ave, Winston, OR 97496

  What an opportunity! Live in 1 unit and rent out the other or turn it back in to a 1600 plus sq ft single family residence. This 2 unit duplex was a total "studs out" remodel back in 2018. Each unit is a 2 bedroom 1 bath and were nicely redone with new roof, new kitchens, bathrooms, flooring and paint inside and out. Large .25 acre flag lot with carport and storage shed. Great rental history and

  Joe Hajos Berkshire Hathaway HomeServices Real Estate Professionals

  

  53 SE Darrell Ave, Winston, OR 97496
• 

  

  /18

  Est $297,025 Not Listed For Sale

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

  220 NW Timothy Ave, Winston, OR 97496

  

  220 NW Timothy Ave, Winston, OR 97496

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