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Winston, OR Homes for Sale with Garage

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  • /45

    $689,900

    • 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

    Agent Photo

    Ashton Faas

    Different Better Real Estate

    (458) 232-3589

    635 Wil Way, Winston, OR 97496
  • /36

    $439,000

    • 7 Beds
    • 4.5 Baths
    • 3,861 Sq Ft

    2414 Brockway Rd, Winston, OR 97496

    Opportunity awaits! Whether you’re a savvy investor seeking passive income, a large family looking for a multi-generational setup, or a single household wanting a home with the luxury of renting out additional units, this three-home property offers countless possibilities.Located on historic Brockway Road, the property spans .58 acres and is lined with mature trees and lush landscaping, creating

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    2414 Brockway Rd, Winston, OR 97496
  • /48

    $469,900 Open Wed 11AM - 3PM

    • 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
  • /45

    $66,000

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

    125 SE Estate Loop, Winston, OR 97496

    Take in breathtaking views of Umpqua Valley and the surrounding mountains from this spacious manufactured home located in a welcoming 55+ community. Unwind on the large covered front porch. Featuring a metal roof, double-pane vinyl windows, and a sturdy concrete block foundation, this home offers lasting durability. Stay comfortable year-round with the newer heat pump installed in 2022.

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    125 SE Estate Loop, Winston, OR 97496
  • /42

    $375,000

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

    700 SE Tokay St, Winston, OR 97496

    Welcome to this inviting one level 3-bedroom, 2-bathroom home offering comfort, convenience, and modern touches throughout. Manicured front yard plus a manicured back yard that is completely fenced. 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

    Mary Gilbert Keller Williams Southern Oregon-Umpqua Valley

    700 SE Tokay St, Winston, OR 97496
  • /39

    $275,000

    • 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
  • /48

    $474,900

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

    13224 Lookingglass Rd, Winston, OR 97496

    Experience 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 with beautiful

    Deleta Dickson eXp Realty, LLC

    13224 Lookingglass Rd, Winston, OR 97496
  • /32

    $469,900

    • 2 Beds
    • 2 Baths
    • 1,764 Sq Ft

    1941 Byron Creek Rd, Winston, OR 97496

    Come home to your own private escape hidden in the trees! Beautiful parklike setting with amazing views and end of the road privacy. Property features include a huge, large covered RV storage, detached guest quarters, a storeroom & workshop. The manufactured home was custom built for the current owners with many custom touches. An expansive deck is perfect for gatherings or taking in the amazing

    Andrew Stoner Roseburg Homes Realty

    1941 Byron Creek Rd, Winston, OR 97496
  • /10

    $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

    $459,000

    • 3 Beds
    • 2.5 Baths
    • 2,067 Sq Ft

    165 Danielle Dr, Winston, OR 97496

    Welcome home! Enjoy the space and warmth of this Safari Estates custom home. Featuring over 2,000 sq ft of living space. 3 bedrooms 2.5 baths with an upstairs laundry room make this home a great family setup. There is an office/Den that also doubles as a 4th bedroom if needed. Dramatic entry way with open concept kitchen/familyroom is what separates this home from the others ! Outside you will

    Brent Yop Winston Realty & Insurance

    165 Danielle Dr, Winston, OR 97496
  • /15

    $229,000

    • 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
  • /35

    $405,000

    • 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
  • /41

    $525,000 New Construction

    • 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
  • /20

    $475,000

    • 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
  • /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 is

    Jerry Norman Oregon Life Homes

    120 SE Edwards Ave, Winston, OR 97496
  • /35

    $142,500

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

    112 Twin Oaks Loop, Winston, OR 97496

    WOW! BRAND NEW 2025 manufactured home in the tidy senior living 55+ Twin Oaks community! This 3-bed, 2-bath home features an open floor plan with a large kitchen island, stainless steel appliances, and modern finishes throughout. The primary suite includes double sinks and a walk-in shower. Covered carport and storage shed add convenience. Space rent $725/month and includes water, sewer, and

    Anthony Beckham Different Better Real Estate

    112 Twin Oaks Loop, Winston, OR 97496
  • /32

    $575,000

    • 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
  • /38

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,848 Sq Ft

    210 NW Timothy Ave, Winston, OR 97496

    Extremely nice 1999 triple-wide on a beautiful corner lot. Features 3 bedrooms, 2 baths with a large kitchen, living, and family rooms. There is also a gas fireplace, new heat pump, and an extra large 2-car garage. Outside has a covered deck, patio, mature landscaping, and fenced yard with sprinkler and drip system.

    John McVeigh The Neil Company Real Estate

    210 NW Timothy Ave, Winston, OR 97496
  • /25

    $249,000

    • 3 Beds
    • 1 Bath
    • 994 Sq Ft

    350 SE Park St, Winston, OR 97496

    Perfect home for a first-time buyer or an excellent investment opportunity! Situated on a large corner lot in a desirable neighborhood within walking distance to the city park. This move-in-ready home features beautiful kitchen cabinets and a versatile storage/she shed. Don’t miss out on this great opportunity!

    Michael Brown Oregon Life Homes

    350 SE Park St, Winston, OR 97496
  • /27

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 2,014 Sq Ft

    291 SE Shigley St, Winston, OR 97496

    Contemporary custom 2014 sq ft. tri level home on .21 acre level lot. Has 8x24 green house, deck, hot tub, new furnace, new solar system paid for. Range, refrigerator, dishwasher, freezer, washer dryer included. Quality built home, double garage, RV parking. Views of mountains. Park around the corner. Estate sale. Motivated seller. Needs cosmetics but excellent bones.

    Valynn Currie Currieco Real Estate

    291 SE Shigley St, Winston, OR 97496
  • /49

    $700,000

    • 2 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    9740 Upper Olalla Rd, Winston, OR 97496

    Country setting 29.80 acres, Chalet-style home, 2304 sqft , 2 BR ( could be 3 BR) 2.5 BA. LR has a fireplace with woodstove insert and massive natural stone chimney. Good size kitchen, laundry room with extra sink. Merchantable timber, access to Seneca timber and BLM land for horseback riding, mushroom hunting, ATV's and hiking. Beautiful mountain views, year-round Olalla Creek with water right

    Thuy Chrestenson KNIPE REALTY ERA POWERED

    9740 Upper Olalla Rd, Winston, OR 97496
  • /18

    $272,000

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

    151 Sherry St, Winston, OR 97496

    Charming 3 bedroom (possibly 4 bedroom), 2 bath home with lots of storage & room to roam! Large, fenced corner lot & covered patio for outdoor enjoyment. With a little TLC, this home could sparkle again.

    Judith Zuver Winston Realty & Insurance

    151 Sherry St, Winston, OR 97496
  • /41

    $525,000 New Construction

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

    150 Wil Way, Winston, OR 97496

    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, recessed lighting, and luxury

    Tyler Head Turning Point Realty Group

    150 Wil Way, Winston, OR 97496
  • /47

    $315,000

    • 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
  • /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
  • /44

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft

    380 Sunnyside Dr, Winston, OR 97496

    Welcome home to this beautifully maintained, move-in ready 3-bedroom, 2-bath property featuring an open floor plan, vaulted ceilings, new LVP flooring, fresh paint, and plenty of storage. Located in a friendly, safe neighborhood with wonderful views. Enjoy the well-manicured, low-maintenance yard, private backyard, spacious deck, garden area, and greenhouse—perfect for families or retirees

    Brandy Holder Holder Realty

    380 Sunnyside Dr, Winston, OR 97496
  • /18

    $199,000

    • Land
    • 0.97 Acre
    • $205,155 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
  • /17

    $302,500

    • 3 Beds
    • 2 Baths
    • 1,692 Sq Ft

    600 SE Carrol St, Winston, OR 97496

    Charming, 3 bedroom, 2 bath home home. Large fenced corner lot. Come see it, you'll be pleased!

    Judith Zuver Winston Realty & Insurance

    600 SE Carrol St, Winston, OR 97496
  • /17

    $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 $725/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
  • /44

    $719,000

    • 4 Beds
    • 2 Baths
    • 2,240 Sq Ft

    411 Woodland Dr, Roseburg, OR 97471

    Discover a lifestyle rooted in fresh air, room to roam, and time spent outside. This two-story ranch sits above sweeping views of Abacela Vineyard and offers Lookingglass Creek frontage with irrigation rights, K-line system, and pump already in place. Enjoy your own private swimming hole, raised-bed fenced garden, and greenhouse—perfect for growing, tinkering, and staying active year-round.The

    Nataly Mattox RE/MAX Integrity

    411 Woodland Dr, Roseburg, OR 97471

Home Trends in Winston, OR

Housing Trends

Median Sale Price
$330,500
Median Single Family Sale Price
$340,000
Average Price Per Sq Ft
$229
Number of Homes for Sale
21
Last 12 months Home Sales
66
Months of Supply
3.80
Median List Price
$359,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
-4%
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