Homes for sale under $300k in Winston, OR

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3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
Welcome to 260 SW Ford Ave in the heart of Winston, OR — a beautifully remodeled single-level home offering comfort, style, and exceptional move-in readiness. Fresh exterior paint gives the home a crisp, modern look, while inside you’ll find waterproof luxury vinyl plank flooring in the main living areas—including the living room, kitchen, bonus room, and laundry room—paired with brand-new carpet in the bedrooms for a warm and cozy feel. This home features vinyl double-pane windows and efficient ductless mini-split units for reliable year-round comfort. The spacious primary bedroom includes a nicely sized closet, and the bathroom offers tile flooring and a tub/shower

$289,900

3 beds1 bath1,180 sq ft

260 SW Ford Ave, Winston, OR 97496

Tile flooring • Brand-new cabinetry • 6,098 sq ft lot

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

VIDEO TOUR

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
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 rural living provides. Whether you envision a hobby farm, gardening, or simply your own private retreat, this property delivers a rare blend of beauty, usability, and opportunity, with additional homesites. (Appt only, please no drive bys, do not drive in bridge. ) Cash only, sold as-is.

$275,000

3 beds1 bath1,056 sq ft

617 Poison Oak Dr, Winston, OR 97496

Seasonal creeks • Nearly 14 acres • Stands of timber

Bob Lamonte • Lamonte Real Estate Professionals

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
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.

$272,000

3 beds2 baths1,835 sq ft

151 NW Sherry St, Winston, OR 97496

Covered patio • Fenced corner lot • 0.32 acre lot

Robert Zuver • Winston Realty & Insurance

3D WALKTHROUGH

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
Welcome home to this 3-bedroom, 2-bath manufactured home on your own property in a quiet Winston neighborhood! Enjoy easy one-level living with laminate flooring throughout and vaulted ceilings that create an open, comfortable feel. The kitchen offers a pantry and built-in dishwasher for everyday convenience. Outside, you’ll find RV parking, a carport, a storage shed, and a fully fenced yard—perfect for gardening, pets, or relaxing outdoors. Washer and dryer included! Located on a level lot with mountain views and close to schools, shopping, and parks.

$255,000

3 beds2 baths1,296 sq ft

308 NW Civil Bend Ave, Winston, OR 97496

Pantry • Laminate flooring • Rv parking

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
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!

$249,000

3 beds1 bath994 sq ft

350 SE Park St, Winston, OR 97496

Large corner lot • 7,405 sq ft lot • Built 1955

Michael Brown • Oregon Life Homes

Property at 90 SE Darrell Ave, Winston, OR 97496, 2 beds, 2 baths

$239,000

2 beds2 baths924 sq ft

90 SE Darrell Ave, Winston, OR 97496

Rebekah Sexauer • eXp Realty, LLC

Property at 301 NW Midway St, Winston, OR 97496, 3 beds, 2 baths

$199,000

3 beds2 baths1,156 sq ft

301 NW Midway St, Winston, OR 97496

Tracy Grubbs • eXp Realty, LLC

Property at 110 SE Darrell Ave, Winston, OR 97496, 2 beds, 1 bath

$184,999

2 beds1 bath735 sq ft

110 SE Darrell Ave, Winston, OR 97496

Lacey Williams • Trueblood Real Estate

Property at 112 SE Twin Oaks Loop, Winston, OR 97496, 3 beds, 2 baths

$142,500

3 beds2 baths1,296 sq ft

112 SE Twin Oaks Loop, Winston, OR 97496

Anthony Beckham • Different Better Real Estate

Property at 180 Twin Oaks Loop, Winston, OR 97496, 3 beds, 2 baths

$137,000

3 beds2 baths1,404 sq ft

180 Twin Oaks Loop, Winston, OR 97496

Raymond Coburn • eXp Realty, LLC

Property at 124 Country Side Ln, Winston, OR 97496, 3 beds, 2 baths

$99,500

3 beds2 baths1,296 sq ft

124 Country Side Ln, Winston, OR 97496

Jason Mann • J Mann Realty

Property at 241 Twin Oaks Loop, Winston, OR 97496, 3 beds, 2 baths

$95,000

3 beds2 baths1,296 sq ft

241 Twin Oaks Loop, Winston, OR 97496

Roger Snyder • Berkshire Hathaway HomeServices Real Estate Professionals

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ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
Come check out this charming home, surrounded by the beauty of the mountains. This 1344 sf, 3 bed 2 bath home is set on 2.5 level acres, Property has a septic tank w/ public water, Fenced, there is plenty of room for a garden, or room to let your animals run.

$300,000

3 beds2 baths1,344 sq ft

449 Evergreen Ridge Rd, Riddle, OR 97469

2.54 acre lot • Built 1976 • Listed 627 days

Sandee Ethington • Village Realty

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
Freshened up 3 bed 2 bath, new roof, paint, flooring, and much more. This small acreage parcel has lots of possibilities for your outdoor enthusiasts. Private setting with nice territory view. Close to town and Interstate. Priced to sell. Listing broker related to seller.

$299,900

3 beds2 baths1,152 sq ft

2193 Canyonville Riddle Rd, Riddle, OR 97469

Territory view • Small acreage parcel • Private setting

Michael Barnes • Real Estate 55 Inc

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
Wow Great Price Just Reduced ! Two Lots and Home Financing available Peaceful Retreat with Valley Landscapes 711 & 715 Plin St, Myrtle Creek, OR . 3 Bed | 2 Bath | 0.58 Acres | 2 Tax Lots welcome to your own private haven in the heart of Myrtle Creek! This serene 3-bedroom, 2-bath home sits on two separate tax lots totaling 0.58 acres, offering ample space, privacy, and endless potential. Nestled among whispering Firs and Cedars, this property captures the essence of Oregon living with distant Landscapes of the valley and surrounding mountains—a picturesque backdrop for your daily life. Whether you're sipping your morning coffee on the porch or relaxing in the evening, you&rsquo

$295,000

3 beds2 baths1,539 sq ft

711 Plin St, Myrtle Creek, OR 97457

Abundant parking • Spacious front lot • Ample space

Raymond Coburn • eXp Realty, LLC

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
MOVE IN READY, NICE LOCATION and backed up to farm land. This 2 bedroom home has the perfect amount of space to accommodate your needs and make you feel right at home. Heating and Air Conditioning for all season comfort. Offers a front and back yard with underground sprinklers. Back yard completely fenced. Plus a single car garage with driveway. Low HOA for neighborhood. Call to make a showing appointment today!!!

$290,000

2 beds1 bath832 sq ft

783 Callahan Dr, Roseburg, OR 97471

Single car garage • Front and back yard • 6,969 sq ft lot

Lacey Williams • Trueblood Real Estate

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
LOCATION, LOCATION, LOCATION. .. This 2 bedroom home has the perfect amount of space to accommodate your needs and make you feel right at home. Heating and Air Conditioning for all season comfort. Offers a front and back yard with underground sprinklers. Back yard fairly spacious and completely fenced. Plus a single car garage with driveway and extra driveway area for additional parking. Low HOA for neighborhood. Call to make a showing appointment today!!!

$290,000

2 beds1 bath832 sq ft

807 Callahan Dr, Roseburg, OR 97471

Single car garage • Extra driveway area • Front and back yard

Lacey Williams • Trueblood Real Estate

ABOUT THIS HOME
Homes for sale under $300k in Winston, OR
Country Living with Endless Potential! Tucked away in the rural countryside between Riddle and Canyonville Oregon, this 1979 single-wide manufactured home sits on 5 acres of rolling hillside terrain—offering privacy, space, and plenty of opportunity to make it your own. Featuring 2 bedrooms and 2 bathrooms, this home is ready for a new owner with vision and a little elbow grease to bring it back to life. The property is on city water and private septic, a rare convenience for a country setting. Outside, you’ll find a flourishing garden area with cherry, apple, pear, and plum trees, plus a workshop, tool shed, and a covered area for firewood storage. With some updates and creativ

$289,900

2 beds2 baths924 sq ft

214 Thompson Rd, Riddle, OR 97469

Apple trees • City water • 5 acres

RaNae Sams • Oregon Life Homes

Property at 306 Mclain Ave, Roseburg, OR 97471, 2 beds, 2 baths

$289,000

2 beds2 baths2,491 sq ft

306 Mclain Ave, Roseburg, OR 97471

Scott Barraza • Village Realty

Property at 663 E 4th Ave, Riddle, OR 97469, 3 beds, 1 bath

$285,000

3 beds1 bath1,152 sq ft

663 E 4th Ave, Riddle, OR 97469

Russell Xay • Matin Real Estate

Property at 450 E 3rd Ave, Riddle, OR 97469, 3 beds, 2 baths

$275,000

3 beds2 baths1,800 sq ft

450 E 3rd Ave, Riddle, OR 97469

Shane Mast • Oregon Life Homes

Property at 258 Bobwhite St, Roseburg, OR 97471, 3 beds, 2 baths

$273,000

3 beds2 baths1,296 sq ft

258 Bobwhite St, Roseburg, OR 97471

Catherine Shipley • RE/MAX Integrity

Property at 1973 Castle Ave, Roseburg, OR 97471, 3 beds, 2 baths

$269,500

3 beds2 baths1,350 sq ft

1973 Castle Ave, Roseburg, OR 97471

Scot Spalding • Oregon Life Homes

Property at 165 Loop Rd, Myrtle Creek, OR 97457, 4 beds, 2 baths

$265,000

4 beds2 baths1,920 sq ft

165 Loop Rd, Myrtle Creek, OR 97457

Stefanie Bernier • Paramount Real Estate LLC

Property at 157 Creekside Ct, Roseburg, OR 97471, 3 beds, 2 baths

$259,000

3 beds2 baths1,568 sq ft

157 Creekside Ct, Roseburg, OR 97471

Jody Tatone • RE/MAX Integrity

Property at 1951 Austin Rd, Roseburg, OR 97471, 2 beds, 1 bath

$235,000

2 beds1 bath946 sq ft

1951 Austin Rd, Roseburg, OR 97471

Jennifer Cox • RE/MAX Integrity

Property at 105 I St, Riddle, OR 97469, 3 beds, 2 baths

$229,000

3 beds2 baths1,188 sq ft

105 I St, Riddle, OR 97469

Anthony Beckham • Different Better Real Estate

Property at 510 Boyer Rd, Riddle, OR 97469, 2 beds, 1 bath

$219,900

2 beds1 bath680 sq ft

510 Boyer Rd, Riddle, OR 97469

Ashton Faas • Different Better Real Estate

Property at 4913 Melody Ln, Roseburg, OR 97471, 2 beds, 1 bath

$170,000

2 beds1 bath672 sq ft

4913 Melody Ln, Roseburg, OR 97471

Theresa Poitner • Oregon Life Homes

Property at 164 Jacob Hale Way, Roseburg, OR 97471, 4 beds, 2 baths

$159,000

4 beds2 baths1,756 sq ft

164 Jacob Hale Way, Roseburg, OR 97471

Najla Slater • Stellar Realty Northwest

Property at 9643 Old Highway 99, Dillard, OR 97432, 2 beds, 1 bath

$159,000

2 beds1 bath550 sq ft

9643 Old Highway 99, Dillard, OR 97432

Beverly Walters • Gold Standard Realty

Property at 275 Littlebrook Ln, Roseburg, OR 97471, 3 beds, 2 baths

$155,000

3 beds2 baths1,768 sq ft

275 Littlebrook Ln, Roseburg, OR 97471

Mary Gilbert • Keller Williams Southern Oregon-Umpqua Valley

Homes for sale under $300k in Winston

There are currently 12 homes for sale under $300k in Winston. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winston stay on the market for 70 days and receive 1 offers. This map is refreshed with the newest listings in Winston every 15 minutes.

In the past month, 6 homes have been sold in Winston. In addition to houses in Winston, there were also 0 condos, 1 townhouse, and 2 multi-family units for sale in Winston last month. Find your dream home in Winston using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winston are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winston. Our Winston real estate stats and trends will give you more information about home buying and selling trends in Winston. If you're looking to sell your home in the Winston area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winston with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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All information provided is deemed reliable but is not guaranteed and should be independently verified. The content relating to real estate for sale on this web site comes in part from the IDX program of the RMLS of Portland Oregon. Real estate listings held by brokerage firms other than Redfin are marked with the RMLS logo and detailed information about these properties includes the names of the listing brokers. Copyright © 2025 RMLS, Portland, Oregon. Data Last Updated Tue Dec 23 2025

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