Looking For Real Estate For Sale in Winston, Oregon?

 The G Team is the top experts on Selling or Buying a home in Winston. Browse available Winston listings

below and reach out to us for questions or to see a

property in person.

Why Winston, Oregon?

Winston is a small city in Douglas County, Oregon and is located about 10 miles southwest of Roseburg. Residing along the South Umpqua River, Winston is the gateway to several outdoor recreational opportunities, like picnicking, catching an outdoor concert at Riverbend Park & Skatepark, swimming in the river or taking advantage of the numerous fishing opportunities in the area. The local skate park is a popular attraction for the kids. Winston is also home to a variety of housing opportunities, from new construction to well established homes and rolling farmland.

Winston is also home to Wildlife Safari, featuring a 4.5-mile drive-thru tour with a look at more than 500 animals of 80 species. Wild residents include hippos, rhinos and zebras in the Africa section, with grizzly bears, bison and elk in the American area. The drive-thru portion of the park offers up-close access to tigers, lions and giraffes among other large creatures. You can also take advantage of the free walk-through area of the Safari Village, which features a botanical wonderland, animal exhibits, gift shop and a children’s petting zoo.

The G Team has sold many homes in the Winston area, and we are ready to help you too! If you’re thinking about relocating to Winston or need to sell your home, put our experience to work for you and hire the best real estate team to help you navigate the process!

Homes for sale in Winston, Oregon

For Sale Recently Sold

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$995,000

1260 IRELAND RD #A
Winston, OR 97496

1

3
Beds

2
Baths

2,600
SqFt

(48)

1260 IRELAND RD #A, Winston, OR 97496 

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#658523583 | House

This Listing Courtesy of Engel & Volkers West Portland westportland@engelvoelkers.com

$874,900

1800 E WILLIS CREEK RD
Winston, OR 97496

2

2
Beds

1
Baths

1,080
SqFt

(48)

1800 E WILLIS CREEK RD, Winston, OR 97496 

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#24065869 | House

This Listing Courtesy of Knipe Realty ERA Powered 503-551-0081

$775,000

411 NW WOODLAND DR
Winston, OR 97496

3

4
Beds

2
Baths

2,240
SqFt

(48)

411 NW WOODLAND DR, Winston, OR 97496 

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#24526415 | House

This Listing Courtesy of RE/MAX Integrity

$774,900

1470 E WILLIS CREEK RD
Winston, OR 97496

4

3
Beds

2 | 1
Baths

1,845
SqFt

(38)

1470 E WILLIS CREEK RD, Winston, OR 97496 

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#370595488 | House

This Listing Courtesy of Knipe Realty ERA Powered 503-551-0081

$670,000

1260 IRELAND RD
Winston, OR 97496

5

3
Beds

2
Baths

2,600
SqFt

(41)

1260 IRELAND RD, Winston, OR 97496 

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#255604831 | House

This Listing Courtesy of Engel & Volkers West Portland westportland@engelvoelkers.com

$649,900

490 DAWSON DR
Winston, OR 97496

6

4
Beds

2 | 1
Baths

2,144
SqFt

(47)

490 DAWSON DR, Winston, OR 97496 

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#700991209 | House

This Listing Courtesy of Different Better Real Estate

$625,000

7941 UPPER OLALLA RD
Winston, OR 97496

7

3
Beds

2
Baths

2,167
SqFt

(48)

7941 UPPER OLALLA RD, Winston, OR 97496 

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#697236893 | House

This Listing Courtesy of The Neil Company Real Estate

$609,000

102 SARAH BEAR LN
Winston, OR 97496

8

4
Beds

3
Baths

2,660
SqFt

(32)

102 SARAH BEAR LN, Winston, OR 97496 

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#475121789 | House

This Listing Courtesy of Currieco Real Estate

$525,303

240 Wil WAY
Winston, OR 97496

9

3
Beds

2
Baths

2,186
SqFt

(32)

240 Wil WAY, Winston, OR 97496 

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#246531491 | House

This Listing Courtesy of Next Generation Real Estate LLC

$469,900

113 CITATION CT
Winston, OR 97496

10

3
Beds

2
Baths

1,770
SqFt

(46)

113 CITATION CT, Winston, OR 97496 

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#141991471 | House

This Listing Courtesy of Keller Williams Southern Oregon-Umpqua Valley 541-371-5500

$469,000

197 WIL WAY
Winston, OR 97496

11

4
Beds

2
Baths

1,994
SqFt

(35)

197 WIL WAY, Winston, OR 97496 

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#24118196 | House

This Listing Courtesy of Oregon Life Homes 541-430-3442

$465,000

13130 LOOKINGGLASS RD
Winston, OR 97496

12

3
Beds

3
Baths

1,636
SqFt

(35)

13130 LOOKINGGLASS RD, Winston, OR 97496 

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#114213472 | House

This Listing Courtesy of Sarah Sherman Real Estate

$464,000

7950 UPPER OLALLA RD
Winston, OR 97496

13

3
Beds

2
Baths

1,393
SqFt

(48)

7950 UPPER OLALLA RD, Winston, OR 97496 

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#553297171 | House

This Listing Courtesy of eXp Realty, LLC 541-530-0409

$449,500

127 NW TEAL ST
Winston, OR 97496

14

4
Beds

2
Baths

1,830
SqFt

(39)

127 NW TEAL ST, Winston, OR 97496 

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#24597560 | House

This Listing Courtesy of Keller Williams Southern Oregon-Umpqua Valley 541-784-7179

$399,000

2651 NW BROCKWAY RD
Winston, OR 97496

15

3
Beds

2 | 1
Baths

1,980
SqFt

(39)

2651 NW BROCKWAY RD, Winston, OR 97496 

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#24626954 | House

This Listing Courtesy of The Neil Company Real Estate

$389,000

765 SE LANOLA ST
Winston, OR 97496

16

3
Beds

2
Baths

1,468
SqFt

(36)

765 SE LANOLA ST, Winston, OR 97496 

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#189495910 | House

This Listing Courtesy of Oregon Life Homes 541-670-5898

$375,000

139 TERESA LN
Winston, OR 97496

17

3
Beds

2
Baths

1,280
SqFt

(22)

139 TERESA LN, Winston, OR 97496 

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#24044509 | House

This Listing Courtesy of Trueblood Real Estate

$359,000

185 SE LEBLEU LN
Winston, OR 97496

18

3
Beds

2
Baths

1,257
SqFt

(5)

185 SE LEBLEU LN, Winston, OR 97496 

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#571231646 | House

This Listing Courtesy of Keller Williams Realty Eugene and Springfield 541-221-8771

$358,900

40 NW CARY ST
Winston, OR 97496

19

4
Beds

2 | 1
Baths

1,798
SqFt

(31)

40 NW CARY ST, Winston, OR 97496 

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#24533411 | Condo

This Listing Courtesy of Safari Village Real Estate

$350,000

151 NW SHERRY ST
Winston, OR 97496

20

3
Beds

2
Baths

1,835
SqFt

(39)

151 NW SHERRY ST, Winston, OR 97496 

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#712884097 | House

This Listing Courtesy of Oregon Life Homes 541-603-8465

$335,000

231 NE DARRELL AVE
Winston, OR 97496

21

3
Beds

2
Baths

1,374
SqFt

(47)

231 NE DARRELL AVE, Winston, OR 97496 

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#492618457 | House

This Listing Courtesy of Johnson Group Real Estate, LLC

$329,500

310 NW LOST LN
Winston, OR 97496

22

4
Beds

2
Baths

1,769
SqFt

(27)

310 NW LOST LN, Winston, OR 97496 

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#186874892 | Condo

This Listing Courtesy of Safari Village Real Estate

$297,900

551 NW T ST
Winston, OR 97496

23

3
Beds

1
Baths

1,668
SqFt

(23)

551 NW T ST, Winston, OR 97496 

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#184512147 | House

This Listing Courtesy of Lamonte Real Estate Professionals

$294,900

401 SE PARK ST
Winston, OR 97496

24

3
Beds

1
Baths

1,056
SqFt

(35)

401 SE PARK ST, Winston, OR 97496 

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#359474307 | House

This Listing Courtesy of Different Better Real Estate

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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 eXp Realty, LLC are marked with the RMLS™ logo, and detailed information about these properties includes the names of the listing brokers.
Listing content is copyright © 2025 RMLS™, Portland, Oregon.
IDX content is updated approximately every two hours. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available. All information provided is deemed reliable but is not guaranteed and should be independently verified.

RMLS - Oregon data last updated at April 27, 2025, 5:36 PM PT

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