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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$1,100,000

6700 UPPER OLALLA RD
Winston, OR 97496

1

3
Beds

2 | 1
Baths

2,720
SqFt

(48)

6700 UPPER OLALLA RD, Winston, OR 97496 

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#549641726 | House

This Listing Courtesy of Real Broker 458-209-0163

$1,099,900

1349 WILLIS CREEK RD
Winston, OR 97496

2

3
Beds

2 | 1
Baths

2,856
SqFt

(48)

1349 WILLIS CREEK RD, Winston, OR 97496 

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#493365103 | House

This Listing Courtesy of The Anderson Agency sold@jordanandersonhomes.com

$735,000

9114 Old Highway 99 S
Winston, OR 97496

3

3
Beds

3
Baths

2,722
SqFt

(48)

9114 Old Highway 99 S, Winston, OR 97496 

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#177934538 | House

This Listing Courtesy of Umpqua Legacy Realty

$699,000

1068 RICE CREEK RD
Winston, OR 97496

4

4
Beds

2 | 1
Baths

2,362
SqFt

(48)

1068 RICE CREEK RD, Winston, OR 97496 

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#467999836 | House

This Listing Courtesy of The Neil Company Real Estate

$685,000

411 WOODLAND DR
Winston, OR 97496

5

4
Beds

2
Baths

2,240
SqFt

(44)

411 WOODLAND DR, Winston, OR 97496 

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#289799981 | House

This Listing Courtesy of RE/MAX Integrity

$619,900

635 WIL WAY
Winston, OR 97496

6

4
Beds

3 | 1
Baths

3,072
SqFt

(48)

635 WIL WAY, Winston, OR 97496 

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#506617845 | House

This Listing Courtesy of Different Better Real Estate

$499,900

2620 NW Brockway RD
Winston, OR 97496

7

3
Beds

2
Baths

4,024
SqFt

(45)

2620 NW Brockway RD, Winston, OR 97496 

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#493398074 | House

This Listing Courtesy of Turning Point Realty Group apryl@tprghomes.com

$499,900

2581 BROCKWAY RD
Winston, OR 97496

8

3
Beds

2 | 1
Baths

2,576
SqFt

(44)

2581 BROCKWAY RD, Winston, OR 97496 

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#189686409 | House

This Listing Courtesy of Turning Point Realty Group apryl@tprghomes.com

$499,900

160 WIL WAY
Winston, OR 97496

9

3
Beds

2 | 1
Baths

2,089
SqFt

(41)

160 WIL WAY, Winston, OR 97496 

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#788491236 | House

This Listing Courtesy of Turning Point Realty Group apryl@tprghomes.com

$499,900

150 WIL WAY
Winston, OR 97496

10

3
Beds

2 | 1
Baths

1,999
SqFt

(40)

150 WIL WAY, Winston, OR 97496 

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#726498556 | House

This Listing Courtesy of Turning Point Realty Group apryl@tprghomes.com

$498,000

572 DILLARD GARDENS RD
Winston, OR 97496

11

2
Beds

2
Baths

1,440
SqFt

(20)

572 DILLARD GARDENS RD, Winston, OR 97496 

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#264021443 | House

This Listing Courtesy of MORE Realty, Inc. 541-944-7708

$489,900

263 WIL WAY
Winston, OR 97496

12

3
Beds

2
Baths

1,928
SqFt

(47)

263 WIL WAY, Winston, OR 97496 

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#773435924 | House

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

$487,000

104 KENYA CT
Winston, OR 97496

13

3
Beds

2
Baths

1,800
SqFt

(48)

104 KENYA CT, Winston, OR 97496 

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Open House: Aug 29, 2026, 11:00 AM - 2:00 PM

 

#571430035 | House

This Listing Courtesy of Platinum Realty

$469,900

161 COLLINS CT
Winston, OR 97496

14

3
Beds

2
Baths

1,770
SqFt

(23)

161 COLLINS CT, Winston, OR 97496 

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#714486794 | House

This Listing Courtesy of The Neil Company Real Estate

$459,000

311 SE GRAPE AVE
Winston, OR 97496

15

3
Beds

1
Baths

1,250
SqFt

(36)

311 SE GRAPE AVE, Winston, OR 97496 

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#679087027 | House

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

$439,900

158 COLLINS CT
Winston, OR 97496

16

3
Beds

2
Baths

1,564
SqFt

(10)

158 COLLINS CT, Winston, OR 97496 

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#656558615 | House

This Listing Courtesy of The Neil Company Real Estate

$439,900

535 SE PARKWAY DR
Winston, OR 97496

17

3
Beds

2
Baths

1,442
SqFt

(48)

535 SE PARKWAY DR, Winston, OR 97496 

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#349138850 | House

This Listing Courtesy of RE/MAX Integrity

$439,900

128 WATUSI CT
Winston, OR 97496

18

3
Beds

2
Baths

1,832
SqFt

(33)

128 WATUSI CT, Winston, OR 97496 

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#284288718 | House

This Listing Courtesy of Heritage Real Estate

$409,900

623 SE GARDEN WAY DR
Winston, OR 97496

19

3
Beds

2
Baths

1,680
SqFt

(38)

623 SE GARDEN WAY DR, Winston, OR 97496 

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#431179209 | House

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

$399,000

675 SE BRUSH CT
Winston, OR 97496

20

3
Beds

2
Baths

1,498
SqFt

(30)

675 SE BRUSH CT, Winston, OR 97496 

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#434537222 | House

This Listing Courtesy of J Mann Realty

$366,000

186 WOODDUCK ST
Winston, OR 97496

21

3
Beds

2
Baths

1,613
SqFt

(48)

186 WOODDUCK ST, Winston, OR 97496 

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#405578083 | House

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

$364,900

10 SW PEACH LN
Winston, OR 97496

22

3
Beds

1
Baths

1,440
SqFt

(23)

10 SW PEACH LN, Winston, OR 97496 

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#489660913 | House

This Listing Courtesy of Stellar Realty Northwest

$350,000

380 NW CARY ST
Winston, OR 97496

23

4
Beds

2
Baths

1,710
SqFt

(34)

380 NW CARY ST, Winston, OR 97496 

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#726088318 | House

This Listing Courtesy of Oregon Life Homes 541-817-3798

$335,000

185 SE LEBLEU LN
Winston, OR 97496

24

3
Beds

2
Baths

1,257
SqFt

(17)

185 SE LEBLEU LN, Winston, OR 97496 

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#625199164 | House

This Listing Courtesy of The Neil Company 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 © 2026 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 August 23, 2026, 1:38 PM PT

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