Real Estate Investment Properties for Sale in Winston, OR
Looking for investment property in Winston, OR with high ROI ?
Explore a variety of short-term homes & houses in Winston, OR. Invest wisely with VRBO & Winston, OR Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winston, OR
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
165 Danielle DrWinston, ORCustom English Tudor style home in beautiful Safari Estates. This 3 bed, 2 1/2 bath home f... |
3 beds | 2 baths | 2,067 sq.ft. |
$455,000 |
Airbnb cash on cash: N/A
|
9740 UPPER OLALLA RdWinston, ORCountry setting 29.80 acres, A-frame Cedar home with vaulted ceilings. Master on main leve... |
3 beds | 2 baths | 2,304 sq.ft. |
$700,000 |
Airbnb cash on cash: N/A
|
110 SE Darrell AveWinston, ORCute 2 bedroom 1 bath home on a fenced corner lot. Great established neighborhood. Needs s... |
2 beds | 1 baths | 735 sq.ft. |
$184,999 |
Airbnb cash on cash: 1.95%
|
0 Rice Creek RdWinston, ORIf you seek seclusion, passive solar design, & a quiet setting: LOOK here! Seller construc... |
2 beds | 1 baths | 2,056 sq.ft. |
$454,000 |
Airbnb cash on cash: 0.37%
|
364 NW Teal StWinston, ORVery nice home in a nice neighborhood. 3 car garage, 3 bedrooms plus den, and fenced back ... |
3 beds | 2 baths | 1,684 sq.ft. |
$399,900 |
Airbnb cash on cash: N/A
|
380 Sunnyside DrWinston, ORLovely 2004 contemporary built 3 bedroom 2 bath home with double garage, vaulted ceilings,... |
3 beds | 2 baths | 1,433 sq.ft. |
$375,000 |
Airbnb cash on cash: N/A
|
139 Teresa LnWinston, ORLook no further than this Beautiful home in a newer neighborhood! This home has bright, na... |
3 beds | 2 baths | 1,280 sq.ft. |
$375,000 |
Airbnb cash on cash: N/A
|
270 Sabrina LnWinston, ORSuper cute brand new cottage-style home on semi-private 8+ acres 15-20 min. from town. You... |
2 beds | 1 baths | 1,040 sq.ft. |
$425,000 |
Airbnb cash on cash: 0.2%
|
1470 E WILLIS CREEK RdWinston, ORNestled on 90 acres of private land, this stunning 3-bedroom, 2.5-bath log home offers the... |
3 beds | 2 baths | 1,845 sq.ft. |
$699,000 |
Airbnb cash on cash: N/A
|
2414 BROCKWAY RdWinston, OROpportunity awaits! Whether you're a savvy investor seeking passive income, a large family... |
7 beds | N/A baths | N/A |
$419,000 |
Airbnb cash on cash: N/A
|
271 NW Sherry StWinston, ORWelcome to 271 NW Sherry St., a delightful home located in the charming town of Winston, O... |
3 beds | 1 baths | 1,260 sq.ft. |
$285,000 |
Airbnb cash on cash: N/A
|
102 SARAH BEAR LnWinston, ORStately quality 4 br 3 bath home, real wood floors, 2 gas fireplaces, central vac, top qua... |
4 beds | 3 baths | 2,660 sq.ft. |
$575,000 |
Airbnb cash on cash: N/A
|
231 NE DARRELL AveWinston, ORGreat location with a custom built one level home located on .39 of an acre at the end of ... |
3 beds | 2 baths | 1,374 sq.ft. |
$315,000 |
Airbnb cash on cash: N/A
|
13224 SE LOOKINGGLASS RdWinston, ORExperience this beautifully updated, original homestead farmhouse nestled in Safari Estate... |
4 beds | 2 baths | 2,534 sq.ft. |
$474,900 |
Airbnb cash on cash: N/A
|
700 SE TOKAY StWinston, ORWelcome to this inviting one level 3-bedroom, 2-bathroom home offering comfort, convenienc... |
3 beds | 2 baths | 1,404 sq.ft. |
$375,000 |
Airbnb cash on cash: N/A
|
800 BYRON CREEK RdWinston, ORWelcome to this charming country home set on over 5 acres of flat, usable land with Firewi... |
3 beds | 2 baths | 1,320 sq.ft. |
$485,000 |
Airbnb cash on cash: N/A
|
180 TWIN OAKS LoopWinston, ORapplication and park requirements, No other fees to HOA except basic space rent 604$+121$ ... |
3 beds | 2 baths | 1,404 sq.ft. |
$137,000 |
Airbnb cash on cash: N/A
|
150 WIL WayWinston, ORNew Home by JW Construction Inc.This beautifully crafted 2,143 sq ft home offers 3 bedroom... |
3 beds | 2 baths | 1,999 sq.ft. |
$525,000 |
Airbnb cash on cash: N/A
|
160 WIL WayWinston, ORNew Home by JW Construction Inc.This beautiful one-level home offers just over 2,000 squar... |
3 beds | 2 baths | 2,089 sq.ft. |
$525,000 |
Airbnb cash on cash: N/A
|
109 CITATION CtWinston, ORWelcome to 109 Citation Ct, a brand-new single-level home nestled in the highly sought-aft... |
3 beds | 2 baths | 1,770 sq.ft. |
$469,900 |
Airbnb cash on cash: N/A
|
90 SE DARRELL AveWinston, ORThis charming 2-bedroom, 2-bathroom manufactured home in Winston, Oregon offers comfortabl... |
2 beds | 2 baths | 924 sq.ft. |
$229,000 |
Airbnb cash on cash: 1.34%
|
411 WOODLAND DrWinston, ORDiscover a lifestyle rooted in fresh air, room to roam, and time spent outside. This two-s... |
4 beds | 2 baths | 2,240 sq.ft. |
$719,000 |
Airbnb cash on cash: N/A
|
308 NW CIVIL BEND AveWinston, ORWelcome home to this 3-bedroom, 2-bath manufactured home on your own property in a quiet W... |
3 beds | 2 baths | 1,296 sq.ft. |
$255,000 |
Airbnb cash on cash: N/A
|
210 NW TIMOTHY AveWinston, ORExtremely nice 1999 triple-wide on a beautiful corner lot. Features 3 bedrooms, 2 baths wi... |
3 beds | 2 baths | 1,848 sq.ft. |
$310,000 |
Airbnb cash on cash: N/A
|
301 NW MIDWAY StWinston, ORAMAZING INVESTMENT OPPORTUNITY!!! Cosmetic fixer upper features 3 Bedrooms, 2 baths, 2 car... |
3 beds | 2 baths | 1,156 sq.ft. |
$199,000 |
Airbnb cash on cash: N/A
|
291 SE SHIGLEY StWinston, ORContemporary custom 2014 sq ft. tri level home on .21 acre level lot. Has 8x24 green house... |
3 beds | 2 baths | 2,014 sq.ft. |
$375,000 |
Airbnb cash on cash: N/A
|
624 WILLIS CREEK RdWinston, ORThis rare riverfront horse property on the South Umpqua River is not to be missed! The hom... |
3 beds | 2 baths | 1,782 sq.ft. |
$625,000 |
Airbnb cash on cash: N/A
|
617 Poison Oak DrWinston, OR617 Poison Oak Dr, Winston, OR 97496 | Single Family Residential |
3 beds | 1 baths | 1,056 sq.ft. |
$265,000 |
Airbnb cash on cash: N/A
|
151 NW Sherry StWinston, OR151 NW Sherry St, Winston, OR 97496 | Single Family Residential |
3 beds | 2 baths | 1,835 sq.ft. |
$272,000 |
Airbnb cash on cash: N/A
|
600 SE Carrol StWinston, OR600 SE Carrol St, Winston, OR 97496 | Single Family Residential |
3 beds | 2 baths | 1,692 sq.ft. |
$302,500 |
Airbnb cash on cash: N/A
|
112 SE Twin Oaks LoopWinston, OR112 SE Twin Oaks Loop, Winston, OR 97496 | Manufactured Home |
3 beds | 2 baths | 1,296 sq.ft. |
$142,500 |
Airbnb cash on cash: N/A
|
350 SE Park StWinston, OR350 SE Park St, Winston, OR 97496 | Single Family Residential |
3 beds | 1 baths | 994 sq.ft. |
$249,000 |
Airbnb cash on cash: N/A
|
308 Helweg RdWinston, OR308 Helweg Rd, Winston, OR 97496 | Single Family Residential |
3 beds | 1 baths | 2,026 sq.ft. |
$475,000 |
Airbnb cash on cash: N/A
|
635 Wil WayWinston, OR635 Wil Way, Winston, OR 97496 | Single Family Residential |
4 beds | 3 baths | 3,072 sq.ft. |
$689,900 |
Airbnb cash on cash: N/A
|
1941 Byron Creek RdWinston, OR1941 Byron Creek Rd, Winston, OR 97496 | Manufactured Home |
2 beds | 2 baths | 1,764 sq.ft. |
$469,900 |
Airbnb cash on cash: -0.59%
|
120 SE Edwards AveWinston, OR120 SE Edwards Ave, Winston, OR 97496 | Single Family Residential |
3 beds | 2 baths | 1,421 sq.ft. |
$325,000 |
Airbnb cash on cash: N/A
|
80 NW Lost LnWinston, OR80 NW Lost Ln, Winston, OR 97496 | Manufactured Home |
4 beds | 2 baths | 1,992 sq.ft. |
$2,000,000 |
Airbnb cash on cash: N/A
|
740 Ireland RdWinston, OR740 Ireland Rd, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$199,000 |
Airbnb cash on cash: N/A
|
271 SE Robinson StWinston, OR271 SE Robinson St, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$80,000 |
Airbnb cash on cash: N/A
|
0 SW Main StWinston, OR0 SW Main St, Winston, OR 97496 | Other |
N/A beds | N/A baths | N/A |
$249,500 |
Airbnb cash on cash: N/A
|
Real Estate investment in Winston, OR
There are 49 properties for sale in the city of Winston . The median list price in Winston is $350,000 and the average price per square foot is $216. In January 2026, the average monthly cash on cash return in Winston is 5.00%. The average monthly rental income in Winston is $1,883.