Real Estate Investment Properties for Sale in Winchester, OR

Looking for investment property in Winchester, OR with high ROI ?

Explore a variety of short-term homes & houses in Winchester, OR. Invest wisely with VRBO & Winchester, 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 Winchester, OR

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
556 NORTH VIEW DR Winchester, OR Pride of ownership! Wonderful 4 bedroom home in North Roseburg Oak Valley Loop area that h...	4 beds \| 3 baths \| 2,581 sq.ft.	$595,000	Airbnb cash on cash: 3.46% Traditional cash on cash: 4.89% Airbnb Rental Income: $3571 Traditional Rental Income: $3584 Airbnb ROI: 3.46% Traditional ROI: 4.89%
230 SINGING WATERS RD Winchester, OR Welcome to your own slice of paradise along the North Umpqua River! Nestled on a tranquil,...	2 beds \| 3 baths \| 1,706 sq.ft.	$675,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 2.09% Airbnb Rental Income: $2592 Traditional Rental Income: $2392 Airbnb ROI: 1.42% Traditional ROI: 2.09%
459 OAK VALLEY LOOP Winchester, OR Custom Built Craftsman Style Home on Coveted Oak Valley Loop in Winchester, OR. Welcome to...	4 beds \| 4 baths \| 2,935 sq.ft.	$785,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 4.26% Airbnb Rental Income: $3571 Traditional Rental Income: $4293 Airbnb ROI: 2.2% Traditional ROI: 4.26%
Investment Properties for Sale in Other Cities of Oregon
4950 SE FRANKLIN ST #2 Portland , OR Rare Richmond ground floor condo in a boutique contemporary building. This spacious and we...	2 beds \| 1 baths \| 917 sq.ft.	$325,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 4.16% Airbnb Rental Income: $2990 Traditional Rental Income: $2404 Airbnb ROI: 3.83% Traditional ROI: 4.16%
1125 NW 9TH AVE #203 Portland , OR Lovely unit in the well-located Lexis Condominiums. Nice morning light - Easy urban livin...	1 beds \| 1 baths \| 707 sq.ft.	$280,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 2.39% Airbnb Rental Income: $2337 Traditional Rental Income: $1888 Airbnb ROI: 1.9% Traditional ROI: 2.39%
19421 Ironwood Circle Bend , OR Beautifully remodeled Broken Top townhome in the Tyrion Sky neighborhood. This stunning ho...	3 beds \| 4 baths \| 2,310 sq.ft.	$975,000	Airbnb cash on cash: 0.18% Traditional cash on cash: 1.22% Airbnb Rental Income: $3340 Traditional Rental Income: $3535 Airbnb ROI: 0.18% Traditional ROI: 1.22%
19595 Simpson Avenue Bend , OR This beautiful, free-standing, unattached SINGLE LEVEL TOWN HOME is a unique find in the p...	2 beds \| 3 baths \| 2,296 sq.ft.	$897,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 0.34% Airbnb Rental Income: $1915 Traditional Rental Income: $2727 Airbnb ROI: -1.24% Traditional ROI: 0.34%
19602 Painted Ridge Loop Bend , OR This townhome in Broken Top is surrounded by beautiful landscaping and serene ponds, provi...	3 beds \| 4 baths \| 2,110 sq.ft.	$1,030,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.76% Airbnb Rental Income: $2790 Traditional Rental Income: $3356 Airbnb ROI: -0.51% Traditional ROI: 0.76%
628 NE Vail Lane Bend , OR Looking for a lower interest rate? This townhome offers an assumable mortgage with a highl...	3 beds \| 3 baths \| 1,580 sq.ft.	$549,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 4.23% Airbnb Rental Income: $3481 Traditional Rental Income: $3283 Airbnb ROI: 3.12% Traditional ROI: 4.23%
15 SW Quail Butte Place Bend , OR Owner carry available at 4.25%! Rare, transferable STR license (with proven high-volume in...	3 beds \| 3 baths \| 3,923 sq.ft.	$2,099,999	Airbnb cash on cash: 0.24% Traditional cash on cash: 0.37% Airbnb Rental Income: $4543 Traditional Rental Income: $3862 Airbnb ROI: 0.24% Traditional ROI: 0.37%
56699 Lunar Drive Bend , OR Embrace the ultimate Central Oregon lifestyle just minutes from Sunriver, where outdoor ad...	5 beds \| 4 baths \| 2,908 sq.ft.	$888,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 3.99% Airbnb Rental Income: $6024 Traditional Rental Income: $4650 Airbnb ROI: 4.21% Traditional ROI: 3.99%
1841 CENTENNIAL BLVD Springfield , OR PRICE IMPROVED!! A must see in person to appreciate updates & space! This home is a newly ...	4 beds \| 1 baths \| 1,800 sq.ft.	$399,500	Airbnb cash on cash: 9.11% Traditional cash on cash: 4.57% Airbnb Rental Income: $5161 Traditional Rental Income: $2412 Airbnb ROI: 9.11% Traditional ROI: 4.57%
356 20TH ST Springfield , OR This charming 3 bedroom, 2 bathroom home close to schools, parks, shopping and recreation!...	3 beds \| 2 baths \| 1,222 sq.ft.	$393,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 5.4% Airbnb Rental Income: $3338 Traditional Rental Income: $2772 Airbnb ROI: 4.91% Traditional ROI: 5.4%
2125 ORR LN Eugene , OR Tastefully updated home located on a large, fully-fenced lot. Low-traffic neighborhood wit...	2 beds \| 1 baths \| 960 sq.ft.	$365,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 4.25% Airbnb Rental Income: $1928 Traditional Rental Income: $2191 Airbnb ROI: 1.99% Traditional ROI: 4.25%
3116 N VANCOUVER AVE Portland , OR Old school charm home in the hot Williams Ave corridor. Many updates have been done to th...	3 beds \| 1 baths \| 2,251 sq.ft.	$614,526	Airbnb cash on cash: 4.21% Traditional cash on cash: 2.47% Airbnb Rental Income: $4355 Traditional Rental Income: $2442 Airbnb ROI: 4.21% Traditional ROI: 2.47%
212 NE 80TH AVE Portland , OR Turnkey, modern, meticulously maintained 2-story live/work property could be used for many...	4 beds \| 3 baths \| 1,976 sq.ft.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $3549 Airbnb ROI: N/A Traditional ROI: 3.24%
8415 SE 17TH AVE Portland , OR The commercially zoned property is ideal for an office space, a live/work situation or for...	2 beds \| 2 baths \| 1,000 sq.ft.	$529,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 2.55% Airbnb Rental Income: $3019 Traditional Rental Income: $2236 Airbnb ROI: 2.73% Traditional ROI: 2.55%
1323 Alpine Lakes St SE Salem , OR Accepted Offer with Contingencies. This meticulously maintained two-story home features 4 ...	4 beds \| 3 baths \| 2,174 sq.ft.	$443,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.9% Airbnb Rental Income: $null Traditional Rental Income: $3771 Airbnb ROI: N/A Traditional ROI: 6.9%

Real Estate investment in Winchester, OR

There are 3 properties for sale in the city of Winchester . The median list price in Winchester is $675,000 and the average price per square foot is $280. In January 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $3,584.

Winchester, OR Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 3 investment properties available for sale in Winchester.

In 2025, the best neighborhood to buy investment property is Winchester.

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $3,584.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, OR

556 NORTH VIEW DR

Winchester, OR

4 beds | 3 baths | 2,581 sq.ft.

$595,000

Airbnb cash on cash: 3.46%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $3571

Traditional Rental Income: $3584

Airbnb ROI: 3.46%

Traditional ROI: 4.89%

230 SINGING WATERS RD

Winchester, OR

2 beds | 3 baths | 1,706 sq.ft.

$675,000

Airbnb cash on cash: 1.42%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $2592

Traditional Rental Income: $2392

Airbnb ROI: 1.42%

Traditional ROI: 2.09%

459 OAK VALLEY LOOP

Winchester, OR

4 beds | 4 baths | 2,935 sq.ft.

$785,000

Airbnb cash on cash: 2.2%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $3571

Traditional Rental Income: $4293

Airbnb ROI: 2.2%

Traditional ROI: 4.26%

Investment Properties for Sale in Other Cities of Oregon

Portland , OR

2 beds | 1 baths | 917 sq.ft.

$325,000

Airbnb cash on cash: 3.83%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $2990

Traditional Rental Income: $2404

Airbnb ROI: 3.83%

Traditional ROI: 4.16%

Portland , OR

1 beds | 1 baths | 707 sq.ft.

$280,000

Airbnb cash on cash: 1.9%

Traditional cash on cash: 2.39%

Airbnb Rental Income: $2337

Traditional Rental Income: $1888

Airbnb ROI: 1.9%

Traditional ROI: 2.39%

Bend , OR

3 beds | 4 baths | 2,310 sq.ft.

$975,000

Airbnb cash on cash: 0.18%

Traditional cash on cash: 1.22%

Airbnb Rental Income: $3340

Traditional Rental Income: $3535

Airbnb ROI: 0.18%

Traditional ROI: 1.22%

Bend , OR

2 beds | 3 baths | 2,296 sq.ft.

$897,000

Airbnb cash on cash: -1.24%

Traditional cash on cash: 0.34%

Airbnb Rental Income: $1915

Traditional Rental Income: $2727

Airbnb ROI: -1.24%

Traditional ROI: 0.34%

Bend , OR

3 beds | 4 baths | 2,110 sq.ft.

$1,030,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $2790

Traditional Rental Income: $3356

Airbnb ROI: -0.51%

Traditional ROI: 0.76%

Bend , OR

3 beds | 3 baths | 1,580 sq.ft.

$549,000