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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
464 OAK VALLEY LOOP Winchester, OR PRICE IMPROVEMENT to $675,500 !! Discover this lovely, well-kept single-level home, perfec...	4 beds \| 3 baths \| 2,760 sq.ft.	$669,500	Airbnb cash on cash: 0% Traditional cash on cash: 4.69% Airbnb Rental Income: $1519 Traditional Rental Income: $4007 Airbnb ROI: 0% Traditional ROI: 4.69%
148 WILD FERN DR Winchester, OR Located in one of the most desirable subdivisions in Douglas County, this stunning chalet ...	3 beds \| 3 baths \| 3,460 sq.ft.	$549,900	Airbnb cash on cash: 0.21% Traditional cash on cash: 5.59% Airbnb Rental Income: $1558 Traditional Rental Income: $3872 Airbnb ROI: 0.21% Traditional ROI: 5.59%
290 SINGING WATERS RD Winchester, OR Peaceful setting on the North Umpqua River close to town. Paved, private boat access ramp ...	3 beds \| 2 baths \| 1,904 sq.ft.	$749,900	Airbnb cash on cash: -0.03% Traditional cash on cash: 3.35% Airbnb Rental Income: $1558 Traditional Rental Income: $3469 Airbnb ROI: -0.03% Traditional ROI: 3.35%
356 WILD FERN DR Winchester, OR Welcome to this beautifully appointed 2,688 sq ft home nestled on a serene 0.41-acre lot i...	5 beds \| 4 baths \| 2,688 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.85% Airbnb Rental Income: $null Traditional Rental Income: $3622 Airbnb ROI: N/A Traditional ROI: 5.85%
Investment Properties for Sale in Other Cities of Oregon
6120 N MONTANA AVE Portland , OR Classic North Portland living! This tri-level home offers a smart layout with 3 bedrooms u...	4 beds \| 2 baths \| 3,080 sq.ft.	$559,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 3.98% Airbnb Rental Income: $1732 Traditional Rental Income: $3170 Airbnb ROI: 0.31% Traditional ROI: 3.98%
1500 SW PARK AVE #119 Portland , OR Welcome to this beautifully updated, quiet corner unit located in a desirable building jus...	1 beds \| 1 baths \| 727 sq.ft.	$290,000	Airbnb cash on cash: -2.36% Traditional cash on cash: 1.92% Airbnb Rental Income: $1270 Traditional Rental Income: $2039 Airbnb ROI: -2.36% Traditional ROI: 1.92%
1125 NW 9TH AVE #203 Portland , OR Lovely unit in the well-located Lexis Condominiums. Gorgeous morning light - Easy urban l...	1 beds \| 1 baths \| 707 sq.ft.	$225,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 3.6% Airbnb Rental Income: $1365 Traditional Rental Income: $2002 Airbnb ROI: -1.35% Traditional ROI: 3.6%
3409 LAKESIDE DR Eugene , OR This one level stunning custom home offers comfort, style, and thoughtful design in the de...	4 beds \| 4 baths \| 3,042 sq.ft.	$998,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 3.26% Airbnb Rental Income: $1634 Traditional Rental Income: $5481 Airbnb ROI: -1.38% Traditional ROI: 3.26%
3237 TIMBERLINE DR Eugene , OR Beautifully updated home in the coveted Southwest Hills! This 5-bedroom (or 4 + large bonu...	5 beds \| 3 baths \| 2,728 sq.ft.	$799,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $4282 Airbnb ROI: N/A Traditional ROI: 3.31%
19442 Chip Shot Lane Bend , OR Seller Financing Available-save money and ''buy'' yourself some time for interest rates to...	3 beds \| 4 baths \| 2,703 sq.ft.	$875,000	Airbnb cash on cash: -1.46% Traditional cash on cash: 1.97% Airbnb Rental Income: $1733 Traditional Rental Income: $4045 Airbnb ROI: -1.46% Traditional ROI: 1.97%
20560 Boyd Court Bend , OR Stunningly remodeled home in a prime location! Enjoy convenient access to Hwy 97 and the c...	4 beds \| 3 baths \| 2,584 sq.ft.	$679,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.89% Airbnb Rental Income: $1136 Traditional Rental Income: $3631 Airbnb ROI: -0.64% Traditional ROI: 3.89%
15 SW Quail Butte Place Bend , OR MOTIVATED SELLERS! 3923 sq ft home on a stunning .62 acre lot, offering breathtaking sunse...	4 beds \| 3 baths \| 3,923 sq.ft.	$1,999,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.4% Airbnb Rental Income: $1822 Traditional Rental Income: $3862 Airbnb ROI: -0.97% Traditional ROI: 0.4%
56081 Snow Goose Court Bend , OR Welcome to your private Central Oregon retreat with breathtaking views and direct access t...	3 beds \| 3 baths \| 2,715 sq.ft.	$1,395,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 1.49% Airbnb Rental Income: $1144 Traditional Rental Income: $3812 Airbnb ROI: -0.86% Traditional ROI: 1.49%
17155 Avocet Drive Bend , OR Escape the bustle of Bend to your serene family retreat -- a charming 3 bed, 2.5 bath cust...	3 beds \| 3 baths \| 1,420 sq.ft.	$589,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 3.05% Airbnb Rental Income: $1144 Traditional Rental Income: $2703 Airbnb ROI: -0.47% Traditional ROI: 3.05%
16973 Downey Road Bend , OR Located minutes to Sunriver, Deschutes River and Cascade Lakes. Downey road ends at the De...	3 beds \| 2 baths \| 1,712 sq.ft.	$425,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.22% Airbnb Rental Income: $1144 Traditional Rental Income: $2874 Airbnb ROI: -0.07% Traditional ROI: 5.22%
3516 SW 1ST AVE Portland , OR Donât miss this charming SW Portland bungalow, perfectly tucked away on a quiet street w...	2 beds \| 2 baths \| 1,354 sq.ft.	$499,900	Airbnb cash on cash: 0.8% Traditional cash on cash: 2.9% Airbnb Rental Income: $2060 Traditional Rental Income: $2506 Airbnb ROI: 0.8% Traditional ROI: 2.9%
1926 W BURNSIDE ST #301 Portland , OR Truly live among all the action when you live at The Civic, a LEED Gold certified building...	2 beds \| 2 baths \| 1,331 sq.ft.	$449,000	Airbnb cash on cash: -2.72% Traditional cash on cash: 0.44% Airbnb Rental Income: $1458 Traditional Rental Income: $2354 Airbnb ROI: -2.72% Traditional ROI: 0.44%
2850 SE 50TH AVE Portland , OR Light and bright condo close to everything! Within a couple of blocks to Franklin High and...	2 beds \| 1 baths \| 920 sq.ft.	$274,900	Airbnb cash on cash: 0.35% Traditional cash on cash: 2.47% Airbnb Rental Income: $1955 Traditional Rental Income: $1990 Airbnb ROI: 0.35% Traditional ROI: 2.47%
443 Geri St NW Albany , OR Beautiful home w/open floor plan, 9' ceilings, gas FP, & updated powder rm on main. Kitche...	3 beds \| 3 baths \| 1,740 sq.ft.	$459,900	Airbnb cash on cash: 0.58% Traditional cash on cash: 5.25% Airbnb Rental Income: $1646 Traditional Rental Income: $3191 Airbnb ROI: 0.58% Traditional ROI: 5.25%

Real Estate investment in Winchester, OR

There are 4 properties for sale in the city of Winchester . The median list price in Winchester is $609,700 and the average price per square foot is $226. In November 2025, the average monthly cash on cash return in Winchester is 5.00%. The average monthly rental income in Winchester is $3,747.

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

There are 4 investment properties available for sale in Winchester.

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

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $1,558.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, OR

464 OAK VALLEY LOOP

Winchester, OR

4 beds | 3 baths | 2,760 sq.ft.

$669,500

Airbnb cash on cash: 0%

Traditional cash on cash: 4.69%

Airbnb Rental Income: $1519

Traditional Rental Income: $4007

Airbnb ROI: 0%

Traditional ROI: 4.69%

148 WILD FERN DR

Winchester, OR

3 beds | 3 baths | 3,460 sq.ft.

$549,900

Airbnb cash on cash: 0.21%

Traditional cash on cash: 5.59%

Airbnb Rental Income: $1558

Traditional Rental Income: $3872

Airbnb ROI: 0.21%

Traditional ROI: 5.59%

290 SINGING WATERS RD

Winchester, OR

3 beds | 2 baths | 1,904 sq.ft.

$749,900

Airbnb cash on cash: -0.03%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $1558

Traditional Rental Income: $3469

Airbnb ROI: -0.03%

Traditional ROI: 3.35%

356 WILD FERN DR

Winchester, OR

5 beds | 4 baths | 2,688 sq.ft.

$499,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.85%

Airbnb Rental Income: $null

Traditional Rental Income: $3622

Airbnb ROI: N/A

Traditional ROI: 5.85%

Investment Properties for Sale in Other Cities of Oregon

Portland , OR

4 beds | 2 baths | 3,080 sq.ft.

$559,000

Airbnb cash on cash: 0.31%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $1732

Traditional Rental Income: $3170

Airbnb ROI: 0.31%

Traditional ROI: 3.98%

Portland , OR

1 beds | 1 baths | 727 sq.ft.

$290,000

Airbnb cash on cash: -2.36%

Traditional cash on cash: 1.92%

Airbnb Rental Income: $1270

Traditional Rental Income: $2039

Airbnb ROI: -2.36%

Traditional ROI: 1.92%

Portland , OR

1 beds | 1 baths | 707 sq.ft.

$225,000

Airbnb cash on cash: -1.35%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $1365

Traditional Rental Income: $2002

Airbnb ROI: -1.35%

Traditional ROI: 3.6%

Eugene , OR

4 beds | 4 baths | 3,042 sq.ft.

$998,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 3.26%

Airbnb Rental Income: $1634

Traditional Rental Income: $5481

Airbnb ROI: -1.38%

Traditional ROI: 3.26%

Eugene , OR

5 beds | 3 baths | 2,728 sq.ft.