Real Estate Investment Properties for Sale in Pleasanthill, OR

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
37308 HIGHWAY 58 Pleasanthill, OR Experience the best of Oregon's natural beauty and refined design with this extraordinary ...	5 beds \| 3 baths \| 3,288 sq.ft.	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $4693 Airbnb ROI: N/A Traditional ROI: 2%
35956 HIGHWAY 58 Pleasanthill, OR Amazing home and huge two story shop privately sited at the end of a 1/2 mile paved drivew...	2 beds \| 2 baths \| 3,216 sq.ft.	$1,195,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.68% Airbnb Rental Income: $886 Traditional Rental Income: $2544 Airbnb ROI: -1.11% Traditional ROI: 0.68%
37381 RIVERSIDE Dr Pleasanthill, OR New Price Improvement! Experience the ultimate in riverfront living on 3.31 private acres ...	4 beds \| 3 baths \| 2,930 sq.ft.	$1,095,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 3.2% Airbnb Rental Income: $1426 Traditional Rental Income: $4964 Airbnb ROI: -0.69% Traditional ROI: 3.2%
84545 DREW Ln Pleasanthill, OR Custom-designed by Arbor South and nestled on a private road in beautiful Pleasant Hill, t...	4 beds \| 2 baths \| 3,173 sq.ft.	$989,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.69% Airbnb Rental Income: $1426 Traditional Rental Income: $4185 Airbnb ROI: -0.77% Traditional ROI: 2.69%
Investment Properties for Sale in Other Cities of Oregon
8038 SE Salmon St Portland , OR You can have it all in this updated ranchalow at the foot of Mt. Tabor! All systems are up...	4 beds \| 2 baths \| 1,905 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $3239 Airbnb ROI: N/A Traditional ROI: 3.31%
1430 SW Highland Rd Portland , OR Privately tucked away and thoughtfully renovated, this one-of-a-kind home sits in one of P...	4 beds \| 3 baths \| 3,721 sq.ft.	$1,450,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.1% Airbnb Rental Income: $2294 Traditional Rental Income: $4123 Airbnb ROI: -0.68% Traditional ROI: 1.1%
20670 Comet Court Bend , OR Nestled in NE Bend, this home offers the perfect blend of modern comfort and natural beaut...	4 beds \| 3 baths \| 2,552 sq.ft.	$830,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $3876 Airbnb ROI: N/A Traditional ROI: 2.93%
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: N/A Traditional cash on cash: 3.89% Airbnb Rental Income: $null Traditional Rental Income: $3631 Airbnb ROI: N/A 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: -0.86% Traditional cash on cash: 0.4% Airbnb Rental Income: $2071 Traditional Rental Income: $3862 Airbnb ROI: -0.86% Traditional ROI: 0.4%
1134 SW Jefferson St #309 Portland , OR 1134 SW Jefferson St #309, Portland, OR 97201 \| Condo/Coop	1 beds \| 1 baths \| 756 sq.ft.	$175,000	Airbnb cash on cash: -2.93% Traditional cash on cash: 1.85% Airbnb Rental Income: $1139 Traditional Rental Income: $1600 Airbnb ROI: -2.93% Traditional ROI: 1.85%
922 NW 11th Ave #806 Portland , OR 922 NW 11th Ave #806, Portland, OR 97209 \| Condo/Coop	1 beds \| 2 baths \| 1,460 sq.ft.	$599,000	Airbnb cash on cash: -2.87% Traditional cash on cash: -0.44% Airbnb Rental Income: $1186 Traditional Rental Income: $2159 Airbnb ROI: -2.87% Traditional ROI: -0.44%
391 W 1st St Halsey , OR Vintage 1930âs farmhouse on a 0.23-acre commercially zoned lot in the heart of Halseyâ...	4 beds \| 2 baths \| 1,924 sq.ft.	$339,999	Airbnb cash on cash: N/A Traditional cash on cash: 9.64% Airbnb Rental Income: $null Traditional Rental Income: $3683 Airbnb ROI: N/A Traditional ROI: 9.64%
231 Dogwood Dr Gates , OR Accepted Offer with Contingencies. Storybook getaway that overlooks the majestic N Santiam...	N/A beds \| N/A baths \| 1,232 sq.ft.	$179,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.74% Airbnb Rental Income: $null Traditional Rental Income: $1961 Airbnb ROI: N/A Traditional ROI: 8.74%
950 Evergreen #309 Rd Woodburn , OR A Bumpable Offer has Been Accepted. Light & bright condo with Sunset and Peek-a-Boo Mounta...	2 beds \| 1 baths \| 921 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.69% Airbnb Rental Income: $null Traditional Rental Income: $1809 Airbnb ROI: N/A Traditional ROI: 7.69%
40615 Rodgers Mountain Lp Scio , OR Accepted Offer with Contingencies. Motivated Seller's! Horse lovers dream! Take a look at ...	3 beds \| 3 baths \| 1,768 sq.ft.	$1,125,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.93% Airbnb Rental Income: $null Traditional Rental Income: $2555 Airbnb ROI: N/A Traditional ROI: 0.93%
922 NW 11th Ave #104 Portland , OR 2 Bedrooms, 2 Full Baths plus loft space and private rooftop terrace. North Pearl living a...	2 beds \| 2 baths \| 1,713 sq.ft.	$825,000	Airbnb cash on cash: -3.75% Traditional cash on cash: -1.24% Airbnb Rental Income: $1227 Traditional Rental Income: $2764 Airbnb ROI: -3.75% Traditional ROI: -1.24%
5418 SW 34th Pl Portland , OR Welcome to this Doschdale gem. You will find this charmer tucked away in the hills of Port...	4 beds \| 3 baths \| 3,094 sq.ft.	$759,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $4405 Airbnb ROI: N/A Traditional ROI: 3.45%
408 NW 12th Ave #306 Portland , OR Priced to sell! Buy this beautiful condo today with the interest rate you have been waitin...	1 beds \| 1 baths \| 1,221 sq.ft.	$399,900	Airbnb cash on cash: -3.95% Traditional cash on cash: 0.36% Airbnb Rental Income: $1186 Traditional Rental Income: $2416 Airbnb ROI: -3.95% Traditional ROI: 0.36%
300 NW 8th Ave #303 Portland , OR 300 NW 8th Ave #303, Portland, OR 97209 \| Condo/Coop	N/A beds \| 1 baths \| 709 sq.ft.	$225,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.49% Airbnb Rental Income: $1336 Traditional Rental Income: $1386 Airbnb ROI: -0.68% Traditional ROI: 1.49%

Real Estate investment in Pleasanthill, OR

There are 4 properties for sale in the city of Pleasanthill . The median list price in Pleasanthill is $1,145,000 and the average price per square foot is $363. In February 2026, the average monthly cash on cash return in Pleasanthill is 2.00%. The average monthly rental income in Pleasanthill is $4,439.

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

There are 4 investment properties available for sale in Pleasanthill.

In 2026, the best neighborhood to buy investment property is Pleasanthill.

The ROI for Long-Term is higher than the Short-Term in Pleasanthill with average rental income of $4,439.

Your search for investment property begins and ends here

Investment Property for Sale in Pleasanthill, OR

37308 HIGHWAY 58

Pleasanthill, OR

5 beds | 3 baths | 3,288 sq.ft.

$1,650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2%

Airbnb Rental Income: $null

Traditional Rental Income: $4693

Airbnb ROI: N/A

Traditional ROI: 2%

35956 HIGHWAY 58

Pleasanthill, OR

2 beds | 2 baths | 3,216 sq.ft.

$1,195,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $886

Traditional Rental Income: $2544

Airbnb ROI: -1.11%

Traditional ROI: 0.68%

37381 RIVERSIDE Dr

Pleasanthill, OR

4 beds | 3 baths | 2,930 sq.ft.

$1,095,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $1426

Traditional Rental Income: $4964

Airbnb ROI: -0.69%

Traditional ROI: 3.2%

84545 DREW Ln

Pleasanthill, OR

4 beds | 2 baths | 3,173 sq.ft.

$989,000

Airbnb cash on cash: -0.77%

Traditional cash on cash: 2.69%

Airbnb Rental Income: $1426

Traditional Rental Income: $4185

Airbnb ROI: -0.77%

Traditional ROI: 2.69%

Investment Properties for Sale in Other Cities of Oregon

Portland , OR

4 beds | 2 baths | 1,905 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.31%

Airbnb Rental Income: $null

Traditional Rental Income: $3239

Airbnb ROI: N/A

Traditional ROI: 3.31%

Portland , OR

4 beds | 3 baths | 3,721 sq.ft.

$1,450,000

Airbnb cash on cash: -0.68%

Traditional cash on cash: 1.1%

Airbnb Rental Income: $2294

Traditional Rental Income: $4123

Airbnb ROI: -0.68%

Traditional ROI: 1.1%

Bend , OR

4 beds | 3 baths | 2,552 sq.ft.

$830,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.93%

Airbnb Rental Income: $null

Traditional Rental Income: $3876

Airbnb ROI: N/A

Traditional ROI: 2.93%

Bend , OR

4 beds | 3 baths | 2,584 sq.ft.

$679,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.89%

Airbnb Rental Income: $null

Traditional Rental Income: $3631

Airbnb ROI: N/A

Traditional ROI: 3.89%

Bend , OR

4 beds | 3 baths | 3,923 sq.ft.