Real Estate Investment Properties for Sale in Oskaloosa, IA

Looking for investment property in Oskaloosa, IA with high ROI ?

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1329 Barclay Street Oskaloosa, IA Spacious Ranch home has 2 large bedrooms and 1 3/4 baths. Current owners have reconfigured...	2 beds \| 2 baths \| 1,347 sq.ft.	$209,900	Airbnb cash on cash: 1.08% Traditional cash on cash: 6.47% Airbnb Rental Income: $1118 Traditional Rental Income: $1815 Airbnb ROI: 1.08% Traditional ROI: 6.47%
712 N H Street Oskaloosa, IA Looking for an awesome garage?? This one is 24x36 with a dividing wall between the 2 stall...	3 beds \| 1 baths \| 1,276 sq.ft.	$162,500	Airbnb cash on cash: N/A Traditional cash on cash: 7.17% Airbnb Rental Income: $null Traditional Rental Income: $1529 Airbnb ROI: N/A Traditional ROI: 7.17%
812 8Th Avenue E Oskaloosa, IA Motivated Sellers! HUGE PRICE REDUCTION!! You've GOT to SEE this for yourself, pictures do...	4 beds \| 2 baths \| 1,632 sq.ft.	$234,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $1907 Airbnb ROI: N/A Traditional ROI: 6.14%
2010 Suffolk Road Oskaloosa, IA Open and spacious berm style home on 10.68 acres located on the edge of Oskaloosa city lim...	4 beds \| 2 baths \| 2,364 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.85% Airbnb Rental Income: $null Traditional Rental Income: $1743 Airbnb ROI: N/A Traditional ROI: 1.85%
436 N 4th Street Oskaloosa, IA Cute 4 bed, 2 bath home in great neighborhood! Walking distance to YMCA, city square, and ...	4 beds \| 2 baths \| 1,460 sq.ft.	$154,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.13% Airbnb Rental Income: $null Traditional Rental Income: $1935 Airbnb ROI: N/A Traditional ROI: 10.13%
1151 Clearview Drive Oskaloosa, IA Great location, large lot, well maintained home. Nicely landscaped and great sized yard, w...	3 beds \| 2 baths \| 1,733 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $1023 Airbnb ROI: N/A Traditional ROI: 1.63%
1409 J Avenue E Oskaloosa, IA Due to work schedules - showings will begin on Saturday March 28th at 9am and available we...	3 beds \| 2 baths \| 1,434 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $1673 Airbnb ROI: N/A Traditional ROI: 4.23%
328 N 6th Street Oskaloosa, IA The transformation is amazing on this property!!! This South Townhome used to be the kitch...	2 beds \| 2 baths \| 2,250 sq.ft.	$324,900	Airbnb cash on cash: -0.43% Traditional cash on cash: 4.03% Airbnb Rental Income: $1118 Traditional Rental Income: $2105 Airbnb ROI: -0.43% Traditional ROI: 4.03%
523 N B Street Oskaloosa, IA Welcome to 523 N B St, a beautifully renovated 3-bedroom, 2-bathroom home with a spacious ...	3 beds \| 2 baths \| 1,367 sq.ft.	$169,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.77% Airbnb Rental Income: $null Traditional Rental Income: $1769 Airbnb ROI: N/A Traditional ROI: 8.77%
605 Fairview Drive Oskaloosa, IA Ready for the next owner - 4 bedrooms - 3 baths - 2 car attached garage - .53-acre lot - L...	4 beds \| 3 baths \| 1,600 sq.ft.	$385,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.54% Airbnb Rental Income: $null Traditional Rental Income: $2901 Airbnb ROI: N/A Traditional ROI: 5.54%
1002 8th Avenue E Oskaloosa, IA ATTENTION INVESTORS & LANDLORDS!!! Investor Special! Great opportunity to add value and bu...	3 beds \| 1 baths \| 1,094 sq.ft.	$129,900	Airbnb cash on cash: N/A Traditional cash on cash: 11.07% Airbnb Rental Income: $null Traditional Rental Income: $1729 Airbnb ROI: N/A Traditional ROI: 11.07%
606 N 3Rd Street Oskaloosa, IA NEW LISTING!!! Check out this Beauitifully renovated 3 bedroom home with an open concept l...	3 beds \| 1 baths \| 1,040 sq.ft.	$183,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $1196 Airbnb ROI: N/A Traditional ROI: 4.73%
330 N 6th Street Oskaloosa, IA One-of-a-kind home blends timeless character with modern luxury. Originally part of a hist...	2 beds \| 2 baths \| 2,250 sq.ft.	$339,900	Airbnb cash on cash: 0.32% Traditional cash on cash: 3.36% Airbnb Rental Income: $1118 Traditional Rental Income: $1715 Airbnb ROI: 0.32% Traditional ROI: 3.36%
516 N G Street Oskaloosa, IA So charming! This one-level home sits on a large corner lot, blending mid-century characte...	3 beds \| 3 baths \| 1,376 sq.ft.	$187,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.04% Airbnb Rental Income: $null Traditional Rental Income: $2257 Airbnb ROI: N/A Traditional ROI: 10.04%
511 5Th Avenue W Oskaloosa, IA HUGE price adjustment!! SO much going for it- Spacious 5 BRs/3Bath Ranch Style home with f...	5 beds \| 3 baths \| 1,680 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.92% Airbnb Rental Income: $null Traditional Rental Income: $2361 Airbnb ROI: N/A Traditional ROI: 5.92%
411 C Avenue W Oskaloosa, IA 4-bedroom, 2 Bath Ranch home has 2 levels of living space. The MAIN FLOOR has an open Livi...	4 beds \| 2 baths \| 2,052 sq.ft.	$259,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.87% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: 6.87%
1215 Mabel Street Oskaloosa, IA Step into this beautifully updated three-bedroom home offering 1,288 sq. ft. of bright, in...	3 beds \| 2 baths \| 1,288 sq.ft.	$125,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.78% Airbnb Rental Income: $null Traditional Rental Income: $1684 Airbnb ROI: N/A Traditional ROI: 11.78%
415 College Hill Ave Oskaloosa, IA Welcome to this charming ranch home built in 1950, offering 2 bedrooms, 2 bathrooms, and 2...	2 beds \| 2 baths \| 1,136 sq.ft.	$165,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 8.61% Airbnb Rental Income: $1118 Traditional Rental Income: $1770 Airbnb ROI: 2.08% Traditional ROI: 8.61%
406 Evans Randolph Street Oskaloosa, IA Turn-key country charm meets outdoor living at 406 Evans Randolph St in Oskaloosa! This in...	2 beds \| 1 baths \| 1,054 sq.ft.	$225,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 5.29% Airbnb Rental Income: $1118 Traditional Rental Income: $1554 Airbnb ROI: 1.48% Traditional ROI: 5.29%
1 Walnut Drive Oskaloosa, IA Imagine yourself in the tranquil setting of this beautiful ranch home on a large lot on th...	4 beds \| 2 baths \| 2,118 sq.ft.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.41% Airbnb Rental Income: $null Traditional Rental Income: $2470 Airbnb ROI: N/A Traditional ROI: 8.41%
2739 255Th Street Oskaloosa, IA Check out this beautiful acreage located within Keomah Village's city limits, with views o...	4 beds \| 3 baths \| 2,597 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $2967 Airbnb ROI: N/A Traditional ROI: 3.79%
1141 Clearview Drive Oskaloosa, IA Be prepared to fall in love with this beautiful Ranch style home in the ever popular Clear...	3 beds \| 2 baths \| 1,040 sq.ft.	$246,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.79% Airbnb Rental Income: $null Traditional Rental Income: $1653 Airbnb ROI: N/A Traditional ROI: 4.79%
123 Geneva Drive Oskaloosa, IA Welcome to 123 Geneva in Oskaloosa! This fully updated 2-bedroom, 1-bath home offers moder...	2 beds \| 1 baths \| 880 sq.ft.	$251,900	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.22% Airbnb Rental Income: $1118 Traditional Rental Income: $1448 Airbnb ROI: 1.26% Traditional ROI: 4.22%
2521 Bill Bone Lane Oskaloosa, IA Nearly new 3-bedroom, 2-bath ranch on a half-acre lot with bonus cottage! Built in late 20...	3 beds \| 2 baths \| 1,512 sq.ft.	$312,800	Airbnb cash on cash: N/A Traditional cash on cash: 5.1% Airbnb Rental Income: $null Traditional Rental Income: $2203 Airbnb ROI: N/A Traditional ROI: 5.1%
811 6th Avenue E Oskaloosa, IA Affordable 1.5 story with fenced in backyard. Would make a good starter or investment prop...	3 beds \| 1 baths \| 1,127 sq.ft.	$85,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.14% Airbnb Rental Income: $null Traditional Rental Income: $1248 Airbnb ROI: N/A Traditional ROI: 11.14%
139 Geneva Drive Oskaloosa, IA This turn-key Ranch has been updated to offer a clean, updated aesthetic in a great neighb...	3 beds \| 2 baths \| 979 sq.ft.	$167,500	Airbnb cash on cash: N/A Traditional cash on cash: 7.79% Airbnb Rental Income: $null Traditional Rental Income: $1647 Airbnb ROI: N/A Traditional ROI: 7.79%
2611 Luminary Lane Oskaloosa, IA NEW LISTING... ACREAGE!!!! Take Note, properties like this do not come on the market often...	3 beds \| 3 baths \| 2,411 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.39% Airbnb Rental Income: $null Traditional Rental Income: $2740 Airbnb ROI: N/A Traditional ROI: 5.39%
303 S 2nd Street #A Oskaloosa, IA Condo Living Opportunity!!! As you enter Unit A, there is a large walk-in closet for coats...	2 beds \| 2 baths \| 1,361 sq.ft.	$159,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 8.56% Airbnb Rental Income: $1118 Traditional Rental Income: $1748 Airbnb ROI: 1.97% Traditional ROI: 8.56%
815 A Avenue E Oskaloosa, IA This beautiful & spacious home is full of charm and character! Hardwood floors, several bu...	4 beds \| 2 baths \| 2,067 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.32% Airbnb Rental Income: $null Traditional Rental Income: $2323 Airbnb ROI: N/A Traditional ROI: 10.32%

Real Estate investment in Oskaloosa, IA

There are 39 properties for sale in the city of Oskaloosa . The median list price in Oskaloosa is $172,411 and the average price per square foot is $103. In June 2026, the average monthly cash on cash return in Oskaloosa is 8.00%. The average monthly rental income in Oskaloosa is $1,769.

Oskaloosa, IA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 39 investment properties available for sale in Oskaloosa.

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

The ROI for Long-Term is higher than the Short-Term in Oskaloosa with average rental income of $1,769.

Your search for investment property begins and ends here

Investment Property for Sale in Oskaloosa, IA

1329 Barclay Street

Oskaloosa, IA

2 beds | 2 baths | 1,347 sq.ft.

$209,900

Airbnb cash on cash: 1.08%

Traditional cash on cash: 6.47%

Airbnb Rental Income: $1118

Traditional Rental Income: $1815

Airbnb ROI: 1.08%

Traditional ROI: 6.47%

712 N H Street

Oskaloosa, IA

3 beds | 1 baths | 1,276 sq.ft.

$162,500

Airbnb cash on cash: N/A

Traditional cash on cash: 7.17%

Airbnb Rental Income: $null

Traditional Rental Income: $1529

Airbnb ROI: N/A

Traditional ROI: 7.17%

812 8Th Avenue E

Oskaloosa, IA

4 beds | 2 baths | 1,632 sq.ft.

$234,500

Airbnb cash on cash: N/A

Traditional cash on cash: 6.14%

Airbnb Rental Income: $null

Traditional Rental Income: $1907

Airbnb ROI: N/A

Traditional ROI: 6.14%

2010 Suffolk Road

Oskaloosa, IA

4 beds | 2 baths | 2,364 sq.ft.

$475,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.85%

Airbnb Rental Income: $null

Traditional Rental Income: $1743

Airbnb ROI: N/A

Traditional ROI: 1.85%

436 N 4th Street

Oskaloosa, IA

4 beds | 2 baths | 1,460 sq.ft.

$154,000

Airbnb cash on cash: N/A

Traditional cash on cash: 10.13%

Airbnb Rental Income: $null

Traditional Rental Income: $1935

Airbnb ROI: N/A

Traditional ROI: 10.13%

1151 Clearview Drive

Oskaloosa, IA

3 beds | 2 baths | 1,733 sq.ft.

$265,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.63%

Airbnb Rental Income: $null

Traditional Rental Income: $1023

Airbnb ROI: N/A

Traditional ROI: 1.63%

1409 J Avenue E

Oskaloosa, IA

3 beds | 2 baths | 1,434 sq.ft.

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.23%

Airbnb Rental Income: $null

Traditional Rental Income: $1673

Airbnb ROI: N/A

Traditional ROI: 4.23%

328 N 6th Street

Oskaloosa, IA

2 beds | 2 baths | 2,250 sq.ft.

$324,900

Airbnb cash on cash: -0.43%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $1118

Traditional Rental Income: $2105

Airbnb ROI: -0.43%