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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
614 S D Street Oskaloosa, IA SELLERS ARE MOTIVATED FOR THIS HOME TO BE YOUR HOME BY CHRISTMAS! Welcome to this stunnin...	4 beds \| 3 baths \| 1,664 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.04% Airbnb Rental Income: $null Traditional Rental Income: $2404 Airbnb ROI: N/A Traditional ROI: 4.04%
602 S H Street Oskaloosa, IA Welcome to this stunning 4 bedroom, 3 bath split-level home that is sure to impress. Built...	4 beds \| 3 baths \| 1,344 sq.ft.	$299,999	Airbnb cash on cash: N/A Traditional cash on cash: 5.43% Airbnb Rental Income: $null Traditional Rental Income: $2352 Airbnb ROI: N/A Traditional ROI: 5.43%
907 G Avenue W Oskaloosa, IA This charming bungalow offers an affordable alternative to renting and is ready for you to...	2 beds \| 1 baths \| 672 sq.ft.	$109,500	Airbnb cash on cash: 4.06% Traditional cash on cash: 10.74% Airbnb Rental Income: $1114 Traditional Rental Income: $1447 Airbnb ROI: 4.06% Traditional ROI: 10.74%
2304 Ridgeway Avenue Oskaloosa, IA Welcome home to this well maintained 3 bedroom, 2 bath located in an established neighborh...	3 beds \| 2 baths \| 1,441 sq.ft.	$248,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.38% Airbnb Rental Income: $null Traditional Rental Income: $1904 Airbnb ROI: N/A Traditional ROI: 5.38%
1109 N 2Nd Street Oskaloosa, IA Welcome to 1109 North 2nd Street, Oskaloosa, IA! This charming home blends timeless charac...	3 beds \| 2 baths \| 1,451 sq.ft.	$162,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.1% Airbnb Rental Income: $null Traditional Rental Income: $1852 Airbnb ROI: N/A Traditional ROI: 9.1%
475 N 9Th Street Oskaloosa, IA Welcome to this beautifully updated 3-bedroom, 2-bath home just minutes from the heart of ...	3 beds \| 2 baths \| 1,872 sq.ft.	$219,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.31% Airbnb Rental Income: $null Traditional Rental Income: $2114 Airbnb ROI: N/A Traditional ROI: 7.31%
417 College Hill Avenue Oskaloosa, IA Welcome to 417 College Hill Avenue, Oskaloosa, IA! This cozy, fully renovated home is move...	3 beds \| 1 baths \| 960 sq.ft.	$164,983	Airbnb cash on cash: N/A Traditional cash on cash: 6.9% Airbnb Rental Income: $null Traditional Rental Income: $1463 Airbnb ROI: N/A Traditional ROI: 6.9%
462 N 9Th Street Oskaloosa, IA If you are looking for exceptional GARAGE space--- this one's for YOU!! Not one, but two! ...	3 beds \| 2 baths \| 2,288 sq.ft.	$227,700	Airbnb cash on cash: N/A Traditional cash on cash: 8.36% Airbnb Rental Income: $null Traditional Rental Income: $2380 Airbnb ROI: N/A Traditional ROI: 8.36%
1117 3Rd Avenue E Oskaloosa, IA Welcome to this charming ranch-style home in Oskaloosa! Built in 1953, this 3-bed, 1-bath ...	3 beds \| 1 baths \| 1,692 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.32% Airbnb Rental Income: $null Traditional Rental Income: $1630 Airbnb ROI: N/A Traditional ROI: 6.32%
1111 Mabel Street Oskaloosa, IA 1.5 Story 3-Bedroom, 2-Bath Home is ready for you to move into! The Main floor has a spaci...	3 beds \| 2 baths \| 1,272 sq.ft.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.82% Airbnb Rental Income: $null Traditional Rental Income: $1808 Airbnb ROI: N/A Traditional ROI: 8.82%
1704 S 5Th Street Oskaloosa, IA Here's an updated Ranch on a quiet street with two beautiful Autumn Blaze Maple trees shad...	3 beds \| 2 baths \| 1,040 sq.ft.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $1687 Airbnb ROI: N/A Traditional ROI: 6.3%
328 N 6th Street Oskaloosa, IA The transformation is amazing on this property!!! This South Duplex used to be the kitche...	2 beds \| 2 baths \| 2,250 sq.ft.	$355,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.96% Airbnb Rental Income: $null Traditional Rental Income: $2105 Airbnb ROI: N/A Traditional ROI: 4.96%
1703 N Park Avenue Oskaloosa, IA IN-TOWN ACREAGE! This updated home sits on 1.17 acres near the hospital and offers the per...	4 beds \| 3 baths \| 4,400 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.65% Airbnb Rental Income: $null Traditional Rental Income: $2813 Airbnb ROI: N/A Traditional ROI: 3.65%
2134 310Th Street Oskaloosa, IA You say you want to enjoy an acreage on hard surface road, not too far from town? You wan...	3 beds \| 2 baths \| 1,636 sq.ft.	$560,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $2121 Airbnb ROI: N/A Traditional ROI: 2.45%
1012 5th Avenue E Oskaloosa, IA Check out this charming home located on a quiet street on the east side of town with a qua...	3 beds \| 2 baths \| 1,028 sq.ft.	$170,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.8% Airbnb Rental Income: $null Traditional Rental Income: $2246 Airbnb ROI: N/A Traditional ROI: 10.8%
502 S Market Street Oskaloosa, IA Great location! Sits on corner lot. Newly updated 2 story home features 4 bedrooms and 1.5...	4 beds \| 2 baths \| 2,009 sq.ft.	$189,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.74% Airbnb Rental Income: $null Traditional Rental Income: $2395 Airbnb ROI: N/A Traditional ROI: 10.74%
2775 Osburn Avenue Oskaloosa, IA Spacious Luxury Home with a Amazing Sized Morton building on 4 gross acres m/l is ready fo...	5 beds \| 5 baths \| 5,040 sq.ft.	$1,140,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $5216 Airbnb ROI: N/A Traditional ROI: 2.88%
1002 8th Avenue E Oskaloosa, IA Welcome to this cozy 3 bedroom bungalow home! With a partially fenced yard and an extra la...	3 beds \| 1 baths \| 1,094 sq.ft.	$139,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.31% Airbnb Rental Income: $null Traditional Rental Income: $1729 Airbnb ROI: N/A Traditional ROI: 10.31%
2120 263rd st. Oskaloosa, IA Location, location, location. Close to town, with some land 8 acres m/l and some privacy! ...	5 beds \| 2 baths \| 2,599 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.44% Airbnb Rental Income: $null Traditional Rental Income: $2572 Airbnb ROI: N/A Traditional ROI: 5.44%
2710 248th Street Oskaloosa, IA Enjoy peaceful country living on 2 acres with the convenience of a hard-surface road. This...	2 beds \| 3 baths \| 1,516 sq.ft.	$299,900	Airbnb cash on cash: 0.47% Traditional cash on cash: 5.44% Airbnb Rental Income: $1114 Traditional Rental Income: $2141 Airbnb ROI: 0.47% Traditional ROI: 5.44%
1105 N 3Rd Street Oskaloosa, IA This ranch-style home features a charming front deck and a spacious living room. The kitch...	3 beds \| 2 baths \| 1,676 sq.ft.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.27% Airbnb Rental Income: $null Traditional Rental Income: $2003 Airbnb ROI: N/A Traditional ROI: 8.27%
611 S Market Street Oskaloosa, IA 2-story home close to downtown. Large kitchen with eat-in area with plenty of cabinets and...	3 beds \| 2 baths \| 1,604 sq.ft.	$165,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.03% Airbnb Rental Income: $null Traditional Rental Income: $1974 Airbnb ROI: N/A Traditional ROI: 10.03%
1117 3rd Avenue Oskaloosa, IA Welcome to this charming ranch-style home in Oskaloosa! Built in 1953, this 3-bed, 1-bath ...	3 beds \| 1 baths \| 992 sq.ft.	$182,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.04% Airbnb Rental Income: $null Traditional Rental Income: $1565 Airbnb ROI: N/A Traditional ROI: 6.04%
306 S 11th Street Oskaloosa, IA A stunning example of modern, maintenance-free living! This newer 2-bedroom, 2-bath townho...	2 beds \| 2 baths \| 1,586 sq.ft.	$325,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 5.7% Airbnb Rental Income: $1114 Traditional Rental Income: $2293 Airbnb ROI: 0.61% Traditional ROI: 5.7%
136 Solar Drive Oskaloosa, IA This charming little gem just hit the market and you wont want to miss checking it out! C...	2 beds \| 2 baths \| 1,428 sq.ft.	$234,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 6.38% Airbnb Rental Income: $1114 Traditional Rental Income: $1925 Airbnb ROI: 1.04% Traditional ROI: 6.38%
129 K Avenue E Oskaloosa, IA Are you looking for an in town acreage? This updated, well-maintained 1920s home is situ...	4 beds \| 3 baths \| 1,646 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $2467 Airbnb ROI: N/A Traditional ROI: 6.02%
714 1st Avenue E Oskaloosa, IA Bursting with character and timeless charm, this inviting home offers the perfect blend of...	4 beds \| 3 baths \| 2,058 sq.ft.	$214,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.99% Airbnb Rental Income: $null Traditional Rental Income: $2744 Airbnb ROI: N/A Traditional ROI: 10.99%
505 A Avenue E Oskaloosa, IA Lots of nice improvements, great potential! Tall ceilings, 2 bedrooms, 1 updated bath, ha...	2 beds \| 1 baths \| 1,188 sq.ft.	$130,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 11.3% Airbnb Rental Income: $1114 Traditional Rental Income: $1744 Airbnb ROI: 3.27% Traditional ROI: 11.3%
1213 9th Avenue E Oskaloosa, IA Welcome to this beautifully maintained 1,816 sq. ft. home offering warmth, character, and ...	3 beds \| 2 baths \| 1,816 sq.ft.	$232,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.16% Airbnb Rental Income: $null Traditional Rental Income: $2159 Airbnb ROI: N/A Traditional ROI: 7.16%
1014 N Market Street Oskaloosa, IA Welcome home! This beautifully maintained 3-bedroom, 2.5-bath residence perfectly blends t...	3 beds \| 3 baths \| 2,739 sq.ft.	$294,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.4% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 7.4%
2226 Lynndale Road Oskaloosa, IA This ranch-style residence is located on the outskirts of town and features three bedrooms...	3 beds \| 3 baths \| 2,491 sq.ft.	$259,500	Airbnb cash on cash: N/A Traditional cash on cash: 8.58% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 8.58%
1616 S 7Th Street Oskaloosa, IA Well kept ranch home In a quiet and desirable neighborhood. This property sits on a corne...	2 beds \| 1 baths \| 960 sq.ft.	$164,900	Airbnb cash on cash: 2.05% Traditional cash on cash: 6.33% Airbnb Rental Income: $1114 Traditional Rental Income: $1413 Airbnb ROI: 2.05% Traditional ROI: 6.33%
1004 4th Avenue E Oskaloosa, IA 2BR, 1 3/4 BA Ranch style home with partially finished basement and additional non-conform...	2 beds \| 2 baths \| 780 sq.ft.	$120,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 10.15% Airbnb Rental Income: $1114 Traditional Rental Income: $1580 Airbnb ROI: 2.89% Traditional ROI: 10.15%
411 College Hill Drive Oskaloosa, IA Welcome home to this charming 2-bedroom, 1-bath residence nestled in a quiet neighborhood ...	2 beds \| 2 baths \| 1,032 sq.ft.	$169,999	Airbnb cash on cash: 1.88% Traditional cash on cash: 7.47% Airbnb Rental Income: $1114 Traditional Rental Income: $1645 Airbnb ROI: 1.88% Traditional ROI: 7.47%
2645 255Th Street Oskaloosa, IA Checking all the boxes with this acreage! 4.29 acres within 5 miles of downtown Oskaloosa....	4 beds \| 2 baths \| 2,752 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $2623 Airbnb ROI: N/A Traditional ROI: 4.89%
1216 Santa Clara Street Oskaloosa, IA Newly updated, paint, flooring, carpet MOVE IN READY ranch! Come see this 2004 built 3 be...	3 beds \| 3 baths \| 1,104 sq.ft.	$218,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $1813 Airbnb ROI: N/A Traditional ROI: 6.02%
2223 290Th Street Oskaloosa, IA Discover this property packed with potential! 3 bedroom, 2 bath manufactured home sits on...	3 beds \| 2 baths \| 1,152 sq.ft.	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 10.23% Airbnb Rental Income: $null Traditional Rental Income: $1631 Airbnb ROI: N/A Traditional ROI: 10.23%
2409 270Th Street Oskaloosa, IA Great location just southeast of Oskaloosa. Be at Oskaloosa Golf or on the square in less...	4 beds \| 3 baths \| 2,352 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.35% Airbnb Rental Income: $null Traditional Rental Income: $2708 Airbnb ROI: N/A Traditional ROI: 4.35%
214 C Avenue E Oskaloosa, IA Well cared for Ranch style home just blocks from the Historic Oskaloosa Downtown Square. I...	3 beds \| 3 baths \| 1,752 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.67% Airbnb Rental Income: $null Traditional Rental Income: $2356 Airbnb ROI: N/A Traditional ROI: 7.67%
708 S 7Th Street Oskaloosa, IA Welcome to 708 South 7th Street in Oskaloosa â a charming, move-in-ready home that might...	2 beds \| 2 baths \| 1,440 sq.ft.	$149,000	Airbnb cash on cash: 2.68% Traditional cash on cash: 10.88% Airbnb Rental Income: $1114 Traditional Rental Income: $1909 Airbnb ROI: 2.68% Traditional ROI: 10.88%

Real Estate investment in Oskaloosa, IA

There are 41 properties for sale in the city of Oskaloosa . The median list price in Oskaloosa is $216,000 and the average price per square foot is $126. In December 2025, the average monthly cash on cash return in Oskaloosa is 7.00%. The average monthly rental income in Oskaloosa is $2,054.

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

There are 41 investment properties available for sale in Oskaloosa.

In 2025, 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 $2,054.

Your search for investment property begins and ends here

Investment Property for Sale in Oskaloosa, IA

614 S D Street

Oskaloosa, IA

4 beds | 3 baths | 1,664 sq.ft.

$349,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.04%

Airbnb Rental Income: $null

Traditional Rental Income: $2404

Airbnb ROI: N/A

Traditional ROI: 4.04%

602 S H Street

Oskaloosa, IA

4 beds | 3 baths | 1,344 sq.ft.

$299,999

Airbnb cash on cash: N/A

Traditional cash on cash: 5.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2352

Airbnb ROI: N/A

Traditional ROI: 5.43%

907 G Avenue W

Oskaloosa, IA

2 beds | 1 baths | 672 sq.ft.

$109,500

Airbnb cash on cash: 4.06%

Traditional cash on cash: 10.74%

Airbnb Rental Income: $1114

Traditional Rental Income: $1447

Airbnb ROI: 4.06%

Traditional ROI: 10.74%

2304 Ridgeway Avenue

Oskaloosa, IA

3 beds | 2 baths | 1,441 sq.ft.

$248,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.38%

Airbnb Rental Income: $null

Traditional Rental Income: $1904

Airbnb ROI: N/A

Traditional ROI: 5.38%

1109 N 2Nd Street

Oskaloosa, IA

3 beds | 2 baths | 1,451 sq.ft.

$162,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.1%

Airbnb Rental Income: $null

Traditional Rental Income: $1852

Airbnb ROI: N/A

Traditional ROI: 9.1%

475 N 9Th Street

Oskaloosa, IA

3 beds | 2 baths | 1,872 sq.ft.

$219,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.31%

Airbnb Rental Income: $null

Traditional Rental Income: $2114

Airbnb ROI: N/A

Traditional ROI: 7.31%

417 College Hill Avenue

Oskaloosa, IA

3 beds | 1 baths | 960 sq.ft.

$164,983

Airbnb cash on cash: N/A

Traditional cash on cash: 6.9%

Airbnb Rental Income: $null

Traditional Rental Income: $1463

Airbnb ROI: N/A

Traditional ROI: 6.9%

462 N 9Th Street

Oskaloosa, IA

3 beds | 2 baths | 2,288 sq.ft.

$227,700

Airbnb cash on cash: N/A

Traditional cash on cash: 8.36%

Airbnb Rental Income: $null

Traditional Rental Income: $2380

Airbnb ROI: N/A