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
614 S D Street Oskaloosa, IA Welcome to this stunning 4-bedroom, 3-bath home offering the perfect blend of comfort and ...	4 beds \| 3 baths \| 1,664 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.65% Airbnb Rental Income: $null Traditional Rental Income: $2404 Airbnb ROI: N/A Traditional ROI: 3.65%
214 Terrace Drive Oskaloosa, IA Stylish four bedroom home in an established neighborhood in a quiet, east part of Oskaloos...	4 beds \| 3 baths \| 2,001 sq.ft.	$279,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.73% Airbnb Rental Income: $null Traditional Rental Income: $2666 Airbnb ROI: N/A Traditional ROI: 7.73%
310 N 8Th Street Oskaloosa, IA Excellent location on a quiet tree lined street in a great neighborhood! Tired of being cr...	3 beds \| 2 baths \| 2,054 sq.ft.	$259,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.83% Airbnb Rental Income: $null Traditional Rental Income: $2316 Airbnb ROI: N/A Traditional ROI: 6.83%
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.	$164,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.93% Airbnb Rental Income: $null Traditional Rental Income: $1852 Airbnb ROI: N/A Traditional ROI: 8.93%
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%
1702 Pella Avenue Oskaloosa, IA Your acreage in the city limits is here! 3-bedroom, 3-bath home located on 4.61 acres. L...	4 beds \| 3 baths \| 1,988 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.43% Airbnb Rental Income: $null Traditional Rental Income: $2447 Airbnb ROI: N/A Traditional ROI: 6.43%
101 4Th Avenue W Oskaloosa, IA This home features three bedrooms and three bathrooms, along with a stylish kitchen that b...	3 beds \| 3 baths \| 1,680 sq.ft.	$212,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.59% Airbnb Rental Income: $null Traditional Rental Income: $1930 Airbnb ROI: N/A Traditional ROI: 6.59%
815 11Th Avenue W Oskaloosa, IA This well-maintained home is ready for you to move in! It boasts a great location, situate...	3 beds \| 3 baths \| 1,512 sq.ft.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $1570 Airbnb ROI: N/A Traditional ROI: 3.74%
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.	$169,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.26% Airbnb Rental Income: $null Traditional Rental Income: $1808 Airbnb ROI: N/A Traditional ROI: 8.26%
1002 Maywood Drive Oskaloosa, IA This 3-bedroom, 2-bath home features a large backyard with shade trees and a nice deck. F...	3 beds \| 2 baths \| 1,232 sq.ft.	$214,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.54% Airbnb Rental Income: $null Traditional Rental Income: $1950 Airbnb ROI: N/A Traditional ROI: 6.54%
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.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.58% Airbnb Rental Income: $null Traditional Rental Income: $2105 Airbnb ROI: N/A Traditional ROI: 4.58%
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.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $2813 Airbnb ROI: N/A Traditional ROI: 3.61%
1815 S 2nd Street Oskaloosa, IA Welcome to this executive 4 bedroom, 3.5 bath ranch. The large primary suite is perfect fo...	4 beds \| 4 baths \| 1,616 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.92% Airbnb Rental Income: $null Traditional Rental Income: $3644 Airbnb ROI: N/A Traditional ROI: 5.92%
407 A Avenue E Oskaloosa, IA 407 A Avenue East is a true architectural gem and a proud piece of Oskaloosaâs rich hist...	5 beds \| 3 baths \| 3,108 sq.ft.	$335,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.96% Airbnb Rental Income: $null Traditional Rental Income: $3102 Airbnb ROI: N/A Traditional ROI: 7.96%
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%
2196 Oxford Avenue Oskaloosa, IA Exceptional acreage located just minutes from town on a hard surface road that has it all....	3 beds \| 3 baths \| 2,834 sq.ft.	$642,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $2374 Airbnb ROI: N/A Traditional ROI: 1.88%
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%
244 Terrace Drive Oskaloosa, IA This spacious home offers over 3,900 square feet of living space, situated on a beautiful ...	4 beds \| 4 baths \| 3,924 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.57% Airbnb Rental Income: $null Traditional Rental Income: $3284 Airbnb ROI: N/A Traditional ROI: 6.57%
1242 C Avenue E Oskaloosa, IA Character and location. This charming two-story home is located near Mahaska Health in a g...	4 beds \| 2 baths \| 1,771 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.81% Airbnb Rental Income: $null Traditional Rental Income: $2145 Airbnb ROI: N/A Traditional ROI: 8.81%
1005 9Th Avenue E Oskaloosa, IA RANCH STYLE 2 BED 1 BATH HOME has had many updates. The previous owner put in many NEW up...	2 beds \| 1 baths \| 1,050 sq.ft.	$159,900	Airbnb cash on cash: 1.82% Traditional cash on cash: 6.1% Airbnb Rental Income: $1132 Traditional Rental Income: $1408 Airbnb ROI: 1.82% Traditional ROI: 6.1%
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.	$205,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.89% Airbnb Rental Income: $null Traditional Rental Income: $2395 Airbnb ROI: N/A Traditional ROI: 9.89%
605 Fairview Oskaloosa, IA PRICE IMPROVEMENT - $365,000 - MOTIVATED SELLERS - 4 bedrooms - 3 baths - attached garage ...	4 beds \| 3 baths \| 3,100 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $2901 Airbnb ROI: N/A Traditional ROI: 5.9%
208 Rosenberger Avenue Oskaloosa, IA Spacious ranch home. Nice location. Oversized 120x120 yard. This home features a spacious...	4 beds \| 3 baths \| 1,240 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $2073 Airbnb ROI: N/A Traditional ROI: 6.02%
514 A Avenue E Oskaloosa, IA The temps are HOT but this new listing is even HOTTER! You don't want to miss seeing this...	3 beds \| 2 baths \| 1,228 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $2018 Airbnb ROI: N/A Traditional ROI: 5.9%
1610 S 5th Street Oskaloosa, IA SPLIT FOYER HOME IS IN A GREAT LOCATION ON A QUIET STREET. MOVE IN READY WITH 5 BEDROOMS,...	5 beds \| 2 baths \| 1,678 sq.ft.	$209,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.36% Airbnb Rental Income: $null Traditional Rental Income: $2170 Airbnb ROI: N/A Traditional ROI: 8.36%
902 S D Street Oskaloosa, IA Updated and Affordable! Come check out this 2 bed, 1 bath home with a modern touch. Perfec...	2 beds \| 1 baths \| 942 sq.ft.	$110,500	Airbnb cash on cash: 4.6% Traditional cash on cash: 11.46% Airbnb Rental Income: $1132 Traditional Rental Income: $1489 Airbnb ROI: 4.6% Traditional ROI: 11.46%
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.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $5216 Airbnb ROI: N/A Traditional ROI: 2.69%
1221 3Rd Avenue W Oskaloosa, IA Welcome to this well-maintained home, where comfort and style come together beautifully! A...	3 beds \| 1 baths \| 1,517 sq.ft.	$184,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.03% Airbnb Rental Income: $null Traditional Rental Income: $1519 Airbnb ROI: N/A Traditional ROI: 6.03%
2201 Edmundson Drive Oskaloosa, IA This property is located in a great area and offers a beautiful view of the golf course. I...	4 beds \| 2 baths \| 1,644 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.73% Airbnb Rental Income: $null Traditional Rental Income: $2114 Airbnb ROI: N/A Traditional ROI: 7.73%
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.	$149,900	Airbnb cash on cash: N/A Traditional cash on cash: 9.51% Airbnb Rental Income: $null Traditional Rental Income: $1729 Airbnb ROI: N/A Traditional ROI: 9.51%
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%
1611 Burlington Road Oskaloosa, IA The living room shines with natural light, featuring a cozy fireplace that invites warmth ...	4 beds \| 3 baths \| 2,278 sq.ft.	$320,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.86% Airbnb Rental Income: $null Traditional Rental Income: $2529 Airbnb ROI: N/A Traditional ROI: 5.86%

Real Estate investment in Oskaloosa, IA

There are 32 properties for sale in the city of Oskaloosa . The median list price in Oskaloosa is $234,900 and the average price per square foot is $123. In September 2025, the average monthly cash on cash return in Oskaloosa is 7.00%. The average monthly rental income in Oskaloosa is $2,118.

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

There are 32 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 $2,118.

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.

$379,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.65%

Airbnb Rental Income: $null

Traditional Rental Income: $2404

Airbnb ROI: N/A

Traditional ROI: 3.65%

214 Terrace Drive

Oskaloosa, IA

4 beds | 3 baths | 2,001 sq.ft.

$279,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2666

Airbnb ROI: N/A

Traditional ROI: 7.73%

310 N 8Th Street

Oskaloosa, IA

3 beds | 2 baths | 2,054 sq.ft.

$259,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.83%

Airbnb Rental Income: $null

Traditional Rental Income: $2316

Airbnb ROI: N/A

Traditional ROI: 6.83%

1109 N 2Nd Street

Oskaloosa, IA

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

$164,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.93%

Airbnb Rental Income: $null

Traditional Rental Income: $1852

Airbnb ROI: N/A

Traditional ROI: 8.93%

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%

1702 Pella Avenue

Oskaloosa, IA

4 beds | 3 baths | 1,988 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.43%

Airbnb Rental Income: $null

Traditional Rental Income: $2447

Airbnb ROI: N/A

Traditional ROI: 6.43%

101 4Th Avenue W

Oskaloosa, IA

3 beds | 3 baths | 1,680 sq.ft.

$212,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.59%

Airbnb Rental Income: $null

Traditional Rental Income: $1930

Airbnb ROI: N/A

Traditional ROI: 6.59%

815 11Th Avenue W

Oskaloosa, IA

3 beds | 3 baths | 1,512 sq.ft.

$265,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.74%

Airbnb Rental Income: $null

Traditional Rental Income: $1570

Airbnb ROI: N/A