Real Estate Investment Properties for Sale in Osceola, WI

Looking for investment property in Osceola, WI with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
890 Maple Drive Osceola, WI Located in a desirable in-town neighborhood within walking distance to parks, trails, and ...	4 beds \| 3 baths \| 2,852 sq.ft.	$294,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.58% Airbnb Rental Income: $null Traditional Rental Income: $3160 Airbnb ROI: N/A Traditional ROI: 8.58%
361 Mill St Osceola, WI The Pinewood Plan: Experience the joy of owning a NEW home. Located in the appealing neigh...	3 beds \| 2 baths \| 1,958 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.6% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 6.6%
512 Seminole Avenue Osceola, WI Exceptional 3 bed, 2 bath rambler offering a dream lifestyle! The open-concept interior fe...	3 beds \| 2 baths \| 1,800 sq.ft.	$344,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $2619 Airbnb ROI: N/A Traditional ROI: 5.74%
380 Staples Road Osceola, WI This charming 4-bedroom, 2-bath home features an open-concept layout that seamlessly conne...	4 beds \| 2 baths \| 1,906 sq.ft.	$339,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $2259 Airbnb ROI: N/A Traditional ROI: 4.5%
606 Big Lake Ct Osceola, WI	4 beds \| 2 baths \| N/A	$285,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.82% Airbnb Rental Income: $null Traditional Rental Income: $2090 Airbnb ROI: N/A Traditional ROI: 5.82%
301 Ladd Lane Osceola, WI The Teton Plan. One level living! Experience the joy and ease of owning a NEW home! Locate...	2 beds \| 1 baths \| 834 sq.ft.	$249,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.9% Airbnb Rental Income: $null Traditional Rental Income: $1736 Airbnb ROI: N/A Traditional ROI: 5.9%
330 Mill Street Osceola, WI New Construction! The Princeton B Plan: Experience the joy of owning a NEW home. Located...	2 beds \| 2 baths \| N/A	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.28% Airbnb Rental Income: $null Traditional Rental Income: $2204 Airbnb ROI: N/A Traditional ROI: 6.28%
1843 60th Ave Osceola, WI Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	4 beds \| 2 baths \| 2,025 sq.ft.	$545,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $2338 Airbnb ROI: N/A Traditional ROI: 2.47%
260 Spring Street Osceola, WI The Penelope Floor Plan.....This highly sought after 1 level living layout include 2 bedro...	2 beds \| 2 baths \| 1,226 sq.ft.	$329,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.5% Airbnb Rental Income: $null Traditional Rental Income: $2129 Airbnb ROI: N/A Traditional ROI: 5.5%
250 Spring Street Osceola, WI New Construction! The Princeton B plan: Experience the joy of owning a NEW home. Located i...	2 beds \| 2 baths \| 1,185 sq.ft.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.21% Airbnb Rental Income: $null Traditional Rental Income: $2184 Airbnb ROI: N/A Traditional ROI: 6.21%
290 Spring Street Osceola, WI New Construction! The Princeton B plan: Experience the joy of owning a NEW home. Located i...	2 beds \| 2 baths \| 1,185 sq.ft.	$305,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.21% Airbnb Rental Income: $null Traditional Rental Income: $2184 Airbnb ROI: N/A Traditional ROI: 6.21%
2486 75th Ave Osceola, WI 2486 75th Ave, Osceola, WI 54020 \| Single Family Residential	5 beds \| 2 baths \| 2,398 sq.ft.	$389,900	Airbnb cash on cash: 7.41% Traditional cash on cash: N/A Airbnb Rental Income: $4833 Traditional Rental Income: $0 Airbnb ROI: 7.41% Traditional ROI: N/A
2383 84th Ave Osceola, WI 2383 84th Ave, Osceola, WI 54020 \| Single Family Residential	3 beds \| 2 baths \| 1,300 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $2126 Airbnb ROI: N/A Traditional ROI: 2.59%
Lot 8 94th Ave Osceola, WI Lot 8 94th Ave, Osceola, WI 54020 \| Other	N/A beds \| N/A baths \| N/A	$79,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.57% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: 5.57%
XXX 65th Ave Osceola, WI XXX 65th Ave, Osceola, WI 54020 \| Other	N/A beds \| N/A baths \| N/A	$1,789,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.45% Airbnb Rental Income: $null Traditional Rental Income: $749 Airbnb ROI: N/A Traditional ROI: -2.45%
602 218th St. Osceola, WI Discover your dream country home! This newer custom built home situated on a peaceful 3 ac...	4 beds \| 3 baths \| 2,496 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.82% Airbnb Rental Income: $null Traditional Rental Income: $3150 Airbnb ROI: N/A Traditional ROI: 5.82%

Real Estate investment in Osceola, WI

There are 16 properties for sale in the city of Osceola . The median list price in Osceola is $299,900 and the average price per square foot is $187. In January 2026, the average monthly cash on cash return in Osceola is 6.00%. The average monthly rental income in Osceola is $2,129.

Osceola, WI Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 16 investment properties available for sale in Osceola.

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

The ROI for Short-Term is higher than the Long-Term in Osceola with average rental income of $4,833.

Your search for investment property begins and ends here

Investment Property for Sale in Osceola, WI

890 Maple Drive

Osceola, WI

4 beds | 3 baths | 2,852 sq.ft.

$294,900

Airbnb cash on cash: N/A

Traditional cash on cash: 8.58%

Airbnb Rental Income: $null

Traditional Rental Income: $3160

Airbnb ROI: N/A

Traditional ROI: 8.58%

361 Mill St

Osceola, WI

3 beds | 2 baths | 1,958 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2624

Airbnb ROI: N/A

Traditional ROI: 6.6%

512 Seminole Avenue

Osceola, WI

3 beds | 2 baths | 1,800 sq.ft.

$344,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2619

Airbnb ROI: N/A

Traditional ROI: 5.74%

380 Staples Road

Osceola, WI

4 beds | 2 baths | 1,906 sq.ft.

$339,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.5%

Airbnb Rental Income: $null

Traditional Rental Income: $2259

Airbnb ROI: N/A

Traditional ROI: 4.5%

606 Big Lake Ct

Osceola, WI

4 beds | 2 baths | N/A

$285,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.82%

Airbnb Rental Income: $null

Traditional Rental Income: $2090

Airbnb ROI: N/A

Traditional ROI: 5.82%

301 Ladd Lane

Osceola, WI

2 beds | 1 baths | 834 sq.ft.

$249,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.9%

Airbnb Rental Income: $null

Traditional Rental Income: $1736

Airbnb ROI: N/A

Traditional ROI: 5.9%

330 Mill Street

Osceola, WI

2 beds | 2 baths | N/A

$305,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.28%

Airbnb Rental Income: $null

Traditional Rental Income: $2204

Airbnb ROI: N/A

Traditional ROI: 6.28%

1843 60th Ave

Osceola, WI

4 beds | 2 baths | 2,025 sq.ft.

$545,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.47%

Airbnb Rental Income: $null

Traditional Rental Income: $2338

Airbnb ROI: N/A