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
8xx 207th St Osceola, WI 8xx 207th St, Osceola, WI 54009 \| Other	N/A beds \| N/A baths \| N/A	$99,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.02% Airbnb Rental Income: $null Traditional Rental Income: $852 Airbnb ROI: N/A Traditional ROI: 5.02%
729 220th Street Osceola, WI This 4-bed, 3-bath home is set on nearly 2.5 acres and offers a thoughtful layout with ple...	4 beds \| 3 baths \| 3,121 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.1% Airbnb Rental Income: $null Traditional Rental Income: $3121 Airbnb ROI: N/A Traditional ROI: 4.1%
307 State Rd 35 Osceola, WI Check out this charming and move-in ready 3-bedroom, 1-bath home offering a perfect blend ...	3 beds \| 1 baths \| 1,056 sq.ft.	$234,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.47% Airbnb Rental Income: $null Traditional Rental Income: $1673 Airbnb ROI: N/A Traditional ROI: 5.47%
2362 84th Ave Osceola, WI Why wait for new, when slightly used will do!! This home features 4 bedrooms, 2 full baths...	4 beds \| 2 baths \| 1,547 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.42% Airbnb Rental Income: $null Traditional Rental Income: $2493 Airbnb ROI: N/A Traditional ROI: 5.42%
918 Geiger St Osceola, WI Discover the perfect blend of comfort and convenience in this charming 3-bedroom, 1-bathro...	3 beds \| 1 baths \| 1,008 sq.ft.	$239,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.69% Airbnb Rental Income: $null Traditional Rental Income: $1338 Airbnb ROI: N/A Traditional ROI: 3.69%
619 Nokomis Dr Osceola, WI Located on Big Lake in Osceola, this four-bedroom, three-bath home offers a modern interio...	4 beds \| 2 baths \| 2,060 sq.ft.	$759,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $3162 Airbnb ROI: N/A Traditional ROI: 2.5%
370 Mill Street Osceola, WI Charming and efficient 1-story home located in the desirable Gateway Meadows neighborhood ...	2 beds \| 2 baths \| 1,185 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $2095 Airbnb ROI: N/A Traditional ROI: 4.66%
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%
330 Mill St 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.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.05% Airbnb Rental Income: $null Traditional Rental Income: $2204 Airbnb ROI: N/A Traditional ROI: 6.05%
250 Spring St 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.	$315,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.98% Airbnb Rental Income: $null Traditional Rental Income: $2184 Airbnb ROI: N/A Traditional ROI: 5.98%
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%
650 Deer Path Osceola, WI One level living in Deer Path Townhomes! This quiet edge of town neighborhood is just what...	2 beds \| 2 baths \| 1,720 sq.ft.	$309,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.51% Airbnb Rental Income: $null Traditional Rental Income: $2328 Airbnb ROI: N/A Traditional ROI: 4.51%
440 Tony St Osceola, WI Welcome to easy living at 440 Tony Street in Osceola! This beautifully maintained detached...	2 beds \| 1 baths \| 1,441 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.86% Airbnb Rental Income: $null Traditional Rental Income: $2340 Airbnb ROI: N/A Traditional ROI: 4.86%
Lot 3 Big Lake Dr Osceola, WI Lot 3 Big Lake Dr, Osceola, WI 54020 \| Other	N/A beds \| N/A baths \| N/A	$133,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $852 Airbnb ROI: N/A Traditional ROI: 3.14%
318 (Lot 25) 238th Street 238th St Osceola, WI 318 (Lot 25) 238th Street 238th St, Osceola, WI 54020 \| Other	N/A beds \| N/A baths \| N/A	$65,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.95% Airbnb Rental Income: $null Traditional Rental Income: $852 Airbnb ROI: N/A Traditional ROI: 8.95%
620 Seminole Ave Osceola, WI Opportunity knocks! This spacious home sits on nearly an acre lot next to the local airpor...	4 beds \| 1 baths \| 2,085 sq.ft.	$195,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.63% Airbnb Rental Income: $null Traditional Rental Income: $2709 Airbnb ROI: N/A Traditional ROI: 11.63%
300 Deer Path #5 Osceola, WI Tucked into a quiet, established neighborhood on the edge of Osceola, Wisconsin, this beau...	2 beds \| 2 baths \| 1,720 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $2347 Airbnb ROI: N/A Traditional ROI: 4.33%
1984 35th Ave Osceola, WI Nestled on nearly 40 acres, this country property blends vast views with mature hardwoods ...	1 beds \| 2 baths \| 1,895 sq.ft.	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.65% Airbnb Rental Income: $null Traditional Rental Income: $2094 Airbnb ROI: N/A Traditional ROI: 0.65%
601 3rd Ave Osceola, WI 601 3rd Ave, Osceola, WI 54020 \| Single Family Residential	4 beds \| 1 baths \| 1,762 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.65% Airbnb Rental Income: $null Traditional Rental Income: $1774 Airbnb ROI: N/A Traditional ROI: 1.65%
908 Martys Way Osceola, WI This stunning in-town home offers something for everyone. A rare find with 20x40 heated in...	4 beds \| 3 baths \| 2,749 sq.ft.	$424,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.78% Airbnb Rental Income: $null Traditional Rental Income: $3001 Airbnb ROI: N/A Traditional ROI: 4.78%
733 220th St Osceola, WI 733 220th St, Osceola, WI 54020 \| Single Family Residential	3 beds \| 2 baths \| 2,233 sq.ft.	$485,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $2362 Airbnb ROI: N/A Traditional ROI: 2.17%
1898 60th Ave Osceola, WI 1898 60th Ave, Osceola, WI 54020 \| Single Family Residential	4 beds \| 3 baths \| 3,452 sq.ft.	$998,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.19% Airbnb Rental Income: $null Traditional Rental Income: $2908 Airbnb ROI: N/A Traditional ROI: 0.19%
298 Zindaus St Osceola, WI 298 Zindaus St, Osceola, WI 54020 \| Other	N/A beds \| N/A baths \| N/A	$689,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.64% Airbnb Rental Income: $null Traditional Rental Income: $861 Airbnb ROI: N/A Traditional ROI: -1.64%
2239 83rd Avenue Osceola, WI Experience the perfect blend of luxury, quality, and convenience in this exceptional home ...	2 beds \| 3 baths \| 2,677 sq.ft.	$605,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.41% Airbnb Rental Income: $null Traditional Rental Income: $2935 Airbnb ROI: N/A Traditional ROI: 3.41%
909 N Cascade St Osceola, WI 909 N Cascade St, Osceola, WI 54020 \| Single Family Residential	3 beds \| 2 baths \| 2,253 sq.ft.	$849,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.27% Airbnb Rental Income: $null Traditional Rental Income: $2126 Airbnb ROI: N/A Traditional ROI: -0.27%
2538 86th Ave Osceola, WI 2538 86th Ave, Osceola, WI 54020 \| Single Family Residential	4 beds \| 3 baths \| 2,640 sq.ft.	$417,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.57% Airbnb Rental Income: $null Traditional Rental Income: $2986 Airbnb ROI: N/A Traditional ROI: 4.57%
2485 50th Ave Osceola, WI 2485 50th Ave, Osceola, WI 54020 \| Single Family Residential	3 beds \| 3 baths \| 2,269 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.35% Airbnb Rental Income: $null Traditional Rental Income: $2639 Airbnb ROI: N/A Traditional ROI: 2.35%
TBD 53rd Osceola, WI TBD 53rd, Osceola, WI 54020 \| Other	N/A beds \| N/A baths \| N/A	$84,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.44% Airbnb Rental Income: $null Traditional Rental Income: $861 Airbnb ROI: N/A Traditional ROI: 6.44%
254 S Cascade Osceola, WI	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.78% Airbnb Rental Income: $null Traditional Rental Income: $861 Airbnb ROI: N/A Traditional ROI: -0.78%
706 Summit Street Osceola, WI Spacious and well-designed home featuring featuring 4 bedrooms all on one level-perfect fo...	4 beds \| 2 baths \| 3,124 sq.ft.	$284,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.7% Airbnb Rental Income: $null Traditional Rental Income: $2866 Airbnb ROI: N/A Traditional ROI: 7.7%
2470 84th Avenue Osceola, WI Beautiful 4BR/2BA 3-level split home on a big 1.57 acre corner lot just NE of Osceola. Hom...	4 beds \| 2 baths \| 2,112 sq.ft.	$419,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $2717 Airbnb ROI: N/A Traditional ROI: 5.01%
2488 91st Avenue Osceola, WI Welcome to 2488 91st Avenue in Osceola, WIâa beautiful 3-bedroom, 2-bath home offering t...	3 beds \| 2 baths \| 1,492 sq.ft.	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.78% Airbnb Rental Income: $null Traditional Rental Income: $2387 Airbnb ROI: N/A Traditional ROI: 5.78%

Real Estate investment in Osceola, WI

There are 34 properties for sale in the city of Osceola . The median list price in Osceola is $314,687 and the average price per square foot is $181. In July 2026, the average monthly cash on cash return in Osceola is 5.00%. The average monthly rental income in Osceola is $2,266.

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

There are 34 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Osceola, WI

8xx 207th St

Osceola, WI

N/A beds | N/A baths | N/A

$99,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.02%

Airbnb Rental Income: $null

Traditional Rental Income: $852

Airbnb ROI: N/A

Traditional ROI: 5.02%

729 220th Street

Osceola, WI

4 beds | 3 baths | 3,121 sq.ft.

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.1%

Airbnb Rental Income: $null

Traditional Rental Income: $3121

Airbnb ROI: N/A

Traditional ROI: 4.1%

307 State Rd 35

Osceola, WI

3 beds | 1 baths | 1,056 sq.ft.

$234,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.47%

Airbnb Rental Income: $null

Traditional Rental Income: $1673

Airbnb ROI: N/A

Traditional ROI: 5.47%

2362 84th Ave

Osceola, WI

4 beds | 2 baths | 1,547 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.42%

Airbnb Rental Income: $null

Traditional Rental Income: $2493

Airbnb ROI: N/A

Traditional ROI: 5.42%

918 Geiger St

Osceola, WI

3 beds | 1 baths | 1,008 sq.ft.

$239,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.69%

Airbnb Rental Income: $null

Traditional Rental Income: $1338

Airbnb ROI: N/A

Traditional ROI: 3.69%

619 Nokomis Dr

Osceola, WI

4 beds | 2 baths | 2,060 sq.ft.

$759,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.5%

Airbnb Rental Income: $null

Traditional Rental Income: $3162

Airbnb ROI: N/A

Traditional ROI: 2.5%

370 Mill Street

Osceola, WI

2 beds | 2 baths | 1,185 sq.ft.

$309,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.66%

Airbnb Rental Income: $null

Traditional Rental Income: $2095

Airbnb ROI: N/A

Traditional ROI: 4.66%

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