Real Estate Investment Properties for Sale in Chili, WI

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
W719 ROSEWOOD DRIVE Chili, WI SERENE LIVING AWAITS YOU AT A DEAD END ROAD! Tucked away on 1.52 acres at the end of the c...	3 beds \| 3 baths \| 1,847 sq.ft.	$311,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.09% Airbnb Rental Income: $null Traditional Rental Income: $2862 Airbnb ROI: N/A Traditional ROI: 7.09%
Investment Properties for Sale in Other Cities of Wisconsin
8037 41st Ave #29C Kenosha , WI Seller will not complete any repairs to the subject property either lender or buyer reques...	2 beds \| 2 baths \| 1,082 sq.ft.	$204,900	Airbnb cash on cash: 5.21% Traditional cash on cash: 6.02% Airbnb Rental Income: $2053 Traditional Rental Income: $1679 Airbnb ROI: 5.21% Traditional ROI: 6.02%
112 E Freistadt Rd #C Thiensville , WI Beautifully updated 3BR/2BA condo in Village Place offers easy one-level living--a perfect...	3 beds \| 2 baths \| 1,156 sq.ft.	$219,900	Airbnb cash on cash: 4.39% Traditional cash on cash: 7.17% Airbnb Rental Income: $1912 Traditional Rental Income: $1983 Airbnb ROI: 4.39% Traditional ROI: 7.17%
N16005 ISLAND LAKE RD Park Falls , WI Privacy at its best featuring a Completely Furnished 4+BR, 3BA home meticulously maintaine...	4 beds \| 3 baths \| N/A	$629,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $3355 Airbnb ROI: N/A Traditional ROI: 3.88%
9811 DEER TRAIL ROAD #3 Tomahawk , WI Beautiful low maintenance condominium on Lake Nokomis! This unit features 3 bedrooms, 3 fu...	3 beds \| 3 baths \| 2,490 sq.ft.	$465,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 6.19% Airbnb Rental Income: $1143 Traditional Rental Income: $3470 Airbnb ROI: -0.03% Traditional ROI: 6.19%
219 Glendale AVENUE Tomah , WI Welcome to this charming 3-bedroom, 2-story home in the heart of Tomah! Step inside to fin...	3 beds \| 1 baths \| 1,350 sq.ft.	$175,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.27% Airbnb Rental Income: $null Traditional Rental Income: $1809 Airbnb ROI: N/A Traditional ROI: 8.27%
7795 S Dublin Road Gratiot , WI Stylish, spacious & serene! This 3 bed, 3.5 bath ranch w/ an oversized 2 car garage sits o...	3 beds \| 4 baths \| 4,588 sq.ft.	$436,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.46% Airbnb Rental Income: $null Traditional Rental Income: $3563 Airbnb ROI: N/A Traditional ROI: 6.46%
1816 17th Avenue Monroe , WI Charming move-in ready 3-bedroom ranch on the south side of Monroe close to schools, parks...	3 beds \| 2 baths \| 1,376 sq.ft.	$224,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 6.9% Airbnb Rental Income: $1407 Traditional Rental Income: $2065 Airbnb ROI: 1.8% Traditional ROI: 6.9%
1728 19th Court Arkdale , WI Welcome to this inviting 2-bedroom, 1-bath ranch that combines comfort w/character. Both b...	2 beds \| 1 baths \| 780 sq.ft.	$229,900	Airbnb cash on cash: 2.96% Traditional cash on cash: 4.73% Airbnb Rental Income: $1504 Traditional Rental Income: $1449 Airbnb ROI: 2.96% Traditional ROI: 4.73%
9811 DEER TRAIL ROAD #5 Tomahawk , WI Beautiful low maintenance condominium on Lake Nokomis! This unit features 3 bedrooms, 3 fu...	3 beds \| 3 baths \| 2,490 sq.ft.	$465,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 6.15% Airbnb Rental Income: $1143 Traditional Rental Income: $3470 Airbnb ROI: -0.07% Traditional ROI: 6.15%
553 Goldsmith Street Chippewa Falls , WI Welcome to 553 Goldsmith Street in Chippewa Falls where your weekends are free of yard wor...	2 beds \| 2 baths \| 1,728 sq.ft.	$215,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 6.01% Airbnb Rental Income: $1822 Traditional Rental Income: $1747 Airbnb ROI: 3.96% Traditional ROI: 6.01%
3712 Glen Crest Court Eau Claire , WI Beautifully maintained home nestled in a private and quiet cul de sac on Eau Claire's sout...	4 beds \| 3 baths \| 3,114 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $3028 Airbnb ROI: N/A Traditional ROI: 2.98%
14817 W Airport Road Hayward , WI Custom home with a private gated driveway situated on 38 acres of serene woodland meadows ...	3 beds \| 3 baths \| 5,000 sq.ft.	$979,900	Airbnb cash on cash: -0.71% Traditional cash on cash: 1.03% Airbnb Rental Income: $1251 Traditional Rental Income: $2447 Airbnb ROI: -0.71% Traditional ROI: 1.03%

Real Estate investment in Chili, WI

There are 1 properties for sale in the city of Chili . The median list price in Chili is $311,900 and the average price per square foot is $169. In November 2025, the average monthly cash on cash return in Chili is 7.00%. The average monthly rental income in Chili is $2,862.

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

There are 1 investment properties available for sale in Chili.

The ROI for Short-Term is higher than the Long-Term in Chili with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Chili, WI

W719 ROSEWOOD DRIVE

Chili, WI

3 beds | 3 baths | 1,847 sq.ft.

$311,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.09%

Airbnb Rental Income: $null

Traditional Rental Income: $2862

Airbnb ROI: N/A

Traditional ROI: 7.09%

Investment Properties for Sale in Other Cities of Wisconsin

Kenosha , WI

2 beds | 2 baths | 1,082 sq.ft.

$204,900

Airbnb cash on cash: 5.21%

Traditional cash on cash: 6.02%

Airbnb Rental Income: $2053

Traditional Rental Income: $1679

Airbnb ROI: 5.21%

Traditional ROI: 6.02%

Thiensville , WI

3 beds | 2 baths | 1,156 sq.ft.

$219,900

Airbnb cash on cash: 4.39%

Traditional cash on cash: 7.17%

Airbnb Rental Income: $1912

Traditional Rental Income: $1983

Airbnb ROI: 4.39%

Traditional ROI: 7.17%

Park Falls , WI

4 beds | 3 baths | N/A

$629,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.88%

Airbnb Rental Income: $null

Traditional Rental Income: $3355

Airbnb ROI: N/A

Traditional ROI: 3.88%

Tomahawk , WI

3 beds | 3 baths | 2,490 sq.ft.

$465,000

Airbnb cash on cash: -0.03%

Traditional cash on cash: 6.19%

Airbnb Rental Income: $1143

Traditional Rental Income: $3470

Airbnb ROI: -0.03%

Traditional ROI: 6.19%

Tomah , WI

3 beds | 1 baths | 1,350 sq.ft.

$175,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.27%

Airbnb Rental Income: $null

Traditional Rental Income: $1809

Airbnb ROI: N/A

Traditional ROI: 8.27%

Gratiot , WI

3 beds | 4 baths | 4,588 sq.ft.

$436,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.46%

Airbnb Rental Income: $null

Traditional Rental Income: $3563

Airbnb ROI: N/A

Traditional ROI: 6.46%

Monroe , WI

3 beds | 2 baths | 1,376 sq.ft.

$224,000

Airbnb cash on cash: 1.8%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $1407

Traditional Rental Income: $2065

Airbnb ROI: 1.8%

Traditional ROI: 6.9%

Arkdale , WI

2 beds | 1 baths | 780 sq.ft.

$229,900

Airbnb cash on cash: 2.96%

Traditional cash on cash: 4.73%