Real Estate Investment Properties for Sale in Winter, WI

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5158 S Main Street Winter, WI This restaurant has been a staple in Winter for generations. The restaurant, kitchen, stor...	2 beds \| 4 baths \| 5,216 sq.ft.	$299,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 7.12% Airbnb Rental Income: $1033 Traditional Rental Income: $2626 Airbnb ROI: 0.17% Traditional ROI: 7.12%
7043 W Fadness Road Winter, WI Rare opportunity to own over 10 acres of beautiful Northwoods land! This property is a hob...	3 beds \| 2 baths \| 1,300 sq.ft.	$369,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 5.4% Airbnb Rental Income: $1513 Traditional Rental Income: $2509 Airbnb ROI: 1.25% Traditional ROI: 5.4%
5167N DOAK RD Winter, WI (226/IK) - Located 4 mi. from Winter, WI on Doak Rd or 30 min. from Hayward on a 733 acre ...	4 beds \| 2 baths \| N/A	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.87% Airbnb Rental Income: $null Traditional Rental Income: $2860 Airbnb ROI: N/A Traditional ROI: 2.87%
3108 W Howard Street Winter, WI Looking for a 4-season Northwoods chalet in the perfect spot to snowmobile, ATV, hunt, or ...	3 beds \| 1 baths \| 1,310 sq.ft.	$275,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 5.18% Airbnb Rental Income: $1513 Traditional Rental Income: $1827 Airbnb ROI: 2.27% Traditional ROI: 5.18%
4878N Fur Farm Trail Winter, WI Your beautiful getaway awaits! This 3 bed, 2 bath home offers one level living with zero e...	3 beds \| 2 baths \| 2,220 sq.ft.	$345,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 6.91% Airbnb Rental Income: $1513 Traditional Rental Income: $2819 Airbnb ROI: 1.52% Traditional ROI: 6.91%
4735 N Lake Winter Road Winter, WI Set along the peaceful shores of Lake Winterâfamous for its excellent musky fishingâth...	2 beds \| 1 baths \| 704 sq.ft.	$255,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.5% Airbnb Rental Income: $1033 Traditional Rental Income: $1556 Airbnb ROI: 0.83% Traditional ROI: 4.5%
7756W Old Hwy 70 Winter, WI Over 114 acres of pure privacy and outdoor beauty! Tucked 1,500 feet back from the road, t...	3 beds \| 1 baths \| 1,786 sq.ft.	$749,900	Airbnb cash on cash: 0.17% Traditional cash on cash: 1.39% Airbnb Rental Income: $1513 Traditional Rental Income: $1926 Airbnb ROI: 0.17% Traditional ROI: 1.39%

Real Estate investment in Winter, WI

There are 7 properties for sale in the city of Winter . The median list price in Winter is $299,900 and the average price per square foot is $149. In January 2026, the average monthly cash on cash return in Winter is 5.00%. The average monthly rental income in Winter is $2,452.

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

There are 7 investment properties available for sale in Winter.

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

The ROI for Long-Term is higher than the Short-Term in Winter with average rental income of $2,452.

Your search for investment property begins and ends here

Investment Property for Sale in Winter, WI

5158 S Main Street

Winter, WI

2 beds | 4 baths | 5,216 sq.ft.

$299,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 7.12%

Airbnb Rental Income: $1033

Traditional Rental Income: $2626

Airbnb ROI: 0.17%

Traditional ROI: 7.12%

7043 W Fadness Road

Winter, WI

3 beds | 2 baths | 1,300 sq.ft.

$369,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $1513

Traditional Rental Income: $2509

Airbnb ROI: 1.25%

Traditional ROI: 5.4%

5167N DOAK RD

Winter, WI

4 beds | 2 baths | N/A

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2860

Airbnb ROI: N/A

Traditional ROI: 2.87%

3108 W Howard Street

Winter, WI

3 beds | 1 baths | 1,310 sq.ft.

$275,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $1513

Traditional Rental Income: $1827

Airbnb ROI: 2.27%

Traditional ROI: 5.18%

4878N Fur Farm Trail

Winter, WI

3 beds | 2 baths | 2,220 sq.ft.

$345,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 6.91%

Airbnb Rental Income: $1513

Traditional Rental Income: $2819

Airbnb ROI: 1.52%

Traditional ROI: 6.91%

4735 N Lake Winter Road

Winter, WI

2 beds | 1 baths | 704 sq.ft.

$255,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1033

Traditional Rental Income: $1556

Airbnb ROI: 0.83%

Traditional ROI: 4.5%

7756W Old Hwy 70

Winter, WI

3 beds | 1 baths | 1,786 sq.ft.

$749,900

Airbnb cash on cash: 0.17%

Traditional cash on cash: 1.39%

Airbnb Rental Income: $1513

Traditional Rental Income: $1926

Airbnb ROI: 0.17%

Traditional ROI: 1.39%

Real Estate investment in Winter, WI

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

How many investment properties are available for sale in Winter?

Which neighborhoods in Winter to invest in 2026?

Long-Term vs. Short-Term Rentals in Winter, Wisconsin: Which will earn the best returns?

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