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: 0.4% Traditional cash on cash: 7.12% Airbnb Rental Income: $1109 Traditional Rental Income: $2626 Airbnb ROI: 0.4% 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: 1.01% Traditional cash on cash: 5.4% Airbnb Rental Income: $1412 Traditional Rental Income: $2509 Airbnb ROI: 1.01% 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 \| 1,700 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.85% Airbnb Rental Income: $null Traditional Rental Income: $2860 Airbnb ROI: N/A Traditional ROI: 2.85%
3480 HWY 70 Winter, WI The Loretta Steakhouse offers the perfect blend of comfort and opportunity, nestled in the...	3 beds \| 4 baths \| 3,604 sq.ft.	$300,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 9.53% Airbnb Rental Income: $1412 Traditional Rental Income: $3231 Airbnb ROI: 1.59% Traditional ROI: 9.53%
6305 N Dam Road Winter, WI Northwoods Living on Dam Rd, 1.8 miles from Big Chip Flowage boat launch, mins from the Wa...	3 beds \| 2 baths \| 1,385 sq.ft.	$242,000	Airbnb cash on cash: 2.67% Traditional cash on cash: 8.01% Airbnb Rental Income: $1412 Traditional Rental Income: $2209 Airbnb ROI: 2.67% Traditional ROI: 8.01%
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: 1.94% Traditional cash on cash: 5.18% Airbnb Rental Income: $1412 Traditional Rental Income: $1827 Airbnb ROI: 1.94% 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: 1.32% Traditional cash on cash: 6.97% Airbnb Rental Income: $1412 Traditional Rental Income: $2819 Airbnb ROI: 1.32% Traditional ROI: 6.97%
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: 1.09% Traditional cash on cash: 4.5% Airbnb Rental Income: $1109 Traditional Rental Income: $1556 Airbnb ROI: 1.09% Traditional ROI: 4.5%
6954n CLOVER RD N Winter, WI (125/KTG) Recreationalist dreams come true! Great location, just 7.5 Miles E of Winter. Ca...	2 beds \| 1 baths \| 768 sq.ft.	$229,900	Airbnb cash on cash: 1.56% Traditional cash on cash: 5.95% Airbnb Rental Income: $1109 Traditional Rental Income: $1689 Airbnb ROI: 1.56% Traditional ROI: 5.95%
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: 0.05% Traditional cash on cash: 1.39% Airbnb Rental Income: $1412 Traditional Rental Income: $1926 Airbnb ROI: 0.05% Traditional ROI: 1.39%
6733w GOLF COURSE RD Winter, WI (228/KTG) Wait! Stop and Look now!! Are you searching for that perfect slice of the Northw...	5 beds \| 1 baths \| 1,420 sq.ft.	$474,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.27% Airbnb Rental Income: $null Traditional Rental Income: $2292 Airbnb ROI: N/A Traditional ROI: 3.27%
8050 N Barker Lake Road Winter, WI Located just north of Winter on the 100+ acre Hunter Lake, this 0.77-acre lot is perfect f...	1 beds \| N/A baths \| 576 sq.ft.	$159,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.79% Airbnb Rental Income: $null Traditional Rental Income: $1513 Airbnb ROI: N/A Traditional ROI: 7.79%

Real Estate investment in Winter, WI

There are 12 properties for sale in the city of Winter . The median list price in Winter is $299,450 and the average price per square foot is $165. In November 2025, the average monthly cash on cash return in Winter is 6.00%. The average monthly rental income in Winter is $2,292.

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

There are 12 investment properties available for sale in Winter.

In 2025, 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 $2,292.

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: 0.4%

Traditional cash on cash: 7.12%

Airbnb Rental Income: $1109

Traditional Rental Income: $2626

Airbnb ROI: 0.4%

Traditional ROI: 7.12%

7043 W Fadness Road

Winter, WI

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

$369,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 5.4%

Airbnb Rental Income: $1412

Traditional Rental Income: $2509

Airbnb ROI: 1.01%

Traditional ROI: 5.4%

5167n DOAK RD

Winter, WI

4 beds | 2 baths | 1,700 sq.ft.

$699,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.85%

Airbnb Rental Income: $null

Traditional Rental Income: $2860

Airbnb ROI: N/A

Traditional ROI: 2.85%

3480 HWY 70

Winter, WI

3 beds | 4 baths | 3,604 sq.ft.

$300,000

Airbnb cash on cash: 1.59%

Traditional cash on cash: 9.53%

Airbnb Rental Income: $1412

Traditional Rental Income: $3231

Airbnb ROI: 1.59%

Traditional ROI: 9.53%

6305 N Dam Road

Winter, WI

3 beds | 2 baths | 1,385 sq.ft.

$242,000

Airbnb cash on cash: 2.67%

Traditional cash on cash: 8.01%

Airbnb Rental Income: $1412

Traditional Rental Income: $2209

Airbnb ROI: 2.67%

Traditional ROI: 8.01%

3108 W Howard Street

Winter, WI

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

$275,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 5.18%

Airbnb Rental Income: $1412

Traditional Rental Income: $1827

Airbnb ROI: 1.94%

Traditional ROI: 5.18%

4878N Fur Farm Trail

Winter, WI

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

$345,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 6.97%

Airbnb Rental Income: $1412

Traditional Rental Income: $2819

Airbnb ROI: 1.32%

Traditional ROI: 6.97%

4735 N Lake Winter Road

Winter, WI

2 beds | 1 baths | 704 sq.ft.

$255,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 4.5%

Airbnb Rental Income: $1109

Traditional Rental Income: $1556

Airbnb ROI: 1.09%