Real Estate Investment Properties for Sale in Windsor, WI

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
L23 Colton Way Windsor, WI L23 Colton Way, Windsor, WI 53590 \| Other	N/A beds \| N/A baths \| N/A	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.69% Airbnb Rental Income: $null Traditional Rental Income: $596 Airbnb ROI: N/A Traditional ROI: -0.69%
L24 Colton Way Windsor, WI A rare opportunity to own a thoughtfully designed signature home by KH Homes + Kayla Haven...	5 beds \| 3 baths \| 4,850 sq.ft.	$1,950,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.78% Airbnb Rental Income: $null Traditional Rental Income: $3830 Airbnb ROI: N/A Traditional ROI: -0.78%
L22 Colton Way Windsor, WI L22 Colton Way, Windsor, WI 53590 \| Other	N/A beds \| N/A baths \| N/A	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.69% Airbnb Rental Income: $null Traditional Rental Income: $596 Airbnb ROI: N/A Traditional ROI: -0.69%
Lot 28 Colton Way Windsor, WI Lot 28 Colton Way, Windsor, WI 53590 \| Other	N/A beds \| N/A baths \| N/A	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.69% Airbnb Rental Income: $null Traditional Rental Income: $596 Airbnb ROI: N/A Traditional ROI: -0.69%
4027 Taunton Rd Windsor, WI This immaculate newly constructed home with designer finishes will surely impress. Open co...	4 beds \| 3 baths \| 3,051 sq.ft.	$649,900	Airbnb cash on cash: 1.83% Traditional cash on cash: 2.09% Airbnb Rental Income: $3732 Traditional Rental Income: $3081 Airbnb ROI: 1.83% Traditional ROI: 2.09%
6586 Wolf Hollow Rd Windsor, WI Nestled in Windsor, this stunning 4-bedroom, 3-bath home effortlessly combines elegance an...	4 beds \| 3 baths \| 3,177 sq.ft.	$725,000	Airbnb cash on cash: 1.99% Traditional cash on cash: 2.4% Airbnb Rental Income: $3732 Traditional Rental Income: $3201 Airbnb ROI: 1.99% Traditional ROI: 2.4%
6689 Highland Dr Windsor, WI 6689 Highland Dr, Windsor, WI 53598 \| Single Family Residential	4 beds \| 2 baths \| 3,355 sq.ft.	$599,900	Airbnb cash on cash: 2.21% Traditional cash on cash: 0.44% Airbnb Rental Income: $3732 Traditional Rental Income: $1927 Airbnb ROI: 2.21% Traditional ROI: 0.44%
6551 Wolf Hollow Road Windsor, WI Welcome to your dream home in sought-after Pleasant Hill Estates! Nestled on a professiona...	4 beds \| 3 baths \| 2,865 sq.ft.	$679,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 1.98% Airbnb Rental Income: $3732 Traditional Rental Income: $2807 Airbnb ROI: 2.16% Traditional ROI: 1.98%
4450 Snowy Ridge Trl Windsor, WI 4450 Snowy Ridge Trl, Windsor, WI 53598 \| Single Family Residential	4 beds \| 3 baths \| 2,724 sq.ft.	$514,900	Airbnb cash on cash: 3.03% Traditional cash on cash: 2.39% Airbnb Rental Income: $3732 Traditional Rental Income: $2611 Airbnb ROI: 3.03% Traditional ROI: 2.39%
6624 Chestnut Cir Windsor, WI 6624 Chestnut Cir, Windsor, WI 53598 \| Single Family Residential	5 beds \| 3 baths \| 3,370 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $2690 Airbnb ROI: N/A Traditional ROI: 1.8%
4498-4500 Maple Ln Windsor, WI 4498-4500 Maple Ln, Windsor, WI 53598 \| Multi Family	6 beds \| 2 baths \| N/A	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $2047 Airbnb ROI: N/A Traditional ROI: 1.15%
6683 Charlie Grimm Rd Windsor, WI 6683 Charlie Grimm Rd, Windsor, WI 53598 \| Condo/Coop	2 beds \| 1 baths \| 1,104 sq.ft.	$275,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 0.65% Airbnb Rental Income: $1188 Traditional Rental Income: $994 Airbnb ROI: -0.09% Traditional ROI: 0.65%
6715 Firehouse Dr Windsor, WI 6715 Firehouse Dr, Windsor, WI 53598 \| Other	N/A beds \| N/A baths \| N/A	$334,900	Airbnb cash on cash: N/A Traditional cash on cash: -1.23% Airbnb Rental Income: $null Traditional Rental Income: $596 Airbnb ROI: N/A Traditional ROI: -1.23%
0 N Towne Rd Windsor, WI 0 N Towne Rd, Windsor, WI 53598 \| Other	N/A beds \| N/A baths \| N/A	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: -1.64% Airbnb Rental Income: $null Traditional Rental Income: $596 Airbnb ROI: N/A Traditional ROI: -1.64%
4528 Scenic View Rd Windsor, WI 4528 Scenic View Rd, Windsor, WI 53598 \| Single Family Residential	4 beds \| 3 baths \| 2,600 sq.ft.	$599,900	Airbnb cash on cash: 2.21% Traditional cash on cash: 1.55% Airbnb Rental Income: $3732 Traditional Rental Income: $2550 Airbnb ROI: 2.21% Traditional ROI: 1.55%

Real Estate investment in Windsor, WI

There are 20 properties for sale in the city of Windsor . The median list price in Windsor is $640,011 and the average price per square foot is $201. In September 2026, the average monthly cash on cash return in Windsor is 2.00%. The average monthly rental income in Windsor is $2,677.

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

There are 20 investment properties available for sale in Windsor.

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

The ROI for Short-Term is higher than the Long-Term in Windsor with average rental income of $3,732.

Your search for investment property begins and ends here

Investment Property for Sale in Windsor, WI

L23 Colton Way

Windsor, WI

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

$249,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.69%

Airbnb Rental Income: $null

Traditional Rental Income: $596

Airbnb ROI: N/A

Traditional ROI: -0.69%

L24 Colton Way

Windsor, WI

5 beds | 3 baths | 4,850 sq.ft.

$1,950,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.78%

Airbnb Rental Income: $null

Traditional Rental Income: $3830

Airbnb ROI: N/A

Traditional ROI: -0.78%

L22 Colton Way

Windsor, WI

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

$249,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.69%

Airbnb Rental Income: $null

Traditional Rental Income: $596

Airbnb ROI: N/A

Traditional ROI: -0.69%

Lot 28 Colton Way

Windsor, WI

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

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.69%

Airbnb Rental Income: $null

Traditional Rental Income: $596

Airbnb ROI: N/A

Traditional ROI: -0.69%

4027 Taunton Rd

Windsor, WI

4 beds | 3 baths | 3,051 sq.ft.

$649,900

Airbnb cash on cash: 1.83%

Traditional cash on cash: 2.09%

Airbnb Rental Income: $3732

Traditional Rental Income: $3081

Airbnb ROI: 1.83%

Traditional ROI: 2.09%

6586 Wolf Hollow Rd

Windsor, WI

4 beds | 3 baths | 3,177 sq.ft.

$725,000

Airbnb cash on cash: 1.99%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3732

Traditional Rental Income: $3201

Airbnb ROI: 1.99%

Traditional ROI: 2.4%

6689 Highland Dr

Windsor, WI

4 beds | 2 baths | 3,355 sq.ft.

$599,900

Airbnb cash on cash: 2.21%

Traditional cash on cash: 0.44%

Airbnb Rental Income: $3732

Traditional Rental Income: $1927

Airbnb ROI: 2.21%

Traditional ROI: 0.44%

6551 Wolf Hollow Road

Windsor, WI

4 beds | 3 baths | 2,865 sq.ft.

$679,900

Airbnb cash on cash: 2.16%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $3732

Traditional Rental Income: $2807

Airbnb ROI: 2.16%