Real Estate Investment Properties for Sale in Greenwood, WI

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
502 E Begley Street Greenwood, WI Spacious 4-bedroom, 2-bath home on a .78-acre lot with a 2-car attached garage. This well-...	4 beds \| 2 baths \| 1,872 sq.ft.	$250,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.18% Airbnb Rental Income: $null Traditional Rental Income: $2138 Airbnb ROI: N/A Traditional ROI: 6.18%
N8296 River Ave Greenwood, WI Nestled near Greenwood and tucked away on a quiet dead-end road, lies your ideal home. If ...	5 beds \| 2 baths \| 4,389 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.73% Airbnb Rental Income: $null Traditional Rental Income: $3858 Airbnb ROI: N/A Traditional ROI: 5.73%
315 W Begley St Greenwood, WI Recently transformed and cute as a button! This home has taken on a huge transformation th...	3 beds \| 1 baths \| 1,084 sq.ft.	$145,000	Airbnb cash on cash: N/A Traditional cash on cash: 8.82% Airbnb Rental Income: $null Traditional Rental Income: $1708 Airbnb ROI: N/A Traditional ROI: 8.82%
609 E Schofield Ave Greenwood, WI 609 E Schofield Ave, Greenwood, WI 54437 \| Single Family Residential	4 beds \| 2 baths \| 1,816 sq.ft.	$179,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.85% Airbnb Rental Income: $null Traditional Rental Income: $2250 Airbnb ROI: N/A Traditional ROI: 9.85%
105 N Hendren Ave Greenwood, WI 105 N Hendren Ave, Greenwood, WI 54437 \| Single Family Residential	4 beds \| 1 baths \| 1,636 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.92% Airbnb Rental Income: $null Traditional Rental Income: $1742 Airbnb ROI: N/A Traditional ROI: 4.92%
114 W School St Greenwood, WI 114 W School St, Greenwood, WI 54437 \| Single Family Residential	4 beds \| 2 baths \| 1,820 sq.ft.	$215,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.92% Airbnb Rental Income: $null Traditional Rental Income: $2281 Airbnb ROI: N/A Traditional ROI: 7.92%
N9126 Highway O Greenwood, WI N9126 Highway O, Greenwood, WI 54437 \| Single Family Residential	2 beds \| 1 baths \| 880 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.03% Airbnb Rental Income: $null Traditional Rental Income: $1219 Airbnb ROI: N/A Traditional ROI: -2.03%
W4768 Capital Rd Greenwood, WI Exceptional quality and craftsmanship shine throughout this spacious five bedroom home! Su...	5 beds \| 4 baths \| 3,380 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.49% Airbnb Rental Income: $null Traditional Rental Income: $4921 Airbnb ROI: N/A Traditional ROI: 9.49%
W8895 North Lake Rd Greenwood, WI Lake living at its best! This beautifully crafted 1.5-story home on Mead Lake offers the p...	3 beds \| 2 baths \| 2,120 sq.ft.	$569,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.86% Airbnb Rental Income: $null Traditional Rental Income: $2840 Airbnb ROI: N/A Traditional ROI: 2.86%
118 N Crocker Ave Greenwood, WI 118 N Crocker Ave, Greenwood, WI 54437 \| Single Family Residential	3 beds \| 2 baths \| 1,928 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.5% Airbnb Rental Income: $null Traditional Rental Income: $2286 Airbnb ROI: N/A Traditional ROI: 6.5%
W5319 Rock Creek Rd Greenwood, WI W5319 Rock Creek Rd, Greenwood, WI 54437 \| Single Family Residential	4 beds \| 2 baths \| 1,582 sq.ft.	$199,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.6% Airbnb Rental Income: $null Traditional Rental Income: $2260 Airbnb ROI: N/A Traditional ROI: 8.6%

Real Estate investment in Greenwood, WI

There are 11 properties for sale in the city of Greenwood . The median list price in Greenwood is $349,450 and the average price per square foot is $134. In May 2026, the average monthly cash on cash return in Greenwood is 6.00%. The average monthly rental income in Greenwood is $2,250.

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

There are 11 investment properties available for sale in Greenwood.

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

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

Your search for investment property begins and ends here

Investment Property for Sale in Greenwood, WI

502 E Begley Street

Greenwood, WI

4 beds | 2 baths | 1,872 sq.ft.

$250,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.18%

Airbnb Rental Income: $null

Traditional Rental Income: $2138

Airbnb ROI: N/A

Traditional ROI: 6.18%

N8296 River Ave

Greenwood, WI

5 beds | 2 baths | 4,389 sq.ft.

$469,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.73%

Airbnb Rental Income: $null

Traditional Rental Income: $3858

Airbnb ROI: N/A

Traditional ROI: 5.73%

315 W Begley St

Greenwood, WI

3 beds | 1 baths | 1,084 sq.ft.

$145,000

Airbnb cash on cash: N/A

Traditional cash on cash: 8.82%

Airbnb Rental Income: $null

Traditional Rental Income: $1708

Airbnb ROI: N/A

Traditional ROI: 8.82%

609 E Schofield Ave

Greenwood, WI

4 beds | 2 baths | 1,816 sq.ft.

$179,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.85%

Airbnb Rental Income: $null

Traditional Rental Income: $2250

Airbnb ROI: N/A

Traditional ROI: 9.85%

105 N Hendren Ave

Greenwood, WI

4 beds | 1 baths | 1,636 sq.ft.

$225,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.92%

Airbnb Rental Income: $null

Traditional Rental Income: $1742

Airbnb ROI: N/A

Traditional ROI: 4.92%

114 W School St

Greenwood, WI

4 beds | 2 baths | 1,820 sq.ft.

$215,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2281

Airbnb ROI: N/A

Traditional ROI: 7.92%

N9126 Highway O

Greenwood, WI

2 beds | 1 baths | 880 sq.ft.

$1,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: -2.03%

Airbnb Rental Income: $null

Traditional Rental Income: $1219

Airbnb ROI: N/A

Traditional ROI: -2.03%

W4768 Capital Rd

Greenwood, WI

5 beds | 4 baths | 3,380 sq.ft.

$450,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.49%

Airbnb Rental Income: $null

Traditional Rental Income: $4921

Airbnb ROI: N/A