Real Estate Investment Properties for Sale in Sheboygan, WI

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2839 Windepoint Ct Sheboygan, WI Neat and clean two bedroom Windepoint condo overlooking Maywood Park. This unit is a lowe...	2 beds \| 2 baths \| 1,600 sq.ft.	$269,000	Airbnb cash on cash: -0.78% Traditional cash on cash: 4.83% Airbnb Rental Income: $1090 Traditional Rental Income: $2141 Airbnb ROI: -0.78% Traditional ROI: 4.83%
5010 S 8th St Sheboygan, WI Discover the Town of Wilson with this beautiful ranch home located at 5010 S. 8th St. in S...	3 beds \| 2 baths \| 2,860 sq.ft.	$359,900	Airbnb cash on cash: 0.15% Traditional cash on cash: 5.45% Airbnb Rental Income: $1165 Traditional Rental Income: $2573 Airbnb ROI: 0.15% Traditional ROI: 5.45%
2117 Arizona Ave Sheboygan, WI 1952, it features a detached garage, aluminum siding, and a quiet residential location. Id...	2 beds \| 1 baths \| 672 sq.ft.	$99,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 8.24% Airbnb Rental Income: $1018 Traditional Rental Income: $1130 Airbnb ROI: 3.39% Traditional ROI: 8.24%
W839 Lake Orchard Ct Sheboygan, WI Once in a lifetime opportunity to own the Wunsch farm that has been in this family's care ...	4 beds \| 3 baths \| 4,000 sq.ft.	$6,500,000	Airbnb cash on cash: -1.05% Traditional cash on cash: -0.74% Airbnb Rental Income: $1941 Traditional Rental Income: $3288 Airbnb ROI: -1.05% Traditional ROI: -0.74%
1316 Indiana Ave Sheboygan, WI This cozy & well-maintained 4-bedroom, 1-bath home offers the perfect blend of comfort & c...	4 beds \| 1 baths \| 1,153 sq.ft.	$149,900	Airbnb cash on cash: 7.22% Traditional cash on cash: 7.87% Airbnb Rental Income: $1941 Traditional Rental Income: $1522 Airbnb ROI: 7.22% Traditional ROI: 7.87%
2825 Stonebrook Dr Sheboygan, WI Sale of home subject to School Board approval (please use this verbiage in any offer). Cu...	3 beds \| 3 baths \| 1,797 sq.ft.	$439,900	Airbnb cash on cash: 0.5% Traditional cash on cash: 4.99% Airbnb Rental Income: $1165 Traditional Rental Income: $2631 Airbnb ROI: 0.5% Traditional ROI: 4.99%
628 End Ct #628A Sheboygan, WI Two-unit duplex located just blocks from Lake Michigan and downtown Sheboygan. Each unit o...	4 beds \| 2 baths \| N/A	$199,000	Airbnb cash on cash: 5.12% Traditional cash on cash: 9.27% Airbnb Rental Income: $1941 Traditional Rental Income: $2213 Airbnb ROI: 5.12% Traditional ROI: 9.27%
810 High Ave Sheboygan, WI This is your chance to live less than two blocks from Lake Michigan at an affordable price...	3 beds \| 2 baths \| 1,694 sq.ft.	$250,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 7.04% Airbnb Rental Income: $1165 Traditional Rental Income: $2256 Airbnb ROI: 0.79% Traditional ROI: 7.04%
2335 N 28th St Sheboygan, WI Welcome to a beautifully maintained 4-bedroom, 2.5-bath ranch on Sheboygan's desirable nor...	4 beds \| 3 baths \| 2,117 sq.ft.	$365,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 5.77% Airbnb Rental Income: $1941 Traditional Rental Income: $2824 Airbnb ROI: 1.7% Traditional ROI: 5.77%
1332 S 9th St Sheboygan, WI Look no further than this one for your next investment opportunity! This property features...	6 beds \| 2 baths \| N/A	$215,000	Airbnb cash on cash: 3.92% Traditional cash on cash: 10.5% Airbnb Rental Income: $1747 Traditional Rental Income: $2608 Airbnb ROI: 3.92% Traditional ROI: 10.5%
2403 Cross Creek Dr #B Sheboygan, WI Welcome to a unique, highly sought after first floor condo at the Creekside Condominiums. ...	3 beds \| 2 baths \| 2,071 sq.ft.	$254,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 7.96% Airbnb Rental Income: $1165 Traditional Rental Income: $2551 Airbnb ROI: 0.61% Traditional ROI: 7.96%
1324 S 17TH Street Sheboygan, WI Welcome home! This charming 3+ bedroom, 1.5 bath home offers comfort and convenience with ...	3 beds \| 2 baths \| 1,470 sq.ft.	$210,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 7.8% Airbnb Rental Income: $1165 Traditional Rental Income: $2068 Airbnb ROI: 1.34% Traditional ROI: 7.8%
2222 N 28th St Sheboygan, WI Spacious 3 Bedroom 2 Bathroom Home features a Bright and Sunny Living Room, Chef's Kitchen...	3 beds \| 2 baths \| 1,844 sq.ft.	$299,900	Airbnb cash on cash: 0.25% Traditional cash on cash: 5.74% Airbnb Rental Income: $1165 Traditional Rental Income: $2332 Airbnb ROI: 0.25% Traditional ROI: 5.74%
429 Beachfront Ct #757 Sheboygan, WI Nicely maintained and updated main floor condo at Blue Harbor that has shown solid rental ...	2 beds \| 2 baths \| 1,242 sq.ft.	$319,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 4.11% Airbnb Rental Income: $1090 Traditional Rental Income: $1831 Airbnb ROI: 0.4% Traditional ROI: 4.11%
650 S Pier Dr #6 Sheboygan, WI Fantastic condo on Sheboygan's riverfront featuring over 1700 square feet, 3 bedrooms, 2 f...	3 beds \| 2 baths \| 1,756 sq.ft.	$429,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 4.51% Airbnb Rental Income: $1165 Traditional Rental Income: $2640 Airbnb ROI: -0.12% Traditional ROI: 4.51%
2523 Henry St Sheboygan, WI So much space in this pristine 4-bedroom, 2-bath Cape Cod conveniently walkable to the par...	4 beds \| 2 baths \| 2,066 sq.ft.	$275,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 7.52% Airbnb Rental Income: $1941 Traditional Rental Income: $2564 Airbnb ROI: 3.14% Traditional ROI: 7.52%
1615 Tennis Ln Sheboygan, WI Lovingly cared for 4BR, 2.5BA home in the Town of Sheboygan, set on nearly 1/2 acre. The i...	4 beds \| 3 baths \| 2,415 sq.ft.	$479,900	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.55% Airbnb Rental Income: $1941 Traditional Rental Income: $2972 Airbnb ROI: 1.11% Traditional ROI: 4.55%
1921 GARFIELD Avenue Sheboygan, WI Starter home or flip opportunity with great potential! Discover this City of Sheboygan 3-...	3 beds \| 2 baths \| 1,577 sq.ft.	$189,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 8.82% Airbnb Rental Income: $1165 Traditional Rental Income: $2115 Airbnb ROI: 1.44% Traditional ROI: 8.82%
1937 Kaat Ln Sheboygan, WI Don't look any further! This ranch style side-by-side condo is the home you've been search...	2 beds \| 2 baths \| 1,636 sq.ft.	$359,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.86% Airbnb Rental Income: $1090 Traditional Rental Income: $2060 Airbnb ROI: -0.11% Traditional ROI: 3.86%
2609 CROSSCREEK Drive #UNIT D Sheboygan, WI Move right in to this amazing Condo tucked away in an ideal southside location. Newer carp...	2 beds \| 1 baths \| 1,016 sq.ft.	$164,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 6.16% Airbnb Rental Income: $1090 Traditional Rental Income: $1387 Airbnb ROI: 1.92% Traditional ROI: 6.16%
1212 ST CLAIR Avenue Sheboygan, WI Seize this fantastic investment opportunity in the vibrant heart of Sheboygan, WI! This we...	N/A beds \| N/A baths \| 2,256 sq.ft.	$189,900	Airbnb cash on cash: 1.45% Traditional cash on cash: 4.33% Airbnb Rental Income: $1090 Traditional Rental Income: $1239 Airbnb ROI: 1.45% Traditional ROI: 4.33%
1106 S 7TH Street #1 Sheboygan, WI Go and Show! Discover your next residential or investment opportunity - offering mid and l...	2 beds \| 1 baths \| 796 sq.ft.	$132,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 6.62% Airbnb Rental Income: $1090 Traditional Rental Income: $1273 Airbnb ROI: 2.26% Traditional ROI: 6.62%
1106 S 7TH Street #2 Sheboygan, WI Go and Show! Discover your next residential or investment opportunity - offering mid and l...	2 beds \| 1 baths \| 796 sq.ft.	$132,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 6.73% Airbnb Rental Income: $1090 Traditional Rental Income: $1271 Airbnb ROI: 2.38% Traditional ROI: 6.73%
2024 N 12TH Avenue Sheboygan, WI Discover this prime investment opportunity in the bustling heart of Sheboygan, WI! This we...	6 beds \| 2 baths \| 2,205 sq.ft.	$215,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 3.52% Airbnb Rental Income: $1090 Traditional Rental Income: $1239 Airbnb ROI: 0.97% Traditional ROI: 3.52%
1325-1327 N 15th Street Sheboygan, WI Centrally located duplex in Sheboyganâs walkable North Railway neighborhood (A Walk Scor...	5 beds \| N/A baths \| N/A	$189,900	Airbnb cash on cash: 4.58% Traditional cash on cash: 9.42% Airbnb Rental Income: $1747 Traditional Rental Income: $2141 Airbnb ROI: 4.58% Traditional ROI: 9.42%
2011 N 9th St Sheboygan, WI Charming 4-bedroom home near Lake Michigan! This property blends character with updates, f...	4 beds \| 2 baths \| 2,661 sq.ft.	$329,900	Airbnb cash on cash: 2.16% Traditional cash on cash: 5.85% Airbnb Rental Income: $1941 Traditional Rental Income: $2573 Airbnb ROI: 2.16% Traditional ROI: 5.85%
3705 N 12th St Sheboygan, WI Welcome home to this beautifully renovated 3-bedroom, 1.5-bath ranch, perfectly situated i...	3 beds \| 2 baths \| 1,496 sq.ft.	$369,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.94% Airbnb Rental Income: $1165 Traditional Rental Income: $2161 Airbnb ROI: -0.04% Traditional ROI: 3.94%
3742 Enterprise Dr Sheboygan, WI Discover the perfect blend of space & potential within this town of Sheboygan home. Situat...	3 beds \| 1 baths \| 1,155 sq.ft.	$249,900	Airbnb cash on cash: 1.28% Traditional cash on cash: 4.94% Airbnb Rental Income: $1165 Traditional Rental Income: $1646 Airbnb ROI: 1.28% Traditional ROI: 4.94%

Real Estate investment in Sheboygan, WI

There are 29 properties for sale in the city of Sheboygan . The median list price in Sheboygan is $249,950 and the average price per square foot is $141. In October 2025, the average monthly cash on cash return in Sheboygan is 5.00%. The average monthly rental income in Sheboygan is $2,141.

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

There are 29 investment properties available for sale in Sheboygan.

In 2025, the best neighborhood to buy investment property is Sheboygan.

The ROI for Long-Term is higher than the Short-Term in Sheboygan with average rental income of $2,141.

Your search for investment property begins and ends here

Investment Property for Sale in Sheboygan, WI

2839 Windepoint Ct

Sheboygan, WI

2 beds | 2 baths | 1,600 sq.ft.

$269,000

Airbnb cash on cash: -0.78%

Traditional cash on cash: 4.83%

Airbnb Rental Income: $1090

Traditional Rental Income: $2141

Airbnb ROI: -0.78%

Traditional ROI: 4.83%

5010 S 8th St

Sheboygan, WI

3 beds | 2 baths | 2,860 sq.ft.

$359,900

Airbnb cash on cash: 0.15%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $1165

Traditional Rental Income: $2573

Airbnb ROI: 0.15%

Traditional ROI: 5.45%

2117 Arizona Ave

Sheboygan, WI

2 beds | 1 baths | 672 sq.ft.

$99,900

Airbnb cash on cash: 3.39%

Traditional cash on cash: 8.24%

Airbnb Rental Income: $1018

Traditional Rental Income: $1130

Airbnb ROI: 3.39%

Traditional ROI: 8.24%

W839 Lake Orchard Ct

Sheboygan, WI

4 beds | 3 baths | 4,000 sq.ft.

$6,500,000

Airbnb cash on cash: -1.05%

Traditional cash on cash: -0.74%

Airbnb Rental Income: $1941

Traditional Rental Income: $3288

Airbnb ROI: -1.05%

Traditional ROI: -0.74%

1316 Indiana Ave

Sheboygan, WI

4 beds | 1 baths | 1,153 sq.ft.

$149,900

Airbnb cash on cash: 7.22%

Traditional cash on cash: 7.87%

Airbnb Rental Income: $1941

Traditional Rental Income: $1522

Airbnb ROI: 7.22%

Traditional ROI: 7.87%

2825 Stonebrook Dr

Sheboygan, WI

3 beds | 3 baths | 1,797 sq.ft.

$439,900

Airbnb cash on cash: 0.5%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $1165

Traditional Rental Income: $2631

Airbnb ROI: 0.5%

Traditional ROI: 4.99%

628 End Ct #628A

Sheboygan, WI

4 beds | 2 baths | N/A

$199,000

Airbnb cash on cash: 5.12%

Traditional cash on cash: 9.27%

Airbnb Rental Income: $1941

Traditional Rental Income: $2213

Airbnb ROI: 5.12%

Traditional ROI: 9.27%

810 High Ave

Sheboygan, WI

3 beds | 2 baths | 1,694 sq.ft.

$250,000

Airbnb cash on cash: 0.79%

Traditional cash on cash: 7.04%

Airbnb Rental Income: $1165

Traditional Rental Income: $2256

Airbnb ROI: 0.79%