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
1430 Virginia Ave Sheboygan, WI What a great spot to call home! This grand ole farmhouse has been here since 1867 and is s...	2 beds \| 1 baths \| 1,160 sq.ft.	$224,900	Airbnb cash on cash: 0.25% Traditional cash on cash: 4.11% Airbnb Rental Income: $1031 Traditional Rental Income: $1492 Airbnb ROI: 0.25% Traditional ROI: 4.11%
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.	$4,900,000	Airbnb cash on cash: -1.06% Traditional cash on cash: -0.74% Airbnb Rental Income: $1876 Traditional Rental Income: $3288 Airbnb ROI: -1.06% Traditional ROI: -0.74%
1223 S 23rd St Sheboygan, WI Find the room you are looking for with this five-bedroom two full bath home sitting on two...	5 beds \| 2 baths \| 1,985 sq.ft.	$254,900	Airbnb cash on cash: 3.99% Traditional cash on cash: 7.7% Airbnb Rental Income: $2190 Traditional Rental Income: $2528 Airbnb ROI: 3.99% Traditional ROI: 7.7%
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.	$423,900	Airbnb cash on cash: 0.59% Traditional cash on cash: 5.12% Airbnb Rental Income: $1196 Traditional Rental Income: $2631 Airbnb ROI: 0.59% Traditional ROI: 5.12%
1217 ALABAMA Avenue Sheboygan, WI Looking for a duplex with great rental history to add to your portfolio? Look no further! ...	N/A beds \| N/A baths \| 1,700 sq.ft.	$140,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 7.09% Airbnb Rental Income: $538 Traditional Rental Income: $1361 Airbnb ROI: -1.11% Traditional ROI: 7.09%
1106 S 7th St #1 Sheboygan, WI Go and Show! Discover your next residential or investment opportunity - offering mid and l...	2 beds \| 1 baths \| 796 sq.ft.	$129,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 4.79% Airbnb Rental Income: $1031 Traditional Rental Income: $1273 Airbnb ROI: -0.04% Traditional ROI: 4.79%
1935 Kaat Ln Sheboygan, WI Custom built two bedroom two bath condo in great location in town of Wilson conveniently l...	2 beds \| 2 baths \| 1,410 sq.ft.	$299,900	Airbnb cash on cash: -0.01% Traditional cash on cash: 4.61% Airbnb Rental Income: $1031 Traditional Rental Income: $2060 Airbnb ROI: -0.01% Traditional ROI: 4.61%
1603 Martin Ave Sheboygan, WI *BACK ON THE MARKET!!*Large completely renovated property waiting for your family to c...	4 beds \| 2 baths \| 1,298 sq.ft.	$210,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 7.55% Airbnb Rental Income: $1876 Traditional Rental Income: $2007 Airbnb ROI: 4.37% Traditional ROI: 7.55%
314 Center Ave #3 Sheboygan, WI Spring is almost here & it's the perfect time to own a condo near the water! This sun-fil...	2 beds \| 1 baths \| 880 sq.ft.	$173,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.9% Airbnb Rental Income: $1031 Traditional Rental Income: $1315 Airbnb ROI: 1.21% Traditional ROI: 4.9%
1217 North Ave Sheboygan, WI Come check out this beautiful 4 bedroom Ranch! Ideally located close to schools, parks, an...	4 beds \| 3 baths \| 1,762 sq.ft.	$299,999	Airbnb cash on cash: 2.48% Traditional cash on cash: 6.55% Airbnb Rental Income: $1876 Traditional Rental Income: $2598 Airbnb ROI: 2.48% Traditional ROI: 6.55%
1106 S 7TH Street unit: 1 Sheboygan, WI Go and Show! Discover your next residential or investment opportunity - offering mid and l...	2 beds \| 1 baths \| 796 sq.ft.	$129,900	Airbnb cash on cash: 2.1% Traditional cash on cash: 4.82% Airbnb Rental Income: $1031 Traditional Rental Income: $1011 Airbnb ROI: 2.1% Traditional ROI: 4.82%
509 Columbus Ave Sheboygan, WI Sought after NE side, Lake Michigan, Mid-century modern home. This stunning, timeless home...	3 beds \| 3 baths \| 2,836 sq.ft.	$1,395,000	Airbnb cash on cash: -1.51% Traditional cash on cash: -0.47% Airbnb Rental Income: $1196 Traditional Rental Income: $2358 Airbnb ROI: -1.51% Traditional ROI: -0.47%
1812 S 10th St Sheboygan, WI ''Better Than New'' & as ''Cute as a Button'' best describes this adorable updated gem off...	3 beds \| 2 baths \| 1,349 sq.ft.	$224,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 5.98% Airbnb Rental Income: $1196 Traditional Rental Income: $1906 Airbnb ROI: 1.23% Traditional ROI: 5.98%
514a S Pier Dr #1 Sheboygan, WI Stunningly stylish, this riverfront corner unit dreams of being your second home, when it'...	3 beds \| 2 baths \| 1,690 sq.ft.	$435,000	Airbnb cash on cash: -1.35% Traditional cash on cash: 2.83% Airbnb Rental Income: $1196 Traditional Rental Income: $2510 Airbnb ROI: -1.35% Traditional ROI: 2.83%
N7330 Lakeshore Rd Sheboygan, WI N7330 Lakeshore Rd, Sheboygan, WI 53083 \| Single Family Residential	3 beds \| 1 baths \| 1,292 sq.ft.	$624,900	Airbnb cash on cash: -1.68% Traditional cash on cash: -1.06% Airbnb Rental Income: $1196 Traditional Rental Income: $1192 Airbnb ROI: -1.68% Traditional ROI: -1.06%
Lt10 N 50th St Sheboygan, WI Lt10 N 50th St, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$49,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 5.26% Airbnb Rental Income: $538 Traditional Rental Income: $500 Airbnb ROI: 0.53% Traditional ROI: 5.26%
Lt9 N 50th St Sheboygan, WI Lt9 N 50th St, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$49,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 5.26% Airbnb Rental Income: $538 Traditional Rental Income: $500 Airbnb ROI: 0.53% Traditional ROI: 5.26%
Lt6 N 50th St Sheboygan, WI Lt6 N 50th St, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$49,900	Airbnb cash on cash: 0.53% Traditional cash on cash: 5.26% Airbnb Rental Income: $538 Traditional Rental Income: $500 Airbnb ROI: 0.53% Traditional ROI: 5.26%
Lt0 Playbird Road Northwest Rd Lot 1 Sheboygan, WI	N/A beds \| N/A baths \| N/A	$32,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 8.23% Airbnb Rental Income: $538 Traditional Rental Income: $498 Airbnb ROI: 1.78% Traditional ROI: 8.23%
Frontage Rd Sheboygan, WI Frontage Rd, Sheboygan, WI 53081 \| Other	N/A beds \| N/A baths \| N/A	$169,900	Airbnb cash on cash: -1.79% Traditional cash on cash: -0.31% Airbnb Rental Income: $538 Traditional Rental Income: $498 Airbnb ROI: -1.79% Traditional ROI: -0.31%
2114 N 19th St Sheboygan, WI 2114 N 19th St, Sheboygan, WI 53081 \| Single Family Residential	4 beds \| 2 baths \| 2,174 sq.ft.	$274,800	Airbnb cash on cash: 1.71% Traditional cash on cash: 3.88% Airbnb Rental Income: $1876 Traditional Rental Income: $1987 Airbnb ROI: 1.71% Traditional ROI: 3.88%
2509 Saemann Ave Sheboygan, WI Take a peek at your dream home seller is moving out of state, this ranch has a ton of upda...	3 beds \| 2 baths \| 1,868 sq.ft.	$324,900	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.52% Airbnb Rental Income: $1196 Traditional Rental Income: $2399 Airbnb ROI: 0.31% Traditional ROI: 5.52%
704 Grand Ave Sheboygan, WI 704 is a GRAND place to be, from the regal manicured formal entrance to romantic white win...	4 beds \| 2 baths \| 1,932 sq.ft.	$334,900	Airbnb cash on cash: 1.91% Traditional cash on cash: 5.03% Airbnb Rental Income: $1876 Traditional Rental Income: $2427 Airbnb ROI: 1.91% Traditional ROI: 5.03%
Lt18 Lincoln Way Sheboygan, WI Lt18 Lincoln Way, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$65,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 8.16% Airbnb Rental Income: $538 Traditional Rental Income: $811 Airbnb ROI: -0.24% Traditional ROI: 8.16%
Lt13 Lincoln Way Sheboygan, WI Lt13 Lincoln Way, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$58,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 9.37% Airbnb Rental Income: $538 Traditional Rental Income: $811 Airbnb ROI: 0.05% Traditional ROI: 9.37%
Lt19 Lincoln Way Sheboygan, WI Lt19 Lincoln Way, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$66,900	Airbnb cash on cash: -0.27% Traditional cash on cash: 8.02% Airbnb Rental Income: $538 Traditional Rental Income: $811 Airbnb ROI: -0.27% Traditional ROI: 8.02%
Lt17 Lincoln Way Sheboygan, WI Lt17 Lincoln Way, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$67,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 7.86% Airbnb Rental Income: $538 Traditional Rental Income: $811 Airbnb ROI: -0.31% Traditional ROI: 7.86%
2407 Henry St Sheboygan, WI 2407 Henry St, Sheboygan, WI 53081 \| Single Family Residential	3 beds \| 1 baths \| 1,456 sq.ft.	$347,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.53% Airbnb Rental Income: $1196 Traditional Rental Income: $1187 Airbnb ROI: -0.64% Traditional ROI: 0.53%
2857 Granite Ct Sheboygan, WI 2857 Granite Ct, Sheboygan, WI 53081 \| Single Family Residential	4 beds \| 3 baths \| 2,549 sq.ft.	$597,900	Airbnb cash on cash: -0.54% Traditional cash on cash: -0.14% Airbnb Rental Income: $1876 Traditional Rental Income: $1600 Airbnb ROI: -0.54% Traditional ROI: -0.14%
1918 S 16th St Sheboygan, WI 1918 S 16th St, Sheboygan, WI 53081 \| Single Family Residential	4 beds \| 1 baths \| 1,465 sq.ft.	$249,900	Airbnb cash on cash: 2.61% Traditional cash on cash: 2.26% Airbnb Rental Income: $1876 Traditional Rental Income: $1292 Airbnb ROI: 2.61% Traditional ROI: 2.26%
1345 Annie Ct Sheboygan, WI Welcome home to this charming Sheboygan residence. This well maintained home offers 3 bedr...	3 beds \| 1 baths \| 1,344 sq.ft.	$257,500	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.63% Airbnb Rental Income: $1196 Traditional Rental Income: $1187 Airbnb ROI: 0.09% Traditional ROI: 1.63%
Lt29 Gettysburg Ln Sheboygan, WI Lt29 Gettysburg Ln, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$68,900	Airbnb cash on cash: -0.33% Traditional cash on cash: 4.09% Airbnb Rental Income: $538 Traditional Rental Income: $562 Airbnb ROI: -0.33% Traditional ROI: 4.09%
750 S Pier Dr #21 Sheboygan, WI 750 S Pier Dr #21, Sheboygan, WI 53081 \| Condo/Coop	2 beds \| 2 baths \| 1,376 sq.ft.	$459,900	Airbnb cash on cash: -2.42% Traditional cash on cash: 0.44% Airbnb Rental Income: $1031 Traditional Rental Income: $1904 Airbnb ROI: -2.42% Traditional ROI: 0.44%
115 Lincoln Ave Sheboygan, WI 115 Lincoln Ave, Sheboygan, WI 53081 \| Single Family Residential	5 beds \| 2 baths \| 2,168 sq.ft.	$355,900	Airbnb cash on cash: 1.79% Traditional cash on cash: N/A Airbnb Rental Income: $2190 Traditional Rental Income: $0 Airbnb ROI: 1.79% Traditional ROI: N/A
3321 N 8TH Street Sheboygan, WI Welcome home! This charming colonial offers four oversized bedrooms and two full baths, gi...	4 beds \| 2 baths \| 2,497 sq.ft.	$314,900	Airbnb cash on cash: 1.99% Traditional cash on cash: 2.75% Airbnb Rental Income: $1876 Traditional Rental Income: $1600 Airbnb ROI: 1.99% Traditional ROI: 2.75%
1328 N 36th St Sheboygan, WI 1328 N 36th St, Sheboygan, WI 53081 \| Single Family Residential	3 beds \| 1 baths \| 931 sq.ft.	$264,900	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.55% Airbnb Rental Income: $1196 Traditional Rental Income: $1187 Airbnb ROI: 0.04% Traditional ROI: 1.55%
Lt33 Gettysburg Ln Sheboygan, WI Lt33 Gettysburg Ln, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$56,900	Airbnb cash on cash: 0.14% Traditional cash on cash: 5.42% Airbnb Rental Income: $538 Traditional Rental Income: $562 Airbnb ROI: 0.14% Traditional ROI: 5.42%
Lt32 Gettysburg Ln Sheboygan, WI Lt32 Gettysburg Ln, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$58,900	Airbnb cash on cash: 0.05% Traditional cash on cash: 9.37% Airbnb Rental Income: $538 Traditional Rental Income: $811 Airbnb ROI: 0.05% Traditional ROI: 9.37%
Lt31 Gettysburg Ln Sheboygan, WI Lt31 Gettysburg Ln, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$61,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 8.84% Airbnb Rental Income: $538 Traditional Rental Income: $811 Airbnb ROI: -0.07% Traditional ROI: 8.84%
1619 Sandstone Ln Sheboygan, WI 1619 Sandstone Ln, Sheboygan, WI 53083 \| Single Family Residential	3 beds \| 3 baths \| 2,756 sq.ft.	$479,900	Airbnb cash on cash: -1.24% Traditional cash on cash: -0.4% Airbnb Rental Income: $1196 Traditional Rental Income: $1187 Airbnb ROI: -1.24% Traditional ROI: -0.4%

Real Estate investment in Sheboygan, WI

There are 83 properties for sale in the city of Sheboygan . The median list price in Sheboygan is $224,900 and the average price per square foot is $154. In March 2026, the average monthly cash on cash return in Sheboygan is 4.00%. The average monthly rental income in Sheboygan is $1,739.

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

There are 83 investment properties available for sale in Sheboygan.

In 2026, 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 $1,739.

Your search for investment property begins and ends here

Investment Property for Sale in Sheboygan, WI

1430 Virginia Ave

Sheboygan, WI

2 beds | 1 baths | 1,160 sq.ft.

$224,900

Airbnb cash on cash: 0.25%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $1031

Traditional Rental Income: $1492

Airbnb ROI: 0.25%

Traditional ROI: 4.11%

W839 Lake Orchard Ct

Sheboygan, WI

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

$4,900,000

Airbnb cash on cash: -1.06%

Traditional cash on cash: -0.74%

Airbnb Rental Income: $1876

Traditional Rental Income: $3288

Airbnb ROI: -1.06%

Traditional ROI: -0.74%

1223 S 23rd St

Sheboygan, WI

5 beds | 2 baths | 1,985 sq.ft.

$254,900

Airbnb cash on cash: 3.99%

Traditional cash on cash: 7.7%

Airbnb Rental Income: $2190

Traditional Rental Income: $2528

Airbnb ROI: 3.99%

Traditional ROI: 7.7%

2825 Stonebrook Dr

Sheboygan, WI

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

$423,900

Airbnb cash on cash: 0.59%

Traditional cash on cash: 5.12%

Airbnb Rental Income: $1196

Traditional Rental Income: $2631

Airbnb ROI: 0.59%

Traditional ROI: 5.12%

1217 ALABAMA Avenue

Sheboygan, WI

N/A beds | N/A baths | 1,700 sq.ft.

$140,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 7.09%

Airbnb Rental Income: $538

Traditional Rental Income: $1361

Airbnb ROI: -1.11%

Traditional ROI: 7.09%

1106 S 7th St #1

Sheboygan, WI

2 beds | 1 baths | 796 sq.ft.

$129,900

Airbnb cash on cash: -0.04%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $1031

Traditional Rental Income: $1273

Airbnb ROI: -0.04%

Traditional ROI: 4.79%

1935 Kaat Ln

Sheboygan, WI

2 beds | 2 baths | 1,410 sq.ft.

$299,900

Airbnb cash on cash: -0.01%

Traditional cash on cash: 4.61%

Airbnb Rental Income: $1031

Traditional Rental Income: $2060

Airbnb ROI: -0.01%

Traditional ROI: 4.61%

1603 Martin Ave

Sheboygan, WI

4 beds | 2 baths | 1,298 sq.ft.

$210,000

Airbnb cash on cash: 4.37%

Traditional cash on cash: 7.55%

Airbnb Rental Income: $1876

Traditional Rental Income: $2007

Airbnb ROI: 4.37%