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
3305 S 18th St Sheboygan, WI What HASN'T been redone is this adorable 3 Bedroom/1 Bath South Side Ranch?? If you're loo...	3 beds \| 1 baths \| 944 sq.ft.	$269,900	Airbnb cash on cash: 2.57% Traditional cash on cash: 3.62% Airbnb Rental Income: $1714 Traditional Rental Income: $1507 Airbnb ROI: 2.57% Traditional ROI: 3.62%
324 St Clair Ave Sheboygan, WI Located in sought-after neighborhood w/ stunning views of Lake Michigan. This classic farm...	3 beds \| 1 baths \| 2,162 sq.ft.	$479,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 0.26% Airbnb Rental Income: $1714 Traditional Rental Income: $1324 Airbnb ROI: 0.07% Traditional ROI: 0.26%
1439 S 10th St Sheboygan, WI This one is not a drive-by!Cute as can be and move in ready. Great home with over 1100' o...	4 beds \| 1 baths \| 1,124 sq.ft.	$179,900	Airbnb cash on cash: 7.46% Traditional cash on cash: 5.06% Airbnb Rental Income: $2243 Traditional Rental Income: $1268 Airbnb ROI: 7.46% Traditional ROI: 5.06%
1135 Logan Ave Sheboygan, WI Very affordable 3 bed, 1.5 bath home. This vinyl sided home offers large living room, spac...	3 beds \| 1 baths \| 1,211 sq.ft.	$220,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 3.77% Airbnb Rental Income: $1714 Traditional Rental Income: $1227 Airbnb ROI: 3.83% Traditional ROI: 3.77%
813 Huron Ave Sheboygan, WI 3BED/1.5 BATH on Sheboygan's Northside. This home has been newly Renovated so your family ...	3 beds \| 1 baths \| 1,247 sq.ft.	$179,900	Airbnb cash on cash: 4.96% Traditional cash on cash: 5.26% Airbnb Rental Income: $1714 Traditional Rental Income: $1291 Airbnb ROI: 4.96% Traditional ROI: 5.26%
1654 S 20th St Sheboygan, WI Time for a new home? Check out this beautiful, 3 bedroom, 1.5 bath, brick Cape Cod on Sheb...	3 beds \| 1 baths \| 1,402 sq.ft.	$255,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.47% Airbnb Rental Income: $1714 Traditional Rental Income: $1429 Airbnb ROI: 2.69% Traditional ROI: 3.47%
1113 High Ave Sheboygan, WI Welcome home to your charming 3-bedroom, 1-bath home in a convenient south-side Sheboygan ...	3 beds \| 1 baths \| 1,177 sq.ft.	$179,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 5.77% Airbnb Rental Income: $1714 Traditional Rental Income: $1441 Airbnb ROI: 4.59% Traditional ROI: 5.77%
3829 Sheridan Ave Sheboygan, WI Country Privacy just outside the City of Sheboygan! This contemporary multifaceted homeste...	4 beds \| 3 baths \| 3,264 sq.ft.	$579,900	Airbnb cash on cash: 1.03% Traditional cash on cash: 5.26% Airbnb Rental Income: $2243 Traditional Rental Income: $3974 Airbnb ROI: 1.03% Traditional ROI: 5.26%
1904 N 28th St Sheboygan, WI Take a look at this beautiful private on a quiet road on the north west side of Sheboygan....	3 beds \| 2 baths \| 1,463 sq.ft.	$280,000	Airbnb cash on cash: 2.51% Traditional cash on cash: 4.69% Airbnb Rental Income: $1714 Traditional Rental Income: $1815 Airbnb ROI: 2.51% Traditional ROI: 4.69%
3805 Sheridan Ave Sheboygan, WI Spacious ranch-style home offering 4 bedrooms, 3.5 bathrooms, an attached garage, and mult...	4 beds \| 3 baths \| 2,755 sq.ft.	$359,000	Airbnb cash on cash: 2.12% Traditional cash on cash: 6.8% Airbnb Rental Income: $2243 Traditional Rental Income: $3258 Airbnb ROI: 2.12% Traditional ROI: 6.8%
514 N 14th St #516 Sheboygan, WI Two family with plenty of room. The lower unit has a nice sized living room, kitchen, 3 be...	6 beds \| 2 baths \| 2,780 sq.ft.	$247,900	Airbnb cash on cash: 4.87% Traditional cash on cash: 8.05% Airbnb Rental Income: $2243 Traditional Rental Income: $2424 Airbnb ROI: 4.87% Traditional ROI: 8.05%
1631 Blocki Ct Sheboygan, WI Cute as can be and very well-maintained home. The main level offers a genuinely nice livin...	3 beds \| 1 baths \| 1,216 sq.ft.	$229,900	Airbnb cash on cash: 3.64% Traditional cash on cash: 3.85% Airbnb Rental Income: $1714 Traditional Rental Income: $1285 Airbnb ROI: 3.64% Traditional ROI: 3.85%
507 Washington Ct Sheboygan, WI Convenient location to Lake Michigan, the Y and other downtown activities. This Blackstock...	4 beds \| 3 baths \| 3,740 sq.ft.	$550,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.34% Airbnb Rental Income: $2243 Traditional Rental Income: $2694 Airbnb ROI: 0.36% Traditional ROI: 2.34%
1636 Main Ave Sheboygan, WI CLOSING TO BE AFTER JANUARY 1, 2023. Located on a dead-end Street; great investment or ow...	2 beds \| 1 baths \| 840 sq.ft.	$182,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 5.27% Airbnb Rental Income: $1416 Traditional Rental Income: $1328 Airbnb ROI: 3.32% Traditional ROI: 5.27%
2029 White Pine Ln Sheboygan, WI This is the ranch you've been waiting for!! The space, the open concept, the view, the wil...	3 beds \| 3 baths \| 3,605 sq.ft.	$559,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 2.24% Airbnb Rental Income: $1714 Traditional Rental Income: $2450 Airbnb ROI: -0.07% Traditional ROI: 2.24%
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.	$4,900,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.66% Airbnb Rental Income: $2243 Traditional Rental Income: $3288 Airbnb ROI: -1.01% Traditional ROI: -0.66%
1106 S 7th St #11 Sheboygan, WI Perfect condo for someone looking for a seasonal or weekend home. This unit is in great s...	2 beds \| 1 baths \| 796 sq.ft.	$157,500	Airbnb cash on cash: 2.22% Traditional cash on cash: 4.31% Airbnb Rental Income: $1416 Traditional Rental Income: $1306 Airbnb ROI: 2.22% Traditional ROI: 4.31%
1529 Indiana Ave Sheboygan, WI Upper Lower Duplex for Sale in Sheboygan! Upper unit has been remodeled with new plank flo...	3 beds \| 2 baths \| 1,212 sq.ft.	$159,900	Airbnb cash on cash: 5.73% Traditional cash on cash: 5.58% Airbnb Rental Income: $1714 Traditional Rental Income: $1217 Airbnb ROI: 5.73% Traditional ROI: 5.58%
1244 Trimberger Ct Sheboygan, WI This inviting Sheboygan home offers a bright and spacious layout with 4 bedrooms and 2.5 b...	4 beds \| 3 baths \| 2,150 sq.ft.	$275,000	Airbnb cash on cash: 4.17% Traditional cash on cash: 7.78% Airbnb Rental Income: $2243 Traditional Rental Income: $2618 Airbnb ROI: 4.17% Traditional ROI: 7.78%
1115 Greendale Rd Sheboygan, WI Beautiful 2015 custom designed home located in Town of Sheboygan (desirable Kohler School ...	4 beds \| 4 baths \| 5,017 sq.ft.	$875,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.44% Airbnb Rental Income: $2243 Traditional Rental Income: $4421 Airbnb ROI: 0.07% Traditional ROI: 3.44%
1106 S 7th St #1 Sheboygan, WI This 2 bedroom condo can either be accessed by a ramp or steps. Located steps away from th...	2 beds \| 1 baths \| 796 sq.ft.	$125,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 5% Airbnb Rental Income: $1416 Traditional Rental Income: $1273 Airbnb ROI: 2.66% Traditional ROI: 5%
1217 North Ave Sheboygan, WI 4-bedroom ranch conveniently located near schools, parks, and local amenities. Spacious li...	4 beds \| 1 baths \| 1,762 sq.ft.	$269,000	Airbnb cash on cash: 4.35% Traditional cash on cash: 7.97% Airbnb Rental Income: $2243 Traditional Rental Income: $2598 Airbnb ROI: 4.35% Traditional ROI: 7.97%
1005 N 38th St Sheboygan, WI 1005 N 38th St, Sheboygan, WI 53081 \| Multi Family	3 beds \| 2 baths \| 1,358 sq.ft.	$239,900	Airbnb cash on cash: 2.23% Traditional cash on cash: 3.56% Airbnb Rental Income: $1714 Traditional Rental Income: $1541 Airbnb ROI: 2.23% Traditional ROI: 3.56%
4026 Hazelnut Ct Sheboygan, WI 4026 Hazelnut Ct, Sheboygan, WI 53081 \| Condo/Coop	2 beds \| 2 baths \| 1,271 sq.ft.	$285,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.77% Airbnb Rental Income: $1416 Traditional Rental Income: $1363 Airbnb ROI: -0.62% Traditional ROI: 0.77%
3322 Main Ave Sheboygan, WI 3322 Main Ave, Sheboygan, WI 53083 \| Single Family Residential	3 beds \| 1 baths \| 1,230 sq.ft.	$279,999	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.34% Airbnb Rental Income: $1714 Traditional Rental Income: $1457 Airbnb ROI: 1.52% Traditional ROI: 2.34%
Lt26 Gettysburg Ln Sheboygan, WI Lt26 Gettysburg Ln, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$58,900	Airbnb cash on cash: 2.81% Traditional cash on cash: 10.1% Airbnb Rental Income: $734 Traditional Rental Income: $854 Airbnb ROI: 2.81% Traditional ROI: 10.1%
Lt178 Green Acres Cir Sheboygan, WI Lt178 Green Acres Cir, Sheboygan, WI 53081 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$66,900	Airbnb cash on cash: 2.19% Traditional cash on cash: 8.66% Airbnb Rental Income: $734 Traditional Rental Income: $854 Airbnb ROI: 2.19% Traditional ROI: 8.66%
Lt164 Schinker Creek Rd Sheboygan, WI Lt164 Schinker Creek Rd, Sheboygan, WI 53081 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$56,900	Airbnb cash on cash: 2.99% Traditional cash on cash: 10.52% Airbnb Rental Income: $734 Traditional Rental Income: $854 Airbnb ROI: 2.99% Traditional ROI: 10.52%
904 Bell Ave Sheboygan, WI Do You Suffer From Old House Love?Knees get weak at the sight of gleaming wood floors?Do b...	4 beds \| 2 baths \| 1,680 sq.ft.	$299,900	Airbnb cash on cash: 3.69% Traditional cash on cash: 4.15% Airbnb Rental Income: $2243 Traditional Rental Income: $1810 Airbnb ROI: 3.69% Traditional ROI: 4.15%
2317 S 9th St Sheboygan, WI 2317 S 9th St, Sheboygan, WI 53081 \| Single Family Residential	4 beds \| 2 baths \| 1,487 sq.ft.	$267,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 3.51% Airbnb Rental Income: $2243 Traditional Rental Income: $1688 Airbnb ROI: 3.48% Traditional ROI: 3.51%
1325 S 11th St Sheboygan, WI 1325 S 11th St, Sheboygan, WI 53081 \| Single Family Residential	4 beds \| 2 baths \| 1,635 sq.ft.	$189,900	Airbnb cash on cash: 5.98% Traditional cash on cash: 7.04% Airbnb Rental Income: $2243 Traditional Rental Income: $1872 Airbnb ROI: 5.98% Traditional ROI: 7.04%
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: 3.74% Traditional cash on cash: 5.26% Airbnb Rental Income: $734 Traditional Rental Income: $500 Airbnb ROI: 3.74% Traditional ROI: 5.26%
Lt3 N 50th St Sheboygan, WI Lt3 N 50th St, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$49,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 7.27% Airbnb Rental Income: $734 Traditional Rental Income: $602 Airbnb ROI: 3.74% Traditional ROI: 7.27%
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: 3.74% Traditional cash on cash: 5.26% Airbnb Rental Income: $734 Traditional Rental Income: $500 Airbnb ROI: 3.74% Traditional ROI: 5.26%
Lt7 N 50th St Sheboygan, WI Lt7 N 50th St, Sheboygan, WI 53083 \| Other	N/A beds \| N/A baths \| N/A	$49,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 5.26% Airbnb Rental Income: $734 Traditional Rental Income: $500 Airbnb ROI: 3.74% Traditional ROI: 5.26%
1813 Washington Ave #1817 Sheboygan, WI 1813 Washington Ave #1817, Sheboygan, WI 53081 \| Single Family Residential	3 beds \| 2 baths \| 1,614 sq.ft.	$215,000	Airbnb cash on cash: 2.81% Traditional cash on cash: 5.53% Airbnb Rental Income: $1714 Traditional Rental Income: $1793 Airbnb ROI: 2.81% Traditional ROI: 5.53%
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: 2.25% Traditional cash on cash: 4.93% Airbnb Rental Income: $734 Traditional Rental Income: $599 Airbnb ROI: 2.25% Traditional ROI: 4.93%
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: 2.81% Traditional cash on cash: 5.79% Airbnb Rental Income: $734 Traditional Rental Income: $599 Airbnb ROI: 2.81% Traditional ROI: 5.79%
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: 2.19% Traditional cash on cash: 4.83% Airbnb Rental Income: $734 Traditional Rental Income: $599 Airbnb ROI: 2.19% Traditional ROI: 4.83%

Real Estate investment in Sheboygan, WI

There are 172 properties for sale in the city of Sheboygan . The median list price in Sheboygan is $229,863 and the average price per square foot is $123. In August 2026, the average monthly cash on cash return in Sheboygan is 4.00%. The average monthly rental income in Sheboygan is $1,656.

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

There are 172 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 $1,656.

Your search for investment property begins and ends here

Investment Property for Sale in Sheboygan, WI

3305 S 18th St

Sheboygan, WI

3 beds | 1 baths | 944 sq.ft.

$269,900

Airbnb cash on cash: 2.57%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $1714

Traditional Rental Income: $1507

Airbnb ROI: 2.57%

Traditional ROI: 3.62%

324 St Clair Ave

Sheboygan, WI

3 beds | 1 baths | 2,162 sq.ft.

$479,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: 0.26%

Airbnb Rental Income: $1714

Traditional Rental Income: $1324

Airbnb ROI: 0.07%

Traditional ROI: 0.26%

1439 S 10th St

Sheboygan, WI

4 beds | 1 baths | 1,124 sq.ft.

$179,900

Airbnb cash on cash: 7.46%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $2243

Traditional Rental Income: $1268

Airbnb ROI: 7.46%

Traditional ROI: 5.06%

1135 Logan Ave

Sheboygan, WI

3 beds | 1 baths | 1,211 sq.ft.

$220,000

Airbnb cash on cash: 3.83%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $1714

Traditional Rental Income: $1227

Airbnb ROI: 3.83%

Traditional ROI: 3.77%

813 Huron Ave

Sheboygan, WI

3 beds | 1 baths | 1,247 sq.ft.

$179,900

Airbnb cash on cash: 4.96%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $1714

Traditional Rental Income: $1291

Airbnb ROI: 4.96%

Traditional ROI: 5.26%

1654 S 20th St

Sheboygan, WI

3 beds | 1 baths | 1,402 sq.ft.

$255,000

Airbnb cash on cash: 2.69%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1714

Traditional Rental Income: $1429

Airbnb ROI: 2.69%

Traditional ROI: 3.47%

1113 High Ave

Sheboygan, WI

3 beds | 1 baths | 1,177 sq.ft.

$179,000

Airbnb cash on cash: 4.59%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $1714

Traditional Rental Income: $1441

Airbnb ROI: 4.59%

Traditional ROI: 5.77%

3829 Sheridan Ave

Sheboygan, WI

4 beds | 3 baths | 3,264 sq.ft.

$579,900

Airbnb cash on cash: 1.03%

Traditional cash on cash: 5.26%

Airbnb Rental Income: $2243

Traditional Rental Income: $3974

Airbnb ROI: 1.03%