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
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.	$349,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 5.63% Airbnb Rental Income: $1196 Traditional Rental Income: $2573 Airbnb ROI: 0.26% Traditional ROI: 5.63%
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: -1.06% Traditional cash on cash: -0.74% Airbnb Rental Income: $1876 Traditional Rental Income: $3288 Airbnb ROI: -1.06% Traditional ROI: -0.74%
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: 0.56% Traditional cash on cash: 4.99% Airbnb Rental Income: $1196 Traditional Rental Income: $2631 Airbnb ROI: 0.56% Traditional ROI: 4.99%
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: 0.9% Traditional cash on cash: 7.04% Airbnb Rental Income: $1196 Traditional Rental Income: $2256 Airbnb ROI: 0.9% Traditional ROI: 7.04%
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: 0.71% Traditional cash on cash: 7.96% Airbnb Rental Income: $1196 Traditional Rental Income: $2551 Airbnb ROI: 0.71% 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: 1.47% Traditional cash on cash: 7.8% Airbnb Rental Income: $1196 Traditional Rental Income: $2068 Airbnb ROI: 1.47% 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.	$279,900	Airbnb cash on cash: 0.44% Traditional cash on cash: 6.22% Airbnb Rental Income: $1196 Traditional Rental Income: $2332 Airbnb ROI: 0.44% Traditional ROI: 6.22%
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.	$349,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.99% Airbnb Rental Income: $1031 Traditional Rental Income: $2060 Airbnb ROI: -0.24% Traditional ROI: 3.99%
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: 1.6% Traditional cash on cash: 6.16% Airbnb Rental Income: $1031 Traditional Rental Income: $1387 Airbnb ROI: 1.6% 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.	$169,900	Airbnb cash on cash: -1.11% Traditional cash on cash: 4.94% Airbnb Rental Income: $538 Traditional Rental Income: $1239 Airbnb ROI: -1.11% Traditional ROI: 4.94%
1106 S 7TH Street unit: 1 #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: 1.92% Traditional cash on cash: 6.74% Airbnb Rental Income: $1031 Traditional Rental Income: $1273 Airbnb ROI: 1.92% Traditional ROI: 6.74%
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% Traditional cash on cash: 6.73% Airbnb Rental Income: $1031 Traditional Rental Income: $1271 Airbnb ROI: 2% Traditional ROI: 6.73%
2024 N 12TH Street Sheboygan, WI Discover this prime investment opportunity in the bustling heart of Sheboygan, WI! This du...	6 beds \| 2 baths \| 2,205 sq.ft.	$199,900	Airbnb cash on cash: 0.75% Traditional cash on cash: 3.75% Airbnb Rental Income: $1031 Traditional Rental Income: $1239 Airbnb ROI: 0.75% Traditional ROI: 3.75%
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: 6.63% Traditional cash on cash: 9.42% Airbnb Rental Income: $2190 Traditional Rental Income: $2141 Airbnb ROI: 6.63% Traditional ROI: 9.42%
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.	$319,900	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%
2305 N 8th St Sheboygan, WI Northeast side of Sheboygan is where you'll find this completely rehabbed two story featur...	3 beds \| 2 baths \| 2,066 sq.ft.	$309,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 5.28% Airbnb Rental Income: $1196 Traditional Rental Income: $2181 Airbnb ROI: 0.55% Traditional ROI: 5.28%
3108 N 21ST Street Sheboygan, WI Welcome home to this beautifully updated 3-bedroom, 1.5-bath ranch. Step inside to find a ...	3 beds \| 2 baths \| 2,074 sq.ft.	$294,900	Airbnb cash on cash: 0.17% Traditional cash on cash: 6.01% Airbnb Rental Income: $1196 Traditional Rental Income: $2430 Airbnb ROI: 0.17% Traditional ROI: 6.01%
1603 Martin Ave Sheboygan, WI Large completely renovated property waiting for your family to call this their home. Ever...	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%
2013 N 13th St Sheboygan, WI This well-maintained home features an inviting main level with a spacious living area, ful...	2 beds \| 1 baths \| 840 sq.ft.	$149,900	Airbnb cash on cash: 2.34% Traditional cash on cash: 6.58% Airbnb Rental Income: $1031 Traditional Rental Income: $1278 Airbnb ROI: 2.34% Traditional ROI: 6.58%
1010 Forest Ave Sheboygan, WI Find the character you've been looking for with this spacious ranch on Sheboygan's south s...	3 beds \| 2 baths \| 1,992 sq.ft.	$334,900	Airbnb cash on cash: 0.06% Traditional cash on cash: 5.33% Airbnb Rental Income: $1196 Traditional Rental Income: $2465 Airbnb ROI: 0.06% Traditional ROI: 5.33%
426 Park Ave Sheboygan, WI Welcome to 426 Park Ave. with grand front staircase leading to covered front porch. If you...	3 beds \| 1 baths \| 1,318 sq.ft.	$230,000	Airbnb cash on cash: 0.9% Traditional cash on cash: 4.7% Airbnb Rental Income: $1196 Traditional Rental Income: $1636 Airbnb ROI: 0.9% Traditional ROI: 4.7%
2602 Camelot Blvd #C Sheboygan, WI Why rent when you can purchase this cozy 2-bedroom, 1-bath condo that checks all the boxes...	2 beds \| 1 baths \| 800 sq.ft.	$107,500	Airbnb cash on cash: 3.68% Traditional cash on cash: 8.66% Airbnb Rental Income: $1031 Traditional Rental Income: $1189 Airbnb ROI: 3.68% Traditional ROI: 8.66%
314 Center Ave #3 Sheboygan, WI Have you been waiting for a condo near the Marina to come up for sale? HERE'S YOUR CHANCE!...	2 beds \| 1 baths \| 880 sq.ft.	$183,900	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%
1411 Marie Ct Sheboygan, WI Welcome to 1411 Marie Ct, where classic 1913 charm meets ''this-could-be-your-next-cashflo...	5 beds \| 2 baths \| N/A	$189,900	Airbnb cash on cash: 6.69% Traditional cash on cash: 11.64% Airbnb Rental Income: $2190 Traditional Rental Income: $2530 Airbnb ROI: 6.69% Traditional ROI: 11.64%
1507b Erie Avenue Sheboygan, WI Centrally located and full of potential, this 3-bed, 1-bath home offers bonus rooms, park ...	3 beds \| 1 baths \| 1,148 sq.ft.	$129,900	Airbnb cash on cash: 3.45% Traditional cash on cash: 9.62% Airbnb Rental Income: $1196 Traditional Rental Income: $1578 Airbnb ROI: 3.45% Traditional ROI: 9.62%
3155 Calumet Dr Sheboygan, WI Enjoy this spacious 5-bedroom, 3 full bath ranch. Just steps away from Jaycee Park, the Q...	5 beds \| 3 baths \| 1,860 sq.ft.	$459,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 4.18% Airbnb Rental Income: $2190 Traditional Rental Income: $2826 Airbnb ROI: 1.41% Traditional ROI: 4.18%
922 Kentucky Ave Sheboygan, WI Small but mighty!! Move right into this completely renovated home. Simply bring your belon...	3 beds \| 1 baths \| 808 sq.ft.	$179,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 6.41% Airbnb Rental Income: $1196 Traditional Rental Income: $1431 Airbnb ROI: 2.77% Traditional ROI: 6.41%

Real Estate investment in Sheboygan, WI

There are 29 properties for sale in the city of Sheboygan . The median list price in Sheboygan is $210,000 and the average price per square foot is $129. In December 2025, the average monthly cash on cash return in Sheboygan is 5.00%. The average monthly rental income in Sheboygan is $2,060.

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 $2,060.

Your search for investment property begins and ends here

Investment Property for Sale in Sheboygan, WI

5010 S 8th St

Sheboygan, WI

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

$349,900

Airbnb cash on cash: 0.26%

Traditional cash on cash: 5.63%

Airbnb Rental Income: $1196

Traditional Rental Income: $2573

Airbnb ROI: 0.26%

Traditional ROI: 5.63%

W839 Lake Orchard Ct

Sheboygan, WI

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

$6,500,000

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%

2825 Stonebrook Dr

Sheboygan, WI

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

$439,900

Airbnb cash on cash: 0.56%

Traditional cash on cash: 4.99%

Airbnb Rental Income: $1196

Traditional Rental Income: $2631

Airbnb ROI: 0.56%

Traditional ROI: 4.99%

810 High Ave

Sheboygan, WI

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

$250,000

Airbnb cash on cash: 0.9%

Traditional cash on cash: 7.04%

Airbnb Rental Income: $1196

Traditional Rental Income: $2256

Airbnb ROI: 0.9%

Traditional ROI: 7.04%

2403 Cross Creek Dr #B

Sheboygan, WI

3 beds | 2 baths | 2,071 sq.ft.

$254,900

Airbnb cash on cash: 0.71%

Traditional cash on cash: 7.96%

Airbnb Rental Income: $1196

Traditional Rental Income: $2551

Airbnb ROI: 0.71%

Traditional ROI: 7.96%

1324 S 17TH Street

Sheboygan, WI

3 beds | 2 baths | 1,470 sq.ft.

$210,000

Airbnb cash on cash: 1.47%

Traditional cash on cash: 7.8%

Airbnb Rental Income: $1196

Traditional Rental Income: $2068

Airbnb ROI: 1.47%

Traditional ROI: 7.8%

2222 N 28th St

Sheboygan, WI

3 beds | 2 baths | 1,844 sq.ft.

$279,900

Airbnb cash on cash: 0.44%

Traditional cash on cash: 6.22%

Airbnb Rental Income: $1196

Traditional Rental Income: $2332

Airbnb ROI: 0.44%

Traditional ROI: 6.22%

1937 Kaat Ln

Sheboygan, WI

2 beds | 2 baths | 1,636 sq.ft.

$349,900

Airbnb cash on cash: -0.24%

Traditional cash on cash: 3.99%

Airbnb Rental Income: $1031

Traditional Rental Income: $2060

Airbnb ROI: -0.24%