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.	$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%
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.	$429,900	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%
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%
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%
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%
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: -0.04% Traditional cash on cash: 4.79% Airbnb Rental Income: $1031 Traditional Rental Income: $1273 Airbnb ROI: -0.04% Traditional ROI: 4.79%
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%
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%
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 *BACK ON THE MARKET!! Buyers financing fell through* Large completely renovated proper...	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%
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%
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%
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: 1.33% Traditional cash on cash: 4.1% Airbnb Rental Income: $2190 Traditional Rental Income: $2826 Airbnb ROI: 1.33% Traditional ROI: 4.1%
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%
915 North Ave Sheboygan, WI You simply must see this absolutely adorable north side Sheboygan home to fully appreciate...	3 beds \| 2 baths \| 1,128 sq.ft.	$269,900	Airbnb cash on cash: 0.61% Traditional cash on cash: 4.59% Airbnb Rental Income: $1196 Traditional Rental Income: $1822 Airbnb ROI: 0.61% Traditional ROI: 4.59%
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.	$320,000	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%

Real Estate investment in Sheboygan, WI

There are 71 properties for sale in the city of Sheboygan . The median list price in Sheboygan is $212,499 and the average price per square foot is $152. In January 2026, the average monthly cash on cash return in Sheboygan is 5.00%. The average monthly rental income in Sheboygan is $1,727.

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

There are 71 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 $1,727.

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.

$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%

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.

$429,900

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%

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%

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%

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%

Traditional ROI: 3.99%

2609 CROSSCREEK Drive #UNIT D

Sheboygan, WI

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%