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: 0.99% Traditional cash on cash: 3.62% Airbnb Rental Income: $1232 Traditional Rental Income: $1507 Airbnb ROI: 0.99% Traditional ROI: 3.62%
620 Oak Tree Rd Sheboygan, WI Experience the beauty of Lake Michigan living in this exceptional home. Stunning views, th...	3 beds \| 5 baths \| 5,107 sq.ft.	$1,477,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 1.95% Airbnb Rental Income: $1232 Traditional Rental Income: $5181 Airbnb ROI: -1.22% Traditional ROI: 1.95%
3829 Sheridan Ave Sheboygan, WI Country Privacy just outside the City of Sheboygan! This contemporary multifaceted homeste...	4 beds \| 4 baths \| 3,264 sq.ft.	$589,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 5.16% Airbnb Rental Income: $1755 Traditional Rental Income: $3974 Airbnb ROI: 0.26% Traditional ROI: 5.16%
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: -0.84% Traditional cash on cash: 2.24% Airbnb Rental Income: $1232 Traditional Rental Income: $2450 Airbnb ROI: -0.84% 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: -1.1% Traditional cash on cash: -0.66% Airbnb Rental Income: $1755 Traditional Rental Income: $3288 Airbnb ROI: -1.1% Traditional ROI: -0.66%
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: 2.6% Traditional cash on cash: 7.78% Airbnb Rental Income: $1755 Traditional Rental Income: $2618 Airbnb ROI: 2.6% Traditional ROI: 7.78%
1106 S 7TH Street #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: 2.65% Traditional cash on cash: 5% Airbnb Rental Income: $1415 Traditional Rental Income: $1273 Airbnb ROI: 2.65% Traditional ROI: 5%
1217 North Ave Sheboygan, WI 4-bedroom ranch conveniently located near schools, parks, and local amenities. Spacious li...	4 beds \| 3 baths \| 1,762 sq.ft.	$279,900	Airbnb cash on cash: 2.6% Traditional cash on cash: 7.62% Airbnb Rental Income: $1755 Traditional Rental Income: $2598 Airbnb ROI: 2.6% Traditional ROI: 7.62%
1538 N 27TH Street Sheboygan, WI Charming and beautifully updated, this cozy 2-bedroom, 1.5 bath home blends comfort and st...	2 beds \| 2 baths \| 602 sq.ft.	$164,500	Airbnb cash on cash: 3.92% Traditional cash on cash: 6.07% Airbnb Rental Income: $1415 Traditional Rental Income: $1327 Airbnb ROI: 3.92% Traditional ROI: 6.07%
750 S Pier Dr #3 Sheboygan, WI Absolutely mint condition second floor riverfront condo featuring large great room kitchen...	2 beds \| 2 baths \| 1,330 sq.ft.	$429,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 2.78% Airbnb Rental Income: $1415 Traditional Rental Income: $2523 Airbnb ROI: -1.04% Traditional ROI: 2.78%
1429 S 9th St Sheboygan, WI This charmer has recent updates including new electrical breakers, new flooring throughout...	3 beds \| 1 baths \| 1,568 sq.ft.	$167,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 6.85% Airbnb Rental Income: $1232 Traditional Rental Income: $1582 Airbnb ROI: 2.18% Traditional ROI: 6.85%
4607 County Road J - Sheboygan, WI This is the charming 2 story farmhouse you have been searching for! Located in sought afte...	4 beds \| 2 baths \| 1,908 sq.ft.	$319,000	Airbnb cash on cash: 2.21% Traditional cash on cash: 6.31% Airbnb Rental Income: $1755 Traditional Rental Income: $2505 Airbnb ROI: 2.21% Traditional ROI: 6.31%
1729 S 12th St Sheboygan, WI Versatile corner mixed-use property offering four 2BR/1BA residential units, commercial sp...	N/A beds \| N/A baths \| N/A	$206,900	Airbnb cash on cash: -1.22% Traditional cash on cash: 4.62% Airbnb Rental Income: $602 Traditional Rental Income: $1459 Airbnb ROI: -1.22% Traditional ROI: 4.62%
N6475 Rangeline Road Sheboygan, WI Fresh spring curb appeal and a light-filled interior make this 3 bedroom, 3 bathroom ranch...	3 beds \| 3 baths \| 2,028 sq.ft.	$432,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 4.39% Airbnb Rental Income: $1232 Traditional Rental Income: $2695 Airbnb ROI: -0.2% Traditional ROI: 4.39%
W2131 Playbird Rd Sheboygan, WI Country living with city convenience! This well-maintained 4-bedroom, 2-bath bi-level home...	4 beds \| 2 baths \| 1,976 sq.ft.	$350,000	Airbnb cash on cash: 1.79% Traditional cash on cash: 6.07% Airbnb Rental Income: $1755 Traditional Rental Income: $2682 Airbnb ROI: 1.79% Traditional ROI: 6.07%
2146 Waverly Ct Sheboygan, WI This timeless 2 story colonial is the home you have been searching for. Located in sought ...	3 beds \| 3 baths \| 2,746 sq.ft.	$400,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 5.59% Airbnb Rental Income: $1232 Traditional Rental Income: $2946 Airbnb ROI: -0.03% Traditional ROI: 5.59%
2114 N 22nd St Sheboygan, WI Vinyl sided 2-story home located near schools, parks and other conveniences. Enjoy a spac...	2 beds \| 2 baths \| 1,264 sq.ft.	$204,900	Airbnb cash on cash: 2.48% Traditional cash on cash: 6.86% Airbnb Rental Income: $1415 Traditional Rental Income: $1842 Airbnb ROI: 2.48% Traditional ROI: 6.86%
826 Geele Ave Sheboygan, WI Charm & Character shines both inside and outside of this open concept style 4br/1.5ba gem!...	4 beds \| 2 baths \| 2,030 sq.ft.	$269,900	Airbnb cash on cash: 2.71% Traditional cash on cash: 7.64% Airbnb Rental Income: $1755 Traditional Rental Income: $2528 Airbnb ROI: 2.71% Traditional ROI: 7.64%
1722 N 11th St Sheboygan, WI Affordable two family on Sheboygan's northeast side. Aluminum siding, large lots, replace...	4 beds \| 3 baths \| N/A	$219,900	Airbnb cash on cash: 3.73% Traditional cash on cash: 9.53% Airbnb Rental Income: $1755 Traditional Rental Income: $2480 Airbnb ROI: 3.73% Traditional ROI: 9.53%
617 N 28th St Sheboygan, WI Welcome to 617 N 28th Street, a beautiful 3-bedroom, 1.5-bath ranch offering 2,026 square ...	3 beds \| 2 baths \| 2,026 sq.ft.	$314,900	Airbnb cash on cash: 0.13% Traditional cash on cash: 5.86% Airbnb Rental Income: $1232 Traditional Rental Income: $2535 Airbnb ROI: 0.13% Traditional ROI: 5.86%
3205 N 10th St Sheboygan, WI Opportunity awaits with this spacious 4 bed, 2 bath tri-level offering over 2,100 sq/ft on...	4 beds \| 2 baths \| 2,108 sq.ft.	$375,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 5.14% Airbnb Rental Income: $1755 Traditional Rental Income: $2604 Airbnb ROI: 1.36% Traditional ROI: 5.14%
2316 Main Ave Sheboygan, WI Looking for an affordable home with major updates already completed? This charming 3-bedro...	3 beds \| 1 baths \| 1,026 sq.ft.	$215,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 4.85% Airbnb Rental Income: $1232 Traditional Rental Income: $1467 Airbnb ROI: 1.76% Traditional ROI: 4.85%
2506 Geele Ave Sheboygan, WI Enjoy the gorgeous Park View from this quality built 2+ BD/1.5 BA Brick Ranch on Sheboyga...	2 beds \| 2 baths \| 1,610 sq.ft.	$274,900	Airbnb cash on cash: 0.76% Traditional cash on cash: 4.99% Airbnb Rental Income: $1415 Traditional Rental Income: $2087 Airbnb ROI: 0.76% Traditional ROI: 4.99%
1823 N 7th St Sheboygan, WI This beautifully renovated 5-bedroom, 2-bath home has been thoughtfully updated from top t...	5 beds \| 2 baths \| 2,156 sq.ft.	$339,900	Airbnb cash on cash: 4.16% Traditional cash on cash: 6.14% Airbnb Rental Income: $2620 Traditional Rental Income: $2627 Airbnb ROI: 4.16% Traditional ROI: 6.14%
3107 Cherokee Dr Sheboygan, WI Beautifully refurbished 4-bedroom, 2.5 bath colonial on a quiet, tree-lined northside Dr. ...	4 beds \| 3 baths \| 2,587 sq.ft.	$433,800	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.07% Airbnb Rental Income: $1755 Traditional Rental Income: $2952 Airbnb ROI: 0.94% Traditional ROI: 5.07%
2727 Highland Ter Sheboygan, WI This prime Lake Michigan waterfront property on the sought-after NE side features an open-...	3 beds \| 3 baths \| 2,079 sq.ft.	$1,195,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.86% Airbnb Rental Income: $1232 Traditional Rental Income: $3059 Airbnb ROI: -1.14% Traditional ROI: 0.86%
3801 S 14th St Sheboygan, WI Charming Southside Ranch - Move-In Ready Comfort! Welcome home to this beautifully maintai...	3 beds \| 2 baths \| 1,358 sq.ft.	$329,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.99% Airbnb Rental Income: $1232 Traditional Rental Income: $2016 Airbnb ROI: 0.19% Traditional ROI: 3.99%
1028 Georgia Ave Sheboygan, WI A Major remodel is complete with all new flooring, interior paint, new porch, new Kitchen ...	3 beds \| 2 baths \| 1,101 sq.ft.	$239,700	Airbnb cash on cash: 1.59% Traditional cash on cash: 5.94% Airbnb Rental Income: $1232 Traditional Rental Income: $1825 Airbnb ROI: 1.59% Traditional ROI: 5.94%
2906 Stonebrook Dr Sheboygan, WI This new construction home is the annual student-built project house constructed by the SA...	3 beds \| 3 baths \| 1,832 sq.ft.	$420,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 5.4% Airbnb Rental Income: $1232 Traditional Rental Income: $2663 Airbnb ROI: 0.76% Traditional ROI: 5.4%
329 Timberlake Road Sheboygan, WI This stunning home, designed by architect Onen Wakefield, was deeply inspired by Frank Llo...	3 beds \| 2 baths \| 2,304 sq.ft.	$700,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.19% Airbnb Rental Income: $1232 Traditional Rental Income: $2513 Airbnb ROI: -0.37% Traditional ROI: 2.19%
2544 Calumet Dr Sheboygan, WI Character, charm, and room to grow -- this beautifully maintained 4BR home checks every bo...	4 beds \| 1 baths \| 1,593 sq.ft.	$270,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 4.36% Airbnb Rental Income: $1755 Traditional Rental Income: $1689 Airbnb ROI: 2.72% Traditional ROI: 4.36%
W2324 North Star Ln Sheboygan, WI Perched high above the Pigeon River on 10 wooded acres, this exceptional home captures swe...	3 beds \| 3 baths \| 3,583 sq.ft.	$979,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 1.35% Airbnb Rental Income: $1232 Traditional Rental Income: $3044 Airbnb ROI: -1.07% Traditional ROI: 1.35%
1341 BLUFF Avenue Sheboygan, WI Your chance to own a unique property. 2 homes on one parcel. Also includes Parcel # 592816...	N/A beds \| N/A baths \| 2,652 sq.ft.	$225,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 5.82% Airbnb Rental Income: $602 Traditional Rental Income: $1563 Airbnb ROI: -0.05% Traditional ROI: 5.82%

Real Estate investment in Sheboygan, WI

There are 34 properties for sale in the city of Sheboygan . The median list price in Sheboygan is $225,384 and the average price per square foot is $107. In June 2026, the average monthly cash on cash return in Sheboygan is 4.00%. The average monthly rental income in Sheboygan is $1,862.

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

There are 34 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 $1,862.

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: 0.99%

Traditional cash on cash: 3.62%

Airbnb Rental Income: $1232

Traditional Rental Income: $1507

Airbnb ROI: 0.99%

Traditional ROI: 3.62%

620 Oak Tree Rd

Sheboygan, WI

3 beds | 5 baths | 5,107 sq.ft.

$1,477,000

Airbnb cash on cash: -1.22%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $1232

Traditional Rental Income: $5181

Airbnb ROI: -1.22%

Traditional ROI: 1.95%

3829 Sheridan Ave

Sheboygan, WI

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

$589,900

Airbnb cash on cash: 0.26%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1755

Traditional Rental Income: $3974

Airbnb ROI: 0.26%

Traditional ROI: 5.16%

2029 White Pine Ln

Sheboygan, WI

3 beds | 3 baths | 3,605 sq.ft.

$559,900

Airbnb cash on cash: -0.84%

Traditional cash on cash: 2.24%

Airbnb Rental Income: $1232

Traditional Rental Income: $2450

Airbnb ROI: -0.84%

Traditional ROI: 2.24%

W839 Lake Orchard Ct

Sheboygan, WI

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

$4,900,000

Airbnb cash on cash: -1.1%

Traditional cash on cash: -0.66%

Airbnb Rental Income: $1755

Traditional Rental Income: $3288

Airbnb ROI: -1.1%

Traditional ROI: -0.66%

1244 Trimberger Ct

Sheboygan, WI

4 beds | 3 baths | 2,150 sq.ft.

$275,000

Airbnb cash on cash: 2.6%

Traditional cash on cash: 7.78%

Airbnb Rental Income: $1755

Traditional Rental Income: $2618

Airbnb ROI: 2.6%

Traditional ROI: 7.78%

1106 S 7TH Street #1

Sheboygan, WI

2 beds | 1 baths | 796 sq.ft.

$125,000

Airbnb cash on cash: 2.65%

Traditional cash on cash: 5%

Airbnb Rental Income: $1415

Traditional Rental Income: $1273

Airbnb ROI: 2.65%

Traditional ROI: 5%

1217 North Ave

Sheboygan, WI

4 beds | 3 baths | 1,762 sq.ft.

$279,900

Airbnb cash on cash: 2.6%

Traditional cash on cash: 7.62%

Airbnb Rental Income: $1755

Traditional Rental Income: $2598

Airbnb ROI: 2.6%