Real Estate Investment Properties for Sale in Winthrop Harbor, IL

Looking for investment property in Winthrop Harbor, IL with high ROI ?

Explore a variety of short-term homes & houses in Winthrop Harbor, IL. Invest wisely with VRBO & Winthrop Harbor, IL 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 Winthrop Harbor, IL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
514 Judith Court Winthrop Harbor, IL Spacious custom built 2 story home features: 4 Bedrooms,2 and half bathrooms, nice size ki...	4 beds \| 3 baths \| 2,381 sq.ft.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.86% Airbnb Rental Income: $null Traditional Rental Income: $2394 Airbnb ROI: N/A Traditional ROI: 2.86%
535 Thompson Avenue Winthrop Harbor, IL Charming 3-bedroom home featuring 1 full bath and 2 half baths, beautiful hardwood floors,...	4 beds \| 3 baths \| 1,232 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $2394 Airbnb ROI: N/A Traditional ROI: 3.84%
1405 Lewis Avenue Winthrop Harbor, IL 7.24 acres of farm land. House needs major updating.	4 beds \| 2 baths \| 1,360 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: 3.56%
210 Oak Lane Winthrop Harbor, IL	5 beds \| 4 baths \| 4,222 sq.ft.	$499,500	Airbnb cash on cash: N/A Traditional cash on cash: 4.85% Airbnb Rental Income: $null Traditional Rental Income: $4274 Airbnb ROI: N/A Traditional ROI: 4.85%
Garnett Avenue Winthrop Harbor, IL PROPOSED NEW CONSTRUCTION BY REPUTABLE LOCAL BUILDER!!! CAN'T FIND YOUR IDEAL HOME??? CALL...	4 beds \| 3 baths \| 2,280 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.86% Airbnb Rental Income: $null Traditional Rental Income: $3036 Airbnb ROI: N/A Traditional ROI: 6.86%
1808 13th Street Winthrop Harbor, IL This charming brick ranch offers a comfortable and spacious layout with a mix of original ...	3 beds \| 2 baths \| 1,400 sq.ft.	$231,000	Airbnb cash on cash: 1.51% Traditional cash on cash: 4.85% Airbnb Rental Income: $2023 Traditional Rental Income: $2227 Airbnb ROI: 1.51% Traditional ROI: 4.85%
1134 Franklin Avenue Winthrop Harbor, IL Welcome to this move-in ready ranch offering exceptional garage space, updated Kitchen, a ...	3 beds \| 1 baths \| 1,647 sq.ft.	$290,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 3.23% Airbnb Rental Income: $2023 Traditional Rental Income: $1807 Airbnb ROI: 2.1% Traditional ROI: 3.23%

Real Estate investment in Winthrop-harbor, IL

There are 11 properties for sale in the city of Winthrop Harbor . The median list price in Winthrop Harbor is $369,500 and the average price per square foot is $213. In March 2026, the average monthly cash on cash return in Winthrop Harbor is 2.00%. The average monthly rental income in Winthrop Harbor is $1,811.

Winthrop-harbor, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 11 investment properties available for sale in Winthrop-harbor.

In 2026, the best neighborhood to buy investment property is Winthrop Harbor.

The ROI for Short-Term is higher than the Long-Term in Winthrop-harbor with average rental income of $2,023.

Your search for investment property begins and ends here

Investment Property for Sale in Winthrop Harbor, IL

514 Judith Court

Winthrop Harbor, IL

4 beds | 3 baths | 2,381 sq.ft.

$399,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.86%

Airbnb Rental Income: $null

Traditional Rental Income: $2394

Airbnb ROI: N/A

Traditional ROI: 2.86%

535 Thompson Avenue

Winthrop Harbor, IL

4 beds | 3 baths | 1,232 sq.ft.

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $2394

Airbnb ROI: N/A

Traditional ROI: 3.84%

1405 Lewis Avenue

Winthrop Harbor, IL

4 beds | 2 baths | 1,360 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.56%

Airbnb Rental Income: $null

Traditional Rental Income: $2337

Airbnb ROI: N/A

Traditional ROI: 3.56%

210 Oak Lane

Winthrop Harbor, IL

5 beds | 4 baths | 4,222 sq.ft.

$499,500

Airbnb cash on cash: N/A

Traditional cash on cash: 4.85%

Airbnb Rental Income: $null

Traditional Rental Income: $4274

Airbnb ROI: N/A

Traditional ROI: 4.85%

Garnett Avenue

Winthrop Harbor, IL

4 beds | 3 baths | 2,280 sq.ft.

$389,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.86%

Airbnb Rental Income: $null

Traditional Rental Income: $3036

Airbnb ROI: N/A

Traditional ROI: 6.86%

1808 13th Street

Winthrop Harbor, IL

3 beds | 2 baths | 1,400 sq.ft.

$231,000

Airbnb cash on cash: 1.51%

Traditional cash on cash: 4.85%

Airbnb Rental Income: $2023

Traditional Rental Income: $2227

Airbnb ROI: 1.51%

Traditional ROI: 4.85%

1134 Franklin Avenue

Winthrop Harbor, IL

3 beds | 1 baths | 1,647 sq.ft.

$290,000

Airbnb cash on cash: 2.1%

Traditional cash on cash: 3.23%

Airbnb Rental Income: $2023

Traditional Rental Income: $1807

Airbnb ROI: 2.1%

Traditional ROI: 3.23%

Real Estate investment in Winthrop-harbor, IL

Winthrop-harbor, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

How many investment properties are available for sale in Winthrop-harbor?

Which neighborhoods in Winthrop-harbor to invest in 2026?

Long-Term vs. Short-Term Rentals in Winthrop-harbor, Illinois: Which will earn the best returns?

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