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: 2.29% Traditional cash on cash: 4.33% Airbnb Rental Income: $2845 Traditional Rental Income: $2946 Airbnb ROI: 2.29% Traditional ROI: 4.33%
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: 3.2% Traditional cash on cash: 3.22% Airbnb Rental Income: $2845 Traditional Rental Income: $2189 Airbnb ROI: 3.2% Traditional ROI: 3.22%
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: 3.14% Traditional cash on cash: 3.56% Airbnb Rental Income: $2845 Traditional Rental Income: $2337 Airbnb ROI: 3.14% Traditional ROI: 3.56%
814 Holdridge Avenue Winthrop Harbor, IL BEAUTIFUL 3 BEDROOM 2 BATH RAISED RANCH WITH STONE WOOD-BURNING FIREPLACE IN THE FAMILY RO...	3 beds \| 2 baths \| 1,788 sq.ft.	$309,900	Airbnb cash on cash: 1.87% Traditional cash on cash: 5.48% Airbnb Rental Income: $1976 Traditional Rental Income: $2510 Airbnb ROI: 1.87% Traditional ROI: 5.48%
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: 4.51% Traditional cash on cash: 6.86% Airbnb Rental Income: $2845 Traditional Rental Income: $3036 Airbnb ROI: 4.51% Traditional ROI: 6.86%
1224 Landon Avenue Winthrop Harbor, IL	3 beds \| 1 baths \| 953 sq.ft.	$259,500	Airbnb cash on cash: 2.84% Traditional cash on cash: 3.54% Airbnb Rental Income: $1976 Traditional Rental Income: $1628 Airbnb ROI: 2.84% Traditional ROI: 3.54%
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.	$285,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 3.31% Airbnb Rental Income: $1976 Traditional Rental Income: $1807 Airbnb ROI: 2.01% Traditional ROI: 3.31%
4914 3rd Street Winthrop Harbor, IL DID SOMEONE SAY THEY NEEDED SPACE? Beautifully situated in desirable Oak View Estates, thi...	4 beds \| 4 baths \| 2,383 sq.ft.	$429,900	Airbnb cash on cash: 2.69% Traditional cash on cash: 5.61% Airbnb Rental Income: $2845 Traditional Rental Income: $3360 Airbnb ROI: 2.69% Traditional ROI: 5.61%
646 Meadow Lane Winthrop Harbor, IL	3 beds \| 3 baths \| 2,327 sq.ft.	$375,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 4.73% Airbnb Rental Income: $1976 Traditional Rental Income: $2981 Airbnb ROI: 0.4% Traditional ROI: 4.73%

Real Estate investment in Winthrop-harbor, IL

There are 14 properties for sale in the city of Winthrop Harbor . The median list price in Winthrop Harbor is $362,500 and the average price per square foot is $186. In May 2026, the average monthly cash on cash return in Winthrop Harbor is 3.00%. 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 14 investment properties available for sale in Winthrop-harbor.

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

The ROI for Long-Term is higher than the Short-Term in Winthrop-harbor with average rental income of $1,811.

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: 2.29%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $2845

Traditional Rental Income: $2946

Airbnb ROI: 2.29%

Traditional ROI: 4.33%

535 Thompson Avenue

Winthrop Harbor, IL

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

$350,000

Airbnb cash on cash: 3.2%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $2845

Traditional Rental Income: $2189

Airbnb ROI: 3.2%

Traditional ROI: 3.22%

1405 Lewis Avenue

Winthrop Harbor, IL

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

$395,000

Airbnb cash on cash: 3.14%

Traditional cash on cash: 3.56%

Airbnb Rental Income: $2845

Traditional Rental Income: $2337

Airbnb ROI: 3.14%

Traditional ROI: 3.56%

814 Holdridge Avenue

Winthrop Harbor, IL

3 beds | 2 baths | 1,788 sq.ft.

$309,900

Airbnb cash on cash: 1.87%

Traditional cash on cash: 5.48%

Airbnb Rental Income: $1976

Traditional Rental Income: $2510

Airbnb ROI: 1.87%

Traditional ROI: 5.48%

Garnett Avenue

Winthrop Harbor, IL

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

$389,000

Airbnb cash on cash: 4.51%

Traditional cash on cash: 6.86%

Airbnb Rental Income: $2845

Traditional Rental Income: $3036

Airbnb ROI: 4.51%

Traditional ROI: 6.86%

1224 Landon Avenue

Winthrop Harbor, IL

3 beds | 1 baths | 953 sq.ft.

$259,500

Airbnb cash on cash: 2.84%

Traditional cash on cash: 3.54%

Airbnb Rental Income: $1976

Traditional Rental Income: $1628

Airbnb ROI: 2.84%

Traditional ROI: 3.54%

1134 Franklin Avenue

Winthrop Harbor, IL

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

$285,000

Airbnb cash on cash: 2.01%

Traditional cash on cash: 3.31%

Airbnb Rental Income: $1976

Traditional Rental Income: $1807

Airbnb ROI: 2.01%

Traditional ROI: 3.31%

4914 3rd Street

Winthrop Harbor, IL

4 beds | 4 baths | 2,383 sq.ft.

$429,900

Airbnb cash on cash: 2.69%

Traditional cash on cash: 5.61%

Airbnb Rental Income: $2845

Traditional Rental Income: $3360

Airbnb ROI: 2.69%