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
2109 7th Street Winthrop Harbor, IL Welcome home to this freshly updated 3-bedroom, 2-bath ranch situated on a spacious (.32 A...	3 beds \| 2 baths \| 1,008 sq.ft.	$325,900	Airbnb cash on cash: 1.97% Traditional cash on cash: 3.03% Airbnb Rental Income: $2213 Traditional Rental Income: $1981 Airbnb ROI: 1.97% Traditional ROI: 3.03%
514 Judith Court Winthrop Harbor, IL Welcome pretty an spacious custom built 2 story home features: 4 Bedrooms,2 and half bathr...	4 beds \| 3 baths \| 2,381 sq.ft.	$350,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 5.04% Airbnb Rental Income: $2136 Traditional Rental Income: $2946 Airbnb ROI: 0.92% Traditional ROI: 5.04%
1405 Lewis Avenue Winthrop Harbor, IL 7.24 acres of farm land. House needs major updating.	4 beds \| 2 baths \| 1,360 sq.ft.	$379,000	Airbnb cash on cash: 1.65% Traditional cash on cash: 3.75% Airbnb Rental Income: $2136 Traditional Rental Income: $2337 Airbnb ROI: 1.65% Traditional ROI: 3.75%
1206 Monroe Avenue Winthrop Harbor, IL BE PREPARED TO HAVE YOUR HEART SKIP A BEAT-THIS HOME IS ABSOLUTELY BREATHTAKING! This is n...	3 beds \| 3 baths \| 2,146 sq.ft.	$449,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.8% Airbnb Rental Income: $2213 Traditional Rental Income: $2881 Airbnb ROI: 0.89% Traditional ROI: 3.8%
301 English Lane Winthrop Harbor, IL Exceptional space, timeless style, and extensive modern updates come together in this beau...	4 beds \| 3 baths \| 2,544 sq.ft.	$460,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 2.8% Airbnb Rental Income: $2136 Traditional Rental Income: $2747 Airbnb ROI: 0.12% Traditional ROI: 2.8%
1038 Landon Avenue Winthrop Harbor, IL Welcome home to this charming ranch-style gem offering the perfect blend of comfort, space...	3 beds \| 1 baths \| 960 sq.ft.	$210,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 7.03% Airbnb Rental Income: $2213 Traditional Rental Income: $2102 Airbnb ROI: 4.79% Traditional ROI: 7.03%
2810 15th Street Winthrop Harbor, IL 3 BEDROOM/1.5 BATH, ONE CAR GARAGE AND A CARPORT ATTACHED. This property is eligible under...	3 beds \| 2 baths \| 1,122 sq.ft.	$239,900	Airbnb cash on cash: 3.83% Traditional cash on cash: 7.54% Airbnb Rental Income: $2213 Traditional Rental Income: $2497 Airbnb ROI: 3.83% Traditional ROI: 7.54%
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: 2.89% Traditional cash on cash: 6.86% Airbnb Rental Income: $2136 Traditional Rental Income: $3036 Airbnb ROI: 2.89% Traditional ROI: 6.86%

Real Estate investment in Winthrop-harbor, IL

There are 10 properties for sale in the city of Winthrop Harbor . The median list price in Winthrop Harbor is $314,812 and the average price per square foot is $171. In July 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 10 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

2109 7th Street

Winthrop Harbor, IL

3 beds | 2 baths | 1,008 sq.ft.

$325,900

Airbnb cash on cash: 1.97%

Traditional cash on cash: 3.03%

Airbnb Rental Income: $2213

Traditional Rental Income: $1981

Airbnb ROI: 1.97%

Traditional ROI: 3.03%

514 Judith Court

Winthrop Harbor, IL

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

$350,000

Airbnb cash on cash: 0.92%

Traditional cash on cash: 5.04%

Airbnb Rental Income: $2136

Traditional Rental Income: $2946

Airbnb ROI: 0.92%

Traditional ROI: 5.04%

1405 Lewis Avenue

Winthrop Harbor, IL

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

$379,000

Airbnb cash on cash: 1.65%

Traditional cash on cash: 3.75%

Airbnb Rental Income: $2136

Traditional Rental Income: $2337

Airbnb ROI: 1.65%

Traditional ROI: 3.75%

1206 Monroe Avenue

Winthrop Harbor, IL

3 beds | 3 baths | 2,146 sq.ft.

$449,900

Airbnb cash on cash: 0.89%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $2213

Traditional Rental Income: $2881

Airbnb ROI: 0.89%

Traditional ROI: 3.8%

301 English Lane

Winthrop Harbor, IL

4 beds | 3 baths | 2,544 sq.ft.

$460,000

Airbnb cash on cash: 0.12%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $2136

Traditional Rental Income: $2747

Airbnb ROI: 0.12%

Traditional ROI: 2.8%

1038 Landon Avenue

Winthrop Harbor, IL

3 beds | 1 baths | 960 sq.ft.

$210,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 7.03%

Airbnb Rental Income: $2213

Traditional Rental Income: $2102

Airbnb ROI: 4.79%

Traditional ROI: 7.03%

2810 15th Street

Winthrop Harbor, IL

3 beds | 2 baths | 1,122 sq.ft.

$239,900

Airbnb cash on cash: 3.83%

Traditional cash on cash: 7.54%

Airbnb Rental Income: $2213

Traditional Rental Income: $2497

Airbnb ROI: 3.83%

Traditional ROI: 7.54%

Garnett Avenue

Winthrop Harbor, IL

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

$389,000

Airbnb cash on cash: 2.89%

Traditional cash on cash: 6.86%

Airbnb Rental Income: $2136

Traditional Rental Income: $3036

Airbnb ROI: 2.89%