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
3616 Creekside Court Winthrop Harbor, IL Welcome Home! This beautiful home located on over 1/3 acre and has 3 bedrooms and 2 1/2 ba...	3 beds \| 3 baths \| 1,828 sq.ft.	$380,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.47% Airbnb Rental Income: $1718 Traditional Rental Income: $2484 Airbnb ROI: -0.01% Traditional ROI: 3.47%
1405 Lewis Avenue Winthrop Harbor, IL 7.24 acres of farm land. House is not in livable condition.	4 beds \| 2 baths \| 1,360 sq.ft.	$398,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $2337 Airbnb ROI: N/A Traditional ROI: 3.52%
0 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: 6.85% Airbnb Rental Income: $null Traditional Rental Income: $3036 Airbnb ROI: N/A Traditional ROI: 6.85%
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.	$248,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 4.77% Airbnb Rental Income: $1718 Traditional Rental Income: $2227 Airbnb ROI: 0.56% Traditional ROI: 4.77%
140 Old Darby Lane Winthrop Harbor, IL Step into this beautifully reimagined 3-bedroom, 3-bathroom home, bursting with charm and ...	3 beds \| 3 baths \| 1,930 sq.ft.	$409,700	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.82% Airbnb Rental Income: $1718 Traditional Rental Income: $2712 Airbnb ROI: -0.01% Traditional ROI: 3.82%
242 Thompson Avenue Winthrop Harbor, IL FOUR BEDROOM Cape cod with Quality hardwood floors on 1st & 2nd Floor. BEAUTIFUL NEW tile...	4 beds \| 2 baths \| 1,544 sq.ft.	$310,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.11% Airbnb Rental Income: $null Traditional Rental Income: $2391 Airbnb ROI: N/A Traditional ROI: 4.11%
1228 Pennsylvania Avenue Winthrop Harbor, IL Welcome to this beautiful 5 bed, 3.5 bath Colonial home, offering over 3,000 sq ft of livi...	4 beds \| 4 baths \| 2,608 sq.ft.	$424,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.61% Airbnb Rental Income: $null Traditional Rental Income: $3373 Airbnb ROI: N/A Traditional ROI: 4.61%
1204 Park Avenue Winthrop Harbor, IL GREAT CAPE COD HOME WITH 4 BEDROOMS AND 1 BATH LOCATED ON A LARGE CORNER LOT WITH 2+ CAR D...	4 beds \| 1 baths \| 1,224 sq.ft.	$200,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.64% Airbnb Rental Income: $null Traditional Rental Income: $1830 Airbnb ROI: N/A Traditional ROI: 5.64%

Real Estate investment in Winthrop-harbor, IL

There are 13 properties for sale in the city of Winthrop Harbor . The median list price in Winthrop Harbor is $380,000 and the average price per square foot is $205. In October 2025, the average monthly cash on cash return in Winthrop Harbor is 5.00%. The average monthly rental income in Winthrop Harbor is $2,484.

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

There are 13 investment properties available for sale in Winthrop-harbor.

In 2025, 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 $1,718.

Your search for investment property begins and ends here

Investment Property for Sale in Winthrop Harbor, IL

3616 Creekside Court

Winthrop Harbor, IL

3 beds | 3 baths | 1,828 sq.ft.

$380,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 3.47%

Airbnb Rental Income: $1718

Traditional Rental Income: $2484

Airbnb ROI: -0.01%

Traditional ROI: 3.47%

1405 Lewis Avenue

Winthrop Harbor, IL

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

$398,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.52%

Airbnb Rental Income: $null

Traditional Rental Income: $2337

Airbnb ROI: N/A

Traditional ROI: 3.52%

0 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: 6.85%

Airbnb Rental Income: $null

Traditional Rental Income: $3036

Airbnb ROI: N/A

Traditional ROI: 6.85%

1808 13th Street

Winthrop Harbor, IL

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

$248,000

Airbnb cash on cash: 0.56%

Traditional cash on cash: 4.77%

Airbnb Rental Income: $1718

Traditional Rental Income: $2227

Airbnb ROI: 0.56%

Traditional ROI: 4.77%

140 Old Darby Lane

Winthrop Harbor, IL

3 beds | 3 baths | 1,930 sq.ft.

$409,700

Airbnb cash on cash: -0.01%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $1718

Traditional Rental Income: $2712

Airbnb ROI: -0.01%

Traditional ROI: 3.82%

242 Thompson Avenue

Winthrop Harbor, IL

4 beds | 2 baths | 1,544 sq.ft.

$310,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.11%

Airbnb Rental Income: $null

Traditional Rental Income: $2391

Airbnb ROI: N/A

Traditional ROI: 4.11%

1228 Pennsylvania Avenue

Winthrop Harbor, IL

4 beds | 4 baths | 2,608 sq.ft.

$424,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.61%

Airbnb Rental Income: $null

Traditional Rental Income: $3373

Airbnb ROI: N/A

Traditional ROI: 4.61%

1204 Park Avenue

Winthrop Harbor, IL

4 beds | 1 baths | 1,224 sq.ft.

$200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.64%

Airbnb Rental Income: $null

Traditional Rental Income: $1830

Airbnb ROI: N/A