Real Estate Investment Properties for Sale in Shorewood, IL

Looking for investment property in Shorewood, IL with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
19057 S Saddlebrook Drive SHOREWOOD, IL Come see this beautiful 4 bedroom, 3.5 bath home sitting on a 0.75 acre lot in rarely avai...	4 beds \| 4 baths \| 4,038 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $3860 Airbnb ROI: N/A Traditional ROI: 2.67%
1632 Fieldstone Drive S SHOREWOOD, IL Remarkable unit now available in the highly desirable Kipling Estates. This unit offers in...	2 beds \| 2 baths \| 1,493 sq.ft.	$269,900	Airbnb cash on cash: 0.71% Traditional cash on cash: 4.38% Airbnb Rental Income: $1714 Traditional Rental Income: $2173 Airbnb ROI: 0.71% Traditional ROI: 4.38%
515 David Drive SHOREWOOD, IL This beautifully maintained 5-bedroom, (4 bedrooms upstairs and one in the basement) 2-sto...	4 beds \| 3 baths \| 2,204 sq.ft.	$419,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $2568 Airbnb ROI: N/A Traditional ROI: 3.34%
21240 S Redwood Lane SHOREWOOD, IL Welcome to this stunning Lake Forrest home, thoughtfully designed with comfort, style, and...	4 beds \| 5 baths \| 3,318 sq.ft.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $3290 Airbnb ROI: N/A Traditional ROI: 3.13%
20948 Lakewoods Lane SHOREWOOD, IL Welcome To River Crossing Of Shorewood! Stunning Ranch Home Shows Like A Model And Truly M...	3 beds \| 2 baths \| 2,070 sq.ft.	$590,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 1.28% Airbnb Rental Income: $1416 Traditional Rental Income: $2622 Airbnb ROI: -1.68% Traditional ROI: 1.28%
1111 Country Drive SHOREWOOD, IL Welcome to this beautiful home in Shorewood's sought-after Country West subdivision, where...	3 beds \| 3 baths \| 1,770 sq.ft.	$359,900	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.92% Airbnb Rental Income: $1416 Traditional Rental Income: $2440 Airbnb ROI: -0.37% Traditional ROI: 3.92%
302 Parkside Drive SHOREWOOD, IL Beautiful two story townhome ready for a new chapter! This home has a lot to offer with 3 ...	3 beds \| 2 baths \| 1,484 sq.ft.	$285,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 4.22% Airbnb Rental Income: $1416 Traditional Rental Income: $2175 Airbnb ROI: -0.19% Traditional ROI: 4.22%
24721 W Park River Lane SHOREWOOD, IL Understated elegance is what you will say when you see this warm and cozy, executive home....	5 beds \| 6 baths \| 4,600 sq.ft.	$998,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.41% Airbnb Rental Income: $null Traditional Rental Income: $7782 Airbnb ROI: N/A Traditional ROI: 5.41%
21547 S Nadia Drive SHOREWOOD, IL Impressive stone and cedar home on a large, oversized lot, with side yard. Located in Unin...	5 beds \| 3 baths \| 2,865 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $3356 Airbnb ROI: N/A Traditional ROI: 4.46%
24433 W Bantry Lane SHOREWOOD, IL Introducing the latest gem in the world of real estate - a brand-new construction with an ...	4 beds \| 3 baths \| 3,141 sq.ft.	$655,616	Airbnb cash on cash: N/A Traditional cash on cash: 4.05% Airbnb Rental Income: $null Traditional Rental Income: $3330 Airbnb ROI: N/A Traditional ROI: 4.05%
21246 Woodland Way SHOREWOOD, IL $214,000 in Recent Upgrades!!! Home of the "TWISTED CHIMNEY". This custom all-brick resid...	4 beds \| 6 baths \| 4,865 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $7247 Airbnb ROI: N/A Traditional ROI: 3.88%
1794 Fieldstone N Drive #1794N SHOREWOOD, IL Welcome to this well-maintained 3-bedroom, 2-bath raised ranch townhome featuring an open ...	3 beds \| 2 baths \| 1,659 sq.ft.	$254,900	Airbnb cash on cash: -0.38% Traditional cash on cash: 5.01% Airbnb Rental Income: $1416 Traditional Rental Income: $2289 Airbnb ROI: -0.38% Traditional ROI: 5.01%
704 Flag Drive SHOREWOOD, IL Come enjoy the desirable lifestyle of Del Webb's Shorewood Glens 55+ active adult gated co...	2 beds \| 2 baths \| 1,529 sq.ft.	$339,900	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.82% Airbnb Rental Income: $1714 Traditional Rental Income: $2340 Airbnb ROI: 0.38% Traditional ROI: 3.82%
24409 W Park River Lane SHOREWOOD, IL Sharp two story on 1.61 acre lot Includes a large storage building and an enclosed indoo...	5 beds \| 4 baths \| 6,000 sq.ft.	$1,400,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $4033 Airbnb ROI: N/A Traditional ROI: 0.84%
704 Helene Street SHOREWOOD, IL Shorewood Tri-Level in Prime Location! Fantastic opportunity across the street from the f...	3 beds \| 2 baths \| 2,000 sq.ft.	$324,900	Airbnb cash on cash: -0.17% Traditional cash on cash: 4.72% Airbnb Rental Income: $1416 Traditional Rental Income: $2485 Airbnb ROI: -0.17% Traditional ROI: 4.72%
21037 Coventry Circle SHOREWOOD, IL Stylish and sophisticated, this Dunbar model in Westminster Gardens is better than new! Bu...	3 beds \| 3 baths \| 2,681 sq.ft.	$515,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 3.23% Airbnb Rental Income: $1416 Traditional Rental Income: $3038 Airbnb ROI: -1.02% Traditional ROI: 3.23%
1719 Moran Drive SHOREWOOD, IL Welcome to this beautifully maintained 4-bedroom, 2.2-bath home in the desirable Shorewood...	2 beds \| 4 baths \| 2,880 sq.ft.	$523,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 4.14% Airbnb Rental Income: $1714 Traditional Rental Income: $3639 Airbnb ROI: -0.77% Traditional ROI: 4.14%
21053 Benjamin Drive SHOREWOOD, IL Newer semi-custom ranch in River Crossing, built by Housing Industry Hall of Fame Inductee...	3 beds \| 2 baths \| 2,256 sq.ft.	$560,000	Airbnb cash on cash: -1.64% Traditional cash on cash: 1.68% Airbnb Rental Income: $1416 Traditional Rental Income: $2725 Airbnb ROI: -1.64% Traditional ROI: 1.68%
1052 Moraine Drive SHOREWOOD, IL Welcome to this stunning newer home in the sought-after Park Pointe subdivision, offering ...	3 beds \| 3 baths \| 1,905 sq.ft.	$364,900	Airbnb cash on cash: -1.11% Traditional cash on cash: 4.23% Airbnb Rental Income: $1416 Traditional Rental Income: $2819 Airbnb ROI: -1.11% Traditional ROI: 4.23%
741 River Bluff Drive SHOREWOOD, IL River Bluff Estates is a highly sought after, intimate DUPLEX community consisting of just...	2 beds \| 2 baths \| 1,500 sq.ft.	$360,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.95% Airbnb Rental Income: $1416 Traditional Rental Income: $2156 Airbnb ROI: 0.5% Traditional ROI: 3.95%
24614 Kaylee Street SHOREWOOD, IL Imagine the memories you and your loved ones will create in this 4-bedroom, 2.5-bath home ...	4 beds \| 3 baths \| 2,660 sq.ft.	$490,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $2992 Airbnb ROI: N/A Traditional ROI: 3.28%
1604 Augusta Lane SHOREWOOD, IL Welcome to this beautifully maintained, maintenance-free ranch home offering the ease of s...	2 beds \| 2 baths \| 1,344 sq.ft.	$339,900	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.14% Airbnb Rental Income: $1714 Traditional Rental Income: $2120 Airbnb ROI: 0.38% Traditional ROI: 3.14%
24620 W River Crossing Drive SHOREWOOD, IL AP HOMES PROUDLY SHOWCASES THE "CYPRESS " MODEL,OFFERS A BRICK FRONT, PLUS A 3 CAR GARA...	3 beds \| 2 baths \| 2,442 sq.ft.	$630,689	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.27% Airbnb Rental Income: $1416 Traditional Rental Income: $2756 Airbnb ROI: 0.27% Traditional ROI: 3.27%
18911 S Palomino Drive SHOREWOOD, IL FIRST TIME ON MARKET! THIS GORGEOUS CUSTOM BUILT, ONE OF A KIND TUDOR HOME, FEATURES OVER ...	4 beds \| 5 baths \| 5,715 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.41% Airbnb Rental Income: $null Traditional Rental Income: $3290 Airbnb ROI: N/A Traditional ROI: 0.41%

Real Estate investment in Shorewood, IL

There are 31 properties for sale in the city of Shorewood . The median list price in Shorewood is $460,000 and the average price per square foot is $171. In October 2025, the average monthly cash on cash return in Shorewood is 4.00%. The average monthly rental income in Shorewood is $2,756.

Shorewood, IL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 31 investment properties available for sale in Shorewood.

In 2025, the best neighborhood to buy investment property is SHOREWOOD.

The ROI for Short-Term is higher than the Long-Term in Shorewood with average rental income of $1,416.

Your search for investment property begins and ends here

Investment Property for Sale in Shorewood, IL

19057 S Saddlebrook Drive

SHOREWOOD, IL

4 beds | 4 baths | 4,038 sq.ft.

$725,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.67%

Airbnb Rental Income: $null

Traditional Rental Income: $3860

Airbnb ROI: N/A

Traditional ROI: 2.67%

1632 Fieldstone Drive S

SHOREWOOD, IL

2 beds | 2 baths | 1,493 sq.ft.

$269,900

Airbnb cash on cash: 0.71%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $1714

Traditional Rental Income: $2173

Airbnb ROI: 0.71%

Traditional ROI: 4.38%

515 David Drive

SHOREWOOD, IL

4 beds | 3 baths | 2,204 sq.ft.

$419,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.34%

Airbnb Rental Income: $null

Traditional Rental Income: $2568

Airbnb ROI: N/A

Traditional ROI: 3.34%

21240 S Redwood Lane

SHOREWOOD, IL

4 beds | 5 baths | 3,318 sq.ft.

$549,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.13%

Airbnb Rental Income: $null

Traditional Rental Income: $3290

Airbnb ROI: N/A

Traditional ROI: 3.13%

20948 Lakewoods Lane

SHOREWOOD, IL

3 beds | 2 baths | 2,070 sq.ft.

$590,000

Airbnb cash on cash: -1.68%

Traditional cash on cash: 1.28%

Airbnb Rental Income: $1416

Traditional Rental Income: $2622

Airbnb ROI: -1.68%

Traditional ROI: 1.28%

1111 Country Drive

SHOREWOOD, IL

3 beds | 3 baths | 1,770 sq.ft.

$359,900

Airbnb cash on cash: -0.37%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $1416

Traditional Rental Income: $2440

Airbnb ROI: -0.37%

Traditional ROI: 3.92%

302 Parkside Drive

SHOREWOOD, IL

3 beds | 2 baths | 1,484 sq.ft.

$285,000

Airbnb cash on cash: -0.19%

Traditional cash on cash: 4.22%

Airbnb Rental Income: $1416

Traditional Rental Income: $2175

Airbnb ROI: -0.19%

Traditional ROI: 4.22%

24721 W Park River Lane

SHOREWOOD, IL

5 beds | 6 baths | 4,600 sq.ft.

$998,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.41%

Airbnb Rental Income: $null

Traditional Rental Income: $7782

Airbnb ROI: N/A