Real Estate Investment Properties for Sale in Woodstock, IL

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1322 Bull Valley Drive Woodstock, IL Amazing opportunity to design your dream home with this modern new construction by a famil...	4 beds \| 5 baths \| 5,549 sq.ft.	$2,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.16% Airbnb Rental Income: $null Traditional Rental Income: $5173 Airbnb ROI: N/A Traditional ROI: 1.16%
13616 Route 176 Woodstock, IL Welcome to your private retreat in Woodstock! This beautiful 3-bedroom, 3-bathroom home is...	3 beds \| 3 baths \| 6,521 sq.ft.	$559,500	Airbnb cash on cash: -3.02% Traditional cash on cash: -0.3% Airbnb Rental Income: $1992 Traditional Rental Income: $2893 Airbnb ROI: -3.02% Traditional ROI: -0.3%
8201 Austin Trail Woodstock, IL Proposed new construction! Incredible opportunity to own a brand new home in unincorporate...	4 beds \| 3 baths \| 3,200 sq.ft.	$895,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.66% Airbnb Rental Income: $null Traditional Rental Income: $3360 Airbnb ROI: N/A Traditional ROI: 0.66%
8106 Austin Trail Woodstock, IL Proposed new construction by U.S. Home Builders! This 2,000 sq ft ranch on the Woodstock-C...	4 beds \| 3 baths \| 2,000 sq.ft.	$750,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.98% Airbnb Rental Income: $null Traditional Rental Income: $3052 Airbnb ROI: N/A Traditional ROI: 0.98%
8210 Austin Trail Woodstock, IL Proposed new construction by U.S. Home Builders! This 3,200 sq ft home on the Woodstock-Cr...	4 beds \| 3 baths \| 3,200 sq.ft.	$875,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.59% Airbnb Rental Income: $null Traditional Rental Income: $3230 Airbnb ROI: N/A Traditional ROI: 0.59%
8205 Austin Trail Woodstock, IL Proposed new construction by U.S. Home Builders! This 3,200 sq ft two-story option on the ...	5 beds \| 3 baths \| 3,200 sq.ft.	$949,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.55% Airbnb Rental Income: $3133 Traditional Rental Income: $3458 Airbnb ROI: -0.62% Traditional ROI: 0.55%
14716 Il Route 176 Highway Woodstock, IL This is truly your dream ranch! Ready to welcome you, your horses and business sitting on ...	4 beds \| 3 baths \| 2,910 sq.ft.	$654,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.62% Airbnb Rental Income: $null Traditional Rental Income: $3107 Airbnb ROI: N/A Traditional ROI: 2.62%
526 W Jackson Street Woodstock, IL Step Into Timeless Character In This Classic Tudor Home, Rich With Original Craftsmanship ...	3 beds \| 2 baths \| 1,608 sq.ft.	$429,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.29% Airbnb Rental Income: $1992 Traditional Rental Income: $2342 Airbnb ROI: 1.13% Traditional ROI: 3.29%
3859 Meadowridge Road Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR NOVEMBER DELIVERY! Homesite# 0088. Experienc...	4 beds \| 3 baths \| 2,063 sq.ft.	$459,180	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $2996 Airbnb ROI: N/A Traditional ROI: 3.34%
3871 Meadowridge Road Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR MAY DELIVERY! Homesite #0086. Welcome to the...	3 beds \| 2 baths \| 1,822 sq.ft.	$454,420	Airbnb cash on cash: -0.17% Traditional cash on cash: 2.77% Airbnb Rental Income: $1992 Traditional Rental Income: $2723 Airbnb ROI: -0.17% Traditional ROI: 2.77%
4038 Meadowridge Road Woodstock, IL READY FOR MAY DELIVERY! Homesite# 0031. SUNROOM OPTION-BRICK FRONT * Step into the Siena, ...	3 beds \| 2 baths \| 1,965 sq.ft.	$444,710	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.16% Airbnb Rental Income: $1992 Traditional Rental Income: $2413 Airbnb ROI: -0.1% Traditional ROI: 2.16%
645 E Calhoun Street Woodstock, IL	5 beds \| 4 baths \| 2,632 sq.ft.	$415,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 6.27% Airbnb Rental Income: $3133 Traditional Rental Income: $3425 Airbnb ROI: 3.69% Traditional ROI: 6.27%
4201 Meadowridge Road Woodstock, IL AVAILABLE NOW! SPECIAL FINANCING OFFERS AVAILABLE! Homesite #6702. Step inside and explore...	3 beds \| 3 baths \| 1,853 sq.ft.	$364,990	Airbnb cash on cash: 0.23% Traditional cash on cash: 4.41% Airbnb Rental Income: $1992 Traditional Rental Income: $2901 Airbnb ROI: 0.23% Traditional ROI: 4.41%
1200 Redtail Circle Woodstock, IL Welcome to easy, elegant living in the highly sought-after Sanctuary of Bull Valley commun...	2 beds \| 2 baths \| 1,646 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $2537 Airbnb ROI: N/A Traditional ROI: 3.19%
4003 Meadowridge Drive Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR MAY DELIVERY! * GARDEN BASEMENT OPTION * Hom...	4 beds \| 3 baths \| 2,631 sq.ft.	$479,040	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $3170 Airbnb ROI: N/A Traditional ROI: 3.46%
3829 Meadowridge Road Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! Homesite #0093. Unveil the Starling, an expertly const...	4 beds \| 3 baths \| 2,193 sq.ft.	$469,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $2851 Airbnb ROI: N/A Traditional ROI: 4.67%
4209 Meadowridge Road Woodstock, IL AVAILABLE MAY DELIVERY! SPECIAL FINANCING OFFERS AVAILABLE! Homesite #6602. Introducing th...	3 beds \| 3 baths \| 1,780 sq.ft.	$358,990	Airbnb cash on cash: 2.14% Traditional cash on cash: 6.15% Airbnb Rental Income: $1992 Traditional Rental Income: $2823 Airbnb ROI: 2.14% Traditional ROI: 6.15%

Real Estate investment in Woodstock, IL

There are 59 properties for sale in the city of Woodstock . The median list price in Woodstock is $337,821 and the average price per square foot is $139. In June 2026, the average monthly cash on cash return in Woodstock is 4.00%. The average monthly rental income in Woodstock is $2,791.

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

There are 59 investment properties available for sale in Woodstock.

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

The ROI for Long-Term is higher than the Short-Term in Woodstock with average rental income of $2,791.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, IL

1322 Bull Valley Drive

Woodstock, IL

4 beds | 5 baths | 5,549 sq.ft.

$2,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.16%

Airbnb Rental Income: $null

Traditional Rental Income: $5173

Airbnb ROI: N/A

Traditional ROI: 1.16%

13616 Route 176

Woodstock, IL

3 beds | 3 baths | 6,521 sq.ft.

$559,500

Airbnb cash on cash: -3.02%

Traditional cash on cash: -0.3%

Airbnb Rental Income: $1992

Traditional Rental Income: $2893

Airbnb ROI: -3.02%

Traditional ROI: -0.3%

8201 Austin Trail

Woodstock, IL

4 beds | 3 baths | 3,200 sq.ft.

$895,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.66%

Airbnb Rental Income: $null

Traditional Rental Income: $3360

Airbnb ROI: N/A

Traditional ROI: 0.66%

8106 Austin Trail

Woodstock, IL

4 beds | 3 baths | 2,000 sq.ft.

$750,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.98%

Airbnb Rental Income: $null

Traditional Rental Income: $3052

Airbnb ROI: N/A

Traditional ROI: 0.98%

8210 Austin Trail

Woodstock, IL

4 beds | 3 baths | 3,200 sq.ft.

$875,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.59%

Airbnb Rental Income: $null

Traditional Rental Income: $3230

Airbnb ROI: N/A

Traditional ROI: 0.59%

8205 Austin Trail

Woodstock, IL

5 beds | 3 baths | 3,200 sq.ft.

$949,000

Airbnb cash on cash: -0.62%

Traditional cash on cash: 0.55%

Airbnb Rental Income: $3133

Traditional Rental Income: $3458

Airbnb ROI: -0.62%

Traditional ROI: 0.55%

14716 Il Route 176 Highway

Woodstock, IL

4 beds | 3 baths | 2,910 sq.ft.

$654,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.62%

Airbnb Rental Income: $null

Traditional Rental Income: $3107

Airbnb ROI: N/A

Traditional ROI: 2.62%

526 W Jackson Street

Woodstock, IL

3 beds | 2 baths | 1,608 sq.ft.

$429,900

Airbnb cash on cash: 1.13%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1992

Traditional Rental Income: $2342

Airbnb ROI: 1.13%