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
1891 Wicker Street Woodstock, IL Lovely 3 bedroom, 2 bath home, looking for a new family to love it! First floor boasts rea...	3 beds \| 2 baths \| 1,682 sq.ft.	$287,500	Airbnb cash on cash: -1.57% Traditional cash on cash: 5.66% Airbnb Rental Income: $757 Traditional Rental Income: $2400 Airbnb ROI: -1.57% Traditional ROI: 5.66%
244 Joseph Street Woodstock, IL Spacious Split-Level with Rare Sub-Basement in Prime Woodstock Location! This 4-bedroom, 2...	4 beds \| 3 baths \| 1,680 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.74% Airbnb Rental Income: $null Traditional Rental Income: $2598 Airbnb ROI: N/A Traditional ROI: 4.74%
2019 Aspen Drive Woodstock, IL Open the Door to your Future in this spacious 3-bedroom, 2.5 bath in Applewood. Feel the m...	3 beds \| 3 baths \| 1,240 sq.ft.	$317,500	Airbnb cash on cash: -1.97% Traditional cash on cash: 2.65% Airbnb Rental Income: $757 Traditional Rental Income: $1821 Airbnb ROI: -1.97% Traditional ROI: 2.65%
708 S Rose Farm Road Woodstock, IL Owner will entertain lease offers for the barn, stables separately or as a whole package. ...	5 beds \| 5 baths \| 4,084 sq.ft.	$2,175,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.77% Airbnb Rental Income: $null Traditional Rental Income: $4706 Airbnb ROI: N/A Traditional ROI: 0.77%
1907 Cherry Valley Road Woodstock, IL Tucked away on 4.3 acres of wooded privacy, this custom 4-bedroom, 3.5-bath home is a true...	4 beds \| 4 baths \| 4,500 sq.ft.	$779,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.32% Airbnb Rental Income: $null Traditional Rental Income: $3198 Airbnb ROI: N/A Traditional ROI: 2.32%
16306 Kishwaukee Valley Road Woodstock, IL From the moment you drive through the electronic gates you'll want to call this one home. ...	3 beds \| 3 baths \| 5,000 sq.ft.	$775,000	Airbnb cash on cash: -2.23% Traditional cash on cash: 0.59% Airbnb Rental Income: $757 Traditional Rental Income: $2473 Airbnb ROI: -2.23% Traditional ROI: 0.59%
15917 Kishwaukee Valley Road Woodstock, IL Exceptional 36.4 acre Horse Farm in Woodstock, IL--40 stalls in 3 barns with a fabulous 60...	5 beds \| 3 baths \| N/A	$2,495,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.2% Airbnb Rental Income: $null Traditional Rental Income: $3397 Airbnb ROI: N/A Traditional ROI: -0.2%
914 Pleasant Street Woodstock, IL Rarely available All Brick 2-bedroom Ranch 1/2 Duplex with No Association fees. Very well-...	2 beds \| 1 baths \| 1,012 sq.ft.	$224,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $1440 Airbnb ROI: N/A Traditional ROI: 1.89%
324 FIELDSTONE Drive Woodstock, IL If it looks like new, it's because much of it is! This beautifully updated 4-bedroom, 2.5...	4 beds \| 3 baths \| 3,798 sq.ft.	$459,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $3195 Airbnb ROI: N/A Traditional ROI: 3.8%
1322 Bull Valley Drive Woodstock, IL INCREDIBLE OPPORTUNITY - BUILD YOUR DREAM HOME TODAY! This stunning new construction home ...	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%
3854 Riverwoods Drive Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE!! READY FOR NOVEMBER DELIVERY!! Homesite# 0274 Ta...	4 beds \| 3 baths \| 2,362 sq.ft.	$421,540	Airbnb cash on cash: N/A Traditional cash on cash: 4.3% Airbnb Rental Income: $null Traditional Rental Income: $3144 Airbnb ROI: N/A Traditional ROI: 4.3%
3827 Riverwoods Drive Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE!! READY FOR NOVEMBER DELIVERY!! Homesite# 0262 Unveil...	4 beds \| 3 baths \| 2,201 sq.ft.	$413,640	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3095 Airbnb ROI: N/A Traditional ROI: 4.32%
1626 Wheeler Street Woodstock, IL Cute as a button ranch home with a full basement, fenced yard and showing off some great u...	3 beds \| 2 baths \| 1,500 sq.ft.	$360,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 4.24% Airbnb Rental Income: $757 Traditional Rental Income: $2407 Airbnb ROI: -1.57% Traditional ROI: 4.24%
3848 Riverwoods Drive Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE!! READY FOR NOVEMBER DELIVERY!! Step into the Siena,...	3 beds \| 2 baths \| 1,965 sq.ft.	$422,960	Airbnb cash on cash: -2.54% Traditional cash on cash: 3.54% Airbnb Rental Income: $757 Traditional Rental Income: $2852 Airbnb ROI: -2.54% Traditional ROI: 3.54%
434 Lake Avenue Woodstock, IL Move in Ready! New windows, new water heater, new driveway, even a sparkling pool. Just un...	5 beds \| 3 baths \| 2,088 sq.ft.	$329,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.2% Airbnb Rental Income: $null Traditional Rental Income: $2963 Airbnb ROI: N/A Traditional ROI: 6.2%
1624 Bull Valley Drive Woodstock, IL Imagine a stunning, custom-built home, in an exclusive community, with timeless architectu...	5 beds \| 6 baths \| 5,000 sq.ft.	$930,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $6844 Airbnb ROI: N/A Traditional ROI: 4.89%
233 Arthur Drive Woodstock, IL Retro charm meets endless potential! Welcome to this one-of-a-kind midcentury modern home,...	3 beds \| 3 baths \| 1,620 sq.ft.	$294,900	Airbnb cash on cash: -2.9% Traditional cash on cash: 6.06% Airbnb Rental Income: $757 Traditional Rental Income: $2930 Airbnb ROI: -2.9% Traditional ROI: 6.06%
2108 Aspen Drive Woodstock, IL Welcome to this fully renovated 3-bedroom, 2-bath ranch located just minutes from Woodstoc...	3 beds \| 2 baths \| 1,152 sq.ft.	$325,000	Airbnb cash on cash: -2.36% Traditional cash on cash: 3.02% Airbnb Rental Income: $757 Traditional Rental Income: $2085 Airbnb ROI: -2.36% Traditional ROI: 3.02%
17515 Deep Cut Road Woodstock, IL This property is a HORSE OWNER'S DREAM! Authentic, FULL LOG HOUSE overlooks 20 GORGEOUS A...	3 beds \| 2 baths \| 3,000 sq.ft.	$960,000	Airbnb cash on cash: -1.85% Traditional cash on cash: 0.39% Airbnb Rental Income: $757 Traditional Rental Income: $2448 Airbnb ROI: -1.85% Traditional ROI: 0.39%
1819 Woodside Drive Woodstock, IL OPEN VIEWING TODAY SUNDAY 9/14 HAS BEEN CANCELED Welcome to 1819 Woodside Dr. in Woods...	3 beds \| 3 baths \| 1,466 sq.ft.	$320,000	Airbnb cash on cash: -2.14% Traditional cash on cash: 4.16% Airbnb Rental Income: $757 Traditional Rental Income: $2339 Airbnb ROI: -2.14% Traditional ROI: 4.16%
13616 Route 176 Woodstock, IL Welcome to your private retreat in Woodstock! This beautiful 3-bedroom, 3-bathroom home i...	3 beds \| 3 baths \| 6,521 sq.ft.	$799,900	Airbnb cash on cash: -3.8% Traditional cash on cash: -0.51% Airbnb Rental Income: $757 Traditional Rental Income: $2893 Airbnb ROI: -3.8% Traditional ROI: -0.51%
15201 Il Route 176 Woodstock, IL Bring your horses & embrace the peace of private country living in this move-in ready 2,50...	4 beds \| 2 baths \| 2,500 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $2858 Airbnb ROI: N/A Traditional ROI: 1.63%

Real Estate investment in Woodstock, IL

There are 57 properties for sale in the city of Woodstock . The median list price in Woodstock is $422,960 and the average price per square foot is $160. In October 2025, the average monthly cash on cash return in Woodstock is 4.00%. The average monthly rental income in Woodstock is $2,893.

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

There are 57 investment properties available for sale in Woodstock.

In 2025, 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 $2,893.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, IL

1891 Wicker Street

Woodstock, IL

3 beds | 2 baths | 1,682 sq.ft.

$287,500

Airbnb cash on cash: -1.57%

Traditional cash on cash: 5.66%

Airbnb Rental Income: $757

Traditional Rental Income: $2400

Airbnb ROI: -1.57%

Traditional ROI: 5.66%

244 Joseph Street

Woodstock, IL

4 beds | 3 baths | 1,680 sq.ft.

$360,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2598

Airbnb ROI: N/A

Traditional ROI: 4.74%

2019 Aspen Drive

Woodstock, IL

3 beds | 3 baths | 1,240 sq.ft.

$317,500

Airbnb cash on cash: -1.97%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $757

Traditional Rental Income: $1821

Airbnb ROI: -1.97%

Traditional ROI: 2.65%

708 S Rose Farm Road

Woodstock, IL

5 beds | 5 baths | 4,084 sq.ft.

$2,175,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.77%

Airbnb Rental Income: $null

Traditional Rental Income: $4706

Airbnb ROI: N/A

Traditional ROI: 0.77%

1907 Cherry Valley Road

Woodstock, IL

4 beds | 4 baths | 4,500 sq.ft.

$779,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.32%

Airbnb Rental Income: $null

Traditional Rental Income: $3198

Airbnb ROI: N/A

Traditional ROI: 2.32%

16306 Kishwaukee Valley Road

Woodstock, IL

3 beds | 3 baths | 5,000 sq.ft.

$775,000

Airbnb cash on cash: -2.23%

Traditional cash on cash: 0.59%

Airbnb Rental Income: $757

Traditional Rental Income: $2473

Airbnb ROI: -2.23%

Traditional ROI: 0.59%

15917 Kishwaukee Valley Road

Woodstock, IL

5 beds | 3 baths | N/A

$2,495,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.2%

Airbnb Rental Income: $null

Traditional Rental Income: $3397

Airbnb ROI: N/A

Traditional ROI: -0.2%

914 Pleasant Street

Woodstock, IL

2 beds | 1 baths | 1,012 sq.ft.

$224,900

Airbnb cash on cash: N/A

Traditional cash on cash: 1.89%

Airbnb Rental Income: $null

Traditional Rental Income: $1440

Airbnb ROI: N/A