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
2014 Greenview Drive Woodstock, IL Coming Soon to the highly desired Ponds of Bull Valley community, this 4-bedroom, 2.5-bath...	4 beds \| 3 baths \| 2,657 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $2975 Airbnb ROI: N/A Traditional ROI: 3.94%
2200 Serenity Ln Woodstock, IL Welcome home to this move-in ready 3-bedroom, 2.1-bath quad-level in the desirable Ponds o...	3 beds \| 2 baths \| 2,124 sq.ft.	$392,500	Airbnb cash on cash: 0.74% Traditional cash on cash: 4.18% Airbnb Rental Income: $2039 Traditional Rental Income: $2802 Airbnb ROI: 0.74% Traditional ROI: 4.18%
708 S Rose Farm Rd Woodstock, IL Exceptional 20-Acre Equestrian Estate with Grand Home, Private Apartment & Premier Facilit...	5 beds \| 4 baths \| 4,084 sq.ft.	$2,150,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 0.77% Airbnb Rental Income: $2181 Traditional Rental Income: $4706 Airbnb ROI: -0.75% Traditional ROI: 0.77%
121 Prairie Ridge Drive Woodstock, IL Absolutely Gorgeous and Move-In Ready home featuring 3 bedrooms, 2.5 bathrooms, and a beau...	3 beds \| 3 baths \| 1,769 sq.ft.	$364,900	Airbnb cash on cash: 1.24% Traditional cash on cash: 3.13% Airbnb Rental Income: $2039 Traditional Rental Income: $2157 Airbnb ROI: 1.24% Traditional ROI: 3.13%
1322 Bull Valley Dr 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%
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: -1.13% Traditional cash on cash: 4.89% Airbnb Rental Income: $2181 Traditional Rental Income: $6844 Airbnb ROI: -1.13% Traditional ROI: 4.89%
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.	$589,900	Airbnb cash on cash: -2.74% Traditional cash on cash: -0.38% Airbnb Rental Income: $2039 Traditional Rental Income: $2893 Airbnb ROI: -2.74% Traditional ROI: -0.38%
8201 Austin Trl 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 Trl Woodstock, IL Proposed new construction by U.S. Home Builders! This 2,200 sq ft ranch on the Woodstock-C...	4 beds \| 2 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 Trl Woodstock, IL Proposed new construction by U.S. Home Builders! This 3,200 sq ft home on the Woodstock-Cr...	4 beds \| 2 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 Trl Woodstock, IL Proposed new construction by U.S. Home Builders! This 3,200 sq ft two-story option on the ...	5 beds \| 2 baths \| 3,200 sq.ft.	$949,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 0.55% Airbnb Rental Income: $2181 Traditional Rental Income: $3458 Airbnb ROI: -1.52% Traditional ROI: 0.55%
4220 Meadowridge Rd Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite #5502. Step insid...	3 beds \| 2 baths \| 1,853 sq.ft.	$331,390	Airbnb cash on cash: 0.63% Traditional cash on cash: 5.55% Airbnb Rental Income: $2039 Traditional Rental Income: $3072 Airbnb ROI: 0.63% Traditional ROI: 5.55%
2732 Woodworth Ave Woodstock, IL Welcome home to 2732 Woodworth Ave. In the well sought out Apple Creek Estates subdivision...	3 beds \| 2 baths \| 1,988 sq.ft.	$415,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 4.77% Airbnb Rental Income: $2039 Traditional Rental Income: $3206 Airbnb ROI: 0.41% Traditional ROI: 4.77%
3914 Riverwoods Dr Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR FEBRUARY DELIVERY! Homesite # 0026. Take in ...	4 beds \| 2 baths \| 2,362 sq.ft.	$454,635	Airbnb cash on cash: N/A Traditional cash on cash: 3.71% Airbnb Rental Income: $null Traditional Rental Income: $3187 Airbnb ROI: N/A Traditional ROI: 3.71%
4216 Meadowridge Rd Woodstock, IL AVAILABLE NOW! SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite# 5...	2 beds \| 2 baths \| 1,512 sq.ft.	$309,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.6% Airbnb Rental Income: $null Traditional Rental Income: $2602 Airbnb ROI: N/A Traditional ROI: 4.6%
4228 Meadowridge Rd Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite# 5602. Introducin...	3 beds \| 2 baths \| 1,780 sq.ft.	$326,440	Airbnb cash on cash: 0.74% Traditional cash on cash: 5.16% Airbnb Rental Income: $2039 Traditional Rental Income: $2876 Airbnb ROI: 0.74% Traditional ROI: 5.16%
3920 Riverwoods Dr Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR FEBRUARY DELIVERY! Homesite# 0027. Step into...	3 beds \| 2 baths \| 1,965 sq.ft.	$454,110	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.87% Airbnb Rental Income: $2039 Traditional Rental Income: $2790 Airbnb ROI: -0.11% Traditional ROI: 2.87%
4212 Meadowridge Rd Woodstock, IL AVAILABLE NOW! SPECIAL FINANCING OFFERS AVAILABLE! Homesite# 5402. Introducing the Mariann...	3 beds \| 2 baths \| 1,780 sq.ft.	$326,640	Airbnb cash on cash: 1.34% Traditional cash on cash: 4.09% Airbnb Rental Income: $2039 Traditional Rental Income: $2360 Airbnb ROI: 1.34% Traditional ROI: 4.09%
4241 Meadowridge Rd Woodstock, IL AVAILABLE NOW! SPECIAL FINANCING OFFERS AVAILABLE! Homesite #6202. Step inside and explore...	3 beds \| 2 baths \| 1,853 sq.ft.	$337,740	Airbnb cash on cash: 1.14% Traditional cash on cash: 3.94% Airbnb Rental Income: $2039 Traditional Rental Income: $2417 Airbnb ROI: 1.14% Traditional ROI: 3.94%
4245 Meadowridge Rd Woodstock, IL AVAILABLE NOW! SPECIAL FINANCING OFFERS AVAILABLE! Homesite# 6201. Introducing the Christi...	2 beds \| 2 baths \| 1,512 sq.ft.	$329,340	Airbnb cash on cash: N/A Traditional cash on cash: 3.66% Airbnb Rental Income: $null Traditional Rental Income: $2231 Airbnb ROI: N/A Traditional ROI: 3.66%
412 St Johns Rd #D Woodstock, IL Great condition first-floor unit offering 2 bedrooms and 1.5 baths with nothing to do but ...	2 beds \| 1 baths \| 1,000 sq.ft.	$159,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.44% Airbnb Rental Income: $null Traditional Rental Income: $1733 Airbnb ROI: N/A Traditional ROI: 5.44%
2006 Serenity Ln Woodstock, IL Welcome to this beautiful Dearborn model built in 2022, located in the highly sought-after...	3 beds \| 2 baths \| 2,403 sq.ft.	$415,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.65% Airbnb Rental Income: $2039 Traditional Rental Income: $3006 Airbnb ROI: -0.2% Traditional ROI: 3.65%
705 Marawood Drive Woodstock, IL Discover the perfect blend of rustic charm and modern elegance in this stunning 2011-built...	2 beds \| 2 baths \| 4,524 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.36% Airbnb Rental Income: $null Traditional Rental Income: $2360 Airbnb ROI: N/A Traditional ROI: 1.36%
1829 Havens Drive Woodstock, IL Unlock the Door to your Future! A METICULOUSLY kept 2 bedroom/1.5 bathroom overlooking Swe...	2 beds \| 2 baths \| 1,467 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.42% Airbnb Rental Income: $null Traditional Rental Income: $2206 Airbnb ROI: N/A Traditional ROI: 6.42%
14716 Il Route 176 Hwy 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.	$664,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.46% Airbnb Rental Income: $null Traditional Rental Income: $3107 Airbnb ROI: N/A Traditional ROI: 2.46%
726 S Jefferson St Woodstock, IL Very well maintained income producing 2-unit property just a few blocks from the Historica...	4 beds \| 2 baths \| N/A	$274,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.48% Airbnb Rental Income: $null Traditional Rental Income: $1962 Airbnb ROI: N/A Traditional ROI: 4.48%
526 W Jackson St Woodstock, IL Step Into Timeless Character In This Classic Tudor Home, Rich With Original Craftsmanship ...	3 beds \| 1 baths \| 1,608 sq.ft.	$449,900	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.2% Airbnb Rental Income: $2039 Traditional Rental Income: $2342 Airbnb ROI: 1.18% Traditional ROI: 3.2%

Real Estate investment in Woodstock, IL

There are 103 properties for sale in the city of Woodstock . The median list price in Woodstock is $462,068 and the average price per square foot is $188. In March 2026, the average monthly cash on cash return in Woodstock is 3.00%. The average monthly rental income in Woodstock is $2,802.

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

There are 103 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 $2,802.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, IL

2014 Greenview Drive

Woodstock, IL

4 beds | 3 baths | 2,657 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.94%

Airbnb Rental Income: $null

Traditional Rental Income: $2975

Airbnb ROI: N/A

Traditional ROI: 3.94%

2200 Serenity Ln

Woodstock, IL

3 beds | 2 baths | 2,124 sq.ft.

$392,500

Airbnb cash on cash: 0.74%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $2039

Traditional Rental Income: $2802

Airbnb ROI: 0.74%

Traditional ROI: 4.18%

708 S Rose Farm Rd

Woodstock, IL

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

$2,150,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $2181

Traditional Rental Income: $4706

Airbnb ROI: -0.75%

Traditional ROI: 0.77%

121 Prairie Ridge Drive

Woodstock, IL

3 beds | 3 baths | 1,769 sq.ft.

$364,900

Airbnb cash on cash: 1.24%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $2039

Traditional Rental Income: $2157

Airbnb ROI: 1.24%

Traditional ROI: 3.13%

1322 Bull Valley Dr

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%

1624 Bull Valley Drive

Woodstock, IL

5 beds | 6 baths | 5,000 sq.ft.

$930,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $2181

Traditional Rental Income: $6844

Airbnb ROI: -1.13%

Traditional ROI: 4.89%

13616 Route 176

Woodstock, IL

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

$589,900

Airbnb cash on cash: -2.74%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $2039

Traditional Rental Income: $2893

Airbnb ROI: -2.74%

Traditional ROI: -0.38%

8201 Austin Trl

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