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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1832 Yasgur Drive Woodstock, IL MOVE-IN READY 3 BEDROOM \| 2.1 BATHROOM \| ~2,600SQFT FINISHED LIVING SPACE \| HARDWOOD FLOOR...	3 beds \| 3 baths \| 1,758 sq.ft.	$374,000	Airbnb cash on cash: 1% Traditional cash on cash: 3.77% Airbnb Rental Income: $2039 Traditional Rental Income: $2484 Airbnb ROI: 1% Traditional ROI: 3.77%
244 Joseph Street Woodstock, IL Prime Woodstock Split-Level with Rare Sub-Basement - Priced to Move at $350K This 4-bedro...	4 beds \| 3 baths \| 1,680 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.9% Airbnb Rental Income: $null Traditional Rental Income: $2598 Airbnb ROI: N/A Traditional ROI: 4.9%
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: -0.75% Traditional cash on cash: 0.77% Airbnb Rental Income: $2181 Traditional Rental Income: $4706 Airbnb ROI: -0.75% 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.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.45% Airbnb Rental Income: $null Traditional Rental Income: $3198 Airbnb ROI: N/A Traditional ROI: 2.45%
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.	$729,900	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.68% Airbnb Rental Income: $2039 Traditional Rental Income: $2473 Airbnb ROI: -0.73% Traditional ROI: 0.68%
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: -0.96% Traditional cash on cash: -0.2% Airbnb Rental Income: $2181 Traditional Rental Income: $3397 Airbnb ROI: -0.96% Traditional ROI: -0.2%
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%
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%
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: 0.95% Traditional cash on cash: 6.06% Airbnb Rental Income: $2039 Traditional Rental Income: $2930 Airbnb ROI: 0.95% Traditional ROI: 6.06%
17515 Deep Cut Road Woodstock, IL If you love PRIVACY, nature, GORGEOUS SUNSETS and tranquility you must see this homestead....	3 beds \| 2 baths \| 3,000 sq.ft.	$939,900	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.42% Airbnb Rental Income: $2039 Traditional Rental Income: $2448 Airbnb ROI: -0.65% Traditional ROI: 0.42%
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.	$699,900	Airbnb cash on cash: -2.56% Traditional cash on cash: -0.44% Airbnb Rental Income: $2039 Traditional Rental Income: $2893 Airbnb ROI: -2.56% Traditional ROI: -0.44%
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 2,200 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: -1.52% Traditional cash on cash: 0.55% Airbnb Rental Income: $2181 Traditional Rental Income: $3458 Airbnb ROI: -1.52% Traditional ROI: 0.55%
3839 Riverwoods Drive Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR DECEMBER DELIVERY! Homesite# 0260 Welc...	3 beds \| 2 baths \| 1,822 sq.ft.	$414,150	Airbnb cash on cash: 0.23% Traditional cash on cash: 3.35% Airbnb Rental Income: $2039 Traditional Rental Income: $2723 Airbnb ROI: 0.23% Traditional ROI: 3.35%
920 Pleasant Street Woodstock, IL Fantastic Duplex Near Historic Woodstock Square! Don't miss this rare opportunity to own ...	4 beds \| N/A baths \| N/A	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 1.98% Airbnb Rental Income: $null Traditional Rental Income: $2338 Airbnb ROI: N/A Traditional ROI: 1.98%
2420 Vivaldi Street Woodstock, IL PRICED TO SELL FAST! MOTIVATED SELLER!!! 4 bed room 2.5 bath with fire place and 2 car gar...	4 beds \| 3 baths \| 2,059 sq.ft.	$369,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $2796 Airbnb ROI: N/A Traditional ROI: 4.77%
619 Schumann Street Woodstock, IL Beautiful Abbey end-unit model with gorgeous finishes throughout. This gorgeous home offer...	2 beds \| 2 baths \| 1,683 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $2488 Airbnb ROI: N/A Traditional ROI: 4.06%
2732 Woodworth Avenue Woodstock, IL Welcome home to 2732 Woodworth Ave. In the well sought out Apple Creek Estates subdivision...	3 beds \| 4 baths \| 1,988 sq.ft.	$415,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 4.81% Airbnb Rental Income: $2039 Traditional Rental Income: $3206 Airbnb ROI: 0.45% Traditional ROI: 4.81%
361 Fieldstone Drive Woodstock, IL ALMOST NEW, MOVE-IN READY HOME, BACKS TO OPEN SPACE \| 2,500 SQFT ABOVE GRADE, PLUS 1,224 S...	5 beds \| 3 baths \| 2,500 sq.ft.	$459,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.88% Airbnb Rental Income: $2181 Traditional Rental Income: $3125 Airbnb ROI: 0.4% Traditional ROI: 3.88%
4319 McCauley Road Woodstock, IL Fabulous 3 acre Estate ready for Horses! Lovely 1989 Cedar home with 4 BR, 3 1/2 baths, 3...	4 beds \| 4 baths \| 2,886 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.68% Airbnb Rental Income: $null Traditional Rental Income: $3622 Airbnb ROI: N/A Traditional ROI: 3.68%
2440 Chopin Lane Woodstock, IL Multiple Offers Received. Highest and Best due by 12/11/2025 11:59:00 PM Mountain Time. ...	4 beds \| 3 baths \| 2,778 sq.ft.	$341,250	Airbnb cash on cash: N/A Traditional cash on cash: 5.69% Airbnb Rental Income: $null Traditional Rental Income: $3235 Airbnb ROI: N/A Traditional ROI: 5.69%
912 Clay Street Woodstock, IL Wonderful 2-unit investment opportunity near downtown Woodstock in great location. With 2 ...	4 beds \| N/A baths \| N/A	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.61% Airbnb Rental Income: $null Traditional Rental Income: $1883 Airbnb ROI: N/A Traditional ROI: 3.61%
5609 N Il Route 47 Highway Woodstock, IL Private setting on almost 2 acres with mature trees recently trimmed and enough room to ad...	3 beds \| 2 baths \| N/A	$439,900	Airbnb cash on cash: 0.94% Traditional cash on cash: 3.35% Airbnb Rental Income: $2039 Traditional Rental Income: $2504 Airbnb ROI: 0.94% Traditional ROI: 3.35%
554 Fremont Street Woodstock, IL (Agent-Owned Property) spacious 3-bedroom, 2-bathroom home offering comfort, character, a...	3 beds \| 2 baths \| 2,178 sq.ft.	$295,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 6.87% Airbnb Rental Income: $2039 Traditional Rental Income: $2758 Airbnb ROI: 2.38% Traditional ROI: 6.87%

Real Estate investment in Woodstock, IL

There are 39 properties for sale in the city of Woodstock . The median list price in Woodstock is $427,690 and the average price per square foot is $158. In December 2025, the average monthly cash on cash return in Woodstock is 4.00%. The average monthly rental income in Woodstock is $2,764.

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

There are 39 investment properties available for sale in Woodstock.

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

The ROI for Short-Term is higher than the Long-Term in Woodstock with average rental income of $2,039.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, IL

1832 Yasgur Drive

Woodstock, IL

3 beds | 3 baths | 1,758 sq.ft.

$374,000

Airbnb cash on cash: 1%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2039

Traditional Rental Income: $2484

Airbnb ROI: 1%

Traditional ROI: 3.77%

244 Joseph Street

Woodstock, IL

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

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.9%

Airbnb Rental Income: $null

Traditional Rental Income: $2598

Airbnb ROI: N/A

Traditional ROI: 4.9%

708 S Rose Farm Road

Woodstock, IL

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

$2,175,000

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%

1907 Cherry Valley Road

Woodstock, IL

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

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: 2.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3198

Airbnb ROI: N/A

Traditional ROI: 2.45%

16306 Kishwaukee Valley Road

Woodstock, IL

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

$729,900

Airbnb cash on cash: -0.73%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $2039

Traditional Rental Income: $2473

Airbnb ROI: -0.73%

Traditional ROI: 0.68%

15917 Kishwaukee Valley Road

Woodstock, IL

5 beds | 3 baths | N/A

$2,495,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: -0.2%

Airbnb Rental Income: $2181

Traditional Rental Income: $3397

Airbnb ROI: -0.96%

Traditional ROI: -0.2%

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%

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%