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
1109 Wicker St Woodstock, IL Come and see this cute little ranch home and you will love it and want to move right in. ...	3 beds \| 1 baths \| 1,088 sq.ft.	$299,900	Airbnb cash on cash: 4.29% Traditional cash on cash: 3.46% Airbnb Rental Income: $2525 Traditional Rental Income: $1682 Airbnb ROI: 4.29% Traditional ROI: 3.46%
2440 Bridgewater Dr #2440 Woodstock, IL Bright and airy 3 bedroom, 2 full bath end unit with attached 1 car garage. Great floor p...	3 beds \| 2 baths \| 1,268 sq.ft.	$235,000	Airbnb cash on cash: 5.6% Traditional cash on cash: 6.03% Airbnb Rental Income: $2525 Traditional Rental Income: $2010 Airbnb ROI: 5.6% Traditional ROI: 6.03%
1019 N Madison St Woodstock, IL Imagine yourself living only a short walk from the historic downtown Woodstock, the conven...	2 beds \| 1 baths \| 784 sq.ft.	$215,000	Airbnb cash on cash: 4.91% Traditional cash on cash: 4.29% Airbnb Rental Income: $2093 Traditional Rental Income: $1429 Airbnb ROI: 4.91% Traditional ROI: 4.29%
110 N Seminary Ave Woodstock, IL Two-story home. 3 bedrooms with wood-looking laminated floors. Full basement. Freshly pain...	3 beds \| 1 baths \| 1,125 sq.ft.	$224,900	Airbnb cash on cash: 5.72% Traditional cash on cash: 4.38% Airbnb Rental Income: $2525 Traditional Rental Income: $1630 Airbnb ROI: 5.72% Traditional ROI: 4.38%
1488 White Oak Ln Woodstock, IL Beauty in the Villas of Bull Valley. OPEN Floor Plan and DETAILS make all the difference i...	2 beds \| 3 baths \| 2,026 sq.ft.	$399,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 2.42% Airbnb Rental Income: $2093 Traditional Rental Income: $2389 Airbnb ROI: 0.19% Traditional ROI: 2.42%
1142 Greenwood Cir Woodstock, IL Open and bright describes this 2-bedroom 1.1 bath end unit townhome. Fresh paint throughou...	2 beds \| 1 baths \| 1,102 sq.ft.	$169,900	Airbnb cash on cash: 4.41% Traditional cash on cash: 4.76% Airbnb Rental Income: $2093 Traditional Rental Income: $1611 Airbnb ROI: 4.41% Traditional ROI: 4.76%
731 N Madison St Woodstock, IL Charming 2 flat ready for immediate occupancy. So many updates!!! Fresh neutral paint thro...	4 beds \| 2 baths \| N/A	$279,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 5.39% Airbnb Rental Income: $2093 Traditional Rental Income: $2172 Airbnb ROI: 3.05% Traditional ROI: 5.39%
708 S Rose Farm Rd Woodstock, IL EQUESTRIAN CENTER & HISTORIC HOME----THIS IS A TOTAL TURNKEY LUXURY RIDING ESTATE 20 acres...	5 beds \| 4 baths \| 4,084 sq.ft.	$2,100,000	Airbnb cash on cash: 1.49% Traditional cash on cash: 0.84% Airbnb Rental Income: $7414 Traditional Rental Income: $4706 Airbnb ROI: 1.49% Traditional ROI: 0.84%
1642 Wheeler St Woodstock, IL This charming ranch home with a full English basement is nestled in a quiet neighborhood i...	3 beds \| 2 baths \| 1,642 sq.ft.	$350,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 4% Airbnb Rental Income: $2525 Traditional Rental Income: $2366 Airbnb ROI: 2.63% Traditional ROI: 4%
1002 Castleshire Dr Woodstock, IL Welcome to this beautifully cared-for 2-bedroom, 1.5-bath townhome in a prime Woodstock lo...	2 beds \| 1 baths \| 1,825 sq.ft.	$240,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 6.18% Airbnb Rental Income: $2093 Traditional Rental Income: $2403 Airbnb ROI: 2.45% Traditional ROI: 6.18%
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 2,000 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: 3.42% Traditional cash on cash: 0.55% Airbnb Rental Income: $7414 Traditional Rental Income: $3458 Airbnb ROI: 3.42% Traditional ROI: 0.55%
640 Schumann St Woodstock, IL 640 Schumann St, Woodstock, IL 60098 \| Townhouse	3 beds \| 2 baths \| 1,840 sq.ft.	$305,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 2.05% Airbnb Rental Income: $2525 Traditional Rental Income: $2064 Airbnb ROI: 1.53% Traditional ROI: 2.05%
Wren Plan Woodstock, IL Wren Plan, Woodstock, IL 60098 \| Single Family Residential	4 beds \| 2 baths \| 2,607 sq.ft.	$482,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $2195 Airbnb ROI: N/A Traditional ROI: 1.4%
Siena II Plan Woodstock, IL Siena II Plan, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 1,866 sq.ft.	$449,990	Airbnb cash on cash: 1.08% Traditional cash on cash: 1.31% Airbnb Rental Income: $2525 Traditional Rental Income: $2015 Airbnb ROI: 1.08% Traditional ROI: 1.31%
Rutherford II Plan Woodstock, IL Rutherford II Plan, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 1,723 sq.ft.	$440,990	Airbnb cash on cash: 1.17% Traditional cash on cash: 1.31% Airbnb Rental Income: $2525 Traditional Rental Income: $1973 Airbnb ROI: 1.17% Traditional ROI: 1.31%
Charlotte Plan Woodstock, IL Charlotte Plan, Woodstock, IL 60098 \| Townhouse	3 beds \| 2 baths \| 1,853 sq.ft.	$366,990	Airbnb cash on cash: 2.05% Traditional cash on cash: 2.39% Airbnb Rental Income: $2525 Traditional Rental Income: $2033 Airbnb ROI: 2.05% Traditional ROI: 2.39%
Marianne Plan Woodstock, IL Marianne Plan, Woodstock, IL 60098 \| Townhouse	3 beds \| 2 baths \| 1,780 sq.ft.	$358,990	Airbnb cash on cash: 2.16% Traditional cash on cash: 2.37% Airbnb Rental Income: $2525 Traditional Rental Income: $1986 Airbnb ROI: 2.16% Traditional ROI: 2.37%
Townsend Plan Woodstock, IL Townsend Plan, Woodstock, IL 60098 \| Single Family Residential	4 beds \| 2 baths \| 2,362 sq.ft.	$460,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.53% Airbnb Rental Income: $null Traditional Rental Income: $2155 Airbnb ROI: N/A Traditional ROI: 1.53%
Christie Plan Woodstock, IL Christie Plan, Woodstock, IL 60098 \| Townhouse	2 beds \| 2 baths \| 1,512 sq.ft.	$351,990	Airbnb cash on cash: 1.18% Traditional cash on cash: 1.84% Airbnb Rental Income: $2093 Traditional Rental Income: $1772 Airbnb ROI: 1.18% Traditional ROI: 1.84%
Meadowlark Plan Woodstock, IL Meadowlark Plan, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 2,052 sq.ft.	$443,990	Airbnb cash on cash: 1.13% Traditional cash on cash: 1.67% Airbnb Rental Income: $2525 Traditional Rental Income: $2138 Airbnb ROI: 1.13% Traditional ROI: 1.67%
Starling Plan Woodstock, IL Starling Plan, Woodstock, IL 60098 \| Single Family Residential	4 beds \| 2 baths \| 2,193 sq.ft.	$450,990	Airbnb cash on cash: N/A Traditional cash on cash: 1.6% Airbnb Rental Income: $null Traditional Rental Income: $2139 Airbnb ROI: N/A Traditional ROI: 1.6%
13902 Kishwaukee Valley Rd Woodstock, IL 13902 Kishwaukee Valley Rd, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$600,000	Airbnb cash on cash: -1.42% Traditional cash on cash: -2.37% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -1.42% Traditional ROI: -2.37%
0000 Lake Shore Dr Woodstock, IL	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: 0.39% Traditional cash on cash: -1.49% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 0.39% Traditional ROI: -1.49%
200 E Judd St Woodstock, IL 200 E Judd St, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$479,900	Airbnb cash on cash: -0.97% Traditional cash on cash: -2.15% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -0.97% Traditional ROI: -2.15%
338 Mchenry Ave Woodstock, IL 338 Mchenry Ave, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: 0.4% Traditional cash on cash: -1.48% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 0.4% Traditional ROI: -1.48%
Lot 5 Olmstead Dr Woodstock, IL Lot 5 Olmstead Dr, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$89,000	Airbnb cash on cash: 8.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $1569 Traditional Rental Income: $596 Airbnb ROI: 8.6% Traditional ROI: 2.6%
214 Raffel Rd Woodstock, IL 214 Raffel Rd, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$399,000	Airbnb cash on cash: -0.51% Traditional cash on cash: -1.92% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -0.51% Traditional ROI: -1.92%
709 Mchenry Ave Woodstock, IL	N/A beds \| N/A baths \| N/A	$999,999	Airbnb cash on cash: -2.16% Traditional cash on cash: -2.72% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -2.16% Traditional ROI: -2.72%
999 S Eastwood Dr Woodstock, IL 999 S Eastwood Dr, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$679,000	Airbnb cash on cash: -1.63% Traditional cash on cash: -2.47% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -1.63% Traditional ROI: -2.47%
7 Galaxy Way Woodstock, IL	N/A beds \| N/A baths \| N/A	$189,000	Airbnb cash on cash: 2.48% Traditional cash on cash: -0.47% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 2.48% Traditional ROI: -0.47%
Lot 2 Olmstead Dr Woodstock, IL Lot 2 Olmstead Dr, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$89,000	Airbnb cash on cash: 8.6% Traditional cash on cash: 2.6% Airbnb Rental Income: $1569 Traditional Rental Income: $596 Airbnb ROI: 8.6% Traditional ROI: 2.6%
0 IL Route 47 & Hercules Rd Woodstock, IL 0 IL Route 47 & Hercules Rd, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$11,500,000	Airbnb cash on cash: -3.17% Traditional cash on cash: -3.22% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -3.17% Traditional ROI: -3.22%
Route 14 N Rose Farm Rd Woodstock, IL Route 14 N Rose Farm Rd, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$3,900,000	Airbnb cash on cash: -2.98% Traditional cash on cash: -3.13% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -2.98% Traditional ROI: -3.13%
Lots 8 & 9 Greenwood Cir Woodstock, IL Lots 8 & 9 Greenwood Cir, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$841,000	Airbnb cash on cash: -1.95% Traditional cash on cash: -2.62% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -1.95% Traditional ROI: -2.62%
0 N Seminary Ave Woodstock, IL 0 N Seminary Ave, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$169,500	Airbnb cash on cash: 3.12% Traditional cash on cash: -0.15% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 3.12% Traditional ROI: -0.15%
00 State Route 120 Woodstock, IL 00 State Route 120, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: 2.18% Traditional cash on cash: -0.61% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: 2.18% Traditional ROI: -0.61%
LOT 1 Mcconnell Rd Woodstock, IL LOT 1 Mcconnell Rd, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$1,834,500	Airbnb cash on cash: -2.66% Traditional cash on cash: -2.97% Airbnb Rental Income: $1569 Traditional Rental Income: $589 Airbnb ROI: -2.66% Traditional ROI: -2.97%

Real Estate investment in Woodstock, IL

There are 150 properties for sale in the city of Woodstock . The median list price in Woodstock is $351,789 and the average price per square foot is $143. In August 2026, the average monthly cash on cash return in Woodstock is 3.00%. The average monthly rental income in Woodstock is $2,234.

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

There are 150 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 $2,234.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, IL

1109 Wicker St

Woodstock, IL

3 beds | 1 baths | 1,088 sq.ft.

$299,900

Airbnb cash on cash: 4.29%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $2525

Traditional Rental Income: $1682

Airbnb ROI: 4.29%

Traditional ROI: 3.46%

2440 Bridgewater Dr #2440

Woodstock, IL

3 beds | 2 baths | 1,268 sq.ft.

$235,000

Airbnb cash on cash: 5.6%

Traditional cash on cash: 6.03%

Airbnb Rental Income: $2525

Traditional Rental Income: $2010

Airbnb ROI: 5.6%

Traditional ROI: 6.03%

1019 N Madison St

Woodstock, IL

2 beds | 1 baths | 784 sq.ft.

$215,000

Airbnb cash on cash: 4.91%

Traditional cash on cash: 4.29%

Airbnb Rental Income: $2093

Traditional Rental Income: $1429

Airbnb ROI: 4.91%

Traditional ROI: 4.29%

110 N Seminary Ave

Woodstock, IL

3 beds | 1 baths | 1,125 sq.ft.

$224,900

Airbnb cash on cash: 5.72%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $2525

Traditional Rental Income: $1630

Airbnb ROI: 5.72%

Traditional ROI: 4.38%

1488 White Oak Ln

Woodstock, IL

2 beds | 3 baths | 2,026 sq.ft.

$399,000

Airbnb cash on cash: 0.19%

Traditional cash on cash: 2.42%

Airbnb Rental Income: $2093

Traditional Rental Income: $2389

Airbnb ROI: 0.19%

Traditional ROI: 2.42%

1142 Greenwood Cir

Woodstock, IL

2 beds | 1 baths | 1,102 sq.ft.

$169,900

Airbnb cash on cash: 4.41%

Traditional cash on cash: 4.76%

Airbnb Rental Income: $2093

Traditional Rental Income: $1611

Airbnb ROI: 4.41%

Traditional ROI: 4.76%

731 N Madison St

Woodstock, IL

4 beds | 2 baths | N/A

$279,900

Airbnb cash on cash: 3.05%

Traditional cash on cash: 5.39%

Airbnb Rental Income: $2093

Traditional Rental Income: $2172

Airbnb ROI: 3.05%

Traditional ROI: 5.39%

708 S Rose Farm Rd

Woodstock, IL

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

$2,100,000

Airbnb cash on cash: 1.49%

Traditional cash on cash: 0.84%

Airbnb Rental Income: $7414

Traditional Rental Income: $4706

Airbnb ROI: 1.49%