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
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%
1540 Hickory Rd #1540 Woodstock, IL This 2 bedroom condo in the Trees of Woodstock makes a great starter home or step down. It...	2 beds \| 1 baths \| 990 sq.ft.	$177,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $1597 Airbnb ROI: N/A Traditional ROI: 3.76%
708 S Rose Farm Road Woodstock, IL Exceptional 20-Acre Equestrian Estate with Grand Home, Private Apartment & Premier Facilit...	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%
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 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%
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.	$940,000	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 is...	3 beds \| 3 baths \| 6,521 sq.ft.	$625,900	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 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%
4220 Meadowridge Road Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite #5502. Step insid...	3 beds \| 3 baths \| 1,853 sq.ft.	$337,990	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%
3839 Riverwoods Dr Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR DECEMBER DELIVERY! Homesite# 0260 Welcome to...	3 beds \| 2 baths \| 1,822 sq.ft.	$396,600	Airbnb cash on cash: 0.38% Traditional cash on cash: 3.64% Airbnb Rental Income: $2039 Traditional Rental Income: $2723 Airbnb ROI: 0.38% Traditional ROI: 3.64%
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: 0.41% Traditional cash on cash: 4.77% Airbnb Rental Income: $2039 Traditional Rental Income: $3206 Airbnb ROI: 0.41% Traditional ROI: 4.77%
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%
4016 Meadowridge Rd Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE!! READY FOR FEBRUARY DELIVERY!!!! Homesite# 0028. Exper...	3 beds \| 2 baths \| 2,063 sq.ft.	$438,940	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.73% Airbnb Rental Income: $2039 Traditional Rental Income: $3030 Airbnb ROI: 0.03% Traditional ROI: 3.73%
3914 Riverwoods Drive Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR FEBRUARY DELIVERY! Homesite # 0026. Take in ...	4 beds \| 3 baths \| 2,362 sq.ft.	$464,635	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%
3902 Riverwoods Dr Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite # 0024. Discover ...	4 beds \| 2 baths \| 2,619 sq.ft.	$496,165	Airbnb cash on cash: N/A Traditional cash on cash: 3.54% Airbnb Rental Income: $null Traditional Rental Income: $3311 Airbnb ROI: N/A Traditional ROI: 3.54%
4216 Meadowridge Road Woodstock, IL AVAILABLE NOW! SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite# 5...	2 beds \| 2 baths \| 1,512 sq.ft.	$314,990	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 Road Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite# 5602. Introducin...	3 beds \| 3 baths \| 1,780 sq.ft.	$328,740	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 Drive Woodstock, IL SPECIAL FINANCING OFFERS AVAILABLE! READY FOR FEBRUARY DELIVERY! Homesite# 0027. Step into...	3 beds \| 2 baths \| 1,965 sq.ft.	$459,110	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%
118 W Donovan Avenue Woodstock, IL Unlock the potential of this charming 2 unit property located only a short stroll from the...	4 beds \| 2 baths \| N/A	$289,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.59% Airbnb Rental Income: $null Traditional Rental Income: $2636 Airbnb ROI: N/A Traditional ROI: 6.59%
4208 Meadowridge Rd Woodstock, IL AVAILABLE NOW! SPECIAL FINANCING OFFERS AVAILABLE! READY FOR JANUARY DELIVERY! Homesite# 5...	2 beds \| 2 baths \| 1,512 sq.ft.	$335,990	Airbnb cash on cash: N/A Traditional cash on cash: 4.33% Airbnb Rental Income: $null Traditional Rental Income: $2670 Airbnb ROI: N/A Traditional ROI: 4.33%
8508 W IL RT 120 Woodstock, IL 8508 W IL RT 120, Woodstock, IL 60098 \| Single Family Residential	6 beds \| 5 baths \| 12,175 sq.ft.	$3,495,000	Airbnb cash on cash: -2.79% Traditional cash on cash: -1.87% Airbnb Rental Income: $2181 Traditional Rental Income: $4602 Airbnb ROI: -2.79% Traditional ROI: -1.87%
Lt 2 Mason Hill Rd Woodstock, IL Lt 2 Mason Hill Rd, Woodstock, IL 60098 \| Other	N/A beds \| N/A baths \| N/A	$273,330	Airbnb cash on cash: 2.48% Traditional cash on cash: -1.31% Airbnb Rental Income: $2105 Traditional Rental Income: $589 Airbnb ROI: 2.48% Traditional ROI: -1.31%
12216 Pleasant Valley Rd Woodstock, IL 12216 Pleasant Valley Rd, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,700 sq.ft.	$825,000	Airbnb cash on cash: -1.41% Traditional cash on cash: -1.55% Airbnb Rental Income: $2039 Traditional Rental Income: $1406 Airbnb ROI: -1.41% Traditional ROI: -1.55%
14320 Westwood Trl Woodstock, IL 14320 Westwood Trl, Woodstock, IL 60098 \| Single Family Residential	4 beds \| 3 baths \| 3,876 sq.ft.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.92% Airbnb Rental Income: $null Traditional Rental Income: $2517 Airbnb ROI: N/A Traditional ROI: 1.92%
1110 Redtail Ct Woodstock, IL 1110 Redtail Ct, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 1,660 sq.ft.	$425,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 1.49% Airbnb Rental Income: $2039 Traditional Rental Income: $2130 Airbnb ROI: -0.06% Traditional ROI: 1.49%
419 Dean St Woodstock, IL 419 Dean St, Woodstock, IL 60098 \| Single Family Residential	5 beds \| 2 baths \| 2,412 sq.ft.	$399,900	Airbnb cash on cash: 0.85% Traditional cash on cash: 2.36% Airbnb Rental Income: $2181 Traditional Rental Income: $2194 Airbnb ROI: 0.85% Traditional ROI: 2.36%
4212 Meadowridge Rd Woodstock, IL 4212 Meadowridge Rd, Woodstock, IL 60098 \| Townhouse	3 beds \| 2 baths \| 1,780 sq.ft.	$342,990	Airbnb cash on cash: 1.15% Traditional cash on cash: 3.79% Airbnb Rental Income: $2039 Traditional Rental Income: $2360 Airbnb ROI: 1.15% Traditional ROI: 3.79%
2381 Fairview Cir Woodstock, IL 2381 Fairview Cir, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 2,998 sq.ft.	$429,900	Airbnb cash on cash: 0.22% Traditional cash on cash: 2.82% Airbnb Rental Income: $2039 Traditional Rental Income: $2556 Airbnb ROI: 0.22% Traditional ROI: 2.82%
331 Chestnut St Woodstock, IL 331 Chestnut St, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 1 baths \| 1,395 sq.ft.	$249,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 2.04% Airbnb Rental Income: $2039 Traditional Rental Income: $1339 Airbnb ROI: 2.77% Traditional ROI: 2.04%
872 Victoria Dr Woodstock, IL 872 Victoria Dr, Woodstock, IL 60098 \| Condo/Coop	3 beds \| 2 baths \| 1,293 sq.ft.	$235,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 2.32% Airbnb Rental Income: $2039 Traditional Rental Income: $1762 Airbnb ROI: 1.19% Traditional ROI: 2.32%
615 Dean St Woodstock, IL 615 Dean St, Woodstock, IL 60098 \| Single Family Residential	3 beds \| 2 baths \| 2,780 sq.ft.	$369,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 2.77% Airbnb Rental Income: $2039 Traditional Rental Income: $2177 Airbnb ROI: 0.85% Traditional ROI: 2.77%
640 Schumann St Woodstock, IL 640 Schumann St, Woodstock, IL 60098 \| Townhouse	3 beds \| 2 baths \| 1,905 sq.ft.	$325,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 1.73% Airbnb Rental Income: $2039 Traditional Rental Income: $2064 Airbnb ROI: -0.08% Traditional ROI: 1.73%
4030 Meadowridge Rd Woodstock, IL 4030 Meadowridge Rd, Woodstock, IL 60098 \| Single Family Residential	4 beds \| 2 baths \| 2,193 sq.ft.	$427,990	Airbnb cash on cash: N/A Traditional cash on cash: 2.65% Airbnb Rental Income: $null Traditional Rental Income: $2459 Airbnb ROI: N/A Traditional ROI: 2.65%
722 E Calhoun St Woodstock, IL 722 E Calhoun St, Woodstock, IL 60098 \| Multi Family	2 beds \| 1 baths \| N/A	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.22% Airbnb Rental Income: $null Traditional Rental Income: $848 Airbnb ROI: N/A Traditional ROI: -0.22%

Real Estate investment in Woodstock, IL

There are 102 properties for sale in the city of Woodstock . The median list price in Woodstock is $399,900 and the average price per square foot is $160. In January 2026, the average monthly cash on cash return in Woodstock is 3.00%. The average monthly rental income in Woodstock is $1,502.

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

There are 102 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 $1,502.

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%

1540 Hickory Rd #1540

Woodstock, IL

2 beds | 1 baths | 990 sq.ft.

$177,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.76%

Airbnb Rental Income: $null

Traditional Rental Income: $1597

Airbnb ROI: N/A

Traditional ROI: 3.76%

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%

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 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%

Traditional ROI: 4.89%

17515 Deep Cut Road

Woodstock, IL

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

$940,000

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

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

$625,900

Airbnb cash on cash: -2.74%

Traditional cash on cash: -0.38%

Airbnb Rental Income: $2039

Traditional Rental Income: $2893

Airbnb ROI: -2.74%