Real Estate Investment Properties for Sale in Woodstock, VA

Looking for investment property in Woodstock, VA with high ROI ?

Explore a variety of short-term homes & houses in Woodstock, VA. Invest wisely with VRBO & Woodstock, VA 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, VA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
539 LUPTON Road Woodstock, VA Discover the perfect blend of peaceful country living and in-town convenience. This charmi...	2 beds \| 2 baths \| 1,517 sq.ft.	$339,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 5.16% Airbnb Rental Income: $1455 Traditional Rental Income: $2226 Airbnb ROI: 1.39% Traditional ROI: 5.16%
143 S CHURCH Street Woodstock, VA Welcome to this beautifully updated and maintained townhome in the heart of downtown Woods...	3 beds \| 4 baths \| 2,296 sq.ft.	$315,000	Airbnb cash on cash: 2.08% Traditional cash on cash: 7.16% Airbnb Rental Income: $1688 Traditional Rental Income: $2722 Airbnb ROI: 2.08% Traditional ROI: 7.16%
412 MASSANUTTEN Heights Woodstock, VA Charming 2-bedroom, 1-bath ranch-style home in Woodstock, VA, conveniently located near W....	2 beds \| 1 baths \| 1,053 sq.ft.	$270,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 4.79% Airbnb Rental Income: $1455 Traditional Rental Income: $1687 Airbnb ROI: 2.19% Traditional ROI: 4.79%
714 JACKSON Street Woodstock, VA Welcome to this spacious 3-bedroom, 2.5-bathroom home offering over 2,000 sq. ft. of livin...	3 beds \| 3 baths \| 2,024 sq.ft.	$449,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.81% Airbnb Rental Income: $1688 Traditional Rental Income: $2714 Airbnb ROI: 1.25% Traditional ROI: 4.81%
558 GREAT OAK Court Woodstock, VA Welcome to this stunning newly built duplex in Woodstock - a modern home with endless poss...	4 beds \| 3 baths \| 2,588 sq.ft.	$399,900	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.86% Airbnb Rental Income: $968 Traditional Rental Income: $1788 Airbnb ROI: -0.26% Traditional ROI: 2.86%
508 MASSANUTTEN Heights Woodstock, VA Welcome to this beautifully remodeled brick rancher in the town of Woodstock. Situated on ...	4 beds \| 2 baths \| 1,890 sq.ft.	$369,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 5.69% Airbnb Rental Income: $968 Traditional Rental Income: $2582 Airbnb ROI: 0.01% Traditional ROI: 5.69%
239 N CHURCH Street Woodstock, VA Fully remodeled in 2025, this 4-bedroom, 2.5-bath home welcomes you with a classic front p...	4 beds \| 3 baths \| 2,343 sq.ft.	$494,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 4.24% Airbnb Rental Income: $968 Traditional Rental Income: $2651 Airbnb ROI: -0.16% Traditional ROI: 4.24%
405 SPRING HOLLOW Road Woodstock, VA Meticulously Renovated Colonial on 2.15 Acres with In-Law Suite & Smart Features Welcome t...	4 beds \| 5 baths \| 4,704 sq.ft.	$839,999	Airbnb cash on cash: -0.68% Traditional cash on cash: 4.64% Airbnb Rental Income: $968 Traditional Rental Income: $4774 Airbnb ROI: -0.68% Traditional ROI: 4.64%
615 ALLEGHENY Circle Woodstock, VA Motivated Sellers! Welcome to this charming two-bedroom, three-bath brick duplex that comb...	2 beds \| 3 baths \| 1,782 sq.ft.	$340,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 5.95% Airbnb Rental Income: $1455 Traditional Rental Income: $2486 Airbnb ROI: 1.37% Traditional ROI: 5.95%
123 OAK HILL Drive Woodstock, VA MOTIVATED SELLER. NEW ROOF to be installed. This elegant 3-bedroom, 3-bath Colonial blends...	3 beds \| 3 baths \| 2,884 sq.ft.	$535,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.07% Airbnb Rental Income: $1688 Traditional Rental Income: $2878 Airbnb ROI: 0.75% Traditional ROI: 4.07%
301 S CHURCH Street Woodstock, VA Welcome to 301 S. Church St, a move-in-ready home in the heart of Woodstock. Enjoy brand-n...	3 beds \| 3 baths \| 1,280 sq.ft.	$334,900	Airbnb cash on cash: 2.07% Traditional cash on cash: 5.61% Airbnb Rental Income: $1688 Traditional Rental Income: $2333 Airbnb ROI: 2.07% Traditional ROI: 5.61%
446 N SUMMIT AVE Woodstock, VA Charming 3-Bedroom Ranch with Mountain Views and Modern Updates Welcome home to this beaut...	3 beds \| 2 baths \| 1,396 sq.ft.	$339,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 5.09% Airbnb Rental Income: $1688 Traditional Rental Income: $2188 Airbnb ROI: 2.04% Traditional ROI: 5.09%
359 W SPRING Street Woodstock, VA Investment opportunity! Two-story frame home built in 1952, converted into two apartments....	2 beds \| 2 baths \| 1,486 sq.ft.	$169,900	Airbnb cash on cash: 4.01% Traditional cash on cash: 11.03% Airbnb Rental Income: $1455 Traditional Rental Income: $2160 Airbnb ROI: 4.01% Traditional ROI: 11.03%
420 ROLAND Woodstock, VA Welcome home to this beautifully built 2023 residence in Woodstock, VA, where modern comfo...	3 beds \| 2 baths \| 1,457 sq.ft.	$410,000	Airbnb cash on cash: 1.36% Traditional cash on cash: 4.2% Airbnb Rental Income: $1688 Traditional Rental Income: $2310 Airbnb ROI: 1.36% Traditional ROI: 4.2%
80 HONEYSUCKLE Avenue Woodstock, VA This spacious 2-bedroom, 2-bath home is perfectly situated just outside of town limits but...	2 beds \| 2 baths \| 1,464 sq.ft.	$295,000	Airbnb cash on cash: 1.95% Traditional cash on cash: 6.48% Airbnb Rental Income: $1455 Traditional Rental Income: $2280 Airbnb ROI: 1.95% Traditional ROI: 6.48%
446 SUMMIT N Woodstock, VA Charming 3-Bedroom Ranch with Mountain Views and Modern Updates Welcome home to this beaut...	3 beds \| 2 baths \| 1,396 sq.ft.	$339,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 5.2% Airbnb Rental Income: $1688 Traditional Rental Income: $2223 Airbnb ROI: 2.04% Traditional ROI: 5.2%
616 ALLEGHENY Circle Woodstock, VA Welcome home to this low-maintenance 2BR/2BA home in a quiet Woodstock location minutes to...	2 beds \| 2 baths \| 1,476 sq.ft.	$335,000	Airbnb cash on cash: 1.44% Traditional cash on cash: 2.4% Airbnb Rental Income: $1455 Traditional Rental Income: $1325 Airbnb ROI: 1.44% Traditional ROI: 2.4%
24295 SENEDO Road Woodstock, VA Welcome to this charming farmhouse-style home in Woodstock, VA, perfectly placed on a litt...	4 beds \| 2 baths \| 2,194 sq.ft.	$299,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 7.59% Airbnb Rental Income: $968 Traditional Rental Income: $2681 Airbnb ROI: 0.26% Traditional ROI: 7.59%
418 EPARD Lane Woodstock, VA Welcome to this charming 3-bedroom, 2 bath brick ranch style home offering 1,726 sq. ft of...	3 beds \| 2 baths \| 2,144 sq.ft.	$459,000	Airbnb cash on cash: 1.07% Traditional cash on cash: 4.05% Airbnb Rental Income: $1688 Traditional Rental Income: $2501 Airbnb ROI: 1.07% Traditional ROI: 4.05%
163 E RESERVOIR RD Woodstock, VA Convenient, Comfortable, and Move-In Ready in the Heart of Woodstock! Welcome home to 163 ...	2 beds \| 2 baths \| 1,680 sq.ft.	$262,500	Airbnb cash on cash: 2.17% Traditional cash on cash: 3.06% Airbnb Rental Income: $1455 Traditional Rental Income: $1243 Airbnb ROI: 2.17% Traditional ROI: 3.06%
336 HOLLINGSWORTH RD Woodstock, VA	4 beds \| 3 baths \| 2,553 sq.ft.	$499,900	Airbnb cash on cash: -0.31% Traditional cash on cash: 5.1% Airbnb Rental Income: $968 Traditional Rental Income: $3149 Airbnb ROI: -0.31% Traditional ROI: 5.1%

Real Estate investment in Woodstock, VA

There are 21 properties for sale in the city of Woodstock . The median list price in Woodstock is $339,000 and the average price per square foot is $171. In December 2025, the average monthly cash on cash return in Woodstock is 5.00%. The average monthly rental income in Woodstock is $2,333.

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

There are 21 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 $2,333.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, VA

539 LUPTON Road

Woodstock, VA

2 beds | 2 baths | 1,517 sq.ft.

$339,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1455

Traditional Rental Income: $2226

Airbnb ROI: 1.39%

Traditional ROI: 5.16%

143 S CHURCH Street

Woodstock, VA

3 beds | 4 baths | 2,296 sq.ft.

$315,000

Airbnb cash on cash: 2.08%

Traditional cash on cash: 7.16%

Airbnb Rental Income: $1688

Traditional Rental Income: $2722

Airbnb ROI: 2.08%

Traditional ROI: 7.16%

412 MASSANUTTEN Heights

Woodstock, VA

2 beds | 1 baths | 1,053 sq.ft.

$270,000

Airbnb cash on cash: 2.19%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $1455

Traditional Rental Income: $1687

Airbnb ROI: 2.19%

Traditional ROI: 4.79%

714 JACKSON Street

Woodstock, VA

3 beds | 3 baths | 2,024 sq.ft.

$449,000

Airbnb cash on cash: 1.25%

Traditional cash on cash: 4.81%

Airbnb Rental Income: $1688

Traditional Rental Income: $2714

Airbnb ROI: 1.25%

Traditional ROI: 4.81%

558 GREAT OAK Court

Woodstock, VA

4 beds | 3 baths | 2,588 sq.ft.

$399,900

Airbnb cash on cash: -0.26%

Traditional cash on cash: 2.86%

Airbnb Rental Income: $968

Traditional Rental Income: $1788

Airbnb ROI: -0.26%

Traditional ROI: 2.86%

508 MASSANUTTEN Heights

Woodstock, VA

4 beds | 2 baths | 1,890 sq.ft.

$369,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $968

Traditional Rental Income: $2582

Airbnb ROI: 0.01%

Traditional ROI: 5.69%

239 N CHURCH Street

Woodstock, VA

4 beds | 3 baths | 2,343 sq.ft.

$494,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $968

Traditional Rental Income: $2651

Airbnb ROI: -0.16%

Traditional ROI: 4.24%

405 SPRING HOLLOW Road

Woodstock, VA

4 beds | 5 baths | 4,704 sq.ft.

$839,999

Airbnb cash on cash: -0.68%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $968

Traditional Rental Income: $4774

Airbnb ROI: -0.68%