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
126 Fairground Road Woodstock, VA Priced below 2026 assessment! Found in the sought-after Grand View Estates, this charming ...	3 beds \| 2 baths \| 1,636 sq.ft.	$340,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 3.35% Airbnb Rental Income: $1688 Traditional Rental Income: $1615 Airbnb ROI: 2.1% Traditional ROI: 3.35%
539 LUPTON RD 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%
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.	$425,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 5.08% Airbnb Rental Income: $968 Traditional Rental Income: $2651 Airbnb ROI: -0.02% Traditional ROI: 5.08%
717 W LOCUST Street Woodstock, VA This spacious 5 bedroom, 3 full bath home sits on an expansive lot of more than 5 acres, c...	5 beds \| 3 baths \| 3,850 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.73% Airbnb Rental Income: $null Traditional Rental Income: $2552 Airbnb ROI: N/A Traditional ROI: 2.73%
769 S WATER Street Woodstock, VA One of a kind, hidden gem in the heart of the Town of Woodstock. This 4 BR, 2 Bath split l...	4 beds \| 2 baths \| 1,419 sq.ft.	$550,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.27% Airbnb Rental Income: $968 Traditional Rental Income: $2442 Airbnb ROI: -0.28% Traditional ROI: 3.27%
123 OAK HILL Drive Woodstock, VA MOTIVATED SELLER. NEW ROOF - Nov. 2025. This elegant 3-bedroom, 3-bath Colonial blends cla...	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.	$329,900	Airbnb cash on cash: 2.12% Traditional cash on cash: 5.71% Airbnb Rental Income: $1688 Traditional Rental Income: $2333 Airbnb ROI: 2.12% Traditional ROI: 5.71%
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.	$334,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 5.16% Airbnb Rental Income: $1688 Traditional Rental Income: $2188 Airbnb ROI: 2.08% Traditional ROI: 5.16%
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.	$334,900	Airbnb cash on cash: 2.08% Traditional cash on cash: 5.27% Airbnb Rental Income: $1688 Traditional Rental Income: $2223 Airbnb ROI: 2.08% Traditional ROI: 5.27%
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%
422 N MAIN Street Woodstock, VA Colonial Revival Elegance Meets Modern Comfort. Step into timeless charm with this beautif...	5 beds \| 4 baths \| 3,324 sq.ft.	$949,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.32% Airbnb Rental Income: $null Traditional Rental Income: $4072 Airbnb ROI: N/A Traditional ROI: 3.32%
56 SMOOT RD Woodstock, VA Welcome to your own peaceful retreat tucked away on **2.83 acres of unrestricted Virginia ...	5 beds \| 3 baths \| N/A	$660,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $3089 Airbnb ROI: N/A Traditional ROI: 3.29%
521 S MAIN Street Woodstock, VA The bones of this house are wonderful. House needs renovation including plumbing, electric...	5 beds \| 4 baths \| 3,670 sq.ft.	$495,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2780 Airbnb ROI: N/A Traditional ROI: 4.37%

Real Estate investment in Woodstock, VA

There are 17 properties for sale in the city of Woodstock . The median list price in Woodstock is $450,000 and the average price per square foot is $183. In January 2026, the average monthly cash on cash return in Woodstock is 4.00%. The average monthly rental income in Woodstock is $2,552.

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

There are 17 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 $2,552.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, VA

126 Fairground Road

Woodstock, VA

3 beds | 2 baths | 1,636 sq.ft.

$340,000

Airbnb cash on cash: 2.1%

Traditional cash on cash: 3.35%

Airbnb Rental Income: $1688

Traditional Rental Income: $1615

Airbnb ROI: 2.1%

Traditional ROI: 3.35%

539 LUPTON RD

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%

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.

$425,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: 5.08%

Airbnb Rental Income: $968

Traditional Rental Income: $2651

Airbnb ROI: -0.02%

Traditional ROI: 5.08%

717 W LOCUST Street

Woodstock, VA

5 beds | 3 baths | 3,850 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.73%

Airbnb Rental Income: $null

Traditional Rental Income: $2552

Airbnb ROI: N/A

Traditional ROI: 2.73%

769 S WATER Street

Woodstock, VA

4 beds | 2 baths | 1,419 sq.ft.

$550,000

Airbnb cash on cash: -0.28%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $968

Traditional Rental Income: $2442

Airbnb ROI: -0.28%