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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2123 BACK Road Woodstock, VA Welcome to 2123 Back Rd in Woodstock, a 4 bedroom, 3 bath brick rancher offering a flexibl...	4 beds \| 3 baths \| 2,912 sq.ft.	$500,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 5.09% Airbnb Rental Income: $1454 Traditional Rental Income: $3187 Airbnb ROI: 0.46% Traditional ROI: 5.09%
203 OAK HILL Drive Woodstock, VA *Price improvement. Back on the market at no fault of seller and priced to move. Inspectio...	3 beds \| 3 baths \| 3,422 sq.ft.	$499,900	Airbnb cash on cash: -0.15% Traditional cash on cash: 3.7% Airbnb Rental Income: $1161 Traditional Rental Income: $2579 Airbnb ROI: -0.15% Traditional ROI: 3.7%
380 E RESERVOIR Road Woodstock, VA Charming 4-bedroom, 2.5-bath ranch situated on almost an acre in a desirable Woodstock loc...	4 beds \| 3 baths \| 2,231 sq.ft.	$365,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 6.67% Airbnb Rental Income: $1454 Traditional Rental Income: $2847 Airbnb ROI: 1.34% Traditional ROI: 6.67%
143 N WATER ST Woodstock, VA Step into timeless charm and modern comfort in this beautifully renovated 2-bedroom, 2-bat...	2 beds \| 2 baths \| N/A	$249,900	Airbnb cash on cash: 1.3% Traditional cash on cash: 3.3% Airbnb Rental Income: $1099 Traditional Rental Income: $1200 Airbnb ROI: 1.3% Traditional ROI: 3.3%
405 SPRING HOLLOW Road Woodstock, VA NEW PRICE REDUCTION !! Meticulously Renovated Colonial on 2.15 Acres with In-Law Suite & S...	4 beds \| 5 baths \| 4,700 sq.ft.	$699,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 5.67% Airbnb Rental Income: $1454 Traditional Rental Income: $4774 Airbnb ROI: -0.07% Traditional ROI: 5.67%
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: 0.5% Traditional cash on cash: 3.27% Airbnb Rental Income: $1454 Traditional Rental Income: $2442 Airbnb ROI: 0.5% Traditional ROI: 3.27%
56 SMOOT RD Woodstock, VA Tucked into the scenic beauty of the Shenandoah Valley, this well-maintained property offe...	5 beds \| 3 baths \| N/A	$614,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $3089 Airbnb ROI: N/A Traditional ROI: 3.6%
207 S MUHLENBERG Street Woodstock, VA This lovely Victorian greets you with it's bold and commanding presence softened by perenn...	4 beds \| 2 baths \| 2,302 sq.ft.	$575,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.37% Airbnb Rental Income: $1454 Traditional Rental Income: $2614 Airbnb ROI: 0.4% Traditional ROI: 3.37%
131 UPPER SPRINGS LN Woodstock, VA LARGE DETACHED GARAGE ADDED TO THIS LISTING 30 X 40 WITH 14' DOORS. Nestled on 6 beautiful...	3 beds \| 4 baths \| 2,028 sq.ft.	$674,900	Airbnb cash on cash: -0.34% Traditional cash on cash: 2.75% Airbnb Rental Income: $1161 Traditional Rental Income: $2725 Airbnb ROI: -0.34% Traditional ROI: 2.75%
1292-F5 OX Road Woodstock, VA FHA and other government financing is now OK thanks to new sprinkler system installed insp...	2 beds \| 2 baths \| 1,195 sq.ft.	$145,900	Airbnb cash on cash: 0.22% Traditional cash on cash: 10.8% Airbnb Rental Income: $1099 Traditional Rental Income: $2205 Airbnb ROI: 0.22% Traditional ROI: 10.8%
316 S MUHLENBERG Street Woodstock, VA A welcoming front porch sets the tone for this stately home-an inviting space to relax and...	5 beds \| 4 baths \| 2,892 sq.ft.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.06% Airbnb Rental Income: $null Traditional Rental Income: $3412 Airbnb ROI: N/A Traditional ROI: 5.06%
2212 SWARTZ Road Woodstock, VA Come see this 3 Bedroom Ranch Style Home with One Bath. This adorable house in the country...	3 beds \| 1 baths \| 1,104 sq.ft.	$319,999	Airbnb cash on cash: 0.93% Traditional cash on cash: 4.06% Airbnb Rental Income: $1161 Traditional Rental Income: $1721 Airbnb ROI: 0.93% Traditional ROI: 4.06%
1081 HISEY Avenue Woodstock, VA Charming ranch in the heart of Woodstock - just one block from shopping and dining. This s...	4 beds \| 2 baths \| 1,949 sq.ft.	$389,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 5.53% Airbnb Rental Income: $1454 Traditional Rental Income: $2643 Airbnb ROI: 1.08% Traditional ROI: 5.53%
515 HOLLINGSWORTH RD Woodstock, VA	3 beds \| 3 baths \| 2,832 sq.ft.	$425,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 5.14% Airbnb Rental Income: $1161 Traditional Rental Income: $2751 Airbnb ROI: 0.19% Traditional ROI: 5.14%
137 HOOVER Road Woodstock, VA Welcome to this charming 2-bedroom, 2 full bath rancher perfectly situated on 1.3 scenic a...	2 beds \| 2 baths \| 1,512 sq.ft.	$435,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 4.12% Airbnb Rental Income: $1099 Traditional Rental Income: $2358 Airbnb ROI: 0.11% Traditional ROI: 4.12%
609 KESTREL Court Woodstock, VA Spacious All-Brick Duplex, beautifully maintained and offering 4000 sq. ft. of comfortable...	4 beds \| 3 baths \| 2,924 sq.ft.	$515,000	Airbnb cash on cash: 0.31% Traditional cash on cash: 4.49% Airbnb Rental Income: $1454 Traditional Rental Income: $3034 Airbnb ROI: 0.31% Traditional ROI: 4.49%
741 HISEY AVE Woodstock, VA To-Be-Built new construction townhomes. The "Juniper" floor plan. Welcome to Westbend, the...	3 beds \| 3 baths \| 1,220 sq.ft.	$265,990	Airbnb cash on cash: 0.48% Traditional cash on cash: 6.22% Airbnb Rental Income: $1161 Traditional Rental Income: $2218 Airbnb ROI: 0.48% Traditional ROI: 6.22%
500 STEPHENSON Court Woodstock, VA Charming 3-bedroom, 3-bath ranch home on a beautifully maintained 0.61-acre cul-de-sac lot...	3 beds \| 3 baths \| 2,250 sq.ft.	$415,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 4.92% Airbnb Rental Income: $1161 Traditional Rental Income: $2658 Airbnb ROI: 0.08% Traditional ROI: 4.92%
317 DAWN Avenue Woodstock, VA 4-bedroom, 3-bath ranch home located in Woodstock with convenient access to shopping, dini...	4 beds \| 3 baths \| 2,091 sq.ft.	$373,000	Airbnb cash on cash: 1.12% Traditional cash on cash: 6.33% Airbnb Rental Income: $1454 Traditional Rental Income: $2845 Airbnb ROI: 1.12% Traditional ROI: 6.33%
771 HISEY AVE Woodstock, VA Quick Delivery New Construction Townhome â August/September Delivery - The "Juniper" flo...	3 beds \| 3 baths \| 1,220 sq.ft.	$287,960	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.59% Airbnb Rental Income: $1161 Traditional Rental Income: $2211 Airbnb ROI: 0.31% Traditional ROI: 5.59%
621 KESTREL Court Woodstock, VA Immaculate 2-bedroom, 2-bath duplex offering comfortable one-level living in a convenient ...	2 beds \| 2 baths \| 1,686 sq.ft.	$415,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 3.99% Airbnb Rental Income: $1099 Traditional Rental Income: $2248 Airbnb ROI: 0.08% Traditional ROI: 3.99%
128 FAIRVIEW Circle Woodstock, VA Welcome to this spacious and beautifully designed 5 bedroom, 4 full bathroom home situated...	5 beds \| 4 baths \| 3,494 sq.ft.	$645,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.42% Airbnb Rental Income: $null Traditional Rental Income: $3677 Airbnb ROI: N/A Traditional ROI: 4.42%
418 KERN Street Woodstock, VA Experience firsthand how exceptionally well this home has been maintained. From the moment...	4 beds \| 4 baths \| 3,237 sq.ft.	$510,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 5.8% Airbnb Rental Income: $1454 Traditional Rental Income: $3550 Airbnb ROI: 0.5% Traditional ROI: 5.8%
536 E RESERVOIR Road Woodstock, VA Charming vinyl sided cape cod with great potential. Walking distance to the Shenandoah Riv...	3 beds \| 1 baths \| 2,380 sq.ft.	$349,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.65% Airbnb Rental Income: $1161 Traditional Rental Income: $1763 Airbnb ROI: 0.64% Traditional ROI: 3.65%
1252 WHITE ROCK CT Woodstock, VA Whether you are just starting out or looking to downsize, you should check out this house....	4 beds \| 2 baths \| 2,576 sq.ft.	$355,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 5.94% Airbnb Rental Income: $1454 Traditional Rental Income: $2610 Airbnb ROI: 1.18% Traditional ROI: 5.94%
787 HISEY AVE Woodstock, VA MOVE IN READY â âJUNIPERâ TOWNHOME in our new Westbend community! This Juniper is a ...	3 beds \| 3 baths \| 1,220 sq.ft.	$265,990	Airbnb cash on cash: 0.48% Traditional cash on cash: 6.14% Airbnb Rental Income: $1161 Traditional Rental Income: $2199 Airbnb ROI: 0.48% Traditional ROI: 6.14%
1017 SUN POPPY CT Woodstock, VA Enjoy premium one-level living in the desirable Hisey Park community in Woodstock. This we...	3 beds \| 2 baths \| 1,549 sq.ft.	$404,900	Airbnb cash on cash: 0.09% Traditional cash on cash: 4.22% Airbnb Rental Income: $1161 Traditional Rental Income: $2347 Airbnb ROI: 0.09% Traditional ROI: 4.22%

Real Estate investment in Woodstock, VA

There are 36 properties for sale in the city of Woodstock . The median list price in Woodstock is $334,777 and the average price per square foot is $138. In June 2026, the average monthly cash on cash return in Woodstock is 5.00%. The average monthly rental income in Woodstock is $2,553.

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

There are 36 investment properties available for sale in Woodstock.

In 2026, 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 $1,161.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, VA

2123 BACK Road

Woodstock, VA

4 beds | 3 baths | 2,912 sq.ft.

$500,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $1454

Traditional Rental Income: $3187

Airbnb ROI: 0.46%

Traditional ROI: 5.09%

203 OAK HILL Drive

Woodstock, VA

3 beds | 3 baths | 3,422 sq.ft.

$499,900

Airbnb cash on cash: -0.15%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $1161

Traditional Rental Income: $2579

Airbnb ROI: -0.15%

Traditional ROI: 3.7%

380 E RESERVOIR Road

Woodstock, VA

4 beds | 3 baths | 2,231 sq.ft.

$365,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 6.67%

Airbnb Rental Income: $1454

Traditional Rental Income: $2847

Airbnb ROI: 1.34%

Traditional ROI: 6.67%

143 N WATER ST

Woodstock, VA

2 beds | 2 baths | N/A

$249,900

Airbnb cash on cash: 1.3%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1099

Traditional Rental Income: $1200

Airbnb ROI: 1.3%

Traditional ROI: 3.3%

405 SPRING HOLLOW Road

Woodstock, VA

4 beds | 5 baths | 4,700 sq.ft.

$699,900

Airbnb cash on cash: -0.07%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $1454

Traditional Rental Income: $4774

Airbnb ROI: -0.07%

Traditional ROI: 5.67%

769 S WATER Street

Woodstock, VA

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

$550,000

Airbnb cash on cash: 0.5%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1454

Traditional Rental Income: $2442

Airbnb ROI: 0.5%

Traditional ROI: 3.27%

56 SMOOT RD

Woodstock, VA

5 beds | 3 baths | N/A

$614,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.6%

Airbnb Rental Income: $null

Traditional Rental Income: $3089

Airbnb ROI: N/A

Traditional ROI: 3.6%

207 S MUHLENBERG Street

Woodstock, VA

4 beds | 2 baths | 2,302 sq.ft.

$575,000

Airbnb cash on cash: 0.4%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $1454

Traditional Rental Income: $2614

Airbnb ROI: 0.4%