Real Estate Investment Properties for Sale in Woodstock, VT

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

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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
442 E Woodstock Road #4A Woodstock, VT Airy, tranquil and quiet, this former yoga studio space has been converted into a two bedr...	2 beds \| 1 baths \| 1,190 sq.ft.	$239,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 3.46% Airbnb Rental Income: $4099 Traditional Rental Income: $2147 Airbnb ROI: 8.24% Traditional ROI: 3.46%
37 South Street Woodstock, VT New price! Welcome to this beautifully renovated residence in the vibrant heart of Woodsto...	3 beds \| 2 baths \| 1,660 sq.ft.	$785,000	Airbnb cash on cash: 2.06% Traditional cash on cash: 1.82% Airbnb Rental Income: $4212 Traditional Rental Income: $3145 Airbnb ROI: 2.06% Traditional ROI: 1.82%
16 Church Street Woodstock, VT 16 Church has the most stunning view of the river from any house in the village that we ha...	4 beds \| 3 baths \| 3,089 sq.ft.	$1,295,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 0.8% Airbnb Rental Income: $6518 Traditional Rental Income: $4033 Airbnb ROI: 1.81% Traditional ROI: 0.8%
10 College Hill Road Woodstock, VT 10 College Hill is the perfect in-village residence, off the main road yet walk-to-everyth...	5 beds \| 5 baths \| 4,214 sq.ft.	$1,695,000	Airbnb cash on cash: -1.99% Traditional cash on cash: 0.65% Airbnb Rental Income: $1835 Traditional Rental Income: $5484 Airbnb ROI: -1.99% Traditional ROI: 0.65%
26 Mt Peg Road #D Woodstock, VT Introducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa...	3 beds \| 4 baths \| 2,385 sq.ft.	$1,195,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.57% Airbnb Rental Income: $4212 Traditional Rental Income: $4698 Airbnb ROI: -0.67% Traditional ROI: 0.57%
26 Mt Peg Road #A Woodstock, VT Introducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa...	3 beds \| 4 baths \| 2,592 sq.ft.	$1,195,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.64% Airbnb Rental Income: $4212 Traditional Rental Income: $4776 Airbnb ROI: -0.67% Traditional ROI: 0.64%
26 Mt Peg Road #C Woodstock, VT Introducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa...	3 beds \| 4 baths \| 2,584 sq.ft.	$995,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.35% Airbnb Rental Income: $4212 Traditional Rental Income: $4778 Airbnb ROI: -0.22% Traditional ROI: 1.35%
26 Mt Peg Road #B Woodstock, VT Introducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa...	3 beds \| 4 baths \| 2,584 sq.ft.	$995,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 1.35% Airbnb Rental Income: $4212 Traditional Rental Income: $4776 Airbnb ROI: -0.22% Traditional ROI: 1.35%

Real Estate investment in Woodstock, VT

There are 10 properties for sale in the city of Woodstock . The median list price in Woodstock is $1,095,000 and the average price per square foot is $429. In November 2025, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $4,698.

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

There are 10 investment properties available for sale in Woodstock.

In 2025, 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 $4,212.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, VT

442 E Woodstock Road #4A

Woodstock, VT

2 beds | 1 baths | 1,190 sq.ft.

$239,000

Airbnb cash on cash: 8.24%

Traditional cash on cash: 3.46%

Airbnb Rental Income: $4099

Traditional Rental Income: $2147

Airbnb ROI: 8.24%

Traditional ROI: 3.46%

37 South Street

Woodstock, VT

3 beds | 2 baths | 1,660 sq.ft.

$785,000

Airbnb cash on cash: 2.06%

Traditional cash on cash: 1.82%

Airbnb Rental Income: $4212

Traditional Rental Income: $3145

Airbnb ROI: 2.06%

Traditional ROI: 1.82%

16 Church Street

Woodstock, VT

4 beds | 3 baths | 3,089 sq.ft.

$1,295,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 0.8%

Airbnb Rental Income: $6518

Traditional Rental Income: $4033

Airbnb ROI: 1.81%

Traditional ROI: 0.8%

10 College Hill Road

Woodstock, VT

5 beds | 5 baths | 4,214 sq.ft.

$1,695,000

Airbnb cash on cash: -1.99%

Traditional cash on cash: 0.65%

Airbnb Rental Income: $1835

Traditional Rental Income: $5484

Airbnb ROI: -1.99%

Traditional ROI: 0.65%

26 Mt Peg Road #D

Woodstock, VT

3 beds | 4 baths | 2,385 sq.ft.

$1,195,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $4212

Traditional Rental Income: $4698

Airbnb ROI: -0.67%

Traditional ROI: 0.57%

26 Mt Peg Road #A

Woodstock, VT

3 beds | 4 baths | 2,592 sq.ft.

$1,195,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 0.64%

Airbnb Rental Income: $4212

Traditional Rental Income: $4776

Airbnb ROI: -0.67%

Traditional ROI: 0.64%

26 Mt Peg Road #C

Woodstock, VT

3 beds | 4 baths | 2,584 sq.ft.

$995,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $4212

Traditional Rental Income: $4778

Airbnb ROI: -0.22%

Traditional ROI: 1.35%

26 Mt Peg Road #B

Woodstock, VT

3 beds | 4 baths | 2,584 sq.ft.

$995,000

Airbnb cash on cash: -0.22%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $4212

Traditional Rental Income: $4776

Airbnb ROI: -0.22%