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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
412 Skyland Lane Woodstock, VT Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Fa...	4 beds \| 5 baths \| 5,087 sq.ft.	$6,750,000	Airbnb cash on cash: -1.21% Traditional cash on cash: -0.52% Airbnb Rental Income: $3122 Traditional Rental Income: $6763 Airbnb ROI: -1.21% Traditional ROI: -0.52%
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: -2.06% Traditional cash on cash: 0.57% Airbnb Rental Income: $2348 Traditional Rental Income: $4698 Airbnb ROI: -2.06% 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: -2.06% Traditional cash on cash: 0.64% Airbnb Rental Income: $2348 Traditional Rental Income: $4776 Airbnb ROI: -2.06% 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: -1.9% Traditional cash on cash: 1.35% Airbnb Rental Income: $2348 Traditional Rental Income: $4778 Airbnb ROI: -1.9% 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: -1.9% Traditional cash on cash: 1.35% Airbnb Rental Income: $2348 Traditional Rental Income: $4776 Airbnb ROI: -1.9% Traditional ROI: 1.35%
249 Sawyer Road Woodstock, VT Located in Woodstock, Vermont just one mile from the village green, the Alta House offers ...	3 beds \| 5 baths \| 3,682 sq.ft.	$3,300,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 0.12% Airbnb Rental Income: $2348 Traditional Rental Income: $5752 Airbnb ROI: -1.19% Traditional ROI: 0.12%
99-2 Safford Commons Way Woodstock, VT These 1200 sq. ft., 2-bedroom, 1.5-bathroom condos are being sold for less than half of th...	2 beds \| 2 baths \| 1,200 sq.ft.	$190,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 9.86% Airbnb Rental Income: $2257 Traditional Rental Income: $2697 Airbnb ROI: 4.3% Traditional ROI: 9.86%
57 Townhouse Way #9 Woodstock, VT This beautiful Woodstock West Townhouse offers effortless, low-maintenance living in one o...	3 beds \| 3 baths \| 1,728 sq.ft.	$465,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 2.93% Airbnb Rental Income: $2348 Traditional Rental Income: $3265 Airbnb ROI: -0.51% Traditional ROI: 2.93%

Real Estate investment in Woodstock, VT

There are 12 properties for sale in the city of Woodstock . The median list price in Woodstock is $474,900 and the average price per square foot is $191. In March 2026, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $3,189.

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

There are 12 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 $3,189.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, VT

412 Skyland Lane

Woodstock, VT

4 beds | 5 baths | 5,087 sq.ft.

$6,750,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: -0.52%

Airbnb Rental Income: $3122

Traditional Rental Income: $6763

Airbnb ROI: -1.21%

Traditional ROI: -0.52%

26 Mt Peg Road #D

Woodstock, VT

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

$1,195,000

Airbnb cash on cash: -2.06%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $2348

Traditional Rental Income: $4698

Airbnb ROI: -2.06%

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: -2.06%

Traditional cash on cash: 0.64%

Airbnb Rental Income: $2348

Traditional Rental Income: $4776

Airbnb ROI: -2.06%

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: -1.9%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $2348

Traditional Rental Income: $4778

Airbnb ROI: -1.9%

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: -1.9%

Traditional cash on cash: 1.35%

Airbnb Rental Income: $2348

Traditional Rental Income: $4776

Airbnb ROI: -1.9%

Traditional ROI: 1.35%

249 Sawyer Road

Woodstock, VT

3 beds | 5 baths | 3,682 sq.ft.

$3,300,000

Airbnb cash on cash: -1.19%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $2348

Traditional Rental Income: $5752

Airbnb ROI: -1.19%

Traditional ROI: 0.12%

99-2 Safford Commons Way

Woodstock, VT

2 beds | 2 baths | 1,200 sq.ft.

$190,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 9.86%

Airbnb Rental Income: $2257

Traditional Rental Income: $2697

Airbnb ROI: 4.3%

Traditional ROI: 9.86%

57 Townhouse Way #9

Woodstock, VT

3 beds | 3 baths | 1,728 sq.ft.

$465,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $2348

Traditional Rental Income: $3265

Airbnb ROI: -0.51%