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
2033 South Rd Woodstock, VT Intelligently renovated, well-maintained and move-in ready 4 BR 3 BA historic home with th...	4 beds \| 3 baths \| 3,306 sq.ft.	$1,395,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 1.76% Airbnb Rental Income: $4160 Traditional Rental Income: $4206 Airbnb ROI: 1.04% Traditional ROI: 1.76%
139 Doe Hill Way Woodstock, VT What a prime location being just off the main road with great privacy and room to roam! Th...	3 beds \| 2 baths \| 1,520 sq.ft.	$549,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 0.94% Airbnb Rental Income: $3573 Traditional Rental Income: $1476 Airbnb ROI: 3.5% Traditional ROI: 0.94%
358 Cowdrey Path Woodstock, VT This beautifully renovated, truly move-in-ready home has been thoughtfully updated through...	3 beds \| 3 baths \| 2,638 sq.ft.	$965,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.42% Airbnb Rental Income: $3573 Traditional Rental Income: $3015 Airbnb ROI: 0.17% Traditional ROI: 0.42%
16 Church St 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 \| 3,979 sq.ft.	$1,195,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 0.95% Airbnb Rental Income: $4160 Traditional Rental Income: $4033 Airbnb ROI: 0.27% Traditional ROI: 0.95%
2394 Fletcher Hill Rd Woodstock, VT Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing r...	2 beds \| 2 baths \| 2,944 sq.ft.	$1,695,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.09% Airbnb Rental Income: $3556 Traditional Rental Income: $3546 Airbnb ROI: -0.4% Traditional ROI: 0.09%
2706 E Woodstock Rd Woodstock, VT Gracious Single Family home and Investment Opportunity - This 3 bedroom, 2 bath brick colo...	4 beds \| 3 baths \| 4,800 sq.ft.	$1,645,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 1.29% Airbnb Rental Income: $4160 Traditional Rental Income: $4360 Airbnb ROI: 0.58% Traditional ROI: 1.29%
412 Skyland Ln Woodstock, VT Once the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Fa...	4 beds \| 4 baths \| 5,087 sq.ft.	$5,950,000	Airbnb cash on cash: -1.09% Traditional cash on cash: -0.45% Airbnb Rental Income: $4160 Traditional Rental Income: $6763 Airbnb ROI: -1.09% Traditional ROI: -0.45%
39 Elm St #B Woodstock, VT The Richmond House â Unit B \| Woodstock Village. An enduring Woodstock landmark, the ico...	3 beds \| 3 baths \| 3,294 sq.ft.	$1,600,000	Airbnb cash on cash: -2.29% Traditional cash on cash: -0.71% Airbnb Rental Income: $3573 Traditional Rental Income: $5134 Airbnb ROI: -2.29% Traditional ROI: -0.71%
26 Mt Peg Rd #D Woodstock, VT Introducing the Mt Peg Condos - Beautifully situated at the foot of Mt. Peg in the Village...	3 beds \| 3 baths \| 2,385 sq.ft.	$975,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.12% Airbnb Rental Income: $3573 Traditional Rental Income: $4698 Airbnb ROI: -0.99% Traditional ROI: 1.12%
26 Mt Peg Rd #A Woodstock, VT Introducing the Mt Peg Condos - Beautifully situated at the foot of Mt. Peg in the Village...	3 beds \| 3 baths \| 2,592 sq.ft.	$975,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.2% Airbnb Rental Income: $3573 Traditional Rental Income: $4776 Airbnb ROI: -0.99% Traditional ROI: 1.2%
26 Mt Peg Rd #C Woodstock, VT Introducing the Mt Peg Condos - Beautifully situated at the foot of Mt. Peg in the Village...	3 beds \| 3 baths \| 2,584 sq.ft.	$875,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 1.67% Airbnb Rental Income: $3573 Traditional Rental Income: $4778 Airbnb ROI: -0.77% Traditional ROI: 1.67%
26 Mt Peg Rd #B Woodstock, VT Introducing the Mt Peg Condos - Beautifully situated at the foot of Mt. Peg in the Village...	3 beds \| 3 baths \| 2,584 sq.ft.	$875,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 1.67% Airbnb Rental Income: $3573 Traditional Rental Income: $4776 Airbnb ROI: -0.77% Traditional ROI: 1.67%
249 Sawyer Rd Woodstock, VT Located in Woodstock, Vermont just one mile from the village green, the Alta House offers ...	3 beds \| 4 baths \| 3,682 sq.ft.	$2,950,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.25% Airbnb Rental Income: $3573 Traditional Rental Income: $5752 Airbnb ROI: -0.84% Traditional ROI: 0.25%
598 E Woodstock Rd Woodstock, VT 598 E Woodstock Rd, Woodstock, VT 05091 \| Single Family Residential	4 beds \| 3 baths \| 3,190 sq.ft.	$659,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 3.7% Airbnb Rental Income: $4160 Traditional Rental Income: $4144 Airbnb ROI: 2.29% Traditional ROI: 3.7%
1522 Barnard Rd Woodstock, VT 1522 Barnard Rd, Woodstock, VT 05091 \| Single Family Residential	5 beds \| 3 baths \| 3,648 sq.ft.	$1,395,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 0.27% Airbnb Rental Income: $2771 Traditional Rental Income: $4190 Airbnb ROI: -1.33% Traditional ROI: 0.27%
5798 W Woodstock Rd Woodstock, VT 5798 W Woodstock Rd, Woodstock, VT 05091 \| Single Family Residential	4 beds \| 2 baths \| 1,617 sq.ft.	$349,000	Airbnb cash on cash: 6.84% Traditional cash on cash: 6.42% Airbnb Rental Income: $4160 Traditional Rental Income: $3143 Airbnb ROI: 6.84% Traditional ROI: 6.42%
41 Pleasant St Woodstock, VT 41 Pleasant St, Woodstock, VT 05091 \| Single Family Residential	9 beds \| 11 baths \| 5,993 sq.ft.	$2,599,000	Airbnb cash on cash: -2.05% Traditional cash on cash: -0.26% Airbnb Rental Income: $2771 Traditional Rental Income: $6432 Airbnb ROI: -2.05% Traditional ROI: -0.26%
1782 Randall Rd Woodstock, VT 1782 Randall Rd, Woodstock, VT 05091 \| Single Family Residential	4 beds \| 3 baths \| 2,785 sq.ft.	$865,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 1.84% Airbnb Rental Income: $4160 Traditional Rental Income: $3901 Airbnb ROI: 1.06% Traditional ROI: 1.84%
234 Randall Rd Woodstock, VT 234 Randall Rd, Woodstock, VT 05091 \| Single Family Residential	2 beds \| 1 baths \| 600 sq.ft.	$845,000	Airbnb cash on cash: 0.52% Traditional cash on cash: -1.07% Airbnb Rental Income: $3556 Traditional Rental Income: $1528 Airbnb ROI: 0.52% Traditional ROI: -1.07%
1 Carlton Hill Rd Woodstock, VT 1 Carlton Hill Rd, Woodstock, VT 05091 \| Other	N/A beds \| N/A baths \| N/A	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.64% Airbnb Rental Income: $null Traditional Rental Income: $1169 Airbnb ROI: N/A Traditional ROI: 0.64%
0 Barnard Rd #20.002 Woodstock, VT 0 Barnard Rd #20.002, Woodstock, VT 05091 \| Other	N/A beds \| N/A baths \| N/A	$779,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.4% Airbnb Rental Income: $null Traditional Rental Income: $1169 Airbnb ROI: N/A Traditional ROI: -1.4%
115 Eastman Road Woodstock, VT Sorgenfrei German for "carefree" captures the spirit of this remarkable property in one of...	3 beds \| 4 baths \| 5,384 sq.ft.	$5,875,000	Airbnb cash on cash: -1.26% Traditional cash on cash: -1.08% Airbnb Rental Income: $3573 Traditional Rental Income: $3767 Airbnb ROI: -1.26% Traditional ROI: -1.08%
85 Townhouse Way #14 Woodstock, VT 85 Townhouse Way #14, Woodstock, VT 05091 \| Condo/Coop	2 beds \| 3 baths \| 2,091 sq.ft.	$450,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 2.4% Airbnb Rental Income: $3556 Traditional Rental Income: $3041 Airbnb ROI: 1.77% Traditional ROI: 2.4%
114 Oak Ridge Way Woodstock, VT See the property specific website with video, 3-D tour and more. Set against the timeless ...	4 beds \| 3 baths \| 5,127 sq.ft.	$2,500,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 0.11% Airbnb Rental Income: $4160 Traditional Rental Income: $5304 Airbnb ROI: -0.76% Traditional ROI: 0.11%
334 Log Cabin Dr Woodstock, VT 334 Log Cabin Dr, Woodstock, VT 05067 \| Other	N/A beds \| N/A baths \| N/A	$325,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.99% Airbnb Rental Income: $null Traditional Rental Income: $1275 Airbnb ROI: N/A Traditional ROI: 0.99%
0 Oak Ridge Way Woodstock, VT 0 Oak Ridge Way, Woodstock, VT 05091 \| Other	N/A beds \| N/A baths \| N/A	$345,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.78% Airbnb Rental Income: $null Traditional Rental Income: $1277 Airbnb ROI: N/A Traditional ROI: 0.78%
47 Pleasant St Woodstock, VT Excellent opportunity for residential or office/commercial space with easy access and high...	3 beds \| 1 baths \| 2,285 sq.ft.	$695,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 2.97% Airbnb Rental Income: $3573 Traditional Rental Income: $3240 Airbnb ROI: 2.27% Traditional ROI: 2.97%
11 Maple St Woodstock, VT A rare Woodstock Village opportunity! A Victorian style home located in Woodstock's much d...	4 beds \| 2 baths \| 2,288 sq.ft.	$595,000	Airbnb cash on cash: 3.05% Traditional cash on cash: 2.96% Airbnb Rental Income: $4160 Traditional Rental Income: $3230 Airbnb ROI: 3.05% Traditional ROI: 2.96%
97 Valley View Rd Woodstock, VT 97 Valley View Rd, Woodstock, VT 05091 \| Other	N/A beds \| N/A baths \| N/A	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.39% Airbnb Rental Income: $null Traditional Rental Income: $1280 Airbnb ROI: N/A Traditional ROI: -1.39%
121 Townhouse Way #20 Woodstock, VT 121 Townhouse Way, Woodstock, VT 05091 \| Single Family Residential	2 beds \| 3 baths \| 2,268 sq.ft.	$495,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 1.86% Airbnb Rental Income: $3556 Traditional Rental Income: $3013 Airbnb ROI: 1.35% Traditional ROI: 1.86%
0 Iver Johnson Way Woodstock, VT 0 Iver Johnson Way, Woodstock, VT 05091 \| Other	N/A beds \| N/A baths \| N/A	$169,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $1280 Airbnb ROI: N/A Traditional ROI: 4.5%
3036 W Woodstock Rd Woodstock, VT On a small hill, amongst trees and beautiful gardens, sits this beautifully maintained log...	3 beds \| 2 baths \| 2,600 sq.ft.	$799,999	Airbnb cash on cash: 0.68% Traditional cash on cash: 1.9% Airbnb Rental Income: $3573 Traditional Rental Income: $3700 Airbnb ROI: 0.68% Traditional ROI: 1.9%
2556 Church Hill Rd Woodstock, VT Once an old school house, this home features stone walls, beautiful gardens, and a nice le...	2 beds \| 1 baths \| 1,324 sq.ft.	$400,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.27% Airbnb Rental Income: $3556 Traditional Rental Income: $2192 Airbnb ROI: 4.82% Traditional ROI: 3.27%
217 S Perry Rd Woodstock, VT 217 S Perry Rd, Woodstock, VT 05091 \| Single Family Residential	3 beds \| 3 baths \| 2,667 sq.ft.	$839,500	Airbnb cash on cash: 0.56% Traditional cash on cash: 1.53% Airbnb Rental Income: $3573 Traditional Rental Income: $3550 Airbnb ROI: 0.56% Traditional ROI: 1.53%

Real Estate investment in Woodstock, VT

There are 52 properties for sale in the city of Woodstock . The median list price in Woodstock is $1,020,639 and the average price per square foot is $402. In October 2026, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $3,370.

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

There are 52 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 $3,573.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, VT

2033 South Rd

Woodstock, VT

4 beds | 3 baths | 3,306 sq.ft.

$1,395,000

Airbnb cash on cash: 1.04%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $4160

Traditional Rental Income: $4206

Airbnb ROI: 1.04%

Traditional ROI: 1.76%

139 Doe Hill Way

Woodstock, VT

3 beds | 2 baths | 1,520 sq.ft.

$549,000

Airbnb cash on cash: 3.5%

Traditional cash on cash: 0.94%

Airbnb Rental Income: $3573

Traditional Rental Income: $1476

Airbnb ROI: 3.5%

Traditional ROI: 0.94%

358 Cowdrey Path

Woodstock, VT

3 beds | 3 baths | 2,638 sq.ft.

$965,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $3573

Traditional Rental Income: $3015

Airbnb ROI: 0.17%

Traditional ROI: 0.42%

16 Church St

Woodstock, VT

4 beds | 3 baths | 3,979 sq.ft.

$1,195,000

Airbnb cash on cash: 0.27%

Traditional cash on cash: 0.95%

Airbnb Rental Income: $4160

Traditional Rental Income: $4033

Airbnb ROI: 0.27%

Traditional ROI: 0.95%

2394 Fletcher Hill Rd

Woodstock, VT

2 beds | 2 baths | 2,944 sq.ft.

$1,695,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 0.09%

Airbnb Rental Income: $3556

Traditional Rental Income: $3546

Airbnb ROI: -0.4%

Traditional ROI: 0.09%

2706 E Woodstock Rd

Woodstock, VT

4 beds | 3 baths | 4,800 sq.ft.

$1,645,000

Airbnb cash on cash: 0.58%

Traditional cash on cash: 1.29%

Airbnb Rental Income: $4160

Traditional Rental Income: $4360

Airbnb ROI: 0.58%

Traditional ROI: 1.29%

412 Skyland Ln

Woodstock, VT

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

$5,950,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: -0.45%

Airbnb Rental Income: $4160

Traditional Rental Income: $6763

Airbnb ROI: -1.09%

Traditional ROI: -0.45%

39 Elm St #B

Woodstock, VT

3 beds | 3 baths | 3,294 sq.ft.

$1,600,000

Airbnb cash on cash: -2.29%

Traditional cash on cash: -0.71%

Airbnb Rental Income: $3573

Traditional Rental Income: $5134

Airbnb ROI: -2.29%