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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
3364 W Woodstock RdWoodstock, VTThis wonderfully updated 4 BR/ 3BA 1840âs Cape on two acres is just 5 minutes from the... |
4 beds | 3 baths | 2,470 sq.ft. |
$495,000 |
Airbnb cash on cash: 3.08%
|
1054 W Woodstock RdWoodstock, VTPROPERTY BEING OFFERED VIA AUCTION ON JUNE 12, 2019. List price is suggested opening bid o... |
N/A beds | N/A baths | N/A |
$275,000 |
Airbnb cash on cash: N/A
|
442 E Woodstock Road #4AWoodstock, VTAiry, 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: 1.88%
|
37 South StWoodstock, VTHoliday price reduction! Welcome to this beautifully renovated residence in the vibrant he... |
3 beds | 2 baths | 1,660 sq.ft. |
$749,000 |
Airbnb cash on cash: -0.3%
|
412 Skyland LnWoodstock, VTOnce the site of an 1850s homestead and now reimagined for 21st-century living, Skyland Fa... |
4 beds | 4 baths | 5,087 sq.ft. |
$6,750,000 |
Airbnb cash on cash: -1.2%
|
3961 Hartland Hill RdWoodstock, VTThis lovely,expanded Cape sits just a half mile from Woodstock Village's East End.Surround... |
5 beds | 3 baths | 3,886 sq.ft. |
$825,000 |
Airbnb cash on cash: N/A
|
26 Mt Peg Rd #DWoodstock, VTIntroducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa... |
3 beds | 3 baths | 2,385 sq.ft. |
$1,195,000 |
Airbnb cash on cash: -2.24%
|
26 Mt Peg Rd #AWoodstock, VTIntroducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa... |
3 beds | 3 baths | 2,592 sq.ft. |
$1,195,000 |
Airbnb cash on cash: -2.24%
|
26 Mt Peg Rd #CWoodstock, VTIntroducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa... |
3 beds | 3 baths | 2,584 sq.ft. |
$995,000 |
Airbnb cash on cash: -2.11%
|
26 Mt Peg Rd #BWoodstock, VTIntroducing the Mt Peg Condos â Beautifully situated at the foot of Mt. Peg in the Villa... |
3 beds | 3 baths | 2,584 sq.ft. |
$995,000 |
Airbnb cash on cash: -2.11%
|
33 Mountain AveWoodstock, VTWelcome to 33 Mountain Avenue â a mid-century modern gem poised perfectly on the edge... |
2 beds | 3 baths | 2,280 sq.ft. |
$1,295,000 |
Airbnb cash on cash: -1.28%
|
249 Sawyer RdWoodstock, VTLocated in Woodstock, Vermont just one mile from the village green, the Alta House offers ... |
3 beds | 4 baths | 3,682 sq.ft. |
$3,300,000 |
Airbnb cash on cash: -1.25%
|
598 E Woodstock RdWoodstock, VT
|
4 beds | 3 baths | 3,190 sq.ft. |
$689,000 |
Airbnb cash on cash: 0.85%
|
3914 South RdWoodstock, VT3914 South Rd, Woodstock, VT 05071 | Single Family Residential |
4 beds | 3 baths | 3,584 sq.ft. |
$725,000 |
Airbnb cash on cash: 0.66%
|
1362 Barnard RdWoodstock, VT1362 Barnard Rd, Woodstock, VT 05091 | Single Family Residential |
6 beds | 3 baths | 3,645 sq.ft. |
$2,395,000 |
Airbnb cash on cash: -2.54%
|
125 Shurtleff LnWoodstock, VT125 Shurtleff Ln, Woodstock, VT 05091 | Single Family Residential |
4 beds | 3 baths | 3,195 sq.ft. |
$1,300,000 |
Airbnb cash on cash: -0.9%
|
72 Oak Ridge WayWoodstock, VT72 Oak Ridge Way, Woodstock, VT 05091 | Single Family Residential |
3 beds | 3 baths | 1,920 sq.ft. |
$895,000 |
Airbnb cash on cash: -1.11%
|
1522 Barnard RdWoodstock, VT1522 Barnard Rd, Woodstock, VT 05091 | Single Family Residential |
5 beds | 3 baths | 3,648 sq.ft. |
$1,595,000 |
Airbnb cash on cash: -2.36%
|
7 Slayton TerWoodstock, VT7 Slayton Ter, Woodstock, VT 05091 | Single Family Residential |
4 beds | 2 baths | 2,532 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -1.16%
|
1079 Fletcher Hill RdWoodstock, VT1079 Fletcher Hill Rd, Woodstock, VT 05071 | Single Family Residential |
2 beds | 2 baths | 1,440 sq.ft. |
$425,000 |
Airbnb cash on cash: 1.38%
|
513 Deer Brook Way Lot 16Woodstock, VT513 Deer Brook Way Lot 16, Woodstock, VT 05091 | Single Family Residential |
4 beds | 2 baths | 2,668 sq.ft. |
$1,250,000 |
Airbnb cash on cash: -0.93%
|
5798 W Woodstock RdWoodstock, VT5798 W Woodstock Rd, Woodstock, VT 05091 | Single Family Residential |
4 beds | 2 baths | 1,617 sq.ft. |
$439,000 |
Airbnb cash on cash: 2.96%
|
18 The GrnWoodstock, VT18 The Grn, Woodstock, VT 05091 | Single Family Residential |
6 beds | 6 baths | 5,142 sq.ft. |
$3,500,000 |
Airbnb cash on cash: -2.65%
|
1514 South RdWoodstock, VT1514 South Rd, Woodstock, VT 05091 | Single Family Residential |
3 beds | 2 baths | 1,920 sq.ft. |
$595,000 |
Airbnb cash on cash: -0.22%
|
41 Pleasant StWoodstock, VT41 Pleasant St, Woodstock, VT 05091 | Single Family Residential |
9 beds | 11 baths | 5,993 sq.ft. |
$2,599,000 |
Airbnb cash on cash: -2.57%
|
509 Church HlWoodstock, VT509 Church Hl, Woodstock, VT 05091 | Single Family Residential |
3 beds | 3 baths | 2,150 sq.ft. |
$915,000 |
Airbnb cash on cash: -1.15%
|
1782 Randall RdWoodstock, VT1782 Randall Rd, Woodstock, VT 05091 | Single Family Residential |
4 beds | 3 baths | 2,785 sq.ft. |
$985,000 |
Airbnb cash on cash: -0.27%
|
15 Central StWoodstock, VT15 Central St, Woodstock, VT 05091 | Single Family Residential |
4 beds | N/A baths | 6,014 sq.ft. |
$1,600,000 |
Airbnb cash on cash: -1.28%
|
234 Randall RdWoodstock, VT234 Randall Rd, Woodstock, VT 05091 | Single Family Residential |
2 beds | 1 baths | 600 sq.ft. |
$845,000 |
Airbnb cash on cash: -0.73%
|
00 Carlton Hill RdWoodstock, VT00 Carlton Hill Rd, Woodstock, VT 05091 | Other |
N/A beds | N/A baths | N/A |
$149,000 |
Airbnb cash on cash: N/A
|
1 Carlton Hill RdWoodstock, VT1 Carlton Hill Rd, Woodstock, VT 05091 | Other |
N/A beds | N/A baths | N/A |
$325,000 |
Airbnb cash on cash: N/A
|
0 Barnard Rd #20.002Woodstock, VT0 Barnard Rd #20.002, Woodstock, VT 05091 | Other |
N/A beds | N/A baths | N/A |
$779,000 |
Airbnb cash on cash: N/A
|
137 Laughlin RdWoodstock, VT137 Laughlin Rd, Woodstock, VT 05091 | Single Family Residential |
5 beds | 3 baths | 3,028 sq.ft. |
$725,000 |
Airbnb cash on cash: -1.72%
|
Real Estate investment in Woodstock, VT
There are 34 properties for sale in the city of Woodstock . The median list price in Woodstock is $489,604 and the average price per square foot is $191. In February 2026, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $3,144.