Real Estate Investment Properties for Sale in Woodstock, NY
Looking for investment property in Woodstock, NY with high ROI ?
Explore a variety of short-term homes & houses in Woodstock, NY. Invest wisely with VRBO & Woodstock, NY 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, NY
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
56 Lauren CtWoodstock, NYExceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle liv... |
3 beds | 2 baths | 3,481 sq.ft. |
$2,300,000 |
Airbnb cash on cash: -0.73%
|
14 Lions WayWoodstock, NYThe essence of Woodstock; the artists, the poets, the musicians and the creatives who have... |
1 beds | 2 baths | 1,128 sq.ft. |
$729,000 |
Airbnb cash on cash: -0.05%
|
18 Elting LaneWoodstock, NYCome and see this cute-as-a-button, circa 1950 brick cape on Elting Lane, one of Woodstock... |
2 beds | 2 baths | 1,502 sq.ft. |
$525,000 |
Airbnb cash on cash: 1.93%
|
529 Mt Guardian Road ExtensionWoodstock, NYWelcome to the Mount Guardian Modern. Positioned on nearly four acres on Mount Guardian, t... |
3 beds | 3 baths | 2,064 sq.ft. |
$1,495,000 |
Airbnb cash on cash: 0%
|
19 Blues QuarryWoodstock, NYTucked away on 17 acres just five minutes from the heart of Woodstock, this exceptional pr... |
3 beds | 3 baths | 2,613 sq.ft. |
$1,450,000 |
Airbnb cash on cash: -1.01%
|
56 Lauren CourtWoodstock, NYExceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle liv... |
3 beds | 3 baths | 2,613 sq.ft. |
$2,300,000 |
Airbnb cash on cash: -0.73%
|
5 Lazy Brook LaneWoodstock, NYNEW NEW NEW! If you thought you have seen 5 Lazy Brook Lane, think again! This home is own... |
4 beds | 3 baths | 2,480 sq.ft. |
$799,000 |
Airbnb cash on cash: 2.35%
|
106 Mountain Laurel LaneWoodstock, NYArchitectural. Artistic. Entirely unforgettable. Tucked away on 1.73 private acres just mo... |
3 beds | 4 baths | 3,330 sq.ft. |
$1,499,900 |
Airbnb cash on cash: -0.65%
|
235 California Quarry RoadWoodstock, NYArchitect-Designed Modern Retreat with Unparalleled Views Over Woodstock! Perched high abo... |
3 beds | 3 baths | 2,608 sq.ft. |
$2,375,000 |
Airbnb cash on cash: -1%
|
31 Pond Park RoadWoodstock, NYWoodstock Condo at Maverick Knolls Discover an exceptional opportunity to own a single-lev... |
3 beds | 2 baths | 1,466 sq.ft. |
$775,000 |
Airbnb cash on cash: 0.63%
|
306 Meads Mountain RoadWoodstock, NYInside Swoop House there is a versatile floor plan that includes four en suite bedrooms, o... |
4 beds | 4 baths | 5,272 sq.ft. |
$3,600,000 |
Airbnb cash on cash: -0.75%
|
00 Lauren CtWoodstock, NY00 Lauren Ct, Ruby, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$575,000 |
Airbnb cash on cash: 0.18%
|
100 Zena Rd #sawkill roadWoodstock, NY100 Zena Rd, West Hurley, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$184,900 |
Airbnb cash on cash: 6.12%
|
5 Maverick TerraceWoodstock, NYTucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of pri... |
3 beds | 3 baths | 2,316 sq.ft. |
$849,000 |
Airbnb cash on cash: 0.85%
|
92 Whichtree RoadWoodstock, NYOpen house this Sunday, 4/19 from 12-3pm. Refreshments will be served! Here is that very a... |
3 beds | 2 baths | 1,033 sq.ft. |
$415,000 |
Airbnb cash on cash: 3.26%
|
25-29 Mink Hollow RoadWoodstock, NYOpen House this Sunday, 6/14 from 12:00-3:00 PM -- come experience this exceptional proper... |
4 beds | 3 baths | 2,410 sq.ft. |
$978,000 |
Airbnb cash on cash: 2.42%
|
2465 Glasco TurnpikeWoodstock, NYRare investment opportunity in Woodstock: a collection of five unique cottages on six wood... |
7 beds | 7 baths | 4,331 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -0.62%
|
40 Mamoud Hills RdWoodstock, NY40 Mamoud Hills Rd, Woodstock, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$449,000 |
Airbnb cash on cash: 0.98%
|
5 Downer LaneWoodstock, NYSet on six bucolic acres along one of Woodstock's most scenic country roads, this extraord... |
4 beds | 4 baths | 3,172 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 0.14%
|
5 - 7 Downer LaneWoodstock, NYA Woodstock compound with two distinct residences on eight acres, currently set up as STR.... |
5 beds | 5 baths | 4,628 sq.ft. |
$1,700,000 |
Airbnb cash on cash: -1.54%
|
21 Overlook DriveWoodstock, NYA sweet bright ranch in a friendly neighborhood, only a skip and a jump from the center of... |
3 beds | 1 baths | 1,200 sq.ft. |
$399,999 |
Airbnb cash on cash: 3.92%
|
121 Tinker StreetWoodstock, NYPrime Income Property | Woodstock 2-Family Opportunity Savvy investors and owner-occupants... |
1 beds | 2 baths | 1,012 sq.ft. |
$420,000 |
Airbnb cash on cash: 0.65%
|
123 Tinker StreetWoodstock, NYWoodstock Charm & Income Potential Near the Green Savvy investors and owner-occupants, tak... |
2 beds | 2 baths | 1,284 sq.ft. |
$470,000 |
Airbnb cash on cash: 2.07%
|
125 Tinker StreetWoodstock, NYPrime Income Property | Vacant Woodstock 2-Family Opportunity Delivered Vacant--maximize y... |
N/A beds | 2 baths | 959 sq.ft. |
$425,000 |
Airbnb cash on cash: 1.94%
|
11 Nordic DriveWoodstock, NYWelcome to this distinctive Woodstock retreat, a home shaped by the creativity and vision ... |
2 beds | 2 baths | 2,355 sq.ft. |
$749,000 |
Airbnb cash on cash: 0.52%
|
94 Chestnut Hill RoadWoodstock, NYA rare opportunity to own a truly special piece of the Hudson Valley. Nestled in the heart... |
3 beds | 1 baths | 1,360 sq.ft. |
$1,575,000 |
Airbnb cash on cash: 0.19%
|
15-17 Broadview RoadWoodstock, NYThis exceptional Woodstock property offers a rare blend of privacy and convenience, just m... |
5 beds | 6 baths | 5,163 sq.ft. |
$2,150,000 |
Airbnb cash on cash: -0.82%
|
18 Country Club LaneWoodstock, NYWelcome to 18 Country Club Lane. Located less than half a mile from the picturesque Villag... |
2 beds | 2 baths | 1,208 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.47%
|
36 Summers LaneWoodstock, NYTucked into Woodstock's coveted Upper Byrdcliffe arts enclave, this thoughtfully built con... |
3 beds | 2 baths | 1,817 sq.ft. |
$1,295,000 |
Airbnb cash on cash: -0.32%
|
203 Reynolds RoadWoodstock, NYHere in the heart of Woodstock Village, this lovingly updated home strikes a rare balance ... |
2 beds | 2 baths | 1,322 sq.ft. |
$629,000 |
Airbnb cash on cash: 1.08%
|
39 Whitney DriveWoodstock, NYPerfectly situated just minutes from the vibrant village of Woodstock, while equally conve... |
3 beds | 2 baths | 1,960 sq.ft. |
$549,000 |
Airbnb cash on cash: 1.81%
|
113 Meadow CourtWoodstock, NYTucked at the end of a quiet cul-de-sac in Woodstock, this bright, single-level ranch offe... |
2 beds | 1 baths | 894 sq.ft. |
$175,000 |
Airbnb cash on cash: 8.34%
|
9 Chesters PlaceWoodstock, NYTucked away at the end of a quiet dead-end road, just minutes from the center of Woodstock... |
3 beds | 2 baths | 1,912 sq.ft. |
$950,000 |
Airbnb cash on cash: 0.13%
|
Real Estate investment in Woodstock, NY
There are 42 properties for sale in the city of Woodstock . The median list price in Woodstock is $599,690 and the average price per square foot is $246. In June 2026, the average monthly cash on cash return in Woodstock is 2.00%. The average monthly rental income in Woodstock is $3,355.