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: -0.75%
|
3207-3209 Route 212Woodstock, NYWoodstock Homestead Compound in Bearsville, NY A truly rare and wonderful opportunity aw... |
4 beds | 3 baths | 3,378 sq.ft. |
$1,149,000 |
Airbnb cash on cash: 1.44%
|
15 Lake View DrWoodstock, NY15 Lake View Dr, Woodstock, NY 12448 | Single Family Residential |
2 beds | 1 baths | 1,416 sq.ft. |
$730,000 |
Airbnb cash on cash: 0.04%
|
132 Valley View WayWoodstock, NY132 Valley View Way, Woodstock, NY 12448 | Other |
N/A beds | N/A baths | N/A |
$1,475,000 |
Airbnb cash on cash: -2.02%
|
208 Tinker StWoodstock, NYCharming turn-key Woodstock cottage that is walking distance to the center of town! This ... |
2 beds | 1 baths | 1,191 sq.ft. |
$549,000 |
Airbnb cash on cash: 0.94%
|
19 Blues QuarryWoodstock, NYSeventeen private acres, minutes from the heart of Woodstock. This 3-bedroom, 2.5-bath mod... |
4 beds | 3 baths | 2,613 sq.ft. |
$1,380,000 |
Airbnb cash on cash: 0.05%
|
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: -0.75%
|
177 Tinker StWoodstock, NYNestled in the heart of Woodstock, this expansive estate spans over twelve acres, it is a ... |
5 beds | 4 baths | 2,978 sq.ft. |
$2,400,000 |
Airbnb cash on cash: -1.42%
|
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: 2.54%
|
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: -0.68%
|
42 Dixon AveWoodstock, NYSituated on a large level lot and a quiet road near the heart of town. Some recent updates... |
3 beds | 1 baths | 1,272 sq.ft. |
$335,000 |
Airbnb cash on cash: 4.83%
|
5 Streamside TerWoodstock, NYOPEN HOUSE! Sunday 7/19 from 12:00-2:00! Woodstock Village living doesn't get much better ... |
3 beds | 2 baths | 1,568 sq.ft. |
$550,000 |
Airbnb cash on cash: 2.11%
|
97 John Joy RdWoodstock, NYThe best of both worlds! A boho cottage paradise and a modern ADU (Accessory Dwelling Unit... |
3 beds | 2 baths | 1,532 sq.ft. |
$825,000 |
Airbnb cash on cash: 0.69%
|
235 California Quarry RdWoodstock, 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: -1.02%
|
306 Meads Mountain RdWoodstock, 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: -0.71%
|
00 Lauren CtWoodstock, NY00 Lauren Ct, Ruby, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$575,000 |
Airbnb cash on cash: -0.95%
|
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: 2.68%
|
57 Ohayo Mt. RdWoodstock, NY57 Ohayo Mt. Rd, Woodstock, NY 12498 | Single Family Residential |
1 beds | 1 baths | 841 sq.ft. |
$395,000 |
Airbnb cash on cash: 0%
|
289 Upper Byrdcliffe RdWoodstock, NY289 Upper Byrdcliffe Rd, Woodstock, NY 12498 | Single Family Residential |
4 beds | 3 baths | 3,151 sq.ft. |
$3,500,000 |
Airbnb cash on cash: -1.61%
|
5 Lazy Brook LnWoodstock, NY5 Lazy Brook Ln, Woodstock, NY 12498 | Single Family Residential |
4 beds | 2 baths | 2,480 sq.ft. |
$799,000 |
Airbnb cash on cash: 2.12%
|
20 Country Club LnWoodstock, NY20 Country Club Ln, Woodstock, NY 12498 | Single Family Residential |
8 beds | 8 baths | 12,393 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -1.15%
|
2320 Glasco TpkeWoodstock, NY2320 Glasco Tpke, Woodstock, NY 12498 | Single Family Residential |
8 beds | 5 baths | 4,648 sq.ft. |
$1,325,000 |
Airbnb cash on cash: -0.36%
|
Tbd Wardwell LnWoodstock, NYTbd Wardwell Ln, Woodstock, NY 12498 | Other |
N/A beds | N/A baths | 1,290 sq.ft. |
$435,000 |
Airbnb cash on cash: -0.39%
|
328 John Joy RdWoodstock, NY328 John Joy Rd, Woodstock, NY 12498 | Single Family Residential |
2 beds | 2 baths | 1,300 sq.ft. |
$569,000 |
Airbnb cash on cash: 0.81%
|
106 Mountain Laurel LnWoodstock, NY106 Mountain Laurel Ln, Woodstock, NY 12498 | Single Family Residential |
3 beds | 4 baths | 3,330 sq.ft. |
$1,499,900 |
Airbnb cash on cash: -1.15%
|
5 Maverick TerWoodstock, NYTucked away on a peaceful, wooded lane, this inviting home offers the perfect blend of pri... |
3 beds | 3 baths | 2,316 sq.ft. |
$799,900 |
Airbnb cash on cash: 0.9%
|
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: 2.9%
|
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: -0.27%
|
5 Downer LnWoodstock, 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: 0.27%
|
5 - 7 Downer LnWoodstock, 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: -1.13%
|
171 Van Dale RdWoodstock, NYStep into this meticulously maintained and tastefully updated Woodstock split-level. Set w... |
3 beds | 1 baths | 1,824 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.53%
|
94 Chestnut Hill RdWoodstock, 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. |
$1,325,000 |
Airbnb cash on cash: 0.03%
|
72 Van Dale RdWoodstock, NYNestled in a quiet Woodstock neighborhood five minutes from the village center and a short... |
3 beds | 3 baths | 1,991 sq.ft. |
$699,000 |
Airbnb cash on cash: 0.93%
|
639 W Saugerties RdWoodstock, NYA treehouse retreat on almost 46 Acres - a rare architectural sanctuary. Tucked into the f... |
3 beds | 2 baths | 3,530 sq.ft. |
$2,200,000 |
Airbnb cash on cash: -1.27%
|
60 Boggs Hill RdWoodstock, NYA Rare Byrdcliffe-Era Magical Retreat with Artistic Legacy Built in 1905, just as the hist... |
3 beds | 2 baths | 1,993 sq.ft. |
$1,375,000 |
Airbnb cash on cash: -0.07%
|
29 Maurizi LnWoodstock, NYSet on an almost 3-acre wooded lot, this property has so much to offer in a quiet location... |
4 beds | 2 baths | 2,372 sq.ft. |
$799,999 |
Airbnb cash on cash: 2.77%
|
25 Pine Grove StWoodstock, NY25 Pine Grove St, Woodstock, NY 12498 | Single Family Residential |
2 beds | 2 baths | 1,440 sq.ft. |
$795,000 |
Airbnb cash on cash: -0.19%
|
48 Mountainview AveWoodstock, NY48 Mountainview Ave, Woodstock, NY 12498 | Single Family Residential |
2 beds | 2 baths | 1,248 sq.ft. |
$647,000 |
Airbnb cash on cash: 0.39%
|
2323 Glasco TpkeWoodstock, NY2323 Glasco Tpke, Woodstock, NY 12498 | Single Family Residential |
3 beds | 2 baths | 1,562 sq.ft. |
$799,000 |
Airbnb cash on cash: 0.22%
|
Real Estate investment in Woodstock, NY
There are 68 properties for sale in the city of Woodstock . The median list price in Woodstock is $698,582 and the average price per square foot is $281. In August 2026, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $3,095.