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 |
|---|---|---|---|
220 John Joy RoadWoodstock, NYTucked back from the road, with beautifully landscaped grounds, bluestone walls, and matur... |
3 beds | 3 baths | 2,430 sq.ft. |
$995,000 |
Airbnb cash on cash: -0.36%
|
194 Wittenberg RoadWoodstock, NYTucked away just three miles from the heart of Woodstock, this timeless 1845 farmhouse is ... |
3 beds | 3 baths | 1,592 sq.ft. |
$749,000 |
Airbnb cash on cash: 1.01%
|
86 Rock City RoadWoodstock, NYWoodstock Charm Meets Modern Living at 86 Rock City Road! Step into a piece of Woodstock h... |
4 beds | 3 baths | 1,754 sq.ft. |
$825,000 |
Airbnb cash on cash: 1.23%
|
5 Lazy Brook LaneWoodstock, NYIdeal Woodstock living! This lovely 4 bedroom 3 bath private ranch is set back from the ro... |
4 beds | 3 baths | 2,480 sq.ft. |
$699,000 |
Airbnb cash on cash: 1.6%
|
8 Tannery Brook RoadWoodstock, NYLarge shade trees filter dappled sunlight across this property's private waterside retreat... |
3 beds | 2 baths | 1,776 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 0.12%
|
3251 Route 212Woodstock, NYTucked deep within a private woodland, a long, winding drive opens to a sunny meadow garde... |
2 beds | 2 baths | 1,850 sq.ft. |
$775,000 |
Airbnb cash on cash: 0.53%
|
18 Country Club LaneWoodstock, NYStunning reimagined Ranch, just 1/2 Mile from the Center of Woodstock, 2/10 of a Mile to t... |
2 beds | 2 baths | 1,208 sq.ft. |
$699,000 |
Airbnb cash on cash: 1.22%
|
5 Violet PlaceWoodstock, NYMove right into this lovely 3-4 bedroom home located in a quiet, friendly neighborhood, ju... |
3 beds | 2 baths | 1,804 sq.ft. |
$540,000 |
Airbnb cash on cash: 1.88%
|
66-68 Webster RoadWoodstock, NYRare Opportunity in the Historic Byrdcliffe Arts Colony, Woodstock, NY Discover this charm... |
2 beds | N/A baths | 1,092 sq.ft. |
$599,000 |
Airbnb cash on cash: 0.74%
|
2565 Route 212Woodstock, NYDiscover modern living at its finest with this newly built contemporary home, perfectly ne... |
4 beds | 3 baths | 2,052 sq.ft. |
$1,790,000 |
Airbnb cash on cash: -0.35%
|
97 John Joy RoadWoodstock, NYThe best of both worlds! A boho cottage paradise and a modern ADU (Accessory Dwelling Unit... |
3 beds | 2 baths | 1,532 sq.ft. |
$759,000 |
Airbnb cash on cash: 0.97%
|
4 Munchkin LaneWoodstock, NYHighwoods Haven rests on just over two whisper-quiet acres where sunlight filters through ... |
4 beds | 2 baths | 1,948 sq.ft. |
$799,000 |
Airbnb cash on cash: 1.24%
|
1637 Glasco TurnpikeWoodstock, NYWelcome to the Woodstock Retreat House. This exceptional multi-residential compound has be... |
2 beds | 2 baths | 1,868 sq.ft. |
$749,000 |
Airbnb cash on cash: -0.31%
|
279 Cooper Lake RoadWoodstock, NYNestled along one of the most enchanting, winding roads in Woodstock, this stunning contem... |
4 beds | 4 baths | 3,193 sq.ft. |
$1,375,000 |
Airbnb cash on cash: -0.32%
|
16 Juniper LaneWoodstock, NYWelcome to Juniper Woods. Nestled on four serene acres just minutes from the center of Woo... |
3 beds | 3 baths | 3,076 sq.ft. |
$1,649,000 |
Airbnb cash on cash: -1.2%
|
48 Cooper Hollow RoadWoodstock, NYTucked away on a scenic country road just minutes from historic Woodstock, this stunning c... |
4 beds | 3 baths | 2,125 sq.ft. |
$889,000 |
Airbnb cash on cash: 0.27%
|
99 Cannon CircleWoodstock, NYTucked away in the pristine Ohayo Mountain forest and less than a mile from the heart of W... |
3 beds | 2 baths | 1,948 sq.ft. |
$1,150,000 |
Airbnb cash on cash: -0.04%
|
96 Meads Mountain RoadWoodstock, NYTucked away on 7.26 acres of lush, storybook landscape with a stream-fed pond, this quinte... |
2 beds | 4 baths | 2,727 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -0.51%
|
48 Cooper HollowWoodstock, NYTucked away on a scenic country road just minutes from historic Woodstock, this stunning c... |
4 beds | 3 baths | 2,125 sq.ft. |
$889,000 |
Airbnb cash on cash: 0.27%
|
8 Pine Grove StreetWoodstock, NYDiscover the essence of refined country living in this impeccably restored 1920s farmhouse... |
5 beds | 4 baths | 2,426 sq.ft. |
$895,000 |
Airbnb cash on cash: 1.36%
|
235 California Quarry RoadWoodstock, NYArchitect-Designed Modern Retreat with Unparalleled Views Over Woodstock Perched high abov... |
3 beds | 3 baths | 2,608 sq.ft. |
$2,950,000 |
Airbnb cash on cash: -1.03%
|
11 Fel Qui RoadWoodstock, NYTucked away for the ultimate in privacy. This totally affordable cute ranch needs only a ... |
3 beds | 2 baths | 944 sq.ft. |
$226,100 |
Airbnb cash on cash: 6.93%
|
57 Overlook DriveWoodstock, NYCharming Woodstock Ranch Just Minutes from Town Located in a quiet neighborhood just outsi... |
2 beds | 2 baths | 1,177 sq.ft. |
$329,000 |
Airbnb cash on cash: 3.53%
|
424 John Joy RoadWoodstock, NYThis Woodstock beauty is set on 1.6 private acres on the very desirable John Joy Road. Ste... |
3 beds | 2 baths | 1,812 sq.ft. |
$699,000 |
Airbnb cash on cash: 1.38%
|
20 Overlook DriveWoodstock, NYWoodstock Ranch with Room to Make It Your Own Just minutes from the heart of Woodstock, t... |
3 beds | 1 baths | 917 sq.ft. |
$300,000 |
Airbnb cash on cash: 6.23%
|
1 Blues QuarryWoodstock, NYWelcome to Blues Quarryâwhere tucked-away tranquility meets ''close to everything'' conv... |
3 beds | 2 baths | 2,390 sq.ft. |
$795,000 |
Airbnb cash on cash: 0.48%
|
10 Niles DriveWoodstock, NYMeticulous 4-Bedroom Mid-Century Cape Cod/Ranch in Woodstock. Set on 1 acre in a desirable... |
4 beds | 2 baths | 2,008 sq.ft. |
$679,000 |
Airbnb cash on cash: 1.55%
|
16 Marko GroveWoodstock, NYTucked at the end of a quiet cul-de-sac, the Bearsville Social House is where ease, beauty... |
4 beds | 2 baths | 2,350 sq.ft. |
$795,000 |
Airbnb cash on cash: 1.59%
|
64 Lower Byrdcliffe RoadWoodstock, NYThis historic Woodstock home, complete with a legal short-term rental license, is ready fo... |
3 beds | 2 baths | 1,998 sq.ft. |
$995,000 |
Airbnb cash on cash: 0.27%
|
45 Rose LaneWoodstock, NYQuintessential Woodstock Contemporary tucked away on almost 4 bucolic, private acres minut... |
2 beds | N/A baths | 1,684 sq.ft. |
$995,000 |
Airbnb cash on cash: 0.06%
|
90 Van Dale RoadWoodstock, NYMake your next transition an easy one in this move-in-ready Woodstock home, where timeless... |
4 beds | 3 baths | 2,034 sq.ft. |
$795,000 |
Airbnb cash on cash: 1.28%
|
90 Van DaleWoodstock, NYMake your next transition an easy one in this move-in-ready Woodstock home, where timeless... |
4 beds | 3 baths | 2,034 sq.ft. |
$795,000 |
Airbnb cash on cash: 1.29%
|
9 Cooper Lake RoadWoodstock, NYA secluded mountain escape awaits you in one of Woodstock's preeminent neighborhoods. Tuck... |
3 beds | 3 baths | 3,319 sq.ft. |
$1,850,000 |
Airbnb cash on cash: -0.43%
|
306 Meads Mountain RoadWoodstock, NYSwoop House is a residence with two great rooms, one of which was designed as a profession... |
2 beds | 4 baths | 3,024 sq.ft. |
$4,200,000 |
Airbnb cash on cash: -1.19%
|
18 Niles DriveWoodstock, NYPeek through the trees on this country lane in Woodstock to glimpse a timeless Catskills A... |
3 beds | 3 baths | 1,990 sq.ft. |
$549,000 |
Airbnb cash on cash: 1.47%
|
Real Estate investment in Woodstock, NY
There are 35 properties for sale in the city of Woodstock . The median list price in Woodstock is $795,000 and the average price per square foot is $390. In October 2025, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $3,160.