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 |
|---|---|---|---|
12 Library LaneWoodstock, NYTucked along tranquil Library Lane, this classic red cottage offers a rare blend of in-tow... |
3 beds | 3 baths | 1,864 sq.ft. |
$799,000 |
Airbnb cash on cash: 1.12%
|
8 Tannery Brook RoadWoodstock, NYPositioned just moments from the vibrant energy of Tinker Street and the heart of Woodstoc... |
3 beds | 2 baths | 2,496 sq.ft. |
$1,495,000 |
Airbnb cash on cash: 0%
|
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. |
$749,000 |
Airbnb cash on cash: 1.33%
|
5 Violet PlaceWoodstock, NYLovely 3-4 bedroom home located in a quiet, friendly neighborhood, just minutes from the s... |
3 beds | 2 baths | 1,804 sq.ft. |
$540,000 |
Airbnb cash on cash: 2.22%
|
66-68 Webster RoadWoodstock, NYRare Opportunity in the Historic Byrdcliffe Arts Colony, Woodstock, NY Discover this charm... |
2 beds | 2 baths | 1,092 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.07%
|
33 Cottonwood LaneWoodstock, NYOPEN HOUSE! 7/5/2025 from 11:00 AM- 1:00 PM! Come check out this amazing property! The per... |
3 beds | 2 baths | 1,973 sq.ft. |
$665,000 |
Airbnb cash on cash: 0.62%
|
208 Grogkill RoadWoodstock, NYOPEN HOUSE! 7/5/2025 from 11:00 AM to 2:00 PM. Come check out the amazing views! Perfectly... |
3 beds | 3 baths | 2,640 sq.ft. |
$1,325,000 |
Airbnb cash on cash: -0.44%
|
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: -0.07%
|
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: 1.22%
|
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. |
$859,000 |
Airbnb cash on cash: 2.49%
|
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: -1.09%
|
680 Zena RoadWoodstock, NYTurn key Opportunity - whether you are looking for a full time residence or second home. O... |
2 beds | 2 baths | 1,385 sq.ft. |
$549,000 |
Airbnb cash on cash: 1.17%
|
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: 0.12%
|
76-78 Mid Mountain WayWoodstock, NYNestled atop Mid Mountain, just five minutes from the heart of Woodstock, this enchanting ... |
2 beds | 2 baths | 1,673 sq.ft. |
$1,050,000 |
Airbnb cash on cash: -0.21%
|
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: 1.63%
|
916 Zena RoadWoodstock, NYHighest and best by Wednesday, 7/23 at 12:00 PM! Woodstock ranch home and separate rental ... |
3 beds | 3 baths | 2,442 sq.ft. |
$599,000 |
Airbnb cash on cash: 1.73%
|
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: 2.29%
|
61 W Saugerties Woodstock RdWoodstock, NYHIGHEST & BEST BY TUESDAY 7/29 AT 10AM! Tucked away at the end of a long, winding drive, t... |
1 beds | 2 baths | 1,729 sq.ft. |
$499,000 |
Airbnb cash on cash: -0.01%
|
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: -0.97%
|
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: 7.79%
|
12 Arnold DriveWoodstock, NYLocated on a quiet, country road is this meticulously maintained raised ranch home with am... |
4 beds | 2 baths | 2,376 sq.ft. |
$649,000 |
Airbnb cash on cash: 4.37%
|
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: 1.65%
|
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: 6.85%
|
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: 0.72%
|
Real Estate investment in Woodstock, NY
There are 24 properties for sale in the city of Woodstock . The median list price in Woodstock is $777,000 and the average price per square foot is $401. In September 2025, the average monthly cash on cash return in Woodstock is 2.00%. The average monthly rental income in Woodstock is $3,014.