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 |
|---|---|---|---|
13-16 Torn Hill RoadWoodstock, NYHidden away at the end of a private country lane, just minutes from the heart of Woodstock... |
4 beds | 2 baths | 2,780 sq.ft. |
$1,055,000 |
Airbnb cash on cash: 1.02%
|
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. |
$2,500,000 |
Airbnb cash on cash: -1.57%
|
33 Tannery Brook RdWoodstock, NYPerfect Investment Property located right in the Heart of Woodstock Village! This vibrant ... |
4 beds | N/A baths | 3,622 sq.ft. |
$975,000 |
Airbnb cash on cash: 1.74%
|
5 Lazy Brook LaneWoodstock, NYStep inside for a huge surprise! This tasteful ranch home hides 3 large living spaces, 4 s... |
4 beds | 3 baths | 2,480 sq.ft. |
$599,000 |
Airbnb cash on cash: 2.77%
|
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. |
$649,000 |
Airbnb cash on cash: 0.99%
|
3207-3209 Route 212Woodstock, NYWoodstock Country Compound - A rare three building gem! Move-in/turnkey-ready farmhouse, c... |
5 beds | 3 baths | 3,696 sq.ft. |
$1,199,000 |
Airbnb cash on cash: -0.34%
|
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. |
$799,000 |
Airbnb cash on cash: 0.82%
|
235 California Quarry RoadWoodstock, NYArchitect-Designed Modern Retreat with Unparalleled Views Over Woodstock Perched high abo... |
3 beds | 3 baths | 2,608 sq.ft. |
$2,950,000 |
Airbnb cash on cash: -1.07%
|
2 Fern Hollow HolwWoodstock, NYCharming Two Bedroom Home on a Quiet Dead-End Road Welcome to this serene and private retr... |
2 beds | 1 baths | 1,263 sq.ft. |
$500,000 |
Airbnb cash on cash: 1.3%
|
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. |
$925,000 |
Airbnb cash on cash: 0.23%
|
31 Pond Park RdWoodstock, 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: -0.61%
|
66 Plochmann LnWoodstock, NYSo close yet so far away! Walk to town from your totally private and like-new timber frame... |
2 beds | 2 baths | 1,560 sq.ft. |
$1,340,000 |
Airbnb cash on cash: -0.98%
|
00 Lauren CtWoodstock, NY00 Lauren Ct, Ruby, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$575,000 |
Airbnb cash on cash: 0.42%
|
100 Zena RdWoodstock, NY100 Zena Rd, West Hurley, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$184,900 |
Airbnb cash on cash: 6.86%
|
Tbd Zena RdWoodstock, NYTbd Zena Rd, West Hurley, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$1,888,000 |
Airbnb cash on cash: -1.75%
|
78 Van De Bogart RdWoodstock, NYLocated on quiet road just minutes from the heart of Woodstock, 78 Van de Bogart Road offe... |
4 beds | 1 baths | 1,733 sq.ft. |
$525,000 |
Airbnb cash on cash: 3.62%
|
58 Jones Quarry RdWoodstock, NY58 Jones Quarry Rd, Woodstock, NY 12498 | Single Family Residential |
3 beds | 2 baths | 2,744 sq.ft. |
$949,000 |
Airbnb cash on cash: -0.26%
|
1 Wittenberg RdWoodstock, NY1 Wittenberg Rd, Woodstock, NY 12498 | Single Family Residential |
3 beds | 3 baths | 2,566 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -1.15%
|
34 Forestwood DrWoodstock, NY34 Forestwood Dr, Woodstock, NY 12498 | Single Family Residential |
4 beds | 2 baths | 2,489 sq.ft. |
$499,000 |
Airbnb cash on cash: 3.6%
|
5 Lazy Brook LnWoodstock, NY5 Lazy Brook Ln, Woodstock, NY 12498 | Single Family Residential |
4 beds | 2 baths | 2,480 sq.ft. |
$599,000 |
Airbnb cash on cash: 2.55%
|
19 Livingston CtWoodstock, NY19 Livingston Ct, Woodstock, NY 12498 | Single Family Residential |
4 beds | 2 baths | 2,471 sq.ft. |
$699,000 |
Airbnb cash on cash: 1.8%
|
178 Chestnut Hill RdWoodstock, NY178 Chestnut Hill Rd, Woodstock, NY 12498 | Single Family Residential |
4 beds | 2 baths | 2,942 sq.ft. |
$1,195,000 |
Airbnb cash on cash: -0.06%
|
27 Old Wagon RdWoodstock, NY27 Old Wagon Rd, Woodstock, NY 12498 | Single Family Residential |
4 beds | 5 baths | 3,080 sq.ft. |
$1,295,000 |
Airbnb cash on cash: -0.27%
|
20 Country Club LnWoodstock, NY20 Country Club Ln, Woodstock, NY 12498 | Single Family Residential |
8 beds | 8 baths | 12,393 sq.ft. |
$2,200,000 |
Airbnb cash on cash: -1.42%
|
2320 Glasco TpkeWoodstock, NY2320 Glasco Tpke, Woodstock, NY 12498 | Single Family Residential |
6 beds | 3 baths | 3,023 sq.ft. |
$1,799,000 |
Airbnb cash on cash: -1.13%
|
326 Raycliffe DrWoodstock, NY326 Raycliffe Dr, Woodstock, NY 12498 | Other |
N/A beds | N/A baths | N/A |
$600,000 |
Airbnb cash on cash: -0.3%
|
Tbd Wardwell LnWoodstock, NYTbd Wardwell Ln, Woodstock, NY 12498 | Other |
N/A beds | N/A baths | 1,290 sq.ft. |
$499,000 |
Airbnb cash on cash: 0.89%
|
TBD 60 Acre Zena RdWoodstock, NYTBD 60 Acre Zena Rd, Woodstock, NY 12498 | Other |
N/A beds | N/A baths | 2,068 sq.ft. |
$1,888,000 |
Airbnb cash on cash: -1.75%
|
86 Rock City RoadWoodstock, NYWoodstock Charm Meets Modern Living at 86 Rock City Road! Step into a piece of Woodstock h... |
4 beds | 2 baths | 1,754 sq.ft. |
$795,000 |
Airbnb cash on cash: 1.91%
|
11 Forestwood DriveWoodstock, NYSet in a quiet, welcoming neighborhood just minutes from Woodstock's center, this beautifu... |
3 beds | 2 baths | 2,316 sq.ft. |
$799,000 |
Airbnb cash on cash: 0.42%
|
12 Library LaneWoodstock, NYTucked along tranquil Library Lane, this classic red cottage offers a rare blend of in-tow... |
3 beds | N/A baths | 1,864 sq.ft. |
$769,000 |
Airbnb cash on cash: 0.81%
|
29 Yerry Hill RoadWoodstock, NYThis inviting, light-filled bungalow sits at the base of Ohayo Mountain in a charming Wood... |
3 beds | 1 baths | 894 sq.ft. |
$485,000 |
Airbnb cash on cash: 2.91%
|
5 Violet PlaceWoodstock, NYMove right in to this lovely 3-4 bedroom home located in a quiet, friendly neighborhood, j... |
3 beds | 2 baths | 1,804 sq.ft. |
$540,000 |
Airbnb cash on cash: 1.66%
|
Real Estate investment in Woodstock, NY
There are 47 properties for sale in the city of Woodstock . The median list price in Woodstock is $577,495 and the average price per square foot is $210. In March 2026, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $2,755.