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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9 Munchkin Ln Woodstock, NY Selling fully furnished. 9 Munchkin Lane: A Designer Sanctuary in Woodstock Experience tur...	4 beds \| 3 baths \| 2,448 sq.ft.	$1,150,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 1.31% Airbnb Rental Income: $4701 Traditional Rental Income: $4413 Airbnb ROI: 0.67% Traditional ROI: 1.31%
56 Lauren Ct Woodstock, NY Exceptional 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: -0.67% Traditional cash on cash: 0.45% Airbnb Rental Income: $3156 Traditional Rental Income: $4829 Airbnb ROI: -0.67% Traditional ROI: 0.45%
3207-3209 Route 212 Woodstock, NY Woodstock 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: 1.48% Traditional cash on cash: -0.49% Airbnb Rental Income: $4701 Traditional Rental Income: $1627 Airbnb ROI: 1.48% Traditional ROI: -0.49%
15 Lake View Dr Woodstock, NY 15 Lake View Dr, Woodstock, NY 12448 \| Single Family Residential	2 beds \| 1 baths \| 1,416 sq.ft.	$675,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 1.04% Airbnb Rental Income: $2832 Traditional Rental Income: $2456 Airbnb ROI: 0.59% Traditional ROI: 1.04%
132 Valley View Way Woodstock, NY 132 Valley View Way, Woodstock, NY 12448 \| Other	N/A beds \| N/A baths \| N/A	$1,475,000	Airbnb cash on cash: -1.88% Traditional cash on cash: -1.88% Airbnb Rental Income: $1713 Traditional Rental Income: $1231 Airbnb ROI: -1.88% Traditional ROI: -1.88%
168 Cooper Lake Rd Woodstock, NY If you are looking for the perfect Woodstock home, in the best location, look no further. ...	3 beds \| 2 baths \| 2,264 sq.ft.	$865,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 0.4% Airbnb Rental Income: $3156 Traditional Rental Income: $2598 Airbnb ROI: 0.21% Traditional ROI: 0.4%
208 Tinker St Woodstock, NY Charming 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: 1.34% Traditional cash on cash: 5.89% Airbnb Rental Income: $2832 Traditional Rental Income: $4504 Airbnb ROI: 1.34% Traditional ROI: 5.89%
19 Blues Quarry Woodstock, NY Seventeen private acres, minutes from the heart of Woodstock. This 3-bedroom, 2.5-bath mod...	4 beds \| 3 baths \| 2,613 sq.ft.	$1,350,000	Airbnb cash on cash: 0.11% Traditional cash on cash: -0.06% Airbnb Rental Income: $4701 Traditional Rental Income: $3515 Airbnb ROI: 0.11% Traditional ROI: -0.06%
56 Lauren Court Woodstock, NY Exceptional 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: -0.67% Traditional cash on cash: -0.13% Airbnb Rental Income: $3156 Traditional Rental Income: $3606 Airbnb ROI: -0.67% Traditional ROI: -0.13%
357 Chestnut Hill Rd Woodstock, NY Looking for that adorable Woodstock cottage close to town and tucked away on a quiet windi...	2 beds \| 1 baths \| 1,338 sq.ft.	$595,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 0.19% Airbnb Rental Income: $2832 Traditional Rental Income: $1703 Airbnb ROI: 1.03% Traditional ROI: 0.19%
145 Tinker St Woodstock, NY 1900 cottage in need of TLC in the heart of Woodstock. Listen to the rolling brook as you ...	3 beds \| 2 baths \| 1,553 sq.ft.	$749,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 0.83% Airbnb Rental Income: $3156 Traditional Rental Income: $2561 Airbnb ROI: 0.65% Traditional ROI: 0.83%
175-177 Tinker St Woodstock, NY Nestled 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: -1.35% Traditional cash on cash: -0.06% Airbnb Rental Income: $3990 Traditional Rental Income: $5990 Airbnb ROI: -1.35% Traditional ROI: -0.06%
15 Chipmunk Ln Woodstock, NY Crave country living but couldn't possibly think of giving up city-dweller conveniences? I...	3 beds \| 3 baths \| 2,265 sq.ft.	$895,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.69% Airbnb Rental Income: $3156 Traditional Rental Income: $3186 Airbnb ROI: 0.79% Traditional ROI: 1.69%
106 Mountain Laurel Lane Woodstock, NY Architectural. 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: -0.56% Traditional cash on cash: -0.01% Airbnb Rental Income: $3156 Traditional Rental Income: $3204 Airbnb ROI: -0.56% Traditional ROI: -0.01%
42 Dixon Ave Woodstock, NY Situated 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: 5.37% Traditional cash on cash: 9.04% Airbnb Rental Income: $3156 Traditional Rental Income: $3596 Airbnb ROI: 5.37% Traditional ROI: 9.04%
97 John Joy Rd Woodstock, NY The 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: 0.91% Traditional cash on cash: 1.11% Airbnb Rental Income: $3156 Traditional Rental Income: $2590 Airbnb ROI: 0.91% Traditional ROI: 1.11%
235 California Quarry Rd Woodstock, NY Architect-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: -0.95% Traditional cash on cash: -0.52% Airbnb Rental Income: $3156 Traditional Rental Income: $3394 Airbnb ROI: -0.95% Traditional ROI: -0.52%
00 Lauren Ct Woodstock, NY 00 Lauren Ct, Ruby, NY 12498 \| Other	N/A beds \| N/A baths \| N/A	$575,000	Airbnb cash on cash: -0.57% Traditional cash on cash: -1.02% Airbnb Rental Income: $1713 Traditional Rental Income: $996 Airbnb ROI: -0.57% Traditional ROI: -1.02%
100 Zena Rd #sawkill road Woodstock, NY 100 Zena Rd, West Hurley, NY 12498 \| Other	N/A beds \| N/A baths \| N/A	$184,900	Airbnb cash on cash: 3.83% Traditional cash on cash: 2.52% Airbnb Rental Income: $1713 Traditional Rental Income: $1009 Airbnb ROI: 3.83% Traditional ROI: 2.52%
57 Ohayo Mt. Rd Woodstock, NY 57 Ohayo Mt. Rd, Woodstock, NY 12498 \| Single Family Residential	1 beds \| 1 baths \| 841 sq.ft.	$395,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 0.02% Airbnb Rental Income: $1721 Traditional Rental Income: $1103 Airbnb ROI: 0.41% Traditional ROI: 0.02%
289 Upper Byrdcliffe Rd Woodstock, NY 289 Upper Byrdcliffe Rd, Woodstock, NY 12498 \| Single Family Residential	4 beds \| 3 baths \| 3,151 sq.ft.	$3,500,000	Airbnb cash on cash: -1.59% Traditional cash on cash: -1.64% Airbnb Rental Income: $4701 Traditional Rental Income: $3590 Airbnb ROI: -1.59% Traditional ROI: -1.64%
5 Lazy Brook Ln Woodstock, NY 5 Lazy Brook Ln, Woodstock, NY 12498 \| Single Family Residential	4 beds \| 2 baths \| 2,480 sq.ft.	$799,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 0.89% Airbnb Rental Income: $4701 Traditional Rental Income: $2775 Airbnb ROI: 2.18% Traditional ROI: 0.89%
20 Country Club Ln Woodstock, NY 20 Country Club Ln, Woodstock, NY 12498 \| Single Family Residential	8 beds \| 8 baths \| 12,393 sq.ft.	$1,995,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.45% Airbnb Rental Income: $3990 Traditional Rental Income: $5943 Airbnb ROI: -1.07% Traditional ROI: 0.45%
2320 Glasco Tpke Woodstock, NY 2320 Glasco Tpke, Woodstock, NY 12498 \| Single Family Residential	8 beds \| 5 baths \| 4,648 sq.ft.	$1,325,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 1.67% Airbnb Rental Income: $3990 Traditional Rental Income: $5494 Airbnb ROI: -0.24% Traditional ROI: 1.67%
Tbd Wardwell Ln Woodstock, NY Tbd Wardwell Ln, Woodstock, NY 12498 \| Other	N/A beds \| N/A baths \| 1,290 sq.ft.	$435,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 0.06% Airbnb Rental Income: $1713 Traditional Rental Income: $1218 Airbnb ROI: 0.11% Traditional ROI: 0.06%
328 John Joy Rd Woodstock, NY 328 John Joy Rd, Woodstock, NY 12498 \| Single Family Residential	2 beds \| 2 baths \| 1,300 sq.ft.	$569,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 0.68% Airbnb Rental Income: $2832 Traditional Rental Income: $1895 Airbnb ROI: 1.2% Traditional ROI: 0.68%
106 Mountain Laurel Ln Woodstock, NY 106 Mountain Laurel Ln, Woodstock, NY 12498 \| Single Family Residential	3 beds \| 4 baths \| 3,330 sq.ft.	$1,450,000	Airbnb cash on cash: -0.97% Traditional cash on cash: -0.04% Airbnb Rental Income: $3156 Traditional Rental Income: $3690 Airbnb ROI: -0.97% Traditional ROI: -0.04%
5 Maverick Ter Woodstock, NY Tucked 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: 1.12% Traditional cash on cash: 2.42% Airbnb Rental Income: $3156 Traditional Rental Income: $3409 Airbnb ROI: 1.12% Traditional ROI: 2.42%
92 Whichtree Road Woodstock, NY Open 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: 3.33% Traditional cash on cash: 3.22% Airbnb Rental Income: $3156 Traditional Rental Income: $2395 Airbnb ROI: 3.33% Traditional ROI: 3.22%
2465 Glasco Turnpike Woodstock, NY Rare 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: -0.19% Traditional cash on cash: 1.99% Airbnb Rental Income: $3990 Traditional Rental Income: $7164 Airbnb ROI: -0.19% Traditional ROI: 1.99%
5 Downer Ln Woodstock, NY Set 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: 0.31% Traditional cash on cash: 1.41% Airbnb Rental Income: $4701 Traditional Rental Income: $4957 Airbnb ROI: 0.31% Traditional ROI: 1.41%
5 - 7 Downer Ln Woodstock, NY A 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: -1.03% Traditional cash on cash: 0.96% Airbnb Rental Income: $3990 Traditional Rental Income: $6290 Airbnb ROI: -1.03% Traditional ROI: 0.96%
171 Van Dale Rd Woodstock, NY Step 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: 1.83% Traditional cash on cash: 2.62% Airbnb Rental Income: $3156 Traditional Rental Income: $2885 Airbnb ROI: 1.83% Traditional ROI: 2.62%
123 Tinker St Woodstock, NY Woodstock Charm & Income Potential Near the Green Savvy investors and owner-occupants, tak...	2 beds \| N/A baths \| 1,284 sq.ft.	$470,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.22% Airbnb Rental Income: $1721 Traditional Rental Income: $2395 Airbnb ROI: 0.6% Traditional ROI: 3.22%
11 Nordic Dr Woodstock, NY Welcome to this distinctive Woodstock retreat, a home shaped by the creativity and vision ...	2 beds \| 2 baths \| 2,355 sq.ft.	$599,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 2.13% Airbnb Rental Income: $2832 Traditional Rental Income: $2584 Airbnb ROI: 1.4% Traditional ROI: 2.13%
94 Chestnut Hill Rd Woodstock, NY A 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: 0.17% Traditional cash on cash: -0.15% Airbnb Rental Income: $3156 Traditional Rental Income: $2045 Airbnb ROI: 0.17% Traditional ROI: -0.15%
72 Van Dale Rd Woodstock, NY Nestled 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: 1.19% Traditional cash on cash: 2.51% Airbnb Rental Income: $3156 Traditional Rental Income: $3302 Airbnb ROI: 1.19% Traditional ROI: 2.51%
29 Maurizi Ln Woodstock, NY Set 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: 2.83% Traditional cash on cash: 2.73% Airbnb Rental Income: $4701 Traditional Rental Income: $3658 Airbnb ROI: 2.83% Traditional ROI: 2.73%
25 Pine Grove St Woodstock, NY 25 Pine Grove St, Woodstock, NY 12498 \| Single Family Residential	2 beds \| 2 baths \| 1,440 sq.ft.	$795,000	Airbnb cash on cash: 0.1% Traditional cash on cash: 0.19% Airbnb Rental Income: $2832 Traditional Rental Income: $2242 Airbnb ROI: 0.1% Traditional ROI: 0.19%
48 Mountainview Ave Woodstock, NY 48 Mountainview Ave, Woodstock, NY 12498 \| Single Family Residential	2 beds \| 2 baths \| 1,248 sq.ft.	$599,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 0.59% Airbnb Rental Income: $2832 Traditional Rental Income: $1936 Airbnb ROI: 1.01% Traditional ROI: 0.59%

Real Estate investment in Woodstock, NY

There are 77 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 $283. In October 2026, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $2,949.

Woodstock, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 77 investment properties available for sale in Woodstock.

In 2026, the best neighborhood to buy investment property is Woodstock.

The ROI for Short-Term is higher than the Long-Term in Woodstock with average rental income of $3,156.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, NY

9 Munchkin Ln

Woodstock, NY

4 beds | 3 baths | 2,448 sq.ft.

$1,150,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 1.31%

Airbnb Rental Income: $4701

Traditional Rental Income: $4413

Airbnb ROI: 0.67%

Traditional ROI: 1.31%

56 Lauren Ct

Woodstock, NY

3 beds | 2 baths | 3,481 sq.ft.

$2,300,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 0.45%

Airbnb Rental Income: $3156

Traditional Rental Income: $4829

Airbnb ROI: -0.67%

Traditional ROI: 0.45%

3207-3209 Route 212

Woodstock, NY

4 beds | 3 baths | 3,378 sq.ft.

$1,149,000

Airbnb cash on cash: 1.48%

Traditional cash on cash: -0.49%

Airbnb Rental Income: $4701

Traditional Rental Income: $1627

Airbnb ROI: 1.48%

Traditional ROI: -0.49%

15 Lake View Dr

Woodstock, NY

2 beds | 1 baths | 1,416 sq.ft.

$675,000

Airbnb cash on cash: 0.59%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $2832

Traditional Rental Income: $2456

Airbnb ROI: 0.59%

Traditional ROI: 1.04%

132 Valley View Way

Woodstock, NY

N/A beds | N/A baths | N/A

$1,475,000

Airbnb cash on cash: -1.88%

Traditional cash on cash: -1.88%

Airbnb Rental Income: $1713

Traditional Rental Income: $1231

Airbnb ROI: -1.88%

Traditional ROI: -1.88%

168 Cooper Lake Rd

Woodstock, NY

3 beds | 2 baths | 2,264 sq.ft.

$865,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 0.4%

Airbnb Rental Income: $3156

Traditional Rental Income: $2598

Airbnb ROI: 0.21%

Traditional ROI: 0.4%

208 Tinker St

Woodstock, NY

2 beds | 1 baths | 1,191 sq.ft.

$549,000

Airbnb cash on cash: 1.34%

Traditional cash on cash: 5.89%

Airbnb Rental Income: $2832

Traditional Rental Income: $4504

Airbnb ROI: 1.34%

Traditional ROI: 5.89%

19 Blues Quarry

Woodstock, NY

4 beds | 3 baths | 2,613 sq.ft.

$1,350,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: -0.06%

Airbnb Rental Income: $4701

Traditional Rental Income: $3515

Airbnb ROI: 0.11%