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
220 John Joy Road Woodstock, NY Tucked back from the road, with beautifully landscaped grounds, bluestone walls, and matur...	3 beds \| 3 baths \| 2,430 sq.ft.	$939,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 1.12% Airbnb Rental Income: $2936 Traditional Rental Income: $3622 Airbnb ROI: -0.45% Traditional ROI: 1.12%
86 Rock City Road Woodstock, NY Woodstock Charm Meets Modern Living at 86 Rock City Road! Step into a piece of Woodstock h...	4 beds \| 3 baths \| 1,754 sq.ft.	$795,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 1.3% Airbnb Rental Income: $3867 Traditional Rental Income: $2588 Airbnb ROI: 1.91% Traditional ROI: 1.3%
12 Library Lane Woodstock, NY Tucked 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% Traditional cash on cash: 2.81% Airbnb Rental Income: $2936 Traditional Rental Income: $3694 Airbnb ROI: 0.81% Traditional ROI: 2.81%
5 Lazy Brook Lane Woodstock, NY Ideal Woodstock living! This lovely 4 bedroom 3 bath private ranch is set back from the ro...	4 beds \| 3 baths \| 2,480 sq.ft.	$599,000	Airbnb cash on cash: 2.77% Traditional cash on cash: 4.11% Airbnb Rental Income: $3867 Traditional Rental Income: $3782 Airbnb ROI: 2.77% Traditional ROI: 4.11%
8 Tannery Brook Road Woodstock, NY Large 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: 0.02% Traditional cash on cash: 0.72% Airbnb Rental Income: $2936 Traditional Rental Income: $3041 Airbnb ROI: 0.02% Traditional ROI: 0.72%
3251 Route 212 Woodstock, NY Tucked 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: 0.2% Traditional cash on cash: 1.5% Airbnb Rental Income: $2279 Traditional Rental Income: $2644 Airbnb ROI: 0.2% Traditional ROI: 1.5%
18 Country Club Lane Woodstock, NY Stunning 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.	$689,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 5.19% Airbnb Rental Income: $2279 Traditional Rental Income: $4481 Airbnb ROI: 0.88% Traditional ROI: 5.19%
26-28 Neher Street Woodstock, NY Woodstock Village home and guest house right in town but so quiet and peaceful you would n...	4 beds \| 3 baths \| 2,526 sq.ft.	$849,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 2.25% Airbnb Rental Income: $3867 Traditional Rental Income: $3582 Airbnb ROI: 1.56% Traditional ROI: 2.25%
5 Violet Place Woodstock, NY Move right into this lovely 3-4 bedroom home located in a quiet, friendly neighborhood, ju...	3 beds \| N/A baths \| 1,804 sq.ft.	$540,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 3.1% Airbnb Rental Income: $2936 Traditional Rental Income: $2986 Airbnb ROI: 1.66% Traditional ROI: 3.1%
2565 Ny-212 Woodstock, NY Discover modern living at its finest with this newly built contemporary home, perfectly ne...	4 beds \| 3 baths \| 2,052 sq.ft.	$1,200,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 0.97% Airbnb Rental Income: $3867 Traditional Rental Income: $3728 Airbnb ROI: 0.34% Traditional ROI: 0.97%
97 John Joy Road 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.	$759,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 1.29% Airbnb Rental Income: $2936 Traditional Rental Income: $2590 Airbnb ROI: 0.82% Traditional ROI: 1.29%
235 California Quarry Road Woodstock, NY Architect-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: -1.07% Traditional cash on cash: -0.66% Airbnb Rental Income: $2936 Traditional Rental Income: $3394 Airbnb ROI: -1.07% Traditional ROI: -0.66%
11 Fel Qui Road Woodstock, NY Tucked 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: 6.42% Traditional cash on cash: 7.55% Airbnb Rental Income: $2936 Traditional Rental Income: $2499 Airbnb ROI: 6.42% Traditional ROI: 7.55%
20 Overlook Drive Woodstock, NY Woodstock 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: 5.84% Traditional cash on cash: 5.25% Airbnb Rental Income: $2936 Traditional Rental Income: $2092 Airbnb ROI: 5.84% Traditional ROI: 5.25%
2 Fern Hollow Woodstock, NY Charming Two Bedroom Home on a Quiet Dead-End Road Welcome to this serene and private retr...	2 beds \| 1 baths \| 1,263 sq.ft.	$525,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 1.62% Airbnb Rental Income: $2279 Traditional Rental Income: $1922 Airbnb ROI: 1.19% Traditional ROI: 1.62%
64 Lower Byrdcliffe Road Woodstock, NY This 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% Traditional cash on cash: 0.9% Airbnb Rental Income: $2936 Traditional Rental Income: $2833 Airbnb ROI: 0.23% Traditional ROI: 0.9%
90 Van Dale Road Woodstock, NY Make your next transition an easy one in this move-in-ready Woodstock home, where timeless...	4 beds \| 3 baths \| 2,034 sq.ft.	$793,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 3.04% Airbnb Rental Income: $3867 Traditional Rental Income: $3917 Airbnb ROI: 1.84% Traditional ROI: 3.04%
9 Cooper Lake Road Woodstock, NY A 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: -0.49% Traditional cash on cash: 0.29% Airbnb Rental Income: $2936 Traditional Rental Income: $3601 Airbnb ROI: -0.49% Traditional ROI: 0.29%
306 Meads Mountain Road Woodstock, NY Swoop 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: -1.25% Traditional cash on cash: -0.57% Airbnb Rental Income: $2279 Traditional Rental Income: $4346 Airbnb ROI: -1.25% Traditional ROI: -0.57%
18 Niles Drive Woodstock, NY Peek through the trees on this country lane in Woodstock to glimpse a timeless Catskills A...	3 beds \| N/A baths \| 1,990 sq.ft.	$549,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 1.5% Airbnb Rental Income: $2936 Traditional Rental Income: $2384 Airbnb ROI: 1.25% Traditional ROI: 1.5%
66 Plochmann Lane Woodstock, NY So 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% Traditional cash on cash: -0.16% Airbnb Rental Income: $2279 Traditional Rental Income: $2741 Airbnb ROI: -0.98% Traditional ROI: -0.16%

Real Estate investment in Woodstock, NY

There are 21 properties for sale in the city of Woodstock . The median list price in Woodstock is $793,000 and the average price per square foot is $407. In December 2025, the average monthly cash on cash return in Woodstock is 1.00%. The average monthly rental income in Woodstock is $3,041.

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

There are 21 investment properties available for sale in Woodstock.

In 2025, 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 $2,936.

Your search for investment property begins and ends here

Investment Property for Sale in Woodstock, NY

220 John Joy Road

Woodstock, NY

3 beds | 3 baths | 2,430 sq.ft.

$939,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 1.12%

Airbnb Rental Income: $2936

Traditional Rental Income: $3622

Airbnb ROI: -0.45%

Traditional ROI: 1.12%

86 Rock City Road

Woodstock, NY

4 beds | 3 baths | 1,754 sq.ft.

$795,000

Airbnb cash on cash: 1.91%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $3867

Traditional Rental Income: $2588

Airbnb ROI: 1.91%

Traditional ROI: 1.3%

12 Library Lane

Woodstock, NY

3 beds | N/A baths | 1,864 sq.ft.

$769,000

Airbnb cash on cash: 0.81%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $2936

Traditional Rental Income: $3694

Airbnb ROI: 0.81%

Traditional ROI: 2.81%

5 Lazy Brook Lane

Woodstock, NY

4 beds | 3 baths | 2,480 sq.ft.

$599,000

Airbnb cash on cash: 2.77%

Traditional cash on cash: 4.11%

Airbnb Rental Income: $3867

Traditional Rental Income: $3782

Airbnb ROI: 2.77%

Traditional ROI: 4.11%

8 Tannery Brook Road

Woodstock, NY

3 beds | 2 baths | 1,776 sq.ft.

$1,200,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 0.72%

Airbnb Rental Income: $2936

Traditional Rental Income: $3041

Airbnb ROI: 0.02%

Traditional ROI: 0.72%

3251 Route 212

Woodstock, NY

2 beds | 2 baths | 1,850 sq.ft.

$775,000

Airbnb cash on cash: 0.2%

Traditional cash on cash: 1.5%

Airbnb Rental Income: $2279

Traditional Rental Income: $2644

Airbnb ROI: 0.2%

Traditional ROI: 1.5%

18 Country Club Lane

Woodstock, NY

2 beds | 2 baths | 1,208 sq.ft.

$689,000

Airbnb cash on cash: 0.88%

Traditional cash on cash: 5.19%

Airbnb Rental Income: $2279

Traditional Rental Income: $4481

Airbnb ROI: 0.88%

Traditional ROI: 5.19%

26-28 Neher Street

Woodstock, NY

4 beds | 3 baths | 2,526 sq.ft.

$849,000

Airbnb cash on cash: 1.56%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $3867

Traditional Rental Income: $3582

Airbnb ROI: 1.56%