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.

Multi Family for Sale in Woodstock, NY

Search for Multi Family for Sale in Woodstock, New York. Browse all of Mashvisor’s Multi Family listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1 Multi Family listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
8 Tannery Brook Road Woodstock, NY Positioned 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% Traditional cash on cash: 0.36% Airbnb Rental Income: $3277 Traditional Rental Income: $3041 Airbnb ROI: 0% Traditional ROI: 0.36%
Other Investment Properties for Sale in Woodstock
12 Library Lane Woodstock , NY Tucked 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% Traditional cash on cash: 2.67% Airbnb Rental Income: $3277 Traditional Rental Income: $3694 Airbnb ROI: 1.12% Traditional ROI: 2.67%
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.	$749,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.7% Airbnb Rental Income: $2785 Traditional Rental Income: $4481 Airbnb ROI: 1.33% Traditional ROI: 4.7%
5 Violet Place Woodstock , NY Lovely 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% Traditional cash on cash: 3.1% Airbnb Rental Income: $3277 Traditional Rental Income: $2986 Airbnb ROI: 2.22% Traditional ROI: 3.1%
66-68 Webster Road Woodstock , NY Rare 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% Traditional cash on cash: 1.24% Airbnb Rental Income: $2785 Traditional Rental Income: $2228 Airbnb ROI: 1.07% Traditional ROI: 1.24%
33 Cottonwood Lane Woodstock , NY OPEN 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% Traditional cash on cash: 0.7% Airbnb Rental Income: $3277 Traditional Rental Income: $2593 Airbnb ROI: 0.62% Traditional ROI: 0.7%
208 Grogkill Road Woodstock , NY OPEN 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% Traditional cash on cash: 0.16% Airbnb Rental Income: $3277 Traditional Rental Income: $3279 Airbnb ROI: -0.44% Traditional ROI: 0.16%
2565 Route 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.	$1,790,000	Airbnb cash on cash: -0.07% Traditional cash on cash: -0.08% Airbnb Rental Income: $4723 Traditional Rental Income: $3728 Airbnb ROI: -0.07% Traditional ROI: -0.08%
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: 1.22% Traditional cash on cash: 1.29% Airbnb Rental Income: $3277 Traditional Rental Income: $2590 Airbnb ROI: 1.22% Traditional ROI: 1.29%
4 Munchkin Lane Woodstock , NY Highwoods 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% Traditional cash on cash: 1.73% Airbnb Rental Income: $4723 Traditional Rental Income: $3136 Airbnb ROI: 2.49% Traditional ROI: 1.73%
16 Juniper Lane Woodstock , NY Welcome 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% Traditional cash on cash: -0.46% Airbnb Rental Income: $3277 Traditional Rental Income: $3504 Airbnb ROI: -1.09% Traditional ROI: -0.46%
680 Zena Road Woodstock , NY Turn 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% Traditional cash on cash: 1.77% Airbnb Rental Income: $2785 Traditional Rental Income: $2440 Airbnb ROI: 1.17% Traditional ROI: 1.77%
99 Cannon Circle Woodstock , NY Tucked 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% Traditional cash on cash: 0.53% Airbnb Rental Income: $3277 Traditional Rental Income: $2979 Airbnb ROI: 0.12% Traditional ROI: 0.53%
76-78 Mid Mountain Way Woodstock , NY Nestled 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% Traditional cash on cash: 0.29% Airbnb Rental Income: $2785 Traditional Rental Income: $2624 Airbnb ROI: -0.21% Traditional ROI: 0.29%
48 Cooper Hollow Woodstock , NY Tucked 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% Traditional cash on cash: 1.79% Airbnb Rental Income: $4723 Traditional Rental Income: $3878 Airbnb ROI: 1.63% Traditional ROI: 1.79%

Your search for investment property begins and ends here

Multi Family for Sale in Woodstock, NY

8 Tannery Brook Road

Woodstock, NY

3 beds | 2 baths | 2,496 sq.ft.

$1,495,000

Airbnb cash on cash: 0%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $3277

Traditional Rental Income: $3041

Airbnb ROI: 0%

Traditional ROI: 0.36%

Other Investment Properties for Sale in Woodstock

Woodstock , NY

3 beds | 3 baths | 1,864 sq.ft.

$799,000

Airbnb cash on cash: 1.12%

Traditional cash on cash: 2.67%

Airbnb Rental Income: $3277

Traditional Rental Income: $3694

Airbnb ROI: 1.12%

Traditional ROI: 2.67%

Woodstock , NY

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

$749,000

Airbnb cash on cash: 1.33%

Traditional cash on cash: 4.7%

Airbnb Rental Income: $2785

Traditional Rental Income: $4481

Airbnb ROI: 1.33%

Traditional ROI: 4.7%

Woodstock , NY

3 beds | 2 baths | 1,804 sq.ft.

$540,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 3.1%

Airbnb Rental Income: $3277

Traditional Rental Income: $2986

Airbnb ROI: 2.22%

Traditional ROI: 3.1%

Woodstock , NY

2 beds | 2 baths | 1,092 sq.ft.

$599,000

Airbnb cash on cash: 1.07%

Traditional cash on cash: 1.24%

Airbnb Rental Income: $2785

Traditional Rental Income: $2228

Airbnb ROI: 1.07%

Traditional ROI: 1.24%

Woodstock , NY

3 beds | 2 baths | 1,973 sq.ft.

$665,000

Airbnb cash on cash: 0.62%

Traditional cash on cash: 0.7%

Airbnb Rental Income: $3277

Traditional Rental Income: $2593

Airbnb ROI: 0.62%

Traditional ROI: 0.7%

Woodstock , NY

3 beds | 3 baths | 2,640 sq.ft.

$1,325,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 0.16%

Airbnb Rental Income: $3277

Traditional Rental Income: $3279

Airbnb ROI: -0.44%

Traditional ROI: 0.16%

Woodstock , NY

4 beds | 3 baths | 2,052 sq.ft.

$1,790,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: -0.08%

Airbnb Rental Income: $4723

Traditional Rental Income: $3728

Airbnb ROI: -0.07%

Traditional ROI: -0.08%

Woodstock , NY

3 beds | 2 baths | 1,532 sq.ft.

$759,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 1.29%