Real Estate Investment Properties for Sale in Windham, NY

Looking for investment property in Windham, NY with high ROI ?

Explore a variety of short-term homes & houses in Windham, NY. Invest wisely with VRBO & Windham, NY Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Single Family Homes for Sale in Windham, NY

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

Showing 22 Single Family Residential 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
21 Nauvoo Road Windham, NY Your four season Catskills dream home is calling. This two bedroom mid-century ranch is co...	2 beds \| 2 baths \| 1,072 sq.ft.	$559,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 2.32% Airbnb Rental Income: $1340 Traditional Rental Income: $2120 Airbnb ROI: 0.04% Traditional ROI: 2.32%
77 Beaver Hill Road Windham, NY Designed by a renowned Manhattan architect known for $20M Aspen ski homes, this 4,834-squa...	5 beds \| 4 baths \| 4,834 sq.ft.	$2,099,000	Airbnb cash on cash: -1.68% Traditional cash on cash: -0.24% Airbnb Rental Income: $2755 Traditional Rental Income: $4917 Airbnb ROI: -1.68% Traditional ROI: -0.24%
128 Mount Greenery Road Windham, NY Cozy Up in This Fully Renovated Mountain Home- Just in Time for Fall Colors and Winter Ski...	4 beds \| 3 baths \| 2,759 sq.ft.	$729,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 3.78% Airbnb Rental Income: $2124 Traditional Rental Income: $3832 Airbnb ROI: 0.46% Traditional ROI: 3.78%
769 Mitchell Hollow Road Windham, NY Bright Sparrow Farmhouse - Modern Farmhouse on 8+ Acres with Private Pond, Mountain Views ...	4 beds \| 4 baths \| 2,100 sq.ft.	$799,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.37% Airbnb Rental Income: $2124 Traditional Rental Income: $3801 Airbnb ROI: 0.39% Traditional ROI: 3.37%
25 Vets Road Windham, NY Peaceful Sanctuary in the Heart of WindhamStep into a unique opportunity to own a stunning...	4 beds \| 4 baths \| 2,950 sq.ft.	$599,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 7.08% Airbnb Rental Income: $2124 Traditional Rental Income: $5567 Airbnb ROI: -0.05% Traditional ROI: 7.08%
9 Pinekill Ln Windham, NY Renovated Mountain Retreat house on 2.4 landscaped acres.! This beautifully renovated 3-be...	3 beds \| 3 baths \| 1,680 sq.ft.	$638,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 3.25% Airbnb Rental Income: $2045 Traditional Rental Income: $2936 Airbnb ROI: 0.87% Traditional ROI: 3.25%
274 Route 65 unit: 43 #43 Windham, NY Dreaming of a quick escape from NYC's chaos? Just 2.5 hours from the city, nestled in the ...	4 beds \| 4 baths \| 1,717 sq.ft.	$445,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.28% Airbnb Rental Income: $2124 Traditional Rental Income: $3213 Airbnb ROI: -0.64% Traditional ROI: 3.28%
33 Elm Ridge Road Windham, NY The Mountains Are Calling and I Must Go.'' P.S., I plan to be VERY comfortable when I get ...	5 beds \| 3 baths \| 3,893 sq.ft.	$1,949,000	Airbnb cash on cash: -1.6% Traditional cash on cash: -0.55% Airbnb Rental Income: $2755 Traditional Rental Income: $4003 Airbnb ROI: -1.6% Traditional ROI: -0.55%
61 South Street Windham, NY Sold as is. 3 minutes to the ski slopes and across the street from the golf course and cl...	2 beds \| 3 baths \| 2,026 sq.ft.	$450,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.82% Airbnb Rental Income: $1340 Traditional Rental Income: $2994 Airbnb ROI: -0.09% Traditional ROI: 4.82%
720 Mill Street Windham, NY Privately nestled down a long driveway off one of Windham's most sought-after roads, this ...	4 beds \| 2 baths \| 2,442 sq.ft.	$769,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.98% Airbnb Rental Income: $2124 Traditional Rental Income: $3024 Airbnb ROI: -0.04% Traditional ROI: 1.98%
22 The Loop Windham, NY Walk to the Slopes! Nestled on the scenic slopes of Windham Mountain and just over two hou...	5 beds \| 4 baths \| 4,044 sq.ft.	$1,975,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.81% Airbnb Rental Income: $2755 Traditional Rental Income: $4700 Airbnb ROI: -0.61% Traditional ROI: 0.81%
30 The Loop Windham, NY Walk to the Slopes in the Winter and Listen to the Soothing Sounds of the Cascading Waterf...	5 beds \| 4 baths \| 3,100 sq.ft.	$925,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 2.48% Airbnb Rental Income: $2755 Traditional Rental Income: $4559 Airbnb ROI: -0.37% Traditional ROI: 2.48%
183 County Road 65 Windham, NY Fully Renovated Mountain Retreat with Two Fireplaces and Stunning Views Just 3 Miles from ...	5 beds \| 3 baths \| 2,644 sq.ft.	$585,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 3.91% Airbnb Rental Income: $2755 Traditional Rental Income: $3708 Airbnb ROI: 0.98% Traditional ROI: 3.91%
15 County Route 79 Windham, NY Exceptional Village Investment with Airbnb Track Record & Expansion Potential Welcome to W...	2 beds \| 2 baths \| 1,271 sq.ft.	$530,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 2.8% Airbnb Rental Income: $1340 Traditional Rental Income: $2455 Airbnb ROI: -0.29% Traditional ROI: 2.8%
102 Thunderbird Terrace Windham, NY Custom Log Cabin with Modern Finishes, The Feel of a New Build, and Stunning Mountain View...	5 beds \| 4 baths \| 4,312 sq.ft.	$1,699,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 0.96% Airbnb Rental Income: $2755 Traditional Rental Income: $5891 Airbnb ROI: -1.44% Traditional ROI: 0.96%
16 High W Road Windham, NY Ski Slope Views, Stream, Designer Finishes - Fully Furnished & Move-In Ready! Why Build Wh...	5 beds \| 5 baths \| 4,140 sq.ft.	$1,499,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 2.09% Airbnb Rental Income: $2755 Traditional Rental Income: $5957 Airbnb ROI: -0.68% Traditional ROI: 2.09%
4 Goff Road Windham, NY Are you sitting down? Because this one will take your breath away! This brand new modern m...	5 beds \| 5 baths \| 3,723 sq.ft.	$2,100,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.21% Airbnb Rental Income: $2755 Traditional Rental Income: $6054 Airbnb ROI: -0.82% Traditional ROI: 1.21%
20 Sutton Hollow Road Windham, NY Modern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! Thi...	3 beds \| 3 baths \| 1,335 sq.ft.	$545,000	Airbnb cash on cash: 0.85% Traditional cash on cash: 3.23% Airbnb Rental Income: $2045 Traditional Rental Income: $2727 Airbnb ROI: 0.85% Traditional ROI: 3.23%
4 Estate View Drive Windham, NY To be built. Experience unparalleled luxury in this custom-built mountain retreat. Situate...	5 beds \| 6 baths \| 5,000 sq.ft.	$1,998,500	Airbnb cash on cash: -1.63% Traditional cash on cash: 1.16% Airbnb Rental Income: $2755 Traditional Rental Income: $7279 Airbnb ROI: -1.63% Traditional ROI: 1.16%
315 Begley Road Windham, NY Located just minutes from the heart of Windham, NY, this inviting 3-bedroom, 1.5-bath ranc...	3 beds \| 2 baths \| 1,152 sq.ft.	$399,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 4.29% Airbnb Rental Income: $2045 Traditional Rental Income: $2271 Airbnb ROI: 2.27% Traditional ROI: 4.29%
292 South Street unit: 2 #2 Windham, NY Incredible Investment Opportunity - Proven Short-Term Rental Income! Welcome to 292 South ...	5 beds \| 6 baths \| 3,460 sq.ft.	$1,149,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 3.26% Airbnb Rental Income: $2755 Traditional Rental Income: $6475 Airbnb ROI: -0.83% Traditional ROI: 3.26%
869 County Route 10 Windham, NY Showing by Appointment Only Saturday 8/16. Please RSVP today! Stunning Contemporary Mounta...	5 beds \| 5 baths \| 3,812 sq.ft.	$1,549,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.35% Airbnb Rental Income: $2755 Traditional Rental Income: $5886 Airbnb ROI: -0.27% Traditional ROI: 2.35%

Your search for investment property begins and ends here

Single Family Homes for Sale in Windham, NY

21 Nauvoo Road

Windham, NY

2 beds | 2 baths | 1,072 sq.ft.

$559,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 2.32%

Airbnb Rental Income: $1340

Traditional Rental Income: $2120

Airbnb ROI: 0.04%

Traditional ROI: 2.32%

77 Beaver Hill Road

Windham, NY

5 beds | 4 baths | 4,834 sq.ft.

$2,099,000

Airbnb cash on cash: -1.68%

Traditional cash on cash: -0.24%

Airbnb Rental Income: $2755

Traditional Rental Income: $4917

Airbnb ROI: -1.68%

Traditional ROI: -0.24%

128 Mount Greenery Road

Windham, NY

4 beds | 3 baths | 2,759 sq.ft.

$729,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $2124

Traditional Rental Income: $3832

Airbnb ROI: 0.46%

Traditional ROI: 3.78%

769 Mitchell Hollow Road

Windham, NY

4 beds | 4 baths | 2,100 sq.ft.

$799,000

Airbnb cash on cash: 0.39%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $2124

Traditional Rental Income: $3801

Airbnb ROI: 0.39%

Traditional ROI: 3.37%

25 Vets Road

Windham, NY

4 beds | 4 baths | 2,950 sq.ft.

$599,000

Airbnb cash on cash: -0.05%

Traditional cash on cash: 7.08%

Airbnb Rental Income: $2124

Traditional Rental Income: $5567

Airbnb ROI: -0.05%

Traditional ROI: 7.08%

9 Pinekill Ln

Windham, NY

3 beds | 3 baths | 1,680 sq.ft.

$638,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $2045

Traditional Rental Income: $2936

Airbnb ROI: 0.87%

Traditional ROI: 3.25%

274 Route 65 unit: 43 #43

Windham, NY

4 beds | 4 baths | 1,717 sq.ft.

$445,000

Airbnb cash on cash: -0.64%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $2124

Traditional Rental Income: $3213

Airbnb ROI: -0.64%

Traditional ROI: 3.28%

33 Elm Ridge Road

Windham, NY

5 beds | 3 baths | 3,893 sq.ft.

$1,949,000

Airbnb cash on cash: -1.6%

Traditional cash on cash: -0.55%

Airbnb Rental Income: $2755

Traditional Rental Income: $4003

Airbnb ROI: -1.6%