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 60 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
77 Beaver Hill Road Windham, NY Designed by a renowned Manhattan architect known for 20M dollar Aspen ski homes, this 4,83...	5 beds \| 4 baths \| 4,834 sq.ft.	$1,950,000	Airbnb cash on cash: -1.76% Traditional cash on cash: -0.05% Airbnb Rental Income: $2411 Traditional Rental Income: $4917 Airbnb ROI: -1.76% Traditional ROI: -0.05%
17 Mitchell Hollow Rd Windham, NY Whether your search is for personal use or investment property, this Windham Farmhouse, ju...	4 beds \| 3 baths \| 1,914 sq.ft.	$439,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 5.54% Airbnb Rental Income: $1966 Traditional Rental Income: $3482 Airbnb ROI: 0.6% Traditional ROI: 5.54%
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.	$759,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.6% Airbnb Rental Income: $1966 Traditional Rental Income: $3801 Airbnb ROI: 0.28% Traditional ROI: 3.6%
22 Club Rd Windham, NY New Price, Expanded Deck & New Cable Railings! A home made for mountain lovers, this rusti...	4 beds \| 3 baths \| 3,400 sq.ft.	$2,200,000	Airbnb cash on cash: -2.05% Traditional cash on cash: 1.02% Airbnb Rental Income: $1966 Traditional Rental Income: $7715 Airbnb ROI: -2.05% Traditional ROI: 1.02%
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.	$628,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 3.32% Airbnb Rental Income: $1988 Traditional Rental Income: $2936 Airbnb ROI: 0.82% Traditional ROI: 3.32%
407 Mill St Windham, NY Aesthetically intriguing and vacation homebuyer or investor appealing! This gorgeously ren...	3 beds \| 2 baths \| 2,864 sq.ft.	$849,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 6.37% Airbnb Rental Income: $1988 Traditional Rental Income: $6555 Airbnb ROI: -0.06% Traditional ROI: 6.37%
85 Cambridge Heights Rd. Windham, NY Enjoy the summer months taking in the beautiful views from the large Trex decking. Warm up...	4 beds \| 2 baths \| 1,440 sq.ft.	$650,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 3.19% Airbnb Rental Income: $1966 Traditional Rental Income: $2826 Airbnb ROI: 0.92% Traditional ROI: 3.19%
5134 Route 23 Windham, NY Introducing a treasure in the heart of Windham, where charm and convenience beautifully co...	3 beds \| 1 baths \| 1,200 sq.ft.	$485,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 1.82% Airbnb Rental Income: $1988 Traditional Rental Income: $2144 Airbnb ROI: 0.33% Traditional ROI: 1.82%
2914 Route 10 Windham, NY Welcome to this 3 bed 3 bath home nestled in Ashland, right outside of Windham. The home i...	3 beds \| 3 baths \| 3,683 sq.ft.	$390,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 6.38% Airbnb Rental Income: $1988 Traditional Rental Income: $3415 Airbnb ROI: 1.06% Traditional ROI: 6.38%
129 Club Rd Windham, NY Gorgeous Windham Mountain Contemporary An abundance of natural light and impressive lands...	4 beds \| 3 baths \| 2,204 sq.ft.	$1,295,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 5.29% Airbnb Rental Income: $1966 Traditional Rental Income: $8305 Airbnb ROI: -0.4% Traditional ROI: 5.29%
61 South Street Windham, NY Sold as is. $100,000 YES - $100,000 DISCOUNT FOR A CASH TRANSACTION ! THIS PROPERTY IS ON ...	2 beds \| 3 baths \| 2,026 sq.ft.	$449,999	Airbnb cash on cash: -0.1% Traditional cash on cash: 4.82% Airbnb Rental Income: $1334 Traditional Rental Income: $2994 Airbnb ROI: -0.1% Traditional ROI: 4.82%
17 Stonewall Ln Windham, NY Nestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers...	3 beds \| 3 baths \| 2,400 sq.ft.	$1,400,000	Airbnb cash on cash: -2.45% Traditional cash on cash: -0.26% Airbnb Rental Income: $1988 Traditional Rental Income: $4313 Airbnb ROI: -2.45% Traditional ROI: -0.26%
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.	$1,899,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 0.76% Airbnb Rental Income: $2411 Traditional Rental Income: $4700 Airbnb ROI: -0.87% Traditional ROI: 0.76%
90 Club Rd Windham, NY Spectacular mountain views and steps away from the trails, this chalet is a Windham Mounta...	5 beds \| 4 baths \| 3,600 sq.ft.	$2,250,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 1.26% Airbnb Rental Income: $2411 Traditional Rental Income: $5816 Airbnb ROI: -0.65% Traditional ROI: 1.26%
28 Sutton Hollow Road Windham, NY Are you looking for an affordable country home? Look no further! Welcome to 28 Sutton Holl...	4 beds \| 2 baths \| 1,457 sq.ft.	$299,777	Airbnb cash on cash: 2.04% Traditional cash on cash: 8.1% Airbnb Rental Income: $1966 Traditional Rental Income: $3159 Airbnb ROI: 2.04% Traditional ROI: 8.1%
57 Brainard Ridge unit: 3-E #3-E Windham, NY Just in time for ski season! Make this your base for winter fun at Windham Mountain Club. ...	4 beds \| N/A baths \| 2,100 sq.ft.	$645,000	Airbnb cash on cash: 0.19% Traditional cash on cash: 3.87% Airbnb Rental Income: $1966 Traditional Rental Income: $3668 Airbnb ROI: 0.19% Traditional ROI: 3.87%
110 - 2 High Ridge Rd Windham, NY Located on a private road and a peaceful wooded setting sits this charming three-bedroom r...	3 beds \| 2 baths \| 1,464 sq.ft.	$399,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 4.13% Airbnb Rental Income: $1988 Traditional Rental Income: $2651 Airbnb ROI: 0.97% Traditional ROI: 4.13%
102 Thunderbird Terrace Windham, NY Custom Log Cabin with Modern Finishes, The Feel of a New Build, and Stunning Mountain View...	5 beds \| N/A baths \| 4,312 sq.ft.	$1,699,000	Airbnb cash on cash: -1.62% Traditional cash on cash: 0.96% Airbnb Rental Income: $2411 Traditional Rental Income: $5891 Airbnb ROI: -1.62% 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: -0.88% Traditional cash on cash: 2.09% Airbnb Rental Income: $2411 Traditional Rental Income: $5957 Airbnb ROI: -0.88% 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 \| N/A baths \| 3,723 sq.ft.	$1,899,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 1.44% Airbnb Rental Income: $2411 Traditional Rental Income: $6054 Airbnb ROI: -0.96% Traditional ROI: 1.44%
20 Sutton Hollow Road Windham, NY Modern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! Thi...	3 beds \| N/A baths \| 1,335 sq.ft.	$535,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 3.31% Airbnb Rental Income: $1988 Traditional Rental Income: $2727 Airbnb ROI: 0.79% Traditional ROI: 3.31%
4 Estate View Drive Windham, NY To be built. Experience unparalleled luxury in this custom-built mountain retreat. Situate...	5 beds \| N/A baths \| 5,000 sq.ft.	$1,998,500	Airbnb cash on cash: -1.78% Traditional cash on cash: 1.16% Airbnb Rental Income: $2411 Traditional Rental Income: $7279 Airbnb ROI: -1.78% Traditional ROI: 1.16%
292 South Street unit: 2 #2 Windham, NY Incredible Investment Opportunity - Proven Short-Term Rental Income! Welcome to 292 South ...	5 beds \| N/A baths \| 3,460 sq.ft.	$1,149,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 3.26% Airbnb Rental Income: $2411 Traditional Rental Income: $6475 Airbnb ROI: -1.09% Traditional ROI: 3.26%
93 & 99 Nauvoo Road Windham, NY Come relax in the cool Mediterranean vibes of this lovingly maintained home with gorgeous ...	6 beds \| N/A baths \| 4,284 sq.ft.	$1,450,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 3.76% Airbnb Rental Income: $2411 Traditional Rental Income: $6927 Airbnb ROI: -0.03% Traditional ROI: 3.76%
370 Begley Road Windham, NY Rare Opportunity Surrounded by 700 Acres of State Land That's right-700 acres of forever-p...	3 beds \| 2 baths \| 1,876 sq.ft.	$399,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 5.38% Airbnb Rental Income: $1988 Traditional Rental Income: $2773 Airbnb ROI: 1.89% Traditional ROI: 5.38%
93 Maplewood Road Windham, NY Nestled at the end of a tranquil cul -de-sac, this spacious 3+1 bedroom perched on a hill ...	4 beds \| 4 baths \| 2,088 sq.ft.	$749,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 2.11% Airbnb Rental Income: $1966 Traditional Rental Income: $2698 Airbnb ROI: 0.32% Traditional ROI: 2.11%
292 #3 S Street Windham, NY Turn-Key Windham Ski Retreat \| Modern End Unit with 4 En-Suites, Full Furnishing Option & ...	5 beds \| 6 baths \| 3,643 sq.ft.	$1,125,000	Airbnb cash on cash: -0.91% Traditional cash on cash: -0.12% Airbnb Rental Income: $2411 Traditional Rental Income: $2647 Airbnb ROI: -0.91% Traditional ROI: -0.12%
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 \| N/A baths \| 3,893 sq.ft.	$1,949,000	Airbnb cash on cash: -1.76% Traditional cash on cash: -1.1% Airbnb Rental Income: $2411 Traditional Rental Income: $3013 Airbnb ROI: -1.76% Traditional ROI: -1.1%
60 County Route 65 A Windham, NY Turn-Key Catskills STR \| 75K-80K Income \| Year-Round Demand + Expansion Upside Windham Cre...	4 beds \| 2 baths \| 2,240 sq.ft.	$750,000	Airbnb cash on cash: 0.43% Traditional cash on cash: 2.72% Airbnb Rental Income: $1966 Traditional Rental Income: $3054 Airbnb ROI: 0.43% Traditional ROI: 2.72%
116 Nilson Drive Windham, NY Price Cut! Don't be fooled by first impressions - this ranch-style home is far more expans...	4 beds \| 4 baths \| 3,075 sq.ft.	$875,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 1.51% Airbnb Rental Income: $1966 Traditional Rental Income: $2661 Airbnb ROI: 0.02% Traditional ROI: 1.51%
215 Siam Road Windham, NY Welcome to the Windham Round House, one of the area's most distinctive and architecturally...	3 beds \| 2 baths \| 1,903 sq.ft.	$515,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 3.62% Airbnb Rental Income: $1988 Traditional Rental Income: $2760 Airbnb ROI: 0.94% Traditional ROI: 3.62%
24 Windham Mount Vlg #24 Windham, NY 24 Windham Mount Vlg #24, Windham, NY 12496 \| Single Family Residential	3 beds \| 3 baths \| 1,528 sq.ft.	$649,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 7.96% Airbnb Rental Income: $1988 Traditional Rental Income: $6555 Airbnb ROI: -0.44% Traditional ROI: 7.96%
91 Beaver Hill Rd Windham, NY 91 Beaver Hill Rd, Windham, NY 12496 \| Single Family Residential	4 beds \| 3 baths \| 2,671 sq.ft.	$780,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 1.7% Airbnb Rental Income: $1966 Traditional Rental Income: $3297 Airbnb ROI: -0.84% Traditional ROI: 1.7%
183 South St Windham, NY 183 South St, Windham, NY 12496 \| Single Family Residential	2 beds \| 1 baths \| 1,122 sq.ft.	$550,000	Airbnb cash on cash: -1.09% Traditional cash on cash: -0.22% Airbnb Rental Income: $1334 Traditional Rental Income: $1368 Airbnb ROI: -1.09% Traditional ROI: -0.22%
10 Stonewall Ln Windham, NY 10 Stonewall Ln, Windham, NY 12496 \| Single Family Residential	4 beds \| 3 baths \| 2,770 sq.ft.	$1,650,000	Airbnb cash on cash: -2.6% Traditional cash on cash: 2.81% Airbnb Rental Income: $1966 Traditional Rental Income: $9737 Airbnb ROI: -2.6% Traditional ROI: 2.81%

Your search for investment property begins and ends here

Single Family Homes for Sale in Windham, NY

77 Beaver Hill Road

Windham, NY

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

$1,950,000

Airbnb cash on cash: -1.76%

Traditional cash on cash: -0.05%

Airbnb Rental Income: $2411

Traditional Rental Income: $4917

Airbnb ROI: -1.76%

Traditional ROI: -0.05%

17 Mitchell Hollow Rd

Windham, NY

4 beds | 3 baths | 1,914 sq.ft.

$439,000

Airbnb cash on cash: 0.6%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $1966

Traditional Rental Income: $3482

Airbnb ROI: 0.6%

Traditional ROI: 5.54%

769 Mitchell Hollow Road

Windham, NY

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

$759,000

Airbnb cash on cash: 0.28%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $1966

Traditional Rental Income: $3801

Airbnb ROI: 0.28%

Traditional ROI: 3.6%

22 Club Rd

Windham, NY

4 beds | 3 baths | 3,400 sq.ft.

$2,200,000

Airbnb cash on cash: -2.05%

Traditional cash on cash: 1.02%

Airbnb Rental Income: $1966

Traditional Rental Income: $7715

Airbnb ROI: -2.05%

Traditional ROI: 1.02%

9 Pinekill Ln

Windham, NY

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

$628,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1988

Traditional Rental Income: $2936

Airbnb ROI: 0.82%

Traditional ROI: 3.32%

407 Mill St

Windham, NY

3 beds | 2 baths | 2,864 sq.ft.

$849,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 6.37%

Airbnb Rental Income: $1988

Traditional Rental Income: $6555

Airbnb ROI: -0.06%

Traditional ROI: 6.37%

85 Cambridge Heights Rd.

Windham, NY

4 beds | 2 baths | 1,440 sq.ft.

$650,000

Airbnb cash on cash: 0.92%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1966

Traditional Rental Income: $2826

Airbnb ROI: 0.92%

Traditional ROI: 3.19%

5134 Route 23

Windham, NY

3 beds | 1 baths | 1,200 sq.ft.

$485,000

Airbnb cash on cash: 0.33%

Traditional cash on cash: 1.82%

Airbnb Rental Income: $1988

Traditional Rental Income: $2144

Airbnb ROI: 0.33%