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.

Investment Property for Sale in Windham, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
77 Beaver Hill Rd Windham, NY Designed by a renowned Manhattan architect known for 20M dollar Aspen ski homes, this 4,83...	5 beds \| 3 baths \| 3,656 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%
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.	$2,100,000	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%
5359 Ny-23 Windham, NY 5359 Ny-23, Windham, NY 12496 \| Condo/Coop	2 beds \| 2 baths \| 1,163 sq.ft.	$275,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 1.97% Airbnb Rental Income: $1334 Traditional Rental Income: $1846 Airbnb ROI: -1.41% Traditional ROI: 1.97%
31 Koonan Rd Windham, NY Discover this beautifully renovated haven just minutes from Windham town. Boasting 4 bedro...	4 beds \| 2 baths \| 1,052 sq.ft.	$565,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.05% Airbnb Rental Income: $1966 Traditional Rental Income: $2712 Airbnb ROI: -0.25% Traditional ROI: 2.05%
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: 1.41% Airbnb Rental Income: $1988 Traditional Rental Income: $2630 Airbnb ROI: -0.06% Traditional ROI: 1.41%
85 Cambridge Heights Rd. 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%
13 Brainard Ridge Road Windham, NY 5 Years New! Stylishly Renovated Townhome in the Heart of Windham Mountain Club. Renovated...	3 beds \| 3 baths \| 1,566 sq.ft.	$499,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 3.69% Airbnb Rental Income: $1988 Traditional Rental Income: $2684 Airbnb ROI: 1.08% Traditional ROI: 3.69%
61 South St 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 Rd Windham, NY Walk to the Slopes! Nestled on the scenic slopes of Windham Mountain and just over two hou...	5 beds \| 3 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 Rd Windham, NY Are you looking for an affordable country home? Look no further! Welcome to 28 Sutton Holl...	4 beds \| 1 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 Rd #3-E Windham, NY Another Price Improvement - Exceptional Value for a Turn-Key, Four-Season Mountain Retreat...	4 beds \| 3 baths \| 2,712 sq.ft.	$625,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 4.03% Airbnb Rental Income: $1966 Traditional Rental Income: $3668 Airbnb ROI: 0.22% Traditional ROI: 4.03%
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.	$389,000	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 Ter Windham, NY Custom Log Cabin with Modern Finishes, The Feel of a New Build, and Stunning Mountain View...	5 beds \| 3 baths \| 4,312 sq.ft.	$1,649,000	Airbnb cash on cash: -1.58% Traditional cash on cash: 1.07% Airbnb Rental Income: $2411 Traditional Rental Income: $5891 Airbnb ROI: -1.58% Traditional ROI: 1.07%
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 Rd Windham, NY Are you sitting down? Because this one will take your breath away! This brand new modern m...	5 beds \| 4 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 Rd Windham, NY Modern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! Thi...	3 beds \| 2 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 Dr Windham, NY To be built. Experience unparalleled luxury in this custom-built mountain retreat. Situate...	5 beds \| 5 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%
315 Begley Rd Windham, NY Located just minutes from the heart of Windham, NY, this inviting 3-bedroom, 1.5-bath ranc...	3 beds \| 1 baths \| 1,152 sq.ft.	$349,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 5.03% Airbnb Rental Income: $1988 Traditional Rental Income: $2271 Airbnb ROI: 2.58% Traditional ROI: 5.03%
53 Windham Mountain Village Vlg Windham, NY Renovated Windham Mountain Village Townhouse - Steps to Slopes & Lodge, Walk to Lift, Seas...	2 beds \| 2 baths \| 1,390 sq.ft.	$545,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 2.14% Airbnb Rental Income: $1334 Traditional Rental Income: $2115 Airbnb ROI: -0.2% Traditional ROI: 2.14%
73 Windham Ridge Road unit: 16H #16H Windham, NY Competitively Priced Catskills End Unit Townhouse - Fully Renovated, Furnished & Move-In R...	2 beds \| 2 baths \| 1,058 sq.ft.	$329,999	Airbnb cash on cash: 1.33% Traditional cash on cash: 5.57% Airbnb Rental Income: $1334 Traditional Rental Income: $2239 Airbnb ROI: 1.33% Traditional ROI: 5.57%
79 Windham Ridge Road #17A Windham, NY Nestled in the rolling hills of Windham, this warm and welcoming retreat feels more like a...	2 beds \| 3 baths \| 1,211 sq.ft.	$269,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 6.2% Airbnb Rental Income: $1334 Traditional Rental Income: $2331 Airbnb ROI: 0.65% Traditional ROI: 6.2%
292 South Street St #2 Windham, NY Incredible Investment Opportunity - Proven Short-Term Rental Income! Welcome to 292 South ...	5 beds \| 5 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%
55 Quads Way #55 Windham, NY Sweet 2-Bedroom, 2-Bath Condo - Four-Season Windham Living This charming and affordable, e...	2 beds \| 2 baths \| 2,016 sq.ft.	$249,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 7% Airbnb Rental Income: $1334 Traditional Rental Income: $2163 Airbnb ROI: 1.72% Traditional ROI: 7%
93 & 99 Nauvoo Rd Windham, NY Come relax in the cool Mediterranean vibes of this lovingly maintained home with gorgeous ...	6 beds \| 5 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 Rd Windham, NY Nestled at the end of a tranquil cul -de-sac, this spacious 3+1 bedroom perched on a hill ...	4 beds \| 3 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%
3 Enclave E Drive Windham, NY Luxury Ski Townhouse in the Heart of Windham Mountain Club's Premier Enclave Community Dis...	4 beds \| 4 baths \| 2,893 sq.ft.	$1,499,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.36% Airbnb Rental Income: $1966 Traditional Rental Income: $2492 Airbnb ROI: -1.1% Traditional ROI: -0.36%
292 #3 South St Windham, NY Turn-Key Windham Ski Retreat \| Modern End Unit with 4 En-Suites, Full Furnishing Option & ...	5 beds \| 5 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 Rd Windham, NY The Mountains Are Calling and I Must Go.'' P.S., I plan to be VERY comfortable when I get ...	5 beds \| 2 baths \| 2,554 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%
7 Karlstadt Rd Windham, NY Charming & Freshly Renovated Cottage in the Heart of Windham - Just 1 mile from skiing at ...	4 beds \| 2 baths \| 1,368 sq.ft.	$479,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.93% Airbnb Rental Income: $1966 Traditional Rental Income: $2580 Airbnb ROI: 1.43% Traditional ROI: 3.93%
317 Mitchell Hollow Road Windham, NY PRICE REDUCTION! - calling all investors, DIY buyers, and project-minded designers! Prime ...	5 beds \| 3 baths \| 2,472 sq.ft.	$399,000	Airbnb cash on cash: 2.53% Traditional cash on cash: 7.47% Airbnb Rental Income: $2411 Traditional Rental Income: $3667 Airbnb ROI: 2.53% Traditional ROI: 7.47%

Real Estate investment in Windham, NY

There are 121 properties for sale in the city of Windham . The median list price in Windham is $499,500 and the average price per square foot is $197. In February 2026, the average monthly cash on cash return in Windham is 2.00%. The average monthly rental income in Windham is $2,568.

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

There are 121 investment properties available for sale in Windham.

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

The ROI for Short-Term is higher than the Long-Term in Windham with average rental income of $1,966.

Your search for investment property begins and ends here

Investment Property for Sale in Windham, NY

77 Beaver Hill Rd

Windham, NY

5 beds | 3 baths | 3,656 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%

22 Club Rd

Windham, NY

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

$2,100,000

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%

5359 Ny-23

Windham, NY

2 beds | 2 baths | 1,163 sq.ft.

$275,000

Airbnb cash on cash: -1.41%

Traditional cash on cash: 1.97%

Airbnb Rental Income: $1334

Traditional Rental Income: $1846

Airbnb ROI: -1.41%

Traditional ROI: 1.97%

31 Koonan Rd

Windham, NY

4 beds | 2 baths | 1,052 sq.ft.

$565,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $1966

Traditional Rental Income: $2712

Airbnb ROI: -0.25%

Traditional ROI: 2.05%

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: 1.41%

Airbnb Rental Income: $1988

Traditional Rental Income: $2630

Airbnb ROI: -0.06%

Traditional ROI: 1.41%

85 Cambridge Heights Rd. 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%