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
150 Vining Road Windham, NY 150 Vining Road, Windham, NY Beautifully renovated contemporary mountain retreat set on 1 ...	3 beds \| 2 baths \| 2,182 sq.ft.	$599,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 1.97% Airbnb Rental Income: $1186 Traditional Rental Income: $2455 Airbnb ROI: -0.99% Traditional ROI: 1.97%
769 Mitchell Hollow Road Windham, NY Bright Sparrow Farmhouse - Modern Catskills Farmhouse with Solar Power Backup, Private Pon...	4 beds \| 4 baths \| 2,100 sq.ft.	$759,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.6% Airbnb Rental Income: $1354 Traditional Rental Income: $3801 Airbnb ROI: -0.44% Traditional ROI: 3.6%
25 Vets Road Windham, NY Welcome to your peaceful sanctuary in the heart of Windham, a rare blend of convenience, n...	4 beds \| 4 baths \| 2,950 sq.ft.	$449,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 10.32% Airbnb Rental Income: $1354 Traditional Rental Income: $5567 Airbnb ROI: -0.69% Traditional ROI: 10.32%
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: -0.32% Traditional cash on cash: 3.32% Airbnb Rental Income: $1186 Traditional Rental Income: $2936 Airbnb ROI: -0.32% Traditional ROI: 3.32%
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: 0.08% Traditional cash on cash: 3.19% Airbnb Rental Income: $1354 Traditional Rental Income: $2826 Airbnb ROI: 0.08% Traditional ROI: 3.19%
41 County Road 40 Windham, NY A Great Investment Opportunity with a 5 Unit Multi-family & a Large Barn in Windham - in t...	7 beds \| 6 baths \| 4,800 sq.ft.	$549,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 8.82% Airbnb Rental Income: $1322 Traditional Rental Income: $5565 Airbnb ROI: -0.25% Traditional ROI: 8.82%
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: -0.35% Traditional cash on cash: 3.69% Airbnb Rental Income: $1186 Traditional Rental Income: $2684 Airbnb ROI: -0.35% Traditional ROI: 3.69%
22 The Loop Windham, NY A short 1-2 minute walk to the trail access (870 ft)!! Nestled on the scenic slopes of Win...	5 beds \| 4 baths \| 4,044 sq.ft.	$1,899,000	Airbnb cash on cash: -1.39% Traditional cash on cash: 0.76% Airbnb Rental Income: $1322 Traditional Rental Income: $4700 Airbnb ROI: -1.39% Traditional ROI: 0.76%
28 Sutton Hollow Road Windham, NY REDUCED! Affordable Single Family Home Close to Windham Mountain! Are you looking for ...	4 beds \| 2 baths \| 1,457 sq.ft.	$289,999	Airbnb cash on cash: 0.27% Traditional cash on cash: 8.4% Airbnb Rental Income: $1354 Traditional Rental Income: $3159 Airbnb ROI: 0.27% Traditional ROI: 8.4%
57 Brainard Ridge unit: 3-E Windham, NY Another Price Improvement - Exceptional Value for a Turn-Key, Four-Season Mountain Retreat...	4 beds \| 4 baths \| 2,100 sq.ft.	$625,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 4.03% Airbnb Rental Income: $1354 Traditional Rental Income: $3668 Airbnb ROI: -0.65% Traditional ROI: 4.03%
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.	$1,649,000	Airbnb cash on cash: -2.18% Traditional cash on cash: 1.07% Airbnb Rental Income: $1322 Traditional Rental Income: $5891 Airbnb ROI: -2.18% Traditional ROI: 1.07%
4 Goff Road 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: -1.48% Traditional cash on cash: 1.44% Airbnb Rental Income: $1322 Traditional Rental Income: $6054 Airbnb ROI: -1.48% Traditional ROI: 1.44%
20 Sutton Hollow Road 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: -0.54% Traditional cash on cash: 3.31% Airbnb Rental Income: $1186 Traditional Rental Income: $2727 Airbnb ROI: -0.54% 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 \| 6 baths \| 5,000 sq.ft.	$1,998,500	Airbnb cash on cash: -2.27% Traditional cash on cash: 1.16% Airbnb Rental Income: $1322 Traditional Rental Income: $7279 Airbnb ROI: -2.27% Traditional ROI: 1.16%
315 Begley Rd. Windham, NY Just minutes from the village of Windham, skiing, and golf, this meticulously maintained r...	3 beds \| 2 baths \| 1,152 sq.ft.	$349,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 5% Airbnb Rental Income: $1186 Traditional Rental Income: $2271 Airbnb ROI: 0.51% Traditional ROI: 5%
53 Windham Mountain Village 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: -1.31% Traditional cash on cash: 2.14% Airbnb Rental Income: $658 Traditional Rental Income: $2115 Airbnb ROI: -1.31% Traditional ROI: 2.14%
292 South Street unit: 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: -1.76% Traditional cash on cash: 3.44% Airbnb Rental Income: $1322 Traditional Rental Income: $6475 Airbnb ROI: -1.76% Traditional ROI: 3.44%
55 Quads Way unit: 55 Windham, NY Price Reduced -- Major Value in Windham! This charming turnkey condo delivers affordable f...	2 beds \| 2 baths \| 1,008 sq.ft.	$239,500	Airbnb cash on cash: -0.66% Traditional cash on cash: 7.31% Airbnb Rental Income: $658 Traditional Rental Income: $2163 Airbnb ROI: -0.66% Traditional ROI: 7.31%
93 & 99 Nauvoo Road Windham, NY Come relax in the cool Mediterranean vibes of this lovingly maintained home with gorgeous ...	6 beds \| 6 baths \| 4,284 sq.ft.	$1,450,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 3.75% Airbnb Rental Income: $1322 Traditional Rental Income: $6927 Airbnb ROI: -0.71% Traditional ROI: 3.75%
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: -0.41% Traditional cash on cash: 2.11% Airbnb Rental Income: $1354 Traditional Rental Income: $2698 Airbnb ROI: -0.41% 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: -1.78% Traditional cash on cash: -0.12% Airbnb Rental Income: $1322 Traditional Rental Income: $2647 Airbnb ROI: -1.78% Traditional ROI: -0.12%
60 County Route 65 A Windham, NY Price Cut! Windham Creek Lodge is an active, income-producing short-term rental property g...	4 beds \| 2 baths \| 2,240 sq.ft.	$715,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.9% Airbnb Rental Income: $1354 Traditional Rental Income: $3054 Airbnb ROI: -0.27% Traditional ROI: 2.9%
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: 0.1% Traditional cash on cash: 7.47% Airbnb Rental Income: $1322 Traditional Rental Income: $3667 Airbnb ROI: 0.1% Traditional ROI: 7.47%
116 Nilson Drive Windham, NY Fall in love with the ease of single-level living wrapped in privacy, beauty, and timeless...	4 beds \| 4 baths \| 3,075 sq.ft.	$875,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 1.51% Airbnb Rental Income: $1354 Traditional Rental Income: $2661 Airbnb ROI: -0.6% Traditional ROI: 1.51%
215 Siam Road Windham, NY Incredible buy at this new price! The Windham Round House, one of most distinctive and arc...	3 beds \| 3 baths \| 1,903 sq.ft.	$499,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 3.77% Airbnb Rental Income: $1186 Traditional Rental Income: $2760 Airbnb ROI: -0.43% Traditional ROI: 3.77%
523 Mitchell Hollow Rd Windham, NY Catskills living with standout appeal in Windham-the ultimate four-season destination for ...	5 beds \| 3 baths \| 3,184 sq.ft.	$685,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 3.71% Airbnb Rental Income: $1322 Traditional Rental Income: $3548 Airbnb ROI: -0.41% Traditional ROI: 3.71%
76 Loo Bridge Lane unit: 12 B Windham, NY NEW PRICE 259,000 - MOTIVATED SELLERS \| BUY NOW! This cozy country townhouse-style condo o...	2 beds \| 2 baths \| 1,411 sq.ft.	$259,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 6.48% Airbnb Rental Income: $658 Traditional Rental Income: $2198 Airbnb ROI: -1.04% Traditional ROI: 6.48%
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.	$1,749,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 1.11% Airbnb Rental Income: $1322 Traditional Rental Income: $4155 Airbnb ROI: -0.88% Traditional ROI: 1.11%
16 Hickory Hill rd Windham, NY Windham: ''The place to Be'' for year round outdoor enthusiasts This gem has direct views ...	3 beds \| 2 baths \| 1,125 sq.ft.	$599,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 9.79% Airbnb Rental Income: $1186 Traditional Rental Income: $6555 Airbnb ROI: -0.5% Traditional ROI: 9.79%
71 Windham Mountain Village #71 Windham, NY Windham Mt. Village . This Beautiful Townhouse is located at the base of Windham slopes . ...	3 beds \| 3 baths \| 1,528 sq.ft.	$799,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 6.8% Airbnb Rental Income: $1186 Traditional Rental Income: $6555 Airbnb ROI: -0.93% Traditional ROI: 6.8%
39 Brook Hollow Lane Windham, NY Updated Log Cabin Retreat with Private Fishing Pond & Flowing Stream in the Catskills If y...	3 beds \| 2 baths \| 2,049 sq.ft.	$769,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 2.36% Airbnb Rental Income: $1186 Traditional Rental Income: $3037 Airbnb ROI: -0.76% Traditional ROI: 2.36%

Real Estate investment in Windham, NY

There are 33 properties for sale in the city of Windham . The median list price in Windham is $577,500 and the average price per square foot is $251. In April 2026, the average monthly cash on cash return in Windham is 3.00%. The average monthly rental income in Windham is $3,082.

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

There are 33 investment properties available for sale in Windham.

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

The ROI for Long-Term is higher than the Short-Term in Windham with average rental income of $3,082.

Your search for investment property begins and ends here

Investment Property for Sale in Windham, NY

150 Vining Road

Windham, NY

3 beds | 2 baths | 2,182 sq.ft.

$599,000

Airbnb cash on cash: -0.99%

Traditional cash on cash: 1.97%

Airbnb Rental Income: $1186

Traditional Rental Income: $2455

Airbnb ROI: -0.99%

Traditional ROI: 1.97%

769 Mitchell Hollow Road

Windham, NY

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

$759,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $1354

Traditional Rental Income: $3801

Airbnb ROI: -0.44%

Traditional ROI: 3.6%

25 Vets Road

Windham, NY

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

$449,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 10.32%

Airbnb Rental Income: $1354

Traditional Rental Income: $5567

Airbnb ROI: -0.69%

Traditional ROI: 10.32%

9 Pinekill Ln

Windham, NY

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

$628,000

Airbnb cash on cash: -0.32%

Traditional cash on cash: 3.32%

Airbnb Rental Income: $1186

Traditional Rental Income: $2936

Airbnb ROI: -0.32%

Traditional ROI: 3.32%

85 Cambridge Heights Rd.

Windham, NY

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

$650,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $1354

Traditional Rental Income: $2826

Airbnb ROI: 0.08%

Traditional ROI: 3.19%

41 County Road 40

Windham, NY

7 beds | 6 baths | 4,800 sq.ft.

$549,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 8.82%

Airbnb Rental Income: $1322

Traditional Rental Income: $5565

Airbnb ROI: -0.25%

Traditional ROI: 8.82%

13 Brainard Ridge Road

Windham, NY

3 beds | 3 baths | 1,566 sq.ft.

$499,000

Airbnb cash on cash: -0.35%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $1186

Traditional Rental Income: $2684

Airbnb ROI: -0.35%

Traditional ROI: 3.69%

22 The Loop

Windham, NY

5 beds | 4 baths | 4,044 sq.ft.

$1,899,000

Airbnb cash on cash: -1.39%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $1322

Traditional Rental Income: $4700

Airbnb ROI: -1.39%