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
76 Loo Bridge Lane Windham, NY Cozy Mountain Condo in Windham - Perfect for Family Retreats or Investment Discover th...	2 beds \| 3 baths \| 1,211 sq.ft.	$295,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 6.46% Airbnb Rental Income: $1340 Traditional Rental Income: $2309 Airbnb ROI: 1.48% Traditional ROI: 6.46%
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: -1.8% Traditional cash on cash: -0.05% Airbnb Rental Income: $2326 Traditional Rental Income: $4917 Airbnb ROI: -1.8% Traditional ROI: -0.05%
333 Begley Road Windham, NY What a sweet home only 3 miles from Windham Mountain! Winter, summer or year-round, this o...	3 beds \| 2 baths \| 1,568 sq.ft.	$329,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 6.9% Airbnb Rental Income: $2026 Traditional Rental Income: $2668 Airbnb ROI: 3.12% Traditional ROI: 6.9%
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: 0.24% Traditional cash on cash: 3.78% Airbnb Rental Income: $1941 Traditional Rental Income: $3832 Airbnb ROI: 0.24% 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.	$779,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 3.48% Airbnb Rental Income: $1941 Traditional Rental Income: $3801 Airbnb ROI: 0.22% Traditional ROI: 3.48%
11 Quads Way Windham, NY Beautifully renovated studio style condo in the Quads condominium association just minutes...	1 beds \| 1 baths \| 1 sq.ft.	$195,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 11.58% Airbnb Rental Income: $903 Traditional Rental Income: $2529 Airbnb ROI: 0.96% Traditional ROI: 11.58%
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.	$499,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 9.03% Airbnb Rental Income: $1941 Traditional Rental Income: $5567 Airbnb ROI: 0.16% Traditional ROI: 9.03%
23 Townhouse Ln unit: D 1 #D 1 Windham, NY Welcome to this warm and cozy FULLY FURNISHED townhome in Elm Ridge. Three levels of livin...	3 beds \| N/A baths \| 1,846 sq.ft.	$369,900	Airbnb cash on cash: 1.35% Traditional cash on cash: 5.49% Airbnb Rental Income: $2026 Traditional Rental Income: $2935 Airbnb ROI: 1.35% Traditional ROI: 5.49%
122 Old Road Windham, NY Two-Lot Mountain Retreat in Windham - 4-Bedroom Home on 2 Acres + Contiguous 1.5-Acre Buil...	4 beds \| 3 baths \| 1,823 sq.ft.	$749,000	Airbnb cash on cash: 0.26% Traditional cash on cash: 3.58% Airbnb Rental Income: $1941 Traditional Rental Income: $3746 Airbnb ROI: 0.26% Traditional ROI: 3.58%
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: 0.87% Traditional cash on cash: 3.32% Airbnb Rental Income: $2026 Traditional Rental Income: $2936 Airbnb ROI: 0.87% Traditional ROI: 3.32%
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: -1.01% Traditional cash on cash: 3.28% Airbnb Rental Income: $1941 Traditional Rental Income: $3213 Airbnb ROI: -1.01% Traditional ROI: 3.28%
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: 0.89% Traditional cash on cash: 3.19% Airbnb Rental Income: $1941 Traditional Rental Income: $2826 Airbnb ROI: 0.89% 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 \| N/A baths \| 4,800 sq.ft.	$549,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 9.1% Airbnb Rental Income: $2326 Traditional Rental Income: $5565 Airbnb ROI: 1.66% Traditional ROI: 9.1%
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: -0.09% Traditional cash on cash: 4.82% Airbnb Rental Income: $1340 Traditional Rental Income: $2994 Airbnb ROI: -0.09% Traditional ROI: 4.82%
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: -0.92% Traditional cash on cash: 0.76% Airbnb Rental Income: $2326 Traditional Rental Income: $4700 Airbnb ROI: -0.92% Traditional ROI: 0.76%
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: 0.32% Traditional cash on cash: 3.91% Airbnb Rental Income: $2326 Traditional Rental Income: $3708 Airbnb ROI: 0.32% Traditional ROI: 3.91%
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: 0.4% Traditional cash on cash: 4.12% Airbnb Rental Income: $1941 Traditional Rental Income: $3668 Airbnb ROI: 0.4% Traditional ROI: 4.12%
15 County Route 79 Windham, NY It's Ski Season, and this fully furnished, turn-key Windham home is ready to enjoy or cont...	2 beds \| 2 baths \| 1,271 sq.ft.	$520,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.87% Airbnb Rental Income: $1340 Traditional Rental Income: $2455 Airbnb ROI: -0.27% Traditional ROI: 2.87%
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: -1.66% Traditional cash on cash: 0.96% Airbnb Rental Income: $2326 Traditional Rental Income: $5891 Airbnb ROI: -1.66% 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: -0.93% Traditional cash on cash: 2.09% Airbnb Rental Income: $2326 Traditional Rental Income: $5957 Airbnb ROI: -0.93% 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: -1% Traditional cash on cash: 1.44% Airbnb Rental Income: $2326 Traditional Rental Income: $6054 Airbnb ROI: -1% Traditional ROI: 1.44%
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.	$535,000	Airbnb cash on cash: 0.86% Traditional cash on cash: 3.31% Airbnb Rental Income: $2026 Traditional Rental Income: $2727 Airbnb ROI: 0.86% 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: -1.82% Traditional cash on cash: 1.16% Airbnb Rental Income: $2326 Traditional Rental Income: $7279 Airbnb ROI: -1.82% 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: 2.22% Traditional cash on cash: 4.29% Airbnb Rental Income: $2026 Traditional Rental Income: $2271 Airbnb ROI: 2.22% Traditional ROI: 4.29%
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: -0.19% Traditional cash on cash: 2.14% Airbnb Rental Income: $1340 Traditional Rental Income: $2115 Airbnb ROI: -0.19% 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 \| 3 baths \| 1,058 sq.ft.	$329,999	Airbnb cash on cash: 1.34% Traditional cash on cash: 5.57% Airbnb Rental Income: $1340 Traditional Rental Income: $2239 Airbnb ROI: 1.34% 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: 0.67% Traditional cash on cash: 6.2% Airbnb Rental Income: $1340 Traditional Rental Income: $2331 Airbnb ROI: 0.67% Traditional ROI: 6.2%
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: -1.16% Traditional cash on cash: 3.26% Airbnb Rental Income: $2326 Traditional Rental Income: $6475 Airbnb ROI: -1.16% 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 \| N/A baths \| 3,812 sq.ft.	$1,549,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 2.35% Airbnb Rental Income: $2326 Traditional Rental Income: $5886 Airbnb ROI: -0.52% Traditional ROI: 2.35%
55 Quads Way unit: 55 #55 Windham, NY Sweet 2-Bedroom, 2-Bath Condo - Carefree Mountain Living This charming and affordable cond...	2 beds \| 2 baths \| 1,008 sq.ft.	$249,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 7% Airbnb Rental Income: $1340 Traditional Rental Income: $2163 Airbnb ROI: 1.75% Traditional ROI: 7%
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: -0.08% Traditional cash on cash: 3.76% Airbnb Rental Income: $2326 Traditional Rental Income: $6927 Airbnb ROI: -0.08% Traditional ROI: 3.76%
68 Hilltop Drive Windham, NY Welcome to The Hill, a private enclave of high-end homes tucked away in the scenic hamlet ...	4 beds \| N/A baths \| 3,500 sq.ft.	$999,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 1.04% Airbnb Rental Income: $1941 Traditional Rental Income: $2621 Airbnb ROI: -0.24% Traditional ROI: 1.04%
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: 1.97% Traditional cash on cash: 5.38% Airbnb Rental Income: $2026 Traditional Rental Income: $2773 Airbnb ROI: 1.97% 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.	$849,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 1.75% Airbnb Rental Income: $1941 Traditional Rental Income: $2698 Airbnb ROI: 0.14% Traditional ROI: 1.75%
3 Enclave E Drive Windham, NY Luxury Ski Townhouse in the Heart of Windham Mountain Club's Premier Enclave Community Dis...	4 beds \| 5 baths \| 2,893 sq.ft.	$1,599,000	Airbnb cash on cash: -1.11% Traditional cash on cash: -0.4% Airbnb Rental Income: $1941 Traditional Rental Income: $2492 Airbnb ROI: -1.11% Traditional ROI: -0.4%
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: -0.98% Traditional cash on cash: -0.12% Airbnb Rental Income: $2326 Traditional Rental Income: $2647 Airbnb ROI: -0.98% Traditional ROI: -0.12%
61 Cambridge Heights Road Windham, NY The Catskills Are Calling - Your Private Four-Season Escape With Spectacular Views Awaits!...	5 beds \| N/A baths \| 4,214 sq.ft.	$1,199,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 0.73% Airbnb Rental Income: $2326 Traditional Rental Income: $2778 Airbnb ROI: -0.19% Traditional ROI: 0.73%
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: -1.8% Traditional cash on cash: -1.1% Airbnb Rental Income: $2326 Traditional Rental Income: $3013 Airbnb ROI: -1.8% Traditional ROI: -1.1%
60 County Route 65 A Windham, NY Welcome to Windham Creek Lodge - a modern mountain retreat designed for both luxury living...	4 beds \| 2 baths \| 2,240 sq.ft.	$750,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 2.72% Airbnb Rental Income: $1941 Traditional Rental Income: $3054 Airbnb ROI: 0.4% Traditional ROI: 2.72%
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: 2.34% Traditional cash on cash: 7.47% Airbnb Rental Income: $2326 Traditional Rental Income: $3667 Airbnb ROI: 2.34% Traditional ROI: 7.47%

Real Estate investment in Windham, NY

There are 42 properties for sale in the city of Windham . The median list price in Windham is $645,000 and the average price per square foot is $250. In December 2025, the average monthly cash on cash return in Windham is 3.00%. The average monthly rental income in Windham is $3,004.

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

There are 42 investment properties available for sale in Windham.

In 2025, 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 $1,984.

Your search for investment property begins and ends here

Investment Property for Sale in Windham, NY

76 Loo Bridge Lane

Windham, NY

2 beds | 3 baths | 1,211 sq.ft.

$295,000

Airbnb cash on cash: 1.48%

Traditional cash on cash: 6.46%

Airbnb Rental Income: $1340

Traditional Rental Income: $2309

Airbnb ROI: 1.48%

Traditional ROI: 6.46%

77 Beaver Hill Road

Windham, NY

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

$1,950,000

Airbnb cash on cash: -1.8%

Traditional cash on cash: -0.05%

Airbnb Rental Income: $2326

Traditional Rental Income: $4917

Airbnb ROI: -1.8%

Traditional ROI: -0.05%

333 Begley Road

Windham, NY

3 beds | 2 baths | 1,568 sq.ft.

$329,000

Airbnb cash on cash: 3.12%

Traditional cash on cash: 6.9%

Airbnb Rental Income: $2026

Traditional Rental Income: $2668

Airbnb ROI: 3.12%

Traditional ROI: 6.9%

128 Mount Greenery Road

Windham, NY

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

$729,000

Airbnb cash on cash: 0.24%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $1941

Traditional Rental Income: $3832

Airbnb ROI: 0.24%

Traditional ROI: 3.78%

769 Mitchell Hollow Road

Windham, NY

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

$779,000

Airbnb cash on cash: 0.22%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $1941

Traditional Rental Income: $3801

Airbnb ROI: 0.22%

Traditional ROI: 3.48%

11 Quads Way

Windham, NY

1 beds | 1 baths | 1 sq.ft.

$195,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 11.58%

Airbnb Rental Income: $903

Traditional Rental Income: $2529

Airbnb ROI: 0.96%

Traditional ROI: 11.58%

25 Vets Road

Windham, NY

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

$499,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 9.03%

Airbnb Rental Income: $1941

Traditional Rental Income: $5567

Airbnb ROI: 0.16%

Traditional ROI: 9.03%

23 Townhouse Ln unit: D 1 #D 1

Windham, NY

3 beds | N/A baths | 1,846 sq.ft.

$369,900

Airbnb cash on cash: 1.35%

Traditional cash on cash: 5.49%

Airbnb Rental Income: $2026

Traditional Rental Income: $2935

Airbnb ROI: 1.35%