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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
21 Nauvoo RoadWindham, NYYour 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: 0.11%
|
76 Loo Bridge LaneWindham, NYCozy 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: 1.63%
|
77 Beaver Hill RoadWindham, NYDesigned 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: -1.7%
|
128 Mount Greenery RoadWindham, NYCozy 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: 0.57%
|
769 Mitchell Hollow RoadWindham, NYBright Sparrow Farmhouse - Modern Farmhouse on 8+ Acres with Private Pond, Mountain Views ... |
4 beds | N/A baths | 2,100 sq.ft. |
$799,000 |
Airbnb cash on cash: 0.49%
|
36 Mount Greenery RoadWindham, NYStylish Windham Contemporary Retreat on 5 Private Acres - Turnkey & Fully Furnished. Tucke... |
3 beds | 2 baths | 1,376 sq.ft. |
$599,000 |
Airbnb cash on cash: 0.75%
|
25 Vets RoadWindham, NYPeaceful 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: 0.08%
|
23 Townhouse Ln unit: D 1 #D 1Windham, NYWelcome to this warm and cozy FULLY FURNISHED townhome in Elm Ridge. Three levels of livin... |
3 beds | 3 baths | 1,846 sq.ft. |
$369,900 |
Airbnb cash on cash: 1.26%
|
122 Old RoadWindham, NYTwo-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: 0.58%
|
9 Pinekill LnWindham, NYRenovated 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: 0.79%
|
274 Route 65 unit: 43 #43Windham, NYDreaming of a quick escape from NYC's chaos? Just 2.5 hours from the city, nestled in the ... |
4 beds | N/A baths | 1,717 sq.ft. |
$445,000 |
Airbnb cash on cash: -0.47%
|
85 Cambridge Heights Rd.Windham, NYEnjoy the summer months taking in the beautiful views from the large Trex decking. Warm up... |
4 beds | 2 baths | 1,440 sq.ft. |
$669,000 |
Airbnb cash on cash: 1.19%
|
33 Elm Ridge RoadWindham, NYThe 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: -1.62%
|
61 South StreetWindham, NYSold 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: 0.01%
|
22 The LoopWindham, NYWalk to the Slopes! Nestled on the scenic slopes of Windham Mountain and just over two hou... |
5 beds | N/A baths | 4,044 sq.ft. |
$1,975,000 |
Airbnb cash on cash: -0.63%
|
57 Chase DriveWindham, NYGreat opportunity to own a vacation home in Windham! Lots of room for loved ones & guests.... |
5 beds | 3 baths | 2,460 sq.ft. |
$450,000 |
Airbnb cash on cash: 1.99%
|
30 The LoopWindham, NYWalk 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: -0.41%
|
15 County Route 79Windham, NYExceptional 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: -0.21%
|
102 Thunderbird TerraceWindham, NYCustom 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: -1.46%
|
16 High W RoadWindham, NYSki 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: -0.7%
|
4 Goff RoadWindham, NYAre 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: -0.84%
|
20 Sutton Hollow RoadWindham, NYModern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! Thi... |
3 beds | 3 baths | 1,335 sq.ft. |
$545,000 |
Airbnb cash on cash: 0.76%
|
4 Estate View DriveWindham, NYTo 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: -1.65%
|
315 Begley RoadWindham, NYLocated just minutes from the heart of Windham, NY, this inviting 3-bedroom, 1.5-bath ranc... |
3 beds | N/A baths | 1,152 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.14%
|
53 Windham Mountain VillageWindham, NYRenovated 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: -0.11%
|
73 Windham Ridge Road unit: 16H #16HWindham, NYCompetitively Priced Catskills End Unit Townhouse - Fully Renovated, Furnished & Move-In R... |
2 beds | 3 baths | 1,058 sq.ft. |
$339,000 |
Airbnb cash on cash: 1.41%
|
79 Windham Ridge Road #17AWindham, NYNestled 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: 0.83%
|
292 South Street unit: 2 #2Windham, NYIncredible 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: -0.86%
|
869 County Route 10Windham, NYShowing 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: -0.3%
|
55 Quads Way unit: 55 #55Windham, NYSweet 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: 1.92%
|
93 & 99 Nauvoo RoadWindham, NYCome relax in the cool Mediterranean vibes of this lovingly maintained home with gorgeous ... |
6 beds | 6 baths | 4,284 sq.ft. |
$1,490,000 |
Airbnb cash on cash: 0.13%
|
68 Hilltop DriveWindham, NYWelcome 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%
|
370 Begley RoadWindham, NYRare 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%
|
93 Maplewood RoadWindham, NYNestled 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: 0.43%
|
3 Enclave E DriveWindham, NYLuxury 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: -0.96%
|
292 #3 S StreetWindham, NYTurn-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: -0.67%
|
Real Estate investment in Windham, NY
There are 37 properties for sale in the city of Windham . The median list price in Windham is $729,000 and the average price per square foot is $282. In October 2025, the average monthly cash on cash return in Windham is 3.00%. The average monthly rental income in Windham is $3,104.