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 |
|---|---|---|---|
78 Buckskin LoopWindham, NYWelcome to Windmont--Windham's most exclusive gated community--where luxury living meets t... |
4 beds | 3 baths | 3,977 sq.ft. |
$1,349,000 |
Airbnb cash on cash: -0.92%
|
97 Carrington RdWindham, NYStreamfront Serenity Meets Mountain Views -- Bordering Protected NYC DEP Lands Bordered by... |
4 beds | 2 baths | 1,808 sq.ft. |
$449,000 |
Airbnb cash on cash: 0.74%
|
150 Vining RdWindham, NY150 Vining Road, Windham, NY Beautifully renovated contemporary mountain retreat set on 1 ... |
3 beds | 2 baths | 2,182 sq.ft. |
$569,000 |
Airbnb cash on cash: -0.54%
|
27 Anchor Camp RdWindham, NYLuxury Windham Log Cabin Retreat Near Windham Mountain Club | Air Conditioned, Ski Slope V... |
5 beds | 5 baths | 4,848 sq.ft. |
$1,699,000 |
Airbnb cash on cash: -0.75%
|
769 Mitchell Hollow RdWindham, NYBright Sparrow Farmhouse - Modern Catskills Farmhouse with Solar Power Backup, Private Pon... |
4 beds | 3 baths | 2,100 sq.ft. |
$699,000 |
Airbnb cash on cash: 0.18%
|
25 Vets Road RdWindham, NYWelcome to your peaceful sanctuary in the heart of Windham, a rare blend of convenience, n... |
4 beds | 4 baths | 2,950 sq.ft. |
$425,000 |
Airbnb cash on cash: 0.37%
|
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. |
$599,000 |
Airbnb cash on cash: 0.14%
|
13 Brainard Ridge RoadWindham, NY5 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: 0.17%
|
22 The Loop RdWindham, NYA short 1-2 minute walk to the trail access (870 ft)!! Nestled on the scenic slopes of Win... |
5 beds | 3 baths | 4,044 sq.ft. |
$1,899,000 |
Airbnb cash on cash: -0.91%
|
4 Goff RdWindham, NYAre 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%
|
20 Sutton Hollow RoadWindham, NYModern Farmhouse Getaway with Streamside Serenity - Fully Renovated & Fully Furnished! Thi... |
3 beds | 3 baths | 1,335 sq.ft. |
$525,000 |
Airbnb cash on cash: -0.04%
|
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: -1.81%
|
315 Begley RdWindham, NYJust minutes from the village of Windham, skiing, and golf, this meticulously maintained r... |
3 beds | 1 baths | 1,152 sq.ft. |
$325,000 |
Airbnb cash on cash: 1.42%
|
53 Windham Mountain Village VlgWindham, 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: -0.89%
|
292 South Street St #2Windham, NYTurn-Key Furnished Investment Opportunity Across from Windham Mountain Club with Existing ... |
5 beds | 5 baths | 3,460 sq.ft. |
$1,149,000 |
Airbnb cash on cash: -0.97%
|
55 Quads Way #55Windham, NYPrice 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: 0.28%
|
93 Maplewood RdWindham, NYNestled 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: 0.13%
|
292 #3 South StWindham, NYLuxury STR Investment Opportunity Across from Windham Mountain Club -- turnkey option, inc... |
5 beds | 5 baths | 3,643 sq.ft. |
$1,125,000 |
Airbnb cash on cash: -0.97%
|
7 Karlstadt RoadWindham, NYLuxury Furnished Catskills Cottage Near Windham Mountain Club | Renovated & Rental-Ready J... |
4 beds | 2 baths | 1,008 sq.ft. |
$399,000 |
Airbnb cash on cash: 1.57%
|
60 County Route 65-aWindham, NYWelcome to Windham Creek Lodge. Are you looking for a money maker? a year-round residence?... |
4 beds | N/A baths | 2,240 sq.ft. |
$659,777 |
Airbnb cash on cash: 0.39%
|
116 Nilson DriveWindham, NYFall 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: -0.14%
|
274 County Route 65 #55Windham, NY274 County Route 65 #55, Windham, NY 12496 | Townhouse |
2 beds | 2 baths | 1,295 sq.ft. |
$325,000 |
Airbnb cash on cash: -1.29%
|
274 Brooksburgh Rd #67Windham, NY274 Brooksburgh Rd #67, Windham, NY 12496 | Townhouse |
4 beds | 3 baths | 1,717 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.18%
|
274 Brooksburgh Rd #48Windham, NY274 Brooksburgh Rd #48, Windham, NY 12496 | Townhouse |
4 beds | 3 baths | 2,058 sq.ft. |
$489,000 |
Airbnb cash on cash: -0.64%
|
523 Mitchell Hollow RdWindham, NYCatskills living with standout appeal in Windham-the ultimate four-season destination for ... |
5 beds | 3 baths | 3,184 sq.ft. |
$665,000 |
Airbnb cash on cash: 0.92%
|
76 Loo Bridge Lane #12 BWindham, NYExceptional Value at 259,000 - MOTIVATED SELLERS | BUY NOW! This cozy country townhouse-st... |
2 beds | 3 baths | 1,411 sq.ft. |
$259,000 |
Airbnb cash on cash: -0.17%
|
16 Hickory Hill RdWindham, NYWindham: ''The place to Be'' for year round outdoor enthusiasts This gem has direct views ... |
3 beds | 2 baths | 2,250 sq.ft. |
$599,000 |
Airbnb cash on cash: -0.07%
|
71 Windham Mountain Village #71Windham, NYWindham 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: -0.6%
|
39 Brook Hollow LaneWindham, NYUpdated 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: -0.42%
|
513 County Road 10Windham, NYMountain Majesty Meets Everyday Luxury on 2.8 Serene Acres! Escape to the perfect blend of... |
3 beds | 3 baths | 1,870 sq.ft. |
$599,900 |
Airbnb cash on cash: -0.15%
|
542 Mitchell Hollow RdWindham, NYWelcome to 542 Mitchell Hollow Road, Windham, NY, a charming home set on a beautifully mai... |
3 beds | 1 baths | 1,446 sq.ft. |
$285,000 |
Airbnb cash on cash: 1.68%
|
5359 Route 23 #2EWindham, NYExperience easy mountain living in Windham! This charming 2-bedroom, 2-bath condo features... |
2 beds | 2 baths | 1,163 sq.ft. |
$239,000 |
Airbnb cash on cash: -1.86%
|
5359 #2HWindham, NYPrime Windham Village Location - Step out your door and wander to restaurants, the farmers... |
2 beds | 2 baths | 838 sq.ft. |
$289,000 |
Airbnb cash on cash: 0.09%
|
69 Windham Ridge Rd #16-FWindham, NYWelcome to Windham Ridge with views of Windham Mountain! This 3 Bedroom, 2.5 Bath townhome... |
3 beds | 2 baths | 1,520 sq.ft. |
$365,000 |
Airbnb cash on cash: 0.37%
|
96 56Windham, NYAn amazing opportunity to own the perfect mountain retreat! This legal two-family home off... |
5 beds | 2 baths | N/A |
$565,000 |
Airbnb cash on cash: 1.58%
|
37 The LoopWindham, NYVIEWS -LOCATION Spectacular true log home just a short walk to the slopes of Windham Moun... |
5 beds | 3 baths | 3,740 sq.ft. |
$1,850,000 |
Airbnb cash on cash: -1.05%
|
55 Windham Ridge Rd #15hWindham, NYCompetitively Priced Catskills End Unit Townhouse - Renovated and furnishings are optional... |
2 beds | 2 baths | 1,238 sq.ft. |
$319,000 |
Airbnb cash on cash: -0.3%
|
5678 New York 23Windham, NYTurn-Key Catskills Timber Frame Retreat | Sold Fully Furnished | Mountain Views | Walk to ... |
4 beds | 3 baths | 2,878 sq.ft. |
$799,000 |
Airbnb cash on cash: 0.21%
|
21 French Park Ct #7bWindham, NYIf you know Windham Ridge, you know there are only a handful of units with a front row sea... |
2 beds | 2 baths | 1,392 sq.ft. |
$389,000 |
Airbnb cash on cash: -1.2%
|
Real Estate investment in Windham, NY
There are 104 properties for sale in the city of Windham . The median list price in Windham is $629,623 and the average price per square foot is $287. In July 2026, the average monthly cash on cash return in Windham is 3.00%. The average monthly rental income in Windham is $2,737.