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 |
|---|---|---|---|
22 Brook Hollow LaneWindham, NYTucked away on a secluded dead-end road just minutes from town, this beautifully maintaine... |
4 beds | 2 baths | 2,842 sq.ft. |
$715,000 |
Airbnb cash on cash: 1.85%
|
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. |
$699,000 |
Airbnb cash on cash: 1.92%
|
429 Mill StreetWindham, NYDiscover serenity in this exquisite cedar contemporary home with seasonal slope views nest... |
4 beds | 4 baths | 2,294 sq.ft. |
$889,000 |
Airbnb cash on cash: 0.06%
|
39 Trail View LaneWindham, NYSeize the opportunity to be the inaugural owner of this pristine Windham Mountain Cabin! I... |
3 beds | 3 baths | 3,914 sq.ft. |
$849,000 |
Airbnb cash on cash: 1.2%
|
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 | 3 baths | 3,893 sq.ft. |
$1,949,000 |
Airbnb cash on cash: -0.79%
|
28 Evergreen LaneWindham, NY** Vacation Land ** 5 miles Windham Ski, at epicenter of vacation-land upstate New York -... |
3 beds | 2 baths | 1,056 sq.ft. |
$360,000 |
Airbnb cash on cash: 4.75%
|
4 French Park DriveWindham, NYPriced to sell, this Windham Ridge townhome is the best value on the market. Located in a ... |
2 beds | 2 baths | 1,536 sq.ft. |
$365,000 |
Airbnb cash on cash: 1.21%
|
274 Route 65Windham, NYDiscover the charm of this exquisite 4-bedroom, 3.5-bathroom townhouse. Step into a welcom... |
4 beds | 4 baths | 1,717 sq.ft. |
$460,000 |
Airbnb cash on cash: 2.62%
|
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. |
$675,000 |
Airbnb cash on cash: 0.93%
|
2914 Route 10Windham, NYWelcome to this 3 bed 3 bath home nestled in Ashland, right outside of Windham. The home i... |
3 beds | 4 baths | 2,610 sq.ft. |
$474,900 |
Airbnb cash on cash: 2.27%
|
81 Elm StreetWindham, NYJust a stones throw from the slopes at Windham Mountain, you will find this gem. A 5 bedro... |
5 beds | 3 baths | 2,500 sq.ft. |
$429,000 |
Airbnb cash on cash: 7.24%
|
14 Clarence D LaneWindham, NYWalk to Trails! Move in ready, from this 3 bedroom has the extra large loft space. Fully f... |
3 beds | 2 baths | 1,390 sq.ft. |
$520,000 |
Airbnb cash on cash: 1.84%
|
10 Brainard Ridge RoadWindham, NYAttractive Location for walking to ski trails, this 3 bedroom 2 bath + Sleeping Alcove. Ha... |
3 beds | 2 baths | 1,343 sq.ft. |
$545,000 |
Airbnb cash on cash: 1.63%
|
19 French Park DriveWindham, NYSpacious Windham Ridge, 2 bedroom +End Unit, 2.5 baths, Beautiful Views, wood burning sto... |
3 beds | 3 baths | 1,488 sq.ft. |
$440,000 |
Airbnb cash on cash: 2.66%
|
720 Mill StreetWindham, NYTucked away on a private 5-acre parcel in the heart of Windham, this unique residence boat... |
4 beds | 2 baths | 2,442 sq.ft. |
$849,000 |
Airbnb cash on cash: 0.19%
|
28 Evergreen LaneWindham, NY2.6 miles (as the crow flies), 5.5 miles (driving), to Windam Country Club and Wyndam Vill... |
3 beds | 2 baths | 1,056 sq.ft. |
$360,000 |
Airbnb cash on cash: 3.84%
|
407 Mill Street StreetWindham, NYWelcome to the Windham Round Haus located just minutes from the Windham Resort. A Unique A... |
3 beds | 3 baths | 2,864 sq.ft. |
$889,000 |
Airbnb cash on cash: -0.04%
|
292 South StreetWindham, NYLuxurious Townhouse in Prime Windham Mountain Location Welcome to your dream home or next ... |
5 beds | 6 baths | 3,643 sq.ft. |
$1,249,000 |
Airbnb cash on cash: 0.29%
|
5134 Route 23Windham, NYIntroducing 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: 2.17%
|
821 Mitchell Hollow RoadWindham, NYWarm and welcoming old style country farmhouse. Completely renovated inside with some orig... |
4 beds | 2 baths | 1,303 sq.ft. |
$400,000 |
Airbnb cash on cash: 3.42%
|
3372 County Road 10Windham, NYWelcome to 3372 County Rt 10, a spacious 5-bedroom, 3-bathroom home in the town of Ashland... |
5 beds | 3 baths | 4,480 sq.ft. |
$849,000 |
Airbnb cash on cash: 1.7%
|
26 Townhouse LaneWindham, NYSCORE-One of the last of the affordable townhouse/condos on the mountain top in luxurious ... |
2 beds | 2 baths | 1,200 sq.ft. |
$348,888 |
Airbnb cash on cash: 2.35%
|
91 Windham Ridge RoadWindham, NYTucked away amongst the quiet pines of the Catskill Mts. and just a stone's throw away fro... |
2 beds | 2 baths | 936 sq.ft. |
$279,000 |
Airbnb cash on cash: 3.35%
|
5449-RT 23 Main StreetWindham, NYNEW PRICE -REDUCED !! Farmhouse Venue on Main Street Windham, greets you with a charming r... |
4 beds | 2 baths | 2,360 sq.ft. |
$749,000 |
Airbnb cash on cash: 0.58%
|
274 Brooksburgh RoadWindham, NYEnter this lovely Townhome and feel right at home. This is an end unit, lovely setting. Th... |
2 beds | 3 baths | 1,295 sq.ft. |
$349,000 |
Airbnb cash on cash: 1.39%
|
73 Windham Ridge RoadWindham, NYEnjoy easy country living in this fully renovated, turn-key condo nestled in the desirable... |
2 beds | 3 baths | 1,058 sq.ft. |
$439,000 |
Airbnb cash on cash: 1.39%
|
28 Loo Bridge LaneWindham, NYBeautiful 3-Bedroom, 3-Bathroom Condo in Windham Ridge Community!Discover comfort and conv... |
3 beds | 3 baths | 1,211 sq.ft. |
$389,000 |
Airbnb cash on cash: 3.94%
|
39 French ParkWindham, NYWelcome to 39 French Park Drive, an incredible end-unit townhouse nestled in the highly so... |
3 beds | 2 baths | 1,488 sq.ft. |
$400,000 |
Airbnb cash on cash: 3.19%
|
11 Whisper Creek DriveWindham, NYWelcome to 601 Whisper Creek- a slopeside penthouse with breathtaking views, right at the ... |
3 beds | 3 baths | 1,506 sq.ft. |
$979,900 |
Airbnb cash on cash: -0.29%
|
190 Mitchell Hollow RoadWindham, NYIntroducing Mitchell Hollow Mountain Modern, a newly constructed, spacious home that maste... |
4 beds | 3 baths | 3,198 sq.ft. |
$1,795,000 |
Airbnb cash on cash: 0.36%
|
5 Jakob Strasse RoadWindham, NYContemporary Elegance Meets Mountain Retreat Living at Windham - Discover the perfect blen... |
4 beds | 4 baths | 3,245 sq.ft. |
$1,075,000 |
Airbnb cash on cash: -0.42%
|
128 Mount Pisgah RdWindham, NYSpectacular Windham Home on Nearly 10 Acres with Stunning Views of Windham Mountain Ski Re... |
5 beds | 5 baths | 4,233 sq.ft. |
$1,599,000 |
Airbnb cash on cash: -0.37%
|
22 The LoopWindham, NYNestled on the scenic slopes of Windham Mountain and just over two hours from NYC, this mo... |
5 beds | 4 baths | 4,044 sq.ft. |
$1,975,000 |
Airbnb cash on cash: 0.19%
|
3 Begley RoadWindham, NYPrice Improvement!! Who doesn't want to live in the house on the hill? Perched high above ... |
4 beds | 2 baths | 1,916 sq.ft. |
$499,999 |
Airbnb cash on cash: 2.2%
|
129 Club RoadWindham, NYGorgeous Windham Mountain Contemporary An abundance of natural light and impressive lands... |
4 beds | 4 baths | 2,900 sq.ft. |
$1,375,000 |
Airbnb cash on cash: 0.3%
|
20 Brook Hollow LaneWindham, NYExperience unparalleled luxury living in the heart of Windham, NY, home to the prestigious... |
3 beds | 4 baths | 3,300 sq.ft. |
$1,199,000 |
Airbnb cash on cash: -0.73%
|
77 Beaver Hill RoadWindham, NYWhen the powder is fresh and the sun kisses the peaks, your Windham ski retreat awaits wit... |
5 beds | 4 baths | 4,834 sq.ft. |
$2,300,000 |
Airbnb cash on cash: -1.08%
|
149 Magda LaneWindham, NYSerene Country and Ski Living at its Finest! Discover the ultimate in luxury and sophistic... |
4 beds | 5 baths | 2,140 sq.ft. |
$1,170,000 |
Airbnb cash on cash: 0.69%
|
4 The LoopWindham, NYWelcome to The Loop. Stunningly renovated 4 bedroom, 3 bath 2,536 Sq. Ft. contemporary hom... |
4 beds | 3 baths | 2,536 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -0.3%
|
110 Maplcrest RoadWindham, NYLocated in the heart of the picturesque Catskill Mountains, this enchanting multi-family f... |
8 beds | 4 baths | 3,577 sq.ft. |
$639,000 |
Airbnb cash on cash: 3.13%
|
Real Estate investment in Windham, NY
There are 50 properties for sale in the city of Windham . The median list price in Windham is $675,000 and the average price per square foot is $301. In January 2025, the average monthly cash on cash return in Windham is 3.00%. The average monthly rental income in Windham is $3,024.