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: -1.15%
|
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: 0.05%
|
150 Vining RdWindham, NY150 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: -0.74%
|
769 Mitchell Hollow RdWindham, NYBright Sparrow Farmhouse - Modern Catskills Farmhouse with Solar Power Backup, Private Pon... |
4 beds | 3 baths | 2,100 sq.ft. |
$734,000 |
Airbnb cash on cash: -0.3%
|
22 Club RdWindham, NYNew Price, Expanded Deck & New Cable Railings! A home made for mountain lovers, this rusti... |
4 beds | 3 baths | 3,400 sq.ft. |
$2,100,000 |
Airbnb cash on cash: -2.23%
|
25 Vets Road RdWindham, NYWelcome to your peaceful sanctuary in the heart of Windham, a rare blend of convenience, n... |
4 beds | 4 baths | 2,374 sq.ft. |
$425,000 |
Airbnb cash on cash: -0.35%
|
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: -0.04%
|
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: -0.84%
|
2914 Route 10Windham, NYWelcome to this 3 bed 3 bath home nestled in Ashland, right outside of Windham. The home i... |
3 beds | 3 baths | 3,683 sq.ft. |
$396,000 |
Airbnb cash on cash: -0.42%
|
41 County Road 40Windham, NYA 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: 0.32%
|
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: -0.05%
|
17 Stonewall LnWindham, NYNestled against the breathtaking backdrop of Windham Mountain Club, Stonewall Glen, offers... |
3 beds | 3 baths | 2,400 sq.ft. |
$1,400,000 |
Airbnb cash on cash: -2.85%
|
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: -1.22%
|
90 Club RdWindham, NYSpectacular mountain views and steps away from the trails, this chalet is a Windham Mounta... |
5 beds | 4 baths | 3,600 sq.ft. |
$2,250,000 |
Airbnb cash on cash: -1%
|
31 Windham Farms RdWindham, NYWelcome to Windham's newest addition, situated within the serene Windham Farms subdivision... |
5 beds | 4 baths | 3,218 sq.ft. |
$1,750,000 |
Airbnb cash on cash: -2.04%
|
57 Brainard Ridge unit: 3-EWindham, NYAnother 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: -0.5%
|
110 - 2 High Ridge RdWindham, NYLocated on a private road and a peaceful wooded setting sits this charming three-bedroom r... |
3 beds | 2 baths | 1,464 sq.ft. |
$369,000 |
Airbnb cash on cash: -0.26%
|
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: -1.31%
|
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: -2.11%
|
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: 1.08%
|
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: -1.23%
|
292 South Street St #2Windham, NYIncredible Investment Opportunity - Proven Short-Term Rental Income! Welcome to 292 South ... |
5 beds | 5 baths | 3,460 sq.ft. |
$1,149,000 |
Airbnb cash on cash: -1.49%
|
55 Quads Way #55Windham, NYPrice Reduced -- Major Value in Windham! This charming turnkey condo delivers affordable f... |
2 beds | 2 baths | 2,016 sq.ft. |
$239,500 |
Airbnb cash on cash: -0.5%
|
93 & 99 Nauvoo RdWindham, NYCome 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: -0.5%
|
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: -0.28%
|
292 #3 South StWindham, NYTurn-Key Windham Ski Retreat | Modern End Unit with 4 En-Suites, Full Furnishing Option & ... |
5 beds | 5 baths | 3,643 sq.ft. |
$1,125,000 |
Airbnb cash on cash: -1.5%
|
33 Elm Ridge Road RdWindham, NYThe Mountains Are Calling and I Must Go.'' P.S., I plan to be VERY comfortable when I get ... |
5 beds | 2 baths | 2,554 sq.ft. |
$1,749,000 |
Airbnb cash on cash: -2.03%
|
274 Route 65 unit: 28Windham, NYNot your ordinary townhouse-this Crystal Pond ''builder's special'' is one of only a few t... |
4 beds | 5 baths | 3,190 sq.ft. |
$575,000 |
Airbnb cash on cash: -0.18%
|
0 High PeakWindham, NY0 High Peak, Windham, NY 12496 | Other |
N/A beds | N/A baths | N/A |
$595,000 |
Airbnb cash on cash: -1.47%
|
183 South StWindham, NY183 South St, Windham, NY 12496 | Single Family Residential |
2 beds | 1 baths | 1,122 sq.ft. |
$550,000 |
Airbnb cash on cash: -2.12%
|
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. |
$685,000 |
Airbnb cash on cash: 0.05%
|
209 Club RdWindham, NY209 Club Rd, Windham, NY 12496 | Single Family Residential |
6 beds | 5 baths | 5,015 sq.ft. |
$3,195,000 |
Airbnb cash on cash: -2.34%
|
436 Big Hollow RdWindham, NY436 Big Hollow Rd, Windham, NY 12496 | Single Family Residential |
3 beds | 2 baths | 1,400 sq.ft. |
$379,000 |
Airbnb cash on cash: -0.44%
|
611 Mitchell Hollow RdWindham, NY611 Mitchell Hollow Rd, Windham, NY 12496 | Single Family Residential |
N/A beds | N/A baths | N/A |
$199,000 |
Airbnb cash on cash: 0.96%
|
111 Brainard Ridge Rd #11bWindham, NY111 Brainard Ridge Rd #11b, Windham, NY 12496 | Single Family Residential |
3 beds | 2 baths | 1,471 sq.ft. |
$463,000 |
Airbnb cash on cash: -0.75%
|
274 Route 65 Rte #41Windham, NY274 Route 65 Rte #41, Windham, NY 12496 | Single Family Residential |
2 beds | 2 baths | 1,295 sq.ft. |
$339,000 |
Airbnb cash on cash: -3.85%
|
18 Maplewood AveWindham, NY18 Maplewood Ave, Windham, NY 12496 | Single Family Residential |
4 beds | 2 baths | 2,287 sq.ft. |
$499,000 |
Airbnb cash on cash: -0.7%
|
Real Estate investment in Windham, NY
There are 102 properties for sale in the city of Windham . The median list price in Windham is $499,000 and the average price per square foot is $208. In May 2026, the average monthly cash on cash return in Windham is 2.00%. The average monthly rental income in Windham is $2,271.