Real Estate Investments for Sale in Windham, NY With High ROI
Are you looking for a vacation rental in Windham, NY? Look no further! We have a wide variety of vacation available for sale, including beachfront condos, mountain single-family homes, townhouses, vacation homes and everything in between.
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 |
|---|---|---|---|
24 Windham View RoadWindham, NYWelcome to your dream mountain retreat in the heart of the Catskills! This incredible cont... |
5 beds | 5 baths | 4,605 sq.ft. |
$1,025,000 |
Airbnb cash on cash: 2.99%
|
770 Mitchell Hollow RoadWindham, NYDiscover this turnkey mid-century chalet located on a country road in the heart of the Cat... |
3 beds | 2 baths | 1,622 sq.ft. |
$550,000 |
Airbnb cash on cash: 2.15%
|
28 Evergreen RoadWindham, NY** Vacation Land ** 5 miles Windham Ski, at epicenter of vacation-land upstate New York -... |
3 beds | 2 baths | 1,056 sq.ft. |
$395,000 |
Airbnb cash on cash: 3.54%
|
39 Trail View LaneWindham, NYBecome the first owner of this brand-new Windham Mountain Cabin!If you've seen this home i... |
3 beds | 3 baths | 4,092 sq.ft. |
$849,000 |
Airbnb cash on cash: 0.87%
|
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: -0.15%
|
60 Quads WayWindham, NYDiscover this beautifully updated 2-bedroom, 2-bathroom condo duplex in Windham, a perfect... |
2 beds | 2 baths | 1,008 sq.ft. |
$257,000 |
Airbnb cash on cash: 5.18%
|
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: 4.39%
|
69 Windham Ridge RoadWindham, NYLovely townhouse nestled in one of Windham's most sought-after developments! This delightf... |
3 beds | 3 baths | 1,520 sq.ft. |
$425,000 |
Airbnb cash on cash: 2.19%
|
11 Whisper Creek DriveWindham, NYWelcome to Windham Mt. Club proudly offering this Whisper Creek Condominium! Where you hav... |
4 beds | 5 baths | 1,812 sq.ft. |
$1,395,000 |
Airbnb cash on cash: -0.36%
|
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. |
$375,000 |
Airbnb cash on cash: 2.12%
|
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: 0.98%
|
5628 23 RouteWindham, NYThree unit rental property for sale in beautiful Windham, New York. The main farmhouse off... |
6 beds | 5 baths | N/A |
$995,000 |
Airbnb cash on cash: 2.29%
|
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: 1.3%
|
89 Siam RoadWindham, NYPrice Cut! Classic Ski Chalet nestled in the heart of Windham, is a quiet retreat with clo... |
4 beds | 2 baths | 2,270 sq.ft. |
$525,000 |
Airbnb cash on cash: 3.52%
|
64 Clarence D Lane LaneWindham, NYLocation! Location! Be a part of Windham Family in this Windham Classic Chalet, built in 1... |
3 beds | 2 baths | N/A |
$515,000 |
Airbnb cash on cash: 1.34%
|
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. |
$729,000 |
Airbnb cash on cash: 1.78%
|
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: 1.68%
|
49 County Route 65Windham, NYWindham Mountain! Now's the time to invest in one of the longest running businesses in the... |
1 beds | 3 baths | 4,100 sq.ft. |
$609,000 |
Airbnb cash on cash: -0.96%
|
28 EvergreenWindham, 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. |
$395,000 |
Airbnb cash on cash: 2.56%
|
13 Brainard Ridge RoadWindham, NYReady for Ski Season! This beautifully renovated 3 bedroom, 3 bath townhome is move in rea... |
3 beds | 3 baths | 1,566 sq.ft. |
$569,000 |
Airbnb cash on cash: 0.96%
|
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: 1.12%
|
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: 2.02%
|
720 Mill StreetWindham, NYTucked away on a private 5-acre parcel in the heart of Windham, this unique residence comb... |
4 beds | 2 baths | 2,442 sq.ft. |
$849,000 |
Airbnb cash on cash: 1.15%
|
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: 1.28%
|
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. |
$929,000 |
Airbnb cash on cash: 2.64%
|
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: -0.36%
|
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: 1.59%
|
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. |
$449,000 |
Airbnb cash on cash: 4.56%
|
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: 3.44%
|
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: 4.71%
|
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: 2.48%
|
0 Brooksburgh Rd.Windham, NYBeautiful townhome located in the Town of Windham. Step into this lovely 4+ bedroom 2.5 ba... |
4 beds | 3 baths | 1,717 sq.ft. |
$495,000 |
Airbnb cash on cash: 3.89%
|
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: 2.26%
|
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: 3.22%
|
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: 1.51%
|
0 Boulder BrookWindham, NYWelcome to Boulder Brook Estates! A new and exclusive six-home community tucked away on 37... |
3 beds | 3 baths | 2,251 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 0.72%
|
134 Magda LaneWindham, NYWelcome to paradise! This 5-bedroom, 3 full bathroom home is just minutes to Windham Ski C... |
5 beds | 3 baths | 2,318 sq.ft. |
$745,000 |
Airbnb cash on cash: 4.81%
|
216 Route 296Windham, NYDiscover the perfect blend of modern comfort and serene seclusion in this 2,342 sq ft, 3 b... |
3 beds | 3 baths | 2,342 sq.ft. |
$1,199,000 |
Airbnb cash on cash: 0.14%
|
5449-RT 23 Main StreetWindham, NYREDUCED !! Farmhouse Venue on Main Street Windham, greets you with a charming rocking chai... |
4 beds | 2 baths | 2,360 sq.ft. |
$749,000 |
Airbnb cash on cash: 1.67%
|
11025 Route 23Windham, NYFully renovated circa 1800 colonial on a state maintained road. Close to Windham Mountain ... |
3 beds | 2 baths | 1,647 sq.ft. |
$299,000 |
Airbnb cash on cash: 5.03%
|
Real Estate investment in Windham, NY
There are 42 properties for sale in the city of Windham . The median list price in Windham is $520,000 and the average price per square foot is $250. In October 2024, the average monthly cash on cash return in Windham is 3.00%. The average monthly rental income in Windham is $2,922.