Real Estate Investment Properties for Sale in New Windsor, NY
Looking for investment property in New Windsor, NY with high ROI ?
Explore a variety of short-term homes & houses in New Windsor, NY. Invest wisely with VRBO & New Windsor, 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 New Windsor, NY
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
60 Creamery DriveNew Windsor, NYWelcome to this beautifully maintained 3-bedroom, 2-bath raised ranch in the highly desira... |
3 beds | 2 baths | 1,980 sq.ft. |
$499,999 |
Airbnb cash on cash: 1.04%
|
3 Garden DrNew Windsor, NYLovely 3BR home on over an acre on a dead end street in the Town of New Windsor. Good opp... |
3 beds | 2 baths | 1,790 sq.ft. |
$519,000 |
Airbnb cash on cash: 1.35%
|
1 Staples LnNew Windsor, NYThis adorable Capecod is located on a quiet dead end street offers you the peace and quiet... |
4 beds | 1 baths | 1,400 sq.ft. |
$314,900 |
Airbnb cash on cash: 6.83%
|
24 Quassaick AveNew Windsor, NYThis well-maintained and updated 2-bedroom, 1-bath home is truly move-in ready. Situated o... |
2 beds | 1 baths | 575 sq.ft. |
$235,000 |
Airbnb cash on cash: 4.48%
|
3 Clemence DrNew Windsor, NYTucked in a quiet cul-de-sac in the sought after Cornwall School District this reimagined ... |
4 beds | 2 baths | 3,653 sq.ft. |
$805,000 |
Airbnb cash on cash: 0.58%
|
15 Queen StNew Windsor, NYCheck out this charming brick 3 bedroom 1 bath home in the Town of New Windsor. This home ... |
3 beds | 1 baths | 1,350 sq.ft. |
$410,000 |
Airbnb cash on cash: 1.91%
|
404 Carlton CirNew Windsor, NYMajor Price Improvement. Seller Motivated! Step into a sun-filled living room and enjoy th... |
3 beds | 2 baths | 2,146 sq.ft. |
$475,000 |
Airbnb cash on cash: 1.39%
|
11 Willow LaneNew Windsor, NYWelcome home to this charming L- shaped brick ranch in desirable New Windsor! Featuring 3... |
3 beds | 1 baths | 1,517 sq.ft. |
$437,500 |
Airbnb cash on cash: 1.77%
|
807 Fairway Ct #94New Windsor, NYTwo years young, beautiful townhome in desirable Windsor Crest is now ready for your next ... |
3 beds | 2 baths | 1,890 sq.ft. |
$425,000 |
Airbnb cash on cash: 1.02%
|
917 Balsam DrNew Windsor, NYThis 2 bed 3 bath townhome in New Windsor is a spacious and well-maintained unit, perfect ... |
2 beds | 3 baths | 1,990 sq.ft. |
$459,900 |
Airbnb cash on cash: 0.1%
|
56 Frank StreetNew Windsor, NYLuxury, Comfort, and Convenience Await at Meadowbrook Estates! Discover the Brook Model,... |
4 beds | 4 baths | 2,791 sq.ft. |
$875,000 |
Airbnb cash on cash: 0.78%
|
8 Oak DrNew Windsor, NYWelcome to 8 Oak Drive! This beautifully updated two-home property features a charming mai... |
6 beds | 5 baths | 4,407 sq.ft. |
$849,000 |
Airbnb cash on cash: -0.39%
|
18 Park Hill DrNew Windsor, NYWelcome to 18 Park Hill Drive-a perfect place to start your homeownership journey! This be... |
4 beds | 2 baths | 2,100 sq.ft. |
$479,000 |
Airbnb cash on cash: 3.5%
|
313 Chestnut AvenueNew Windsor, NYWelcome to 313 Chestnut Avenue in New Windsor, NYâan inviting and beautifully maintained... |
4 beds | 3 baths | 2,821 sq.ft. |
$599,000 |
Airbnb cash on cash: 2.52%
|
10 Oakwood Ter #65New Windsor, NYWelcome to this beautifully maintained 1-bedroom co-op located in the desirable Oakwood Te... |
1 beds | 1 baths | 750 sq.ft. |
$139,000 |
Airbnb cash on cash: -0.24%
|
74 Red Maple WayNew Windsor, NYWelcome to 74 Red Maple Way at Windsor Woods, one of New Windsor's premier cul-de-sac comm... |
5 beds | 2 baths | 3,538 sq.ft. |
$679,900 |
Airbnb cash on cash: 0.2%
|
10 Oakwood Ter #110New Windsor, NYSpacious and sun-filled 1-bedroom, 1-bath end unit co-op offering 960 square feet of comfo... |
1 beds | 1 baths | 960 sq.ft. |
$139,900 |
Airbnb cash on cash: -0.45%
|
1404 Hawthorn WayNew Windsor, NYWhen only the best will do this is the town home you have been waiting for! Located in the... |
3 beds | 2 baths | 1,910 sq.ft. |
$475,000 |
Airbnb cash on cash: 0.21%
|
131 Erie AveNew Windsor, NYWelcome to this beautifully maintained contemporary bi-level set on over an acre of land o... |
5 beds | 2 baths | 2,196 sq.ft. |
$575,000 |
Airbnb cash on cash: 0.65%
|
60 Trafalgar Rd #1New Windsor, NYWelcome Home! Newly remodeled 1 Bed and 1 Bath apartment in Squire Village of New Windsor.... |
1 beds | 1 baths | 700 sq.ft. |
$175,000 |
Airbnb cash on cash: 4.14%
|
91 Holloran RdNew Windsor, NYCORNWALL CENTRAL SCHOOLS! Welcome to 91 Holloran Road, a beautifully refreshed 3-bedroom, ... |
3 beds | 2 baths | 1,430 sq.ft. |
$424,999 |
Airbnb cash on cash: 2.2%
|
276 Temple Hill Rd #2604New Windsor, NYWelcome to effortless condo living in the heart of New Windsor. This beautifully maintaine... |
2 beds | 2 baths | 1,176 sq.ft. |
$250,000 |
Airbnb cash on cash: 1.55%
|
106 Station RdNew Windsor, NY106 Station Rd, New Windsor, NY 12553 | Single Family Residential |
4 beds | 5 baths | 3,000 sq.ft. |
$985,000 |
Airbnb cash on cash: 0.48%
|
9 Benedict Ln #5-7New Windsor, NYOffered at $999,900, this legacy investment property in New Windsor within the Cornwall Sc... |
8 beds | 4 baths | N/A |
$999,000 |
Airbnb cash on cash: -0.52%
|
85 Holloran RdNew Windsor, NY85 Holloran Rd, New Windsor, NY 12553 | Single Family Residential |
3 beds | 1 baths | 1,438 sq.ft. |
$395,000 |
Airbnb cash on cash: 2.4%
|
1974 St Rte 32New Windsor, NY1974 St Rte 32, New Windsor, NY 12553 | Single Family Residential |
3 beds | 2 baths | 2,137 sq.ft. |
$499,000 |
Airbnb cash on cash: 1.34%
|
64 Palomino PlNew Windsor, NY64 Palomino Pl, New Windsor, NY 12553 | Single Family Residential |
3 beds | 2 baths | 2,122 sq.ft. |
$534,000 |
Airbnb cash on cash: 1.08%
|
2 Mazies Ln #3New Windsor, NY2 Mazies Ln #3, New Windsor, NY 12553 | Manufactured Home |
1 beds | 1 baths | 650 sq.ft. |
$72,000 |
Airbnb cash on cash: -2.79%
|
8 Jefferson AveNew Windsor, NY8 Jefferson Ave, New Windsor, NY 12553 | Single Family Residential |
4 beds | 3 baths | 3,100 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -0.09%
|
4 Jefferson AveNew Windsor, NY4 Jefferson Ave, New Windsor, NY 12553 | Single Family Residential |
4 beds | 3 baths | 3,100 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 0.15%
|
2898 Route 9W Lot 54New Windsor, NY2898 Route 9W Lot 54, New Windsor, NY 12553 | Manufactured Home |
3 beds | 2 baths | 1,067 sq.ft. |
$148,000 |
Airbnb cash on cash: 3.04%
|
58 Red Maple WayNew Windsor, NY58 Red Maple Way, New Windsor, NY 12553 | Single Family Residential |
4 beds | 2 baths | 2,440 sq.ft. |
$630,000 |
Airbnb cash on cash: 2.27%
|
11 Square Hill Rd #27New Windsor, NY11 Square Hill Rd #27, New Windsor, NY 12553 | Manufactured Home |
2 beds | 2 baths | 784 sq.ft. |
$99,900 |
Airbnb cash on cash: -0.38%
|
105 Shaker Ct NNew Windsor, NY105 Shaker Ct N, New Windsor, NY 12553 | Single Family Residential |
3 beds | 2 baths | 1,764 sq.ft. |
$549,999 |
Airbnb cash on cash: 0.97%
|
117 Sandpiper Ln #1BNew Windsor, NY117 Sandpiper Ln #1B, New Windsor, NY 12553 | Condo/Coop |
3 beds | 2 baths | 1,510 sq.ft. |
$449,000 |
Airbnb cash on cash: 0.59%
|
91 Creamery DrNew Windsor, NY91 Creamery Dr, New Windsor, NY 12553 | Single Family Residential |
5 beds | 2 baths | 2,314 sq.ft. |
$649,950 |
Airbnb cash on cash: 0.58%
|
241 Tamerisk LnNew Windsor, NY241 Tamerisk Ln, New Windsor, NY 12553 | Condo/Coop |
2 beds | 2 baths | 2,132 sq.ft. |
$455,000 |
Airbnb cash on cash: -0.24%
|
1402 Hawthorn WayNew Windsor, NY1402 Hawthorn Way, New Windsor, NY 12553 | Single Family Residential |
3 beds | 2 baths | 2,139 sq.ft. |
$479,999 |
Airbnb cash on cash: 0.39%
|
276 Temple Hill Rd #2513New Windsor, NY276 Temple Hill Rd #2513, New Windsor, NY 12553 | Condo/Coop |
2 beds | 2 baths | 1,176 sq.ft. |
$247,900 |
Airbnb cash on cash: 1.55%
|
10 Oakwood Ter #38New Windsor, NY10 Oakwood Ter #38, New Windsor, NY 12553 | Condo/Coop |
2 beds | 1 baths | 1,200 sq.ft. |
$205,900 |
Airbnb cash on cash: 0.11%
|
Real Estate investment in New-windsor, NY
There are 90 properties for sale in the city of New Windsor . The median list price in New Windsor is $474,999 and the average price per square foot is $251. In January 2026, the average monthly cash on cash return in New Windsor is 4.00%. The average monthly rental income in New Windsor is $2,769.