Real Estate Investment Properties for Sale in Ossining, NY
Looking for investment property in Ossining, NY with high ROI ?
Explore a variety of short-term homes & houses in Ossining, NY. Invest wisely with VRBO & Ossining, 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 Ossining, NY
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
12 Brooke Hollow CourtOssining, NYEnjoy relaxing on your private patio overlooking the spectacular gardens of the The Woods,... |
2 beds | 3 baths | 1,400 sq.ft. |
$585,000 |
Airbnb cash on cash: -0.72%
|
139 Spring StreetOssining, NYNestled in the heart of Ossining, this charming two-family home combines space, flexibilit... |
5 beds | 3 baths | 2,812 sq.ft. |
$828,000 |
Airbnb cash on cash: -1.21%
|
201 Horseshoe CircleOssining, NYMOVE-IN-READY â nothing to do but unpack! Absolutely stunning & rare end unit in desir... |
2 beds | 3 baths | 1,784 sq.ft. |
$699,999 |
Airbnb cash on cash: -1.27%
|
1 Agate AvenueOssining, NYWestchester welcomes you to your new home sweet home! One family house for a first-time ho... |
2 beds | 1 baths | 960 sq.ft. |
$389,000 |
Airbnb cash on cash: -0.55%
|
30 Hunter StreetOssining, NYHere is your chance to take advantage of a rare opportunity to buy a designers honeymoon w... |
2 beds | 1 baths | 1,474 sq.ft. |
$300,000 |
Airbnb cash on cash: -0.24%
|
320 Illington RoadOssining, NYKitchawan Farmhouse built approx. 1850 featuring all up-to-date amenities. Stylish Kitche... |
4 beds | 3 baths | 2,950 sq.ft. |
$1,203,000 |
Airbnb cash on cash: 1.39%
|
20 Maple PlaceOssining, NYAccording to the Town Of Ossining this house is uninhabitable and it is unsafe to enter. ... |
5 beds | 2 baths | 2,880 sq.ft. |
$364,000 |
Airbnb cash on cash: 8.28%
|
459 Illington RoadOssining, NYYorktown School District â Charming Colonial in Sought-After Teatown Neighborhood. Move... |
3 beds | 2 baths | 2,658 sq.ft. |
$775,000 |
Airbnb cash on cash: 1.46%
|
1 Noel DriveOssining, NYSprawling Cape Cod style home with first floor primary suite on a fabulous, private settin... |
4 beds | 3 baths | 3,551 sq.ft. |
$899,222 |
Airbnb cash on cash: 1.64%
|
135 Main Street #203Ossining, NYExciting 2-bedroom condo in the Village of Ossining! Enjoy the lifestyle of convenience. W... |
2 beds | 1 baths | 951 sq.ft. |
$240,000 |
Airbnb cash on cash: 0.05%
|
11c Piping Rock DriveOssining, NYA/O CTS -Nestled at the end of the serene and private Piping Rock Drive, this stunning col... |
4 beds | 4 baths | 2,900 sq.ft. |
$700,000 |
Airbnb cash on cash: 3.28%
|
95 Charter Circle #95Ossining, NYIf you are looking for an extra large 2 bedroom unit with private entrance and no steps, l... |
2 beds | 1 baths | 1,100 sq.ft. |
$298,222 |
Airbnb cash on cash: -2.31%
|
50 Snowden AvenueOssining, NYWelcome to 50 Snowden Avenue, Ossining, NY, a distinguished end unit nestled in the heart ... |
2 beds | 3 baths | 1,444 sq.ft. |
$549,999 |
Airbnb cash on cash: -1.3%
|
16 Rockledge Avenue #5B1Ossining, NYInspirational. Awe inspiring. Witness first-hand the most stunning panoramic Hudson Rive... |
2 beds | 2 baths | 1,580 sq.ft. |
$332,500 |
Airbnb cash on cash: 2%
|
83 McDonald RoadOssining, NYStunning Colonial Home Set on 1.8 Acres in Westchester County, NY Welcome to your dream h... |
5 beds | 3 baths | 3,972 sq.ft. |
$1,099,000 |
Airbnb cash on cash: 0.4%
|
129-1 South Highland Avenue #B6Ossining, NYWelcome to Highland Terrace, 129-1 Unit B6, a spacious 2 bedroom, I bath in a beautiful co... |
2 beds | 1 baths | 900 sq.ft. |
$225,000 |
Airbnb cash on cash: 2.26%
|
20 Pine AvenueOssining, NYThis huge 5-bedroom, 3-bathroom home, is beautifully maintained and tucked away on a quiet... |
5 beds | 3 baths | 2,100 sq.ft. |
$699,000 |
Airbnb cash on cash: 2.54%
|
23-096 Liberty StreetOssining, NYTHIS IS NOT JUST ANOTHER LISTING! Don't miss this RARE opportunity to own a newly construc... |
3 beds | 3 baths | 2,250 sq.ft. |
$850,000 |
Airbnb cash on cash: 3.03%
|
135-2 S Highland Avenue #B5Ossining, NYWelcome to 135 S Highland Avenue Unit #B5, a desirable cooperative in the heart of Ossinin... |
2 beds | 1 baths | 925 sq.ft. |
$199,999 |
Airbnb cash on cash: 2.66%
|
117 S Highland Avenue #6jOssining, NYWelcome to your perfect home-away-from-the-hustle! Step into this beautifully maintained 7... |
1 beds | 1 baths | 750 sq.ft. |
$150,000 |
Airbnb cash on cash: 6.13%
|
17 CAMPWOODS GroundsOssining, NYA home is something so special, it is indescribable. It is not about the structure or the ... |
2 beds | 1 baths | 720 sq.ft. |
$319,888 |
Airbnb cash on cash: 0.76%
|
7 Belleview AvenueOssining, NYThis beautifully maintained & newly renovated 3 bedroom l 2 bathroom home blends cozy char... |
3 beds | 2 baths | 1,283 sq.ft. |
$570,000 |
Airbnb cash on cash: 2.7%
|
14 High Ridge RoadOssining, NYMystic Pointe offers a serene, private lifestyle with resort-style amenities including a c... |
2 beds | 4 baths | 3,240 sq.ft. |
$829,000 |
Airbnb cash on cash: -2%
|
58 Narragansett AvenueOssining, NYWelcome Home to Modern Comfort and Relaxed Living! Tucked back at the end of a tree lined ... |
4 beds | 3 baths | 2,202 sq.ft. |
$840,000 |
Airbnb cash on cash: 2.83%
|
90 BroadwayOssining, NYThis Colonial TWO-FAMILY dwelling is located in the heart of the village. The large 3BR Ap... |
4 beds | 2 baths | 1,935 sq.ft. |
$635,000 |
Airbnb cash on cash: 5.07%
|
3 Forest AvenueOssining, NYWelcome to your ideal forever home! This cozy two bedroom, two bathroom ranch-style house... |
2 beds | 2 baths | 1,046 sq.ft. |
$545,500 |
Airbnb cash on cash: -0.54%
|
42 Campwoods GroundsOssining, NYStep back in time and discover the charm of this turn-of-the-century cottage, nestled in t... |
2 beds | 2 baths | 972 sq.ft. |
$359,222 |
Airbnb cash on cash: 0.44%
|
9 Possum RoadOssining, NYBring your vision to this ranch-style home on an oversized, flat 1.17-acre lot in Ossining... |
3 beds | 2 baths | 1,528 sq.ft. |
$650,000 |
Airbnb cash on cash: 0.43%
|
200 Route 9AOssining, NY2BR Apartment Included! Welcome to this stunning 5-bedroom, 3.5-bath Ossining home offeri... |
5 beds | 4 baths | 2,520 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 0.73%
|
106 Mystic Drive #106Ossining, NYMystic Pointe in Ossinng is a coveted gated community tucked between the Hudson and N. Hig... |
3 beds | 4 baths | 3,638 sq.ft. |
$1,099,000 |
Airbnb cash on cash: -0.17%
|
19 Lincoln Place #55Ossining, NYWelcome to this beautifully maintained unit in the desirable Cedar Garden Townhouses, offe... |
2 beds | 3 baths | 1,658 sq.ft. |
$499,222 |
Airbnb cash on cash: -0.66%
|
125 S Highland Avenue #4BOssining, NYPopular co-op in the heart of Ossining. Convenient to public transportation, shopping, Old... |
2 beds | 1 baths | 950 sq.ft. |
$220,000 |
Airbnb cash on cash: -2.34%
|
22 William StreetOssining, NYCalling all contractors, investors, and end users! This classic two-family home is brimmi... |
4 beds | 2 baths | 2,116 sq.ft. |
$399,222 |
Airbnb cash on cash: -0.76%
|
39 Ann StreetOssining, NYWelcome to this single-family home located in the heart of the vibrant town of Ossining. ... |
3 beds | 1 baths | 1,120 sq.ft. |
$505,000 |
Airbnb cash on cash: 4.47%
|
25 William StreetOssining, NYThis spacious three-family home in Ossining offers three full stories plus a finished base... |
7 beds | 3 baths | 2,224 sq.ft. |
$949,000 |
Airbnb cash on cash: 1.4%
|
18 Adams RoadOssining, NYWelcome to 18 Adams Road! This charming property is tucked away on a quiet dead-end street... |
3 beds | 2 baths | 1,658 sq.ft. |
$799,000 |
Airbnb cash on cash: 1.33%
|
19 Donald LaneOssining, NYLocated along a peaceful cul-de-sac in Ossining, there is a quiet grace to 19 Donald Lane.... |
3 beds | 2 baths | 1,550 sq.ft. |
$695,000 |
Airbnb cash on cash: 1.77%
|
Real Estate investment in Ossining, NY
There are 37 properties for sale in the city of Ossining . The median list price in Ossining is $577,500 and the average price per square foot is $311. In October 2025, the average monthly cash on cash return in Ossining is 3.00%. The average monthly rental income in Ossining is $3,710.