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: -0.8%
|
18 Jenkins CourtOssining, NYTucked away at the end of a quiet cul-de-sac, this charming Cape cod is the kind of home t... |
4 beds | 3 baths | 1,932 sq.ft. |
$698,000 |
Airbnb cash on cash: 6.89%
|
33 Fawn CourtOssining, NYTucked away on a quiet cul-de-sac in the desirable Deerfield community, this meticulously ... |
1 beds | 2 baths | 1,287 sq.ft. |
$499,000 |
Airbnb cash on cash: 2.27%
|
193 Woods Brooke CircleOssining, NYStunning townhouse at The Woods; one of Ossining's most popular communities. This condo ha... |
2 beds | 3 baths | 1,400 sq.ft. |
$635,000 |
Airbnb cash on cash: -0.87%
|
8 Samstag AvenueOssining, NYCome view this stunning, lovingly landscaped private property in Ossining. Charming ranch... |
3 beds | 1 baths | 1,031 sq.ft. |
$489,500 |
Airbnb cash on cash: 1.22%
|
88 Broadway #PH4Ossining, NYExperience the perfect blend of historic charm and modern comfort in this sun-drenched 2 b... |
2 beds | 3 baths | 1,102 sq.ft. |
$529,000 |
Airbnb cash on cash: -1.06%
|
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: -1.34%
|
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: -0.67%
|
23 Ann StreetOssining, NYTWO FAMILY HOME - FULLY AVAILABLE - temp off market 100% renovation. Quality materia... |
5 beds | 2 baths | 1,800 sq.ft. |
$650,000 |
Airbnb cash on cash: 0.01%
|
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: -0.4%
|
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: 3.24%
|
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: N/A
|
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: 4.16%
|
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. |
$250,000 |
Airbnb cash on cash: -0.18%
|
3 Belleview AvenueOssining, NYGreat project! Perfect for a new flipper! Lots of work has already been done. Located clos... |
3 beds | 2 baths | 1,450 sq.ft. |
$399,000 |
Airbnb cash on cash: 2.04%
|
133-3 S Highland Avenue #B4Ossining, NYHighland Terrace is a pet friendly complex with assigned parking, an outdoor pool, & baske... |
2 beds | 1 baths | 900 sq.ft. |
$215,222 |
Airbnb cash on cash: -4.76%
|
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: 6.44%
|
19 Meadowbrook DriveOssining, NYEnjoy sweeping Hudson River views from every room in this turnkey ranch. The sunlit living... |
3 beds | 3 baths | 2,200 sq.ft. |
$799,900 |
Airbnb cash on cash: -0.18%
|
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: -2.47%
|
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: -1.39%
|
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: 1.86%
|
7-05 Briarcliff Drive SOssining, NYEnjoy carefree livingâ¦Embrace comfort and convenience living in this large two-bedroom, ... |
2 beds | 2 baths | 1,288 sq.ft. |
$435,000 |
Airbnb cash on cash: -1.37%
|
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: N/A
|
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: 2.05%
|
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: N/A
|
32 Spring Pond DriveOssining, NYA beautifully maintained end-unit townhome nestled in the desirable Hamlet on Spring Pond ... |
2 beds | 3 baths | 2,100 sq.ft. |
$600,000 |
Airbnb cash on cash: -0.94%
|
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: 1.64%
|
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: 2.42%
|
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: 7.21%
|
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. |
$328,000 |
Airbnb cash on cash: 0.75%
|
7 Belleview AvenueOssining, NYThis beautifully maintained & newly renovated 3 bedroom l 2 bathroom home blends cozy char... |
3 beds | 2 baths | 971 sq.ft. |
$599,000 |
Airbnb cash on cash: 0.55%
|
15 Dale AvenueOssining, NYA rare opportunity to own this well built 1880's Duplex home with covered front porch & pe... |
3 beds | 2 baths | 1,568 sq.ft. |
$629,000 |
Airbnb cash on cash: 0.11%
|
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: -2.06%
|
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: 5.47%
|
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. |
$675,000 |
Airbnb cash on cash: 7.98%
|
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: 0.31%
|
Real Estate investment in Ossining, NY
There are 36 properties for sale in the city of Ossining . The median list price in Ossining is $539,500 and the average price per square foot is $323. In September 2025, the average monthly cash on cash return in Ossining is 3.00%. The average monthly rental income in Ossining is $3,498.