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 |
|---|---|---|---|
124 Cedar LnOssining, NYCome see this great house located on 1.41 lovely acres with mature trees and a .50 acre bu... |
3 beds | 1 baths | 1,930 sq.ft. |
$749,000 |
Airbnb cash on cash: -1.97%
|
398 Illington RoadOssining, NYA Charming Farmhouse Style Home, Carefully Restored to Blend Historic Character with Moder... |
4 beds | 3 baths | 3,128 sq.ft. |
$624,000 |
Airbnb cash on cash: 2.22%
|
27 Ryder RdOssining, NYThis home is Spectacular and set on the most serene of settings. Wide open foyer and stai... |
4 beds | 3 baths | 2,573 sq.ft. |
$1,045,000 |
Airbnb cash on cash: 1.12%
|
17 Knoll VwOssining, NYCommuters dream with jitney to train. Great tri-level townhome which has been lovingly mai... |
1 beds | 2 baths | 1,203 sq.ft. |
$419,000 |
Airbnb cash on cash: -3.09%
|
55 Sherwood AveOssining, NYThis charming Dutch Colonial with rocking chair front porch has been owned by the same fam... |
3 beds | 1 baths | 1,701 sq.ft. |
$729,000 |
Airbnb cash on cash: -1.07%
|
128 Croton AveOssining, NYEverything new! Move right into this centrally located mixed use home and call it your ow... |
3 beds | 1 baths | 1,622 sq.ft. |
$200,000 |
Airbnb cash on cash: 1.34%
|
1 Edward StOssining, NYWell-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and of... |
5 beds | 2 baths | 1,860 sq.ft. |
$699,000 |
Airbnb cash on cash: -1.35%
|
227 Cedar LnOssining, NYEnchanting, historic hand-hewn log cabin on 6+ lush private acres. Stone fireplace, origin... |
2 beds | 1 baths | 900 sq.ft. |
$850,000 |
Airbnb cash on cash: -0.87%
|
22 Oakbrook RdOssining, NYWelcome home to this immaculate cape cod in Ossining! Inviting open floor plan makes enter... |
4 beds | 3 baths | 1,742 sq.ft. |
$684,900 |
Airbnb cash on cash: 2.66%
|
139 Spring StreetOssining, NYNestled in the heart of Ossining, this charming two-family home combines space, flexibilit... |
5 beds | 3 baths | N/A |
$799,000 |
Airbnb cash on cash: 3.44%
|
33 Maurice AveOssining, NYFull of warmth, character, and timeless appeal, this charming colonial home offers a wonde... |
3 beds | 1 baths | 1,280 sq.ft. |
$555,000 |
Airbnb cash on cash: -0.92%
|
16 Rockledge Ave #5P-2Ossining, NYWhen You Have Unobstructed Hudson River And Palisades Mountain Views From Every Window In ... |
2 beds | 2 baths | 1,580 sq.ft. |
$425,000 |
Airbnb cash on cash: -4.79%
|
1 Agate AvenueOssining, NYAre you thinking about making a move? This is the perfect opportunity you were waiting for... |
2 beds | 1 baths | 960 sq.ft. |
$399,000 |
Airbnb cash on cash: -0.02%
|
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: 0.72%
|
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: 0.42%
|
42 Campwoods GroundsOssining, NYThis beautifully updated home now features several new upgrades, including a fully reconst... |
2 beds | 2 baths | 972 sq.ft. |
$329,222 |
Airbnb cash on cash: 0.98%
|
22 Lafayette AvenueOssining, NYOpportunity knocks. Are you looking for a starter house or is it time to downsize? 22 Lafa... |
3 beds | 1 baths | 842 sq.ft. |
$335,000 |
Airbnb cash on cash: 0.77%
|
25 William StreetOssining, NYThis spacious three-family home in Ossining offers three full stories plus a finished base... |
7 beds | 3 baths | N/A |
$899,000 |
Airbnb cash on cash: 2.91%
|
110 Morningside DrOssining, NYWelcome Home and discover this charming ranch-style residence nestled in one of Ossining's... |
3 beds | 2 baths | 1,418 sq.ft. |
$750,000 |
Airbnb cash on cash: -1.76%
|
143 N Highland AveOssining, NYLegal 3-family home, located in the heart of Ossining. Excellent 1st time buyer opportunit... |
4 beds | 3 baths | 1,368 sq.ft. |
$799,000 |
Airbnb cash on cash: 2.03%
|
135 Main Street #203Ossining, NYFully available as f 1/7/2026. Exciting 2-bedroom condo in the Village of Ossining! Enjoy ... |
2 beds | 1 baths | 951 sq.ft. |
$210,000 |
Airbnb cash on cash: 0.83%
|
12 Broad AvenueOssining, NYTwo family home for sale. Each apartment is a very large one bedroom apartment. Private dr... |
2 beds | 3 baths | N/A |
$650,000 |
Airbnb cash on cash: -1.11%
|
335 Croton Dam RdOssining, NY335 Croton Dam Rd, Ossining, NY 10562 | Single Family Residential |
10 beds | 5 baths | 8,881 sq.ft. |
$3,500,000 |
Airbnb cash on cash: -1.19%
|
83 Somerstown RdOssining, NY83 Somerstown Rd, Ossining, NY 10562 | Single Family Residential |
7 beds | 5 baths | 5,502 sq.ft. |
$2,900,000 |
Airbnb cash on cash: -0.88%
|
94-3 Somerstown RdOssining, NY94-3 Somerstown Rd, Ossining, NY 10562 | Single Family Residential |
4 beds | 3 baths | 2,693 sq.ft. |
$1,899,000 |
Airbnb cash on cash: -0.43%
|
433 Arcady RdOssining, NY433 Arcady Rd, Ossining, NY 10562 | Single Family Residential |
7 beds | 5 baths | 5,700 sq.ft. |
$3,995,000 |
Airbnb cash on cash: -1.38%
|
7 Hawkes AveOssining, NY7 Hawkes Ave, Ossining, NY 10562 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$195,000 |
Airbnb cash on cash: -1.06%
|
Van Wyck StOssining, NYVan Wyck St, Ossining, NY 10562 | Other |
N/A beds | N/A baths | 0 sq.ft. |
$1,900,000 |
Airbnb cash on cash: -2.54%
|
131 Spring StreetOssining, NYNow offered at a compelling new price, 131 Spring Street is a restored brick two-family of... |
4 beds | 2 baths | N/A |
$799,000 |
Airbnb cash on cash: 2.42%
|
11 Meadowbrook DrOssining, NY11 Meadowbrook Dr, Ossining, NY 10562 | Single Family Residential |
3 beds | N/A baths | 1,750 sq.ft. |
$729,900 |
Airbnb cash on cash: -0.97%
|
81 Glendale RdOssining, NY81 Glendale Rd, Ossining, NY 10562 | Single Family Residential |
3 beds | 2 baths | 3,990 sq.ft. |
$825,000 |
Airbnb cash on cash: -1.17%
|
54 Allapartus RdOssining, NYSet on two peaceful acres in the desirable New Castle area, this thoughtfully updated home... |
4 beds | 3 baths | 2,606 sq.ft. |
$1,085,000 |
Airbnb cash on cash: 1.12%
|
42 Charter Circle #42Ossining, NYWelcome to 42 Charter Circle in Ossining, a home that offers space, comfort, and an incred... |
2 beds | 1 baths | 860 sq.ft. |
$235,000 |
Airbnb cash on cash: 4.49%
|
65 Morningside DriveOssining, NYTake A Stroll in the Park...The market has waited 50 years for this true gem of a home to ... |
3 beds | 2 baths | 1,563 sq.ft. |
$779,900 |
Airbnb cash on cash: -1.43%
|
16 Rockledge Avenue #5K-1Ossining, NYWelcome to Scarborough Manor, A Co-Op That Offers The Perfect Balance Of Tranquility And C... |
2 beds | 2 baths | 1,580 sq.ft. |
$415,000 |
Airbnb cash on cash: 1.4%
|
155 Charter Circle #155Ossining, NYWelcome to this spacious townhouse-style co-op in Ossining, NY. This inviting home feature... |
3 beds | 2 baths | 1,250 sq.ft. |
$285,000 |
Airbnb cash on cash: 1.7%
|
55 Hoags Cross RoadOssining, NYWelcome to 55 Hoags Cross Rd. in the desirable New Castle area of Ossining. Privately set ... |
3 beds | 2 baths | 2,292 sq.ft. |
$849,000 |
Airbnb cash on cash: -1.87%
|
15 Marshall PlaceOssining, NYWelcome home to a charming two family Dutch Colonial in the Forest Park area of Ossining. ... |
4 beds | 2 baths | N/A |
$750,000 |
Airbnb cash on cash: 2.09%
|
16 Rockledge #2Mm2Ossining, NYPerched gracefully above the majestic Hudson River, this beautifully renovated one-bedroom... |
1 beds | 1 baths | 736 sq.ft. |
$249,999 |
Airbnb cash on cash: -0.29%
|
58 Quakerbridge RdOssining, NY58 Quakerbridge Rd, Ossining, NY 10562 | Single Family Residential |
4 beds | 2 baths | 2,400 sq.ft. |
$765,000 |
Airbnb cash on cash: 2.94%
|
Real Estate investment in Ossining, NY
There are 96 properties for sale in the city of Ossining . The median list price in Ossining is $557,167 and the average price per square foot is $276. In July 2026, the average monthly cash on cash return in Ossining is 2.00%. The average monthly rental income in Ossining is $3,598.