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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
24 Nelson Avenue Ossining, NY Cozy One-Level Cottage on a Quiet Dead-End Street. This inviting home features a large eat...	2 beds \| 1 baths \| 767 sq.ft.	$399,222	Airbnb cash on cash: 0.57% Traditional cash on cash: 3.82% Airbnb Rental Income: $2148 Traditional Rental Income: $2819 Airbnb ROI: 0.57% Traditional ROI: 3.82%
12 Brooke Hollow Court Ossining, NY Enjoy 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: -0.65% Traditional cash on cash: 2.93% Airbnb Rental Income: $2148 Traditional Rental Income: $3554 Airbnb ROI: -0.65% Traditional ROI: 2.93%
9 High Ridge Road Ossining, NY Make an easy lifestyle transition to resort-style living in this beautifully-updated 3 bed...	3 beds \| 3 baths \| 2,715 sq.ft.	$900,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 1.23% Airbnb Rental Income: $3243 Traditional Rental Income: $4178 Airbnb ROI: -0.76% Traditional ROI: 1.23%
139 Spring Street Ossining, NY Nestled 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: 0.02% Traditional cash on cash: 1% Airbnb Rental Income: $3243 Traditional Rental Income: $3267 Airbnb ROI: 0.02% Traditional ROI: 1%
1 Agate Avenue Ossining, NY Westchester 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: -0.44% Traditional cash on cash: 3.04% Airbnb Rental Income: $2148 Traditional Rental Income: $2873 Airbnb ROI: -0.44% Traditional ROI: 3.04%
120 Morningside Drive Ossining, NY STUNNING, Georgous, Elegant, remarkable, a few words that don't even begin to scratch the ...	4 beds \| 3 baths \| 2,392 sq.ft.	$899,999	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.5% Airbnb Rental Income: $3298 Traditional Rental Income: $5485 Airbnb ROI: 0.01% Traditional ROI: 3.5%
30 Hunter Street Ossining, NY Here 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: -0.11% Traditional cash on cash: 4.41% Airbnb Rental Income: $2148 Traditional Rental Income: $2877 Airbnb ROI: -0.11% Traditional ROI: 4.41%
20 Maple Place Ossining, NY According to the Town Of Ossining this house is uninhabitable and it is unsafe to enter. A...	5 beds \| 2 baths \| 2,880 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 10.3% Airbnb Rental Income: $null Traditional Rental Income: $4216 Airbnb ROI: N/A Traditional ROI: 10.3%
459 Illington Road Ossining, NY Yorktown 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: 0.32% Traditional cash on cash: 2.2% Airbnb Rental Income: $3243 Traditional Rental Income: $3868 Airbnb ROI: 0.32% Traditional ROI: 2.2%
1 Noel Drive Ossining, NY Sprawling 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: -1.15% Traditional cash on cash: 1.58% Airbnb Rental Income: $3298 Traditional Rental Income: $4843 Airbnb ROI: -1.15% Traditional ROI: 1.58%
135 Main Street #203 Ossining, NY Exciting 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: 0.22% Traditional cash on cash: 5.18% Airbnb Rental Income: $2148 Traditional Rental Income: $2726 Airbnb ROI: 0.22% Traditional ROI: 5.18%
119 S Highland Avenue #1b Ossining, NY This beautifully updated 2-bedroom, 1-bathroom co-op offers a bright, spacious layout with...	2 beds \| 1 baths \| 900 sq.ft.	$174,999	Airbnb cash on cash: 3.4% Traditional cash on cash: 9.83% Airbnb Rental Income: $2148 Traditional Rental Income: $2673 Airbnb ROI: 3.4% Traditional ROI: 9.83%
50 Snowden Avenue Ossining, NY Welcome 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: -1.22% Traditional cash on cash: 2.34% Airbnb Rental Income: $2148 Traditional Rental Income: $3434 Airbnb ROI: -1.22% Traditional ROI: 2.34%
16 Rockledge Avenue #5B1 Ossining, NY Inspirational. 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: 2.12% Traditional cash on cash: 9.01% Airbnb Rental Income: $2148 Traditional Rental Income: $3753 Airbnb ROI: 2.12% Traditional ROI: 9.01%
129-1 South Highland Avenue #B6 Ossining, NY Welcome 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: 2.44% Traditional cash on cash: 7.44% Airbnb Rental Income: $2148 Traditional Rental Income: $2665 Airbnb ROI: 2.44% Traditional ROI: 7.44%
20 Pine Avenue Ossining, NY This 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 Traditional cash on cash: 3.59% Airbnb Rental Income: $null Traditional Rental Income: $4568 Airbnb ROI: N/A Traditional ROI: 3.59%
23-096 Liberty Street Ossining, NY THIS 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: 1.99% Traditional cash on cash: 5.05% Airbnb Rental Income: $3243 Traditional Rental Income: $4939 Airbnb ROI: 1.99% Traditional ROI: 5.05%
135-2 S Highland Avenue #B5 Ossining, NY Welcome 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: 2.86% Traditional cash on cash: 8.87% Airbnb Rental Income: $2148 Traditional Rental Income: $2742 Airbnb ROI: 2.86% Traditional ROI: 8.87%
117 S Highland Avenue #6j Ossining, NY Welcome 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: 3.15% Traditional cash on cash: 5.34% Airbnb Rental Income: $2748 Traditional Rental Income: $2415 Airbnb ROI: 3.15% Traditional ROI: 5.34%
17 CAMPWOODS Grounds Ossining, NY A 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: 0.89% Traditional cash on cash: 4.39% Airbnb Rental Income: $2148 Traditional Rental Income: $2655 Airbnb ROI: 0.89% Traditional ROI: 4.39%
58 Narragansett Avenue Ossining, NY Welcome 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: -0.15% Traditional cash on cash: 2.58% Airbnb Rental Income: $3298 Traditional Rental Income: $4692 Airbnb ROI: -0.15% Traditional ROI: 2.58%
90 Broadway Ossining, NY This Colonial TWO-FAMILY dwelling is located in the heart of the village. The large 3BR Ap...	4 beds \| 2 baths \| 1,935 sq.ft.	$629,900	Airbnb cash on cash: 1.14% Traditional cash on cash: 3.66% Airbnb Rental Income: $3298 Traditional Rental Income: $4041 Airbnb ROI: 1.14% Traditional ROI: 3.66%
127 S Highland Avenue #A4 Ossining, NY Welcome to 127 S Highland Avenue, Unit A4 in Ossining, NYâa bright and inviting cooperat...	1 beds \| 1 baths \| 750 sq.ft.	$130,000	Airbnb cash on cash: 8.86% Traditional cash on cash: 10.65% Airbnb Rental Income: $2748 Traditional Rental Income: $2324 Airbnb ROI: 8.86% Traditional ROI: 10.65%
42 Campwoods Grounds Ossining, NY This beautifully updated home now features several new upgrades, including a fully reconst...	2 beds \| 2 baths \| 972 sq.ft.	$349,222	Airbnb cash on cash: 0.6% Traditional cash on cash: 5.42% Airbnb Rental Income: $2148 Traditional Rental Income: $3181 Airbnb ROI: 0.6% Traditional ROI: 5.42%
9 Possum Road Ossining, NY Bring 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: -0.93% Traditional cash on cash: 1.57% Airbnb Rental Income: $3243 Traditional Rental Income: $4026 Airbnb ROI: -0.93% Traditional ROI: 1.57%
200 Route 9A Ossining, NY 2BR Apartment Included! Welcome to this stunning 5-bedroom, 3.5-bath Ossining home offerin...	5 beds \| 4 baths \| 2,520 sq.ft.	$1,099,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $5692 Airbnb ROI: N/A Traditional ROI: 2.58%
106 Mystic Drive #106 Ossining, NY Mystic 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: -0.98% Traditional cash on cash: 1.7% Airbnb Rental Income: $3243 Traditional Rental Income: $5256 Airbnb ROI: -0.98% Traditional ROI: 1.7%
19 Lincoln Place #55 Ossining, NY Welcome 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: -0.58% Traditional cash on cash: 4.09% Airbnb Rental Income: $2148 Traditional Rental Income: $3781 Airbnb ROI: -0.58% Traditional ROI: 4.09%
73 Van Cortlandt Avenue Ossining, NY Move right in to this brightly sun lit home. This "Turn Of The Century" Farmhouse with har...	3 beds \| 2 baths \| 1,482 sq.ft.	$595,500	Airbnb cash on cash: 0.6% Traditional cash on cash: 2.65% Airbnb Rental Income: $3243 Traditional Rental Income: $3654 Airbnb ROI: 0.6% Traditional ROI: 2.65%
22 Lafayette Avenue Ossining, NY Opportunity 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: 4.71% Traditional cash on cash: 6.46% Airbnb Rental Income: $3243 Traditional Rental Income: $3065 Airbnb ROI: 4.71% Traditional ROI: 6.46%
125 S Highland Avenue #4B Ossining, NY Popular 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: -2.16% Traditional cash on cash: 3.65% Airbnb Rental Income: $2148 Traditional Rental Income: $2810 Airbnb ROI: -2.16% Traditional ROI: 3.65%
22 William Street Ossining, NY Calling 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: -0.66% Traditional cash on cash: 5.69% Airbnb Rental Income: $2148 Traditional Rental Income: $3978 Airbnb ROI: -0.66% Traditional ROI: 5.69%
39 Ann Street Ossining, NY Welcome 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: 2.72% Traditional cash on cash: 3.69% Airbnb Rental Income: $3243 Traditional Rental Income: $2971 Airbnb ROI: 2.72% Traditional ROI: 3.69%
25 William Street Ossining, NY This 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: N/A Traditional cash on cash: 1.97% Airbnb Rental Income: $null Traditional Rental Income: $4383 Airbnb ROI: N/A Traditional ROI: 1.97%
18 Adams Road Ossining, NY Welcome 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: 0.22% Traditional cash on cash: 1.77% Airbnb Rental Income: $3243 Traditional Rental Income: $3667 Airbnb ROI: 0.22% Traditional ROI: 1.77%
19 Donald Lane Ossining, NY Located along a peaceful cul-de-sac in Ossining, there is a quiet grace to 19 Donald Lane....	3 beds \| 2 baths \| 1,408 sq.ft.	$695,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 2.11% Airbnb Rental Income: $3243 Traditional Rental Income: $3777 Airbnb ROI: 0.16% Traditional ROI: 2.11%
110 Morningside Drive Ossining, NY Welcome Home and discover this charming ranch-style residence nestled in one of Ossiningâ...	3 beds \| 2 baths \| 1,418 sq.ft.	$799,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 1.52% Airbnb Rental Income: $3243 Traditional Rental Income: $3688 Airbnb ROI: -0.05% Traditional ROI: 1.52%
84 Charter Circle unit: 84 #84 Ossining, NY Charming Garden-Style Co-op - Light and airy Unit with Modern Upgrades Welcome to this bea...	2 beds \| 1 baths \| 900 sq.ft.	$245,000	Airbnb cash on cash: -4.67% Traditional cash on cash: -0.29% Airbnb Rental Income: $2148 Traditional Rental Income: $2615 Airbnb ROI: -4.67% Traditional ROI: -0.29%
119 S Highland Avenue unit: 5B #5B Ossining, NY Accepted Offer as of 10/29 - Incredible value! This is a wonderful 2-bedroom home at The P...	2 beds \| 1 baths \| 936 sq.ft.	$179,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 10.52% Airbnb Rental Income: $2148 Traditional Rental Income: $2831 Airbnb ROI: 3.3% Traditional ROI: 10.52%
7 Locust Road Ossining, NY Immaculate Move-In Ready Home in the Heart of Westchester This pristine raised ranch combi...	3 beds \| 2 baths \| 1,747 sq.ft.	$749,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 1.63% Airbnb Rental Income: $3243 Traditional Rental Income: $3774 Airbnb ROI: -0.18% Traditional ROI: 1.63%

Real Estate investment in Ossining, NY

There are 44 properties for sale in the city of Ossining . The median list price in Ossining is $567,500 and the average price per square foot is $342. In December 2025, the average monthly cash on cash return in Ossining is 4.00%. The average monthly rental income in Ossining is $3,721.

Ossining, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 44 investment properties available for sale in Ossining.

In 2025, the best neighborhood to buy investment property is Ossining.

The ROI for Short-Term is higher than the Long-Term in Ossining with average rental income of $2,996.

Your search for investment property begins and ends here

Investment Property for Sale in Ossining, NY

24 Nelson Avenue

Ossining, NY

2 beds | 1 baths | 767 sq.ft.

$399,222

Airbnb cash on cash: 0.57%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $2148

Traditional Rental Income: $2819

Airbnb ROI: 0.57%

Traditional ROI: 3.82%

12 Brooke Hollow Court

Ossining, NY

2 beds | 3 baths | 1,400 sq.ft.

$585,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $2148

Traditional Rental Income: $3554

Airbnb ROI: -0.65%

Traditional ROI: 2.93%

9 High Ridge Road

Ossining, NY

3 beds | 3 baths | 2,715 sq.ft.

$900,000

Airbnb cash on cash: -0.76%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $3243

Traditional Rental Income: $4178

Airbnb ROI: -0.76%

Traditional ROI: 1.23%

139 Spring Street

Ossining, NY

5 beds | 3 baths | 2,812 sq.ft.

$828,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 1%

Airbnb Rental Income: $3243

Traditional Rental Income: $3267

Airbnb ROI: 0.02%

Traditional ROI: 1%

1 Agate Avenue

Ossining, NY

2 beds | 1 baths | 960 sq.ft.

$389,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $2148

Traditional Rental Income: $2873

Airbnb ROI: -0.44%

Traditional ROI: 3.04%

120 Morningside Drive

Ossining, NY

4 beds | 3 baths | 2,392 sq.ft.

$899,999

Airbnb cash on cash: 0.01%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $3298

Traditional Rental Income: $5485

Airbnb ROI: 0.01%

Traditional ROI: 3.5%

30 Hunter Street

Ossining, NY

2 beds | 1 baths | 1,474 sq.ft.

$300,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $2148

Traditional Rental Income: $2877

Airbnb ROI: -0.11%

Traditional ROI: 4.41%

20 Maple Place

Ossining, NY

5 beds | 2 baths | 2,880 sq.ft.

$329,900

Airbnb cash on cash: N/A

Traditional cash on cash: 10.3%

Airbnb Rental Income: $null

Traditional Rental Income: $4216

Airbnb ROI: N/A