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.

Multi Family for Sale in Ossining, NY

Search for Multi Family for Sale in Ossining, New York. Browse all of Mashvisor’s Multi Family listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 3 Multi Family listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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: -1.21% Traditional cash on cash: 1% Airbnb Rental Income: $2102 Traditional Rental Income: $3267 Airbnb ROI: -1.21% Traditional ROI: 1%
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.	$635,000	Airbnb cash on cash: 5.07% Traditional cash on cash: 3.63% Airbnb Rental Income: $6099 Traditional Rental Income: $4041 Airbnb ROI: 5.07% Traditional ROI: 3.63%
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: -0.76% Traditional cash on cash: 5.69% Airbnb Rental Income: $2102 Traditional Rental Income: $3978 Airbnb ROI: -0.76% Traditional ROI: 5.69%
Other Investment Properties for Sale in Ossining
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: -0.72% Traditional cash on cash: 2.93% Airbnb Rental Income: $2102 Traditional Rental Income: $3554 Airbnb ROI: -0.72% Traditional ROI: 2.93%
201 Horseshoe Circle Ossining , NY MOVE-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% Traditional cash on cash: 0.91% Airbnb Rental Income: $2102 Traditional Rental Income: $2986 Airbnb ROI: -1.27% Traditional ROI: 0.91%
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: -0.55% Traditional cash on cash: 3.04% Airbnb Rental Income: $2102 Traditional Rental Income: $2873 Airbnb ROI: -0.55% Traditional ROI: 3.04%
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: -0.24% Traditional cash on cash: 4.41% Airbnb Rental Income: $2102 Traditional Rental Income: $2877 Airbnb ROI: -0.24% Traditional ROI: 4.41%
320 Illington Road Ossining , NY Kitchawan 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% Traditional cash on cash: 1.27% Airbnb Rental Income: $6099 Traditional Rental Income: $4761 Airbnb ROI: 1.39% Traditional ROI: 1.27%
20 Maple Place Ossining , NY According 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% Traditional cash on cash: 9.25% Airbnb Rental Income: $4886 Traditional Rental Income: $4216 Airbnb ROI: 8.28% Traditional ROI: 9.25%
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: 1.46% Traditional cash on cash: 2.2% Airbnb Rental Income: $4234 Traditional Rental Income: $3868 Airbnb ROI: 1.46% 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: 1.64% Traditional cash on cash: 1.58% Airbnb Rental Income: $6099 Traditional Rental Income: $4843 Airbnb ROI: 1.64% 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: 0.05% Traditional cash on cash: 5.18% Airbnb Rental Income: $2102 Traditional Rental Income: $2726 Airbnb ROI: 0.05% Traditional ROI: 5.18%
11c Piping Rock Drive Ossining , NY A/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% Traditional cash on cash: 4.34% Airbnb Rental Income: $6099 Traditional Rental Income: $5585 Airbnb ROI: 3.28% Traditional ROI: 4.34%
95 Charter Circle #95 Ossining , NY If 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% Traditional cash on cash: 2.68% Airbnb Rental Income: $2102 Traditional Rental Income: $2964 Airbnb ROI: -2.31% Traditional ROI: 2.68%
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: -1.3% Traditional cash on cash: 2.34% Airbnb Rental Income: $2102 Traditional Rental Income: $3434 Airbnb ROI: -1.3% 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% Traditional cash on cash: 9.01% Airbnb Rental Income: $2102 Traditional Rental Income: $3753 Airbnb ROI: 2% Traditional ROI: 9.01%
83 McDonald Road Ossining , NY Stunning 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% Traditional cash on cash: 1.73% Airbnb Rental Income: $4886 Traditional Rental Income: $5241 Airbnb ROI: 0.4% Traditional ROI: 1.73%

Your search for investment property begins and ends here

Multi Family for Sale in Ossining, NY

139 Spring Street

Ossining, NY

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

$828,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 1%

Airbnb Rental Income: $2102

Traditional Rental Income: $3267

Airbnb ROI: -1.21%

Traditional ROI: 1%

90 Broadway

Ossining, NY

4 beds | 2 baths | 1,935 sq.ft.

$635,000

Airbnb cash on cash: 5.07%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $6099

Traditional Rental Income: $4041

Airbnb ROI: 5.07%

Traditional ROI: 3.63%

22 William Street

Ossining, NY

4 beds | 2 baths | 2,116 sq.ft.

$399,222

Airbnb cash on cash: -0.76%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $2102

Traditional Rental Income: $3978

Airbnb ROI: -0.76%

Traditional ROI: 5.69%

Other Investment Properties for Sale in Ossining

Ossining , NY

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

$585,000

Airbnb cash on cash: -0.72%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $2102

Traditional Rental Income: $3554

Airbnb ROI: -0.72%

Traditional ROI: 2.93%

Ossining , NY

2 beds | 3 baths | 1,784 sq.ft.

$699,999

Airbnb cash on cash: -1.27%

Traditional cash on cash: 0.91%

Airbnb Rental Income: $2102

Traditional Rental Income: $2986

Airbnb ROI: -1.27%

Traditional ROI: 0.91%

Ossining , NY

2 beds | 1 baths | 960 sq.ft.

$389,000

Airbnb cash on cash: -0.55%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $2102

Traditional Rental Income: $2873

Airbnb ROI: -0.55%

Traditional ROI: 3.04%

Ossining , NY

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

$300,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $2102

Traditional Rental Income: $2877

Airbnb ROI: -0.24%

Traditional ROI: 4.41%

Ossining , NY

4 beds | 3 baths | 2,950 sq.ft.

$1,203,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 1.27%

Airbnb Rental Income: $6099

Traditional Rental Income: $4761

Airbnb ROI: 1.39%

Traditional ROI: 1.27%

Ossining , NY

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

$364,000