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
23 Ann Street Ossining, NY TWO 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% Traditional cash on cash: 3.57% Airbnb Rental Income: $2048 Traditional Rental Income: $3678 Airbnb ROI: 0.01% Traditional ROI: 3.57%
15 Dale Avenue Ossining, NY A 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% Traditional cash on cash: 2.43% Airbnb Rental Income: $2915 Traditional Rental Income: $3601 Airbnb ROI: 0.11% Traditional ROI: 2.43%
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.	$675,000	Airbnb cash on cash: 7.98% Traditional cash on cash: 3.36% Airbnb Rental Income: $8572 Traditional Rental Income: $4041 Airbnb ROI: 7.98% Traditional ROI: 3.36%
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: -0.8% Traditional cash on cash: 2.93% Airbnb Rental Income: $2048 Traditional Rental Income: $3554 Airbnb ROI: -0.8% Traditional ROI: 2.93%
18 Jenkins Court Ossining , NY Tucked 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% Traditional cash on cash: 3.21% Airbnb Rental Income: $8572 Traditional Rental Income: $4557 Airbnb ROI: 6.89% Traditional ROI: 3.21%
33 Fawn Court Ossining , NY Tucked 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% Traditional cash on cash: 3.18% Airbnb Rental Income: $3447 Traditional Rental Income: $3107 Airbnb ROI: 2.27% Traditional ROI: 3.18%
193 Woods Brooke Circle Ossining , NY Stunning 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% Traditional cash on cash: 2.56% Airbnb Rental Income: $2048 Traditional Rental Income: $3550 Airbnb ROI: -0.87% Traditional ROI: 2.56%
8 Samstag Avenue Ossining , NY Come 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% Traditional cash on cash: 2.92% Airbnb Rental Income: $2915 Traditional Rental Income: $3018 Airbnb ROI: 1.22% Traditional ROI: 2.92%
88 Broadway #PH4 Ossining , NY Experience 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% Traditional cash on cash: 2.39% Airbnb Rental Income: $2048 Traditional Rental Income: $3223 Airbnb ROI: -1.06% Traditional ROI: 2.39%
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: -1.34% Traditional cash on cash: 0.91% Airbnb Rental Income: $2048 Traditional Rental Income: $2986 Airbnb ROI: -1.34% 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: -0.67% Traditional cash on cash: 3.04% Airbnb Rental Income: $2048 Traditional Rental Income: $2873 Airbnb ROI: -0.67% 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: -0.4% Traditional cash on cash: 4.41% Airbnb Rental Income: $2048 Traditional Rental Income: $2877 Airbnb ROI: -0.4% 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: 3.24% Traditional cash on cash: 1.27% Airbnb Rental Income: $8572 Traditional Rental Income: $4761 Airbnb ROI: 3.24% 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: N/A Traditional cash on cash: 9.25% Airbnb Rental Income: $null Traditional Rental Income: $4216 Airbnb ROI: N/A Traditional ROI: 9.25%
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: 4.16% Traditional cash on cash: 1.64% Airbnb Rental Income: $8572 Traditional Rental Income: $4843 Airbnb ROI: 4.16% Traditional ROI: 1.64%
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.	$250,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 4.94% Airbnb Rental Income: $2048 Traditional Rental Income: $2726 Airbnb ROI: -0.18% Traditional ROI: 4.94%
3 Belleview Avenue Ossining , NY Great 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% Traditional cash on cash: 5.96% Airbnb Rental Income: $2915 Traditional Rental Income: $3707 Airbnb ROI: 2.04% Traditional ROI: 5.96%

Your search for investment property begins and ends here

Multi Family for Sale in Ossining, NY

23 Ann Street

Ossining, NY

5 beds | 2 baths | 1,800 sq.ft.

$650,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $2048

Traditional Rental Income: $3678

Airbnb ROI: 0.01%

Traditional ROI: 3.57%

15 Dale Avenue

Ossining, NY

3 beds | 2 baths | 1,568 sq.ft.

$629,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 2.43%

Airbnb Rental Income: $2915

Traditional Rental Income: $3601

Airbnb ROI: 0.11%

Traditional ROI: 2.43%

90 Broadway

Ossining, NY

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

$675,000

Airbnb cash on cash: 7.98%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $8572

Traditional Rental Income: $4041

Airbnb ROI: 7.98%

Traditional ROI: 3.36%

Other Investment Properties for Sale in Ossining

Ossining , NY

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

$585,000

Airbnb cash on cash: -0.8%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $2048

Traditional Rental Income: $3554

Airbnb ROI: -0.8%

Traditional ROI: 2.93%

Ossining , NY

4 beds | 3 baths | 1,932 sq.ft.

$698,000

Airbnb cash on cash: 6.89%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $8572

Traditional Rental Income: $4557

Airbnb ROI: 6.89%

Traditional ROI: 3.21%

Ossining , NY

1 beds | 2 baths | 1,287 sq.ft.

$499,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $3447

Traditional Rental Income: $3107

Airbnb ROI: 2.27%

Traditional ROI: 3.18%

Ossining , NY

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

$635,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $2048

Traditional Rental Income: $3550

Airbnb ROI: -0.87%

Traditional ROI: 2.56%

Ossining , NY

3 beds | 1 baths | 1,031 sq.ft.

$489,500

Airbnb cash on cash: 1.22%

Traditional cash on cash: 2.92%

Airbnb Rental Income: $2915

Traditional Rental Income: $3018

Airbnb ROI: 1.22%

Traditional ROI: 2.92%

Ossining , NY

2 beds | 3 baths | 1,102 sq.ft.

$529,000