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.

Condos for Sale in Ossining, NY

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

Showing 7 Condo 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
88 Broadway #Ph1 Ossining, NY Rare opportunity to purchase a stunning 2 Bedroom/2.5 Bath penthouse condo in the heart of...	2 beds \| 3 baths \| 1,332 sq.ft.	$538,888	Airbnb cash on cash: -0.54% Traditional cash on cash: 2.78% Airbnb Rental Income: $2653 Traditional Rental Income: $3690 Airbnb ROI: -0.54% Traditional ROI: 2.78%
135 Main Street #203 Ossining, NY Fully 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: 2.5% Traditional cash on cash: 5.94% Airbnb Rental Income: $2653 Traditional Rental Income: $2705 Airbnb ROI: 2.5% Traditional ROI: 5.94%
806 Eagle Bay Drive Ossining, NY Welcome to beautiful Eagle Bay, a gated community along the Hudson River in Ossining. Enjo...	1 beds \| 2 baths \| 1,233 sq.ft.	$475,900	Airbnb cash on cash: -1.37% Traditional cash on cash: 3.98% Airbnb Rental Income: $946 Traditional Rental Income: $2980 Airbnb ROI: -1.37% Traditional ROI: 3.98%
14 Bridle Path Road Ossining, NY Welcome to this tastefully updated one-bedroom townhouse with loft in the highly desirable...	1 beds \| 2 baths \| 1,152 sq.ft.	$525,000	Airbnb cash on cash: -2.04% Traditional cash on cash: 2.97% Airbnb Rental Income: $946 Traditional Rental Income: $3061 Airbnb ROI: -2.04% Traditional ROI: 2.97%
133-3 S Highland Ave #5B Ossining, NY 133-3 S Highland Ave #5B, Ossining, NY 10562 \| Condo/Coop	2 beds \| 1 baths \| 950 sq.ft.	$215,000	Airbnb cash on cash: 6.78% Traditional cash on cash: 9.65% Airbnb Rental Income: $2653 Traditional Rental Income: $2607 Airbnb ROI: 6.78% Traditional ROI: 9.65%
3 Hudson View Hill Ossining, NY Welcome to 3 Hudson View Hill, a charming end-unit townhome tucked into the sought-after R...	2 beds \| 2 baths \| 1,311 sq.ft.	$475,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 3.77% Airbnb Rental Income: $2653 Traditional Rental Income: $3493 Airbnb ROI: 0.46% Traditional ROI: 3.77%
6 Spring Pond Dr Ossining, NY 6 Spring Pond Dr, Ossining, NY 10562 \| Condo/Coop	1 beds \| 1 baths \| 1,938 sq.ft.	$749,000	Airbnb cash on cash: -2.93% Traditional cash on cash: -0.94% Airbnb Rental Income: $946 Traditional Rental Income: $1992 Airbnb ROI: -2.93% Traditional ROI: -0.94%

Your search for investment property begins and ends here

Condos for Sale in Ossining, NY

88 Broadway #Ph1

Ossining, NY

2 beds | 3 baths | 1,332 sq.ft.

$538,888

Airbnb cash on cash: -0.54%

Traditional cash on cash: 2.78%

Airbnb Rental Income: $2653

Traditional Rental Income: $3690

Airbnb ROI: -0.54%

Traditional ROI: 2.78%

135 Main Street #203

Ossining, NY

2 beds | 1 baths | 951 sq.ft.

$210,000

Airbnb cash on cash: 2.5%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $2653

Traditional Rental Income: $2705

Airbnb ROI: 2.5%

Traditional ROI: 5.94%

806 Eagle Bay Drive

Ossining, NY

1 beds | 2 baths | 1,233 sq.ft.

$475,900

Airbnb cash on cash: -1.37%

Traditional cash on cash: 3.98%

Airbnb Rental Income: $946

Traditional Rental Income: $2980

Airbnb ROI: -1.37%

Traditional ROI: 3.98%

14 Bridle Path Road

Ossining, NY

1 beds | 2 baths | 1,152 sq.ft.

$525,000

Airbnb cash on cash: -2.04%

Traditional cash on cash: 2.97%

Airbnb Rental Income: $946

Traditional Rental Income: $3061

Airbnb ROI: -2.04%

Traditional ROI: 2.97%

133-3 S Highland Ave #5B

Ossining, NY

2 beds | 1 baths | 950 sq.ft.

$215,000

Airbnb cash on cash: 6.78%

Traditional cash on cash: 9.65%

Airbnb Rental Income: $2653

Traditional Rental Income: $2607

Airbnb ROI: 6.78%

Traditional ROI: 9.65%

3 Hudson View Hill

Ossining, NY

2 beds | 2 baths | 1,311 sq.ft.

$475,000

Airbnb cash on cash: 0.46%

Traditional cash on cash: 3.77%

Airbnb Rental Income: $2653

Traditional Rental Income: $3493

Airbnb ROI: 0.46%

Traditional ROI: 3.77%

6 Spring Pond Dr

Ossining, NY

1 beds | 1 baths | 1,938 sq.ft.

$749,000

Airbnb cash on cash: -2.93%

Traditional cash on cash: -0.94%

Airbnb Rental Income: $946

Traditional Rental Income: $1992

Airbnb ROI: -2.93%

Traditional ROI: -0.94%

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