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.

Single Family Homes for Sale in Ossining, NY

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

Showing 23 Single Family Residential 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
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%
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%
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: 3.46% Traditional cash on cash: 9.25% Airbnb Rental Income: $2909 Traditional Rental Income: $4216 Airbnb ROI: 3.46% 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%
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%
133-3 S Highland Avenue #B4 Ossining, NY Highland Terrace is a pet friendly complex with assigned parking, an outdoor pool, & baske...	2 beds \| 1 baths \| 900 sq.ft.	$215,222	Airbnb cash on cash: -4.76% Traditional cash on cash: 1.29% Airbnb Rental Income: $2048 Traditional Rental Income: $2753 Airbnb ROI: -4.76% Traditional ROI: 1.29%
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: 6.44% Traditional cash on cash: 4.34% Airbnb Rental Income: $8572 Traditional Rental Income: $5585 Airbnb ROI: 6.44% Traditional ROI: 4.34%
19 Meadowbrook Drive Ossining, NY Enjoy sweeping Hudson River views from every room in this turnkey ranch. The sunlit living...	3 beds \| 3 baths \| 2,200 sq.ft.	$799,900	Airbnb cash on cash: -0.18% Traditional cash on cash: 2.84% Airbnb Rental Income: $2915 Traditional Rental Income: $4495 Airbnb ROI: -0.18% Traditional ROI: 2.84%
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: -2.47% Traditional cash on cash: 2.68% Airbnb Rental Income: $2048 Traditional Rental Income: $2964 Airbnb ROI: -2.47% Traditional ROI: 2.68%
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: 1.86% Traditional cash on cash: 9.01% Airbnb Rental Income: $2048 Traditional Rental Income: $3753 Airbnb ROI: 1.86% 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: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $5241 Airbnb ROI: N/A Traditional ROI: 1.73%
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: 2.05% Traditional cash on cash: 7.44% Airbnb Rental Income: $2048 Traditional Rental Income: $2665 Airbnb ROI: 2.05% 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: 1.64% Traditional cash on cash: 5.05% Airbnb Rental Income: $2915 Traditional Rental Income: $4939 Airbnb ROI: 1.64% 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: 2.42% Traditional cash on cash: 8.87% Airbnb Rental Income: $2048 Traditional Rental Income: $2742 Airbnb ROI: 2.42% 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: 7.21% Traditional cash on cash: 5.34% Airbnb Rental Income: $3447 Traditional Rental Income: $2415 Airbnb ROI: 7.21% 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.	$328,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.44% Airbnb Rental Income: $2048 Traditional Rental Income: $2655 Airbnb ROI: 0.75% Traditional ROI: 4.44%
7 Belleview Avenue Ossining, NY This beautifully maintained & newly renovated 3 bedroom l 2 bathroom home blends cozy char...	3 beds \| 2 baths \| 971 sq.ft.	$599,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 2.71% Airbnb Rental Income: $2915 Traditional Rental Income: $3446 Airbnb ROI: 0.55% Traditional ROI: 2.71%
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: 5.47% Traditional cash on cash: 2.58% Airbnb Rental Income: $8572 Traditional Rental Income: $4692 Airbnb ROI: 5.47% Traditional ROI: 2.58%
42 Campwoods Grounds Ossining, NY Step back in time and discover the charm of this turn-of-the-century cottage, nestled in t...	2 beds \| 2 baths \| 972 sq.ft.	$359,222	Airbnb cash on cash: 0.31% Traditional cash on cash: 5.24% Airbnb Rental Income: $2048 Traditional Rental Income: $3181 Airbnb ROI: 0.31% Traditional ROI: 5.24%

Your search for investment property begins and ends here

Single Family Homes for Sale in Ossining, NY

18 Jenkins Court

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%

8 Samstag Avenue

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%

1 Agate Avenue

Ossining, NY

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

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

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

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

$364,000

Airbnb cash on cash: 3.46%

Traditional cash on cash: 9.25%

Airbnb Rental Income: $2909

Traditional Rental Income: $4216

Airbnb ROI: 3.46%

Traditional ROI: 9.25%

1 Noel Drive

Ossining, NY

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%

3 Belleview Avenue

Ossining, NY

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%