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 17 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
398 Illington Road Ossining, NY A Charming Farmhouse Style Home, Carefully Restored to Blend Historic Character with Moder...	4 beds \| 3 baths \| 3,128 sq.ft.	$774,000	Airbnb cash on cash: -2.16% Traditional cash on cash: 1.17% Airbnb Rental Income: $1913 Traditional Rental Income: $3806 Airbnb ROI: -2.16% Traditional ROI: 1.17%
4 Spaulding Place Ossining, NY PLEASE NOTE: Home is occupied, appointment required for access to the property. Do not tre...	3 beds \| 2 baths \| 1,636 sq.ft.	$600,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.55% Airbnb Rental Income: $3082 Traditional Rental Income: $3761 Airbnb ROI: 0.08% Traditional ROI: 2.55%
1 Agate Avenue Ossining, NY Are you thinking about making a move? This is the perfect opportunity you were waiting for...	2 beds \| 1 baths \| 960 sq.ft.	$399,000	Airbnb cash on cash: -2.33% Traditional cash on cash: 3.15% Airbnb Rental Income: $1217 Traditional Rental Income: $2873 Airbnb ROI: -2.33% Traditional ROI: 3.15%
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: -2.53% Traditional cash on cash: 1.58% Airbnb Rental Income: $1913 Traditional Rental Income: $4843 Airbnb ROI: -2.53% Traditional ROI: 1.58%
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: 1.82% Traditional cash on cash: 5.05% Airbnb Rental Income: $3082 Traditional Rental Income: $4939 Airbnb ROI: 1.82% Traditional ROI: 5.05%
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.	$329,222	Airbnb cash on cash: -1.81% Traditional cash on cash: 5.8% Airbnb Rental Income: $1217 Traditional Rental Income: $3181 Airbnb ROI: -1.81% Traditional ROI: 5.8%
200 Route 9A Ossining, NY Exceptional residence featuring a fully legal accessory apartment, offering rare flexibili...	5 beds \| 4 baths \| 2,520 sq.ft.	$1,099,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 2.58% Airbnb Rental Income: $5523 Traditional Rental Income: $5692 Airbnb ROI: 1.33% Traditional ROI: 2.58%
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: 4.28% Traditional cash on cash: 6.46% Airbnb Rental Income: $3082 Traditional Rental Income: $3065 Airbnb ROI: 4.28% Traditional ROI: 6.46%
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: 0.04% Traditional cash on cash: 1.77% Airbnb Rental Income: $3082 Traditional Rental Income: $3667 Airbnb ROI: 0.04% Traditional ROI: 1.77%
63 Cedar Lane Ossining, NY Welcome to 63 Cedar Lane - Your Hudson River Retreat! Perched on one of Ossining's most so...	3 beds \| 3 baths \| 2,100 sq.ft.	$849,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 2.15% Airbnb Rental Income: $3082 Traditional Rental Income: $4023 Airbnb ROI: 0.07% Traditional ROI: 2.15%
59 Watson Avenue Ossining, NY Move right in to this beautifully maintained home, freshly painted throughout the interior...	3 beds \| 2 baths \| 1,730 sq.ft.	$649,222	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.85% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: 0.09% Traditional ROI: 1.85%
65 Morningside Drive Ossining, NY Take A Stroll in the Park...The market has waited 50 years for this true gem of a home to ...	3 beds \| 2 baths \| 1,563 sq.ft.	$779,900	Airbnb cash on cash: 0.09% Traditional cash on cash: 1.56% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: 0.09% Traditional ROI: 1.56%
48 Pershing Avenue Ossining, NY Charming and updated Cape Cod-style home in desirable village location. This light-filled ...	4 beds \| 2 baths \| 1,463 sq.ft.	$629,222	Airbnb cash on cash: -1.17% Traditional cash on cash: 3.05% Airbnb Rental Income: $1913 Traditional Rental Income: $3881 Airbnb ROI: -1.17% Traditional ROI: 3.05%
36 Watson Avenue Ossining, NY Perched in the hills above historic downtown Ossining, this artfully renovated colonial wi...	5 beds \| 4 baths \| 2,049 sq.ft.	$745,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 3.16% Airbnb Rental Income: $5523 Traditional Rental Income: $4936 Airbnb ROI: 2.41% Traditional ROI: 3.16%
55 Hoags Cross Road Ossining, NY Welcome to 55 Hoags Cross Rd. in the desirable New Castle area of Ossining. This beautiful...	3 beds \| 2 baths \| 2,292 sq.ft.	$899,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.77% Airbnb Rental Income: $3082 Traditional Rental Income: $3444 Airbnb ROI: -0.5% Traditional ROI: 0.77%
15 Prospect Avenue Ossining, NY Step into a welcoming three-bedroom, two full-bath home that's ready to make your life eas...	3 beds \| 2 baths \| 1,520 sq.ft.	$575,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.99% Airbnb Rental Income: $3082 Traditional Rental Income: $3580 Airbnb ROI: 0.75% Traditional ROI: 2.99%
27 Allapartus Circle Ossining, NY This distinctive Teatown compound made for gatherings and entertainment blends timeless cr...	5 beds \| 3 baths \| 3,867 sq.ft.	$1,200,000	Airbnb cash on cash: 0.63% Traditional cash on cash: N/A Airbnb Rental Income: $5523 Traditional Rental Income: $0 Airbnb ROI: 0.63% Traditional ROI: N/A

Your search for investment property begins and ends here

Single Family Homes for Sale in Ossining, NY

398 Illington Road

Ossining, NY

4 beds | 3 baths | 3,128 sq.ft.

$774,000

Airbnb cash on cash: -2.16%

Traditional cash on cash: 1.17%

Airbnb Rental Income: $1913

Traditional Rental Income: $3806

Airbnb ROI: -2.16%

Traditional ROI: 1.17%

4 Spaulding Place

Ossining, NY

3 beds | 2 baths | 1,636 sq.ft.

$600,000

Airbnb cash on cash: 0.08%

Traditional cash on cash: 2.55%

Airbnb Rental Income: $3082

Traditional Rental Income: $3761

Airbnb ROI: 0.08%

Traditional ROI: 2.55%

1 Agate Avenue

Ossining, NY

2 beds | 1 baths | 960 sq.ft.

$399,000

Airbnb cash on cash: -2.33%

Traditional cash on cash: 3.15%

Airbnb Rental Income: $1217

Traditional Rental Income: $2873

Airbnb ROI: -2.33%

Traditional ROI: 3.15%

1 Noel Drive

Ossining, NY

4 beds | 3 baths | 3,551 sq.ft.

$899,222

Airbnb cash on cash: -2.53%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $1913

Traditional Rental Income: $4843

Airbnb ROI: -2.53%

Traditional ROI: 1.58%

23-096 Liberty Street

Ossining, NY

3 beds | 3 baths | 2,250 sq.ft.

$850,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 5.05%

Airbnb Rental Income: $3082

Traditional Rental Income: $4939

Airbnb ROI: 1.82%

Traditional ROI: 5.05%

42 Campwoods Grounds

Ossining, NY

2 beds | 2 baths | 972 sq.ft.

$329,222

Airbnb cash on cash: -1.81%

Traditional cash on cash: 5.8%

Airbnb Rental Income: $1217

Traditional Rental Income: $3181

Airbnb ROI: -1.81%

Traditional ROI: 5.8%

200 Route 9A

Ossining, NY

5 beds | 4 baths | 2,520 sq.ft.

$1,099,000

Airbnb cash on cash: 1.33%

Traditional cash on cash: 2.58%

Airbnb Rental Income: $5523

Traditional Rental Income: $5692

Airbnb ROI: 1.33%

Traditional ROI: 2.58%

22 Lafayette Avenue

Ossining, NY

3 beds | 1 baths | 842 sq.ft.

$335,000

Airbnb cash on cash: 4.28%

Traditional cash on cash: 6.46%

Airbnb Rental Income: $3082

Traditional Rental Income: $3065

Airbnb ROI: 4.28%