Real Estate Investment Properties for Sale in Shelter Island, NY

Looking for investment property in Shelter Island, NY with high ROI ?

Explore a variety of short-term homes & houses in Shelter Island, NY. Invest wisely with VRBO & Shelter Island, 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 Shelter Island, NY

Search for Single Family Residential for Sale in Shelter Island, 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 7 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
23 Osprey Rd Shelter Island, NY Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach...	4 beds \| 4 baths \| 3,484 sq.ft.	$2,350,000	Airbnb cash on cash: -0.73% Traditional cash on cash: 1.53% Airbnb Rental Income: $1906 Traditional Rental Income: $6326 Airbnb ROI: -0.73% Traditional ROI: 1.53%
4 Duvall Place Shelter Island, NY Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Islan...	3 beds \| 2 baths \| 1,200 sq.ft.	$1,350,000	Airbnb cash on cash: -1.58% Traditional cash on cash: -0.17% Airbnb Rental Income: $2038 Traditional Rental Income: $3277 Airbnb ROI: -1.58% Traditional ROI: -0.17%
141A N Ferry Road Shelter Island, NY Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the ...	4 beds \| 7 baths \| 5,500 sq.ft.	$4,250,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.96% Airbnb Rental Income: $1906 Traditional Rental Income: $8511 Airbnb ROI: -0.84% Traditional ROI: 0.96%
55 Peconic Ave Shelter Island, NY Welcome to 55 Peconic Avenue, a bold, newly built statement home completed in 2022 and set...	4 beds \| 3 baths \| N/A	$2,675,000	Airbnb cash on cash: -2.19% Traditional cash on cash: -0.8% Airbnb Rental Income: $1906 Traditional Rental Income: $4834 Airbnb ROI: -2.19% Traditional ROI: -0.8%
70 Peconic Ave Shelter Island, NY Introducing 70 Peconic Avenue-an irreplaceable, one-of-a-kind waterfront estate commanding...	4 beds \| 5 baths \| N/A	$4,479,000	Airbnb cash on cash: -2.4% Traditional cash on cash: -1.02% Airbnb Rental Income: $1906 Traditional Rental Income: $7130 Airbnb ROI: -2.4% Traditional ROI: -1.02%
8 Hilo Drive Shelter Island, NY This newly constructed modern residence offers stunning south-facing water views over West...	4 beds \| 6 baths \| 3,985 sq.ft.	$3,850,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.97% Airbnb Rental Income: $1906 Traditional Rental Income: $8327 Airbnb ROI: -0.97% Traditional ROI: 0.97%
16 Shelterlands Path Shelter Island, NY This island classic is truly a home for all seasons. The bright and open floor plan is bea...	3 beds \| 3 baths \| 1,950 sq.ft.	$1,175,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 2.28% Airbnb Rental Income: $2038 Traditional Rental Income: $4200 Airbnb ROI: -0.18% Traditional ROI: 2.28%

Your search for investment property begins and ends here

Single Family Homes for Sale in Shelter Island, NY

23 Osprey Rd

Shelter Island, NY

4 beds | 4 baths | 3,484 sq.ft.

$2,350,000

Airbnb cash on cash: -0.73%

Traditional cash on cash: 1.53%

Airbnb Rental Income: $1906

Traditional Rental Income: $6326

Airbnb ROI: -0.73%

Traditional ROI: 1.53%

4 Duvall Place

Shelter Island, NY

3 beds | 2 baths | 1,200 sq.ft.

$1,350,000

Airbnb cash on cash: -1.58%

Traditional cash on cash: -0.17%

Airbnb Rental Income: $2038

Traditional Rental Income: $3277

Airbnb ROI: -1.58%

Traditional ROI: -0.17%

141A N Ferry Road

Shelter Island, NY

4 beds | 7 baths | 5,500 sq.ft.

$4,250,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 0.96%

Airbnb Rental Income: $1906

Traditional Rental Income: $8511

Airbnb ROI: -0.84%

Traditional ROI: 0.96%

55 Peconic Ave

Shelter Island, NY

4 beds | 3 baths | N/A

$2,675,000

Airbnb cash on cash: -2.19%

Traditional cash on cash: -0.8%

Airbnb Rental Income: $1906

Traditional Rental Income: $4834

Airbnb ROI: -2.19%

Traditional ROI: -0.8%

70 Peconic Ave

Shelter Island, NY

4 beds | 5 baths | N/A

$4,479,000

Airbnb cash on cash: -2.4%

Traditional cash on cash: -1.02%

Airbnb Rental Income: $1906

Traditional Rental Income: $7130

Airbnb ROI: -2.4%

Traditional ROI: -1.02%

8 Hilo Drive

Shelter Island, NY

4 beds | 6 baths | 3,985 sq.ft.

$3,850,000

Airbnb cash on cash: -0.97%

Traditional cash on cash: 0.97%

Airbnb Rental Income: $1906

Traditional Rental Income: $8327

Airbnb ROI: -0.97%

Traditional ROI: 0.97%

16 Shelterlands Path

Shelter Island, NY

3 beds | 3 baths | 1,950 sq.ft.

$1,175,000

Airbnb cash on cash: -0.18%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $2038

Traditional Rental Income: $4200

Airbnb ROI: -0.18%

Traditional ROI: 2.28%

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