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.
Investment Property for Sale in Shelter Island, NY
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
9 Margarets DriveShelter Island, NYOriginally conceived as the Laguna Project, 9 Margarets is an AIA award-winning modern res... |
4 beds | 6 baths | 4,250 sq.ft. |
$5,395,000 |
Airbnb cash on cash: -1.01%
|
23 Osprey RdShelter Island, NYSituated in the desirable Sherwood Farms neighborhood, just moments from the private beach... |
4 beds | 4 baths | 3,484 sq.ft. |
$1,995,000 |
Airbnb cash on cash: -0.73%
|
4 Duvall PlaceShelter Island, NYAmazing 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: -1.04%
|
9 Locust Woods DrShelter Island, NYWelcome to Shelter Island - a place where time slows down and nature takes center stage. A... |
4 beds | 3 baths | 3,856 sq.ft. |
$3,499,000 |
Airbnb cash on cash: -0.93%
|
141A N Ferry RdShelter Island, NYWelcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the ... |
4 beds | 5 baths | 5,500 sq.ft. |
$3,999,000 |
Airbnb cash on cash: -0.85%
|
90 Peconic AveShelter Island, NYSome properties are simply irreplaceable. This is one of them. Held by a single family for... |
5 beds | 3 baths | 3,325 sq.ft. |
$4,800,000 |
Airbnb cash on cash: -0.81%
|
11 Sunnyside AveShelter Island, NYAn architecturally significant modern retreat set on two private acres within coveted Shel... |
4 beds | 5 baths | 4,000 sq.ft. |
$5,500,000 |
Airbnb cash on cash: -0.83%
|
8 Hilo DrShelter Island, NYThis newly constructed modern residence offers stunning south-facing water views over West... |
4 beds | 5 baths | 3,985 sq.ft. |
$3,850,000 |
Airbnb cash on cash: -0.99%
|
16 Shelterlands PathShelter Island, NYThis 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: 0.45%
|
5 Marc StShelter Island, NYWelcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newl... |
4 beds | 3 baths | 2,777 sq.ft. |
$2,350,000 |
Airbnb cash on cash: -0.56%
|
28 S Menantic RdShelter Island, NYBuilt in 1888 and thoughtfully renovated by acclaimed architect Lee H. Skolnick in 1988, t... |
4 beds | 6 baths | 3,863 sq.ft. |
$6,495,000 |
Airbnb cash on cash: -1.11%
|
3 Conrad RdShelter Island, NYSet on a quiet street in the Montclair Colony section of Shelter Island, this newly renova... |
4 beds | 4 baths | 2,000 sq.ft. |
$2,695,000 |
Airbnb cash on cash: -0.62%
|
60 W Neck RdShelter Island, NYPool Possible- subject to Permits and approvals. |
2 beds | 2 baths | 1,376 sq.ft. |
$950,000 |
Airbnb cash on cash: 1.32%
|
64A N Midway RdShelter Island, NY64A N Midway Rd, Shelter Island, NY 11964 | Single Family Residential |
5 beds | 4 baths | 2,642 sq.ft. |
$2,199,000 |
Airbnb cash on cash: -1.4%
|
6 Great Circle DrShelter Island, NY6 Great Circle Dr, Shelter Island, NY 11964 | Single Family Residential |
5 beds | 6 baths | 5,535 sq.ft. |
$4,995,000 |
Airbnb cash on cash: -2.13%
|
5 Osprey LnShelter Island, NY5 Osprey Ln, Shelter Island, NY 11964 | Single Family Residential |
4 beds | 4 baths | 1,608 sq.ft. |
$1,850,000 |
Airbnb cash on cash: -2%
|
6 Oxford AveShelter Island, NY6 Oxford Ave, Shelter Island, NY 11964 | Single Family Residential |
4 beds | 2 baths | 2,074 sq.ft. |
$1,495,000 |
Airbnb cash on cash: -1.83%
|
5 Sea Gull RdShelter Island, NY5 Sea Gull Rd, Shelter Island, NY 11964 | Single Family Residential |
5 beds | 5 baths | 3,072 sq.ft. |
$3,795,000 |
Airbnb cash on cash: -1.95%
|
43 Gardiners Bay DrShelter Island, NY43 Gardiners Bay Dr, Shelter Island, NY 11964 | Single Family Residential |
5 beds | 4 baths | 6,106 sq.ft. |
$3,625,000 |
Airbnb cash on cash: -1.92%
|
16 Bowditch RdShelter Island, NY16 Bowditch Rd, Shelter Island, NY 11964 | Single Family Residential |
3 beds | 2 baths | 1,266 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -0.83%
|
2 Prospect AveShelter Island, NY2 Prospect Ave, Shelter Island, NY 11964 | Single Family Residential |
6 beds | 3 baths | 5,900 sq.ft. |
$2,700,000 |
Airbnb cash on cash: -1.64%
|
4 Irene LnShelter Island, NY4 Irene Ln, Shelter Island, NY 11964 | Single Family Residential |
4 beds | 3 baths | 2,600 sq.ft. |
$1,850,000 |
Airbnb cash on cash: -2.04%
|
11 Mimosa PlShelter Island, NY11 Mimosa Pl, Shelter Island, NY 11964 | Single Family Residential |
3 beds | 2 baths | 1,564 sq.ft. |
$1,350,000 |
Airbnb cash on cash: -1.05%
|
12 Terry DrShelter Island, NY12 Terry Dr, Shelter Island, NY 11964 | Single Family Residential |
5 beds | 4 baths | 4,200 sq.ft. |
$2,950,000 |
Airbnb cash on cash: -1.74%
|
21 Tims TrlShelter Island, NY21 Tims Trl, Shelter Island, NY 11964 | Other |
N/A beds | N/A baths | N/A |
$575,000 |
Airbnb cash on cash: -1.94%
|
169 N Ferry RdShelter Island, NY169 N Ferry Rd, Shelter Island, NY 11964 | Single Family Residential |
4 beds | 4 baths | 3,500 sq.ft. |
$4,250,000 |
Airbnb cash on cash: -2.4%
|
Real Estate investment in Shelter-island, NY
There are 28 properties for sale in the city of Shelter Island . The median list price in Shelter Island is $2,398,565 and the average price per square foot is $908. In September 2026, the average monthly cash on cash return in Shelter Island is N/A%. The average monthly rental income in Shelter Island is $5,509.