2026 Rates: August 1-15 $20,000, September $25,000, October $20,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4 spacious bedroomsincluding a luxurious primary en-suiteand 3 full bathrooms, there’s plenty of room for family and guests to unwind in comfort. The heart of the home is a dramatic post and beam Great Room, designed for both relaxing and entertaining, with soaring ceilings and expansive windows that flood the space with natural light. Step out onto the large balcony to take in sweeping views of the Sound, enjoy morning coffee as the sun rises over the water, or end the day with a spectacular sunset. Additional amenities include a 1-car garage, central air, and thoughtfully landscaped grounds that ensure privacy and tranquility. Whether you’re lounging poolside, walking along the shoreline, or enjoying evening breezes from the balcony, this home offers an unforgettable seasonal escape.
| MLS # | 876750 |
|---|---|
| Listing Type | For Lease |
| Style | House |
| Status | Active |
| Year | 1998 |
| Days On Site | 456 |
| Listing Provided By | Daniel Gale Sothebys Intl Rlty | William J. Walters CBR |
| Bed(s) | 5 |
|---|---|
| Bath(s) | 3 Total |
| SQ Feet | 3,700 |
| Garage | 1 |
| Basement | Y |
| Pool | Yes |
| Acreage | 0.57 |
| Water Front | Yes |
| Property View | Water |
| Cooling | Central Air |
|---|---|
| Heating | Forced Air |
| Interior Features | First Floor Bedroom, First Floor Full Bath, Beamed Ceilings, Cathedral Ceiling(s), Chefs Kitchen, Eat-in Kitchen, High Ceilings, High Speed Internet, Primary Bathroom, Master Downstairs, Open Floorplan, Open Kitchen |
| Furnished | Furnished |
| Appliances | Cooktop, Dishwasher, Dryer, Electric Range, Freezer, Microwave, Refrigerator, Washer, Wine Refrigerator |
| Exterior Features | Gas Grill |
|---|---|
| Construction Materials | Frame |
| Garage Yes / No | Yes |
|---|
| Utilities | Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, See Remarks |
|---|---|
| Sewer | Septic Tank |
| State | NY |
|---|---|
| County | Suffolk County |
| City | Greenport |
| Zip Code | 11944 |
| Community Name | Stirling Eastern Shores |
| School District | Greenport High School |
| Elementary School | Greenport Elementary School |
| High School | Greenport High School |
| State | NY |
|---|---|
| County | Suffolk County |
| City | Greenport |
| Zip Code | 11944 |
| Community Name | Stirling Eastern Shores |
| School District | Greenport High School |
| Elementary School | Greenport Elementary School |
| High School | Greenport High School |
![]() | $1,695,00090 Caiola CourtGreenport, NY 11944 |