Entire home
Charming historic house on Sterling Harbor, water views, 5-min walk to village
Holiday home in Greenport with kitchen and balcony
Photo gallery for Charming historic house on Sterling Harbor, water views, 5-min walk to village





Reviews
10 out of 10
Exceptional
3 bedrooms 2+ bathrooms Sleeps 5 2000 sq ft
Popular amenities
Explore the area

Greenport, NY
- Place, Eastern Long Island Hospital6 min walk
- Place, Kontokosta Winery16 min walk
- Place, 67 Steps Beach3 min drive
- Airport, New Haven, CT (HVN-Tweed - New Haven Regional)
Rooms & beds
3 bedrooms (sleeps 5)
Bedroom 1 - Queen bed
1 Queen Bed
Bedroom 2 - Queen bed
1 Queen Bed
Bedroom 3 - Full bed
1 Double Bed
2 bathrooms, 1 half bathroom
Bathroom 1
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo · Hair dryer
Bathroom 2
Soap · Towels provided · Bathtub or shower · Bathtub · Toilet · Shampoo
Bathroom 3
Soap · Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden
Dining area
About this property
Charming historic house on Sterling Harbor, water views, 5-min walk to village
REDUCED RATE FOR MONTH OF OCTOBER!!
Tucked away in Sterling Harbor in the Historic District on Greenport's most desired street is this lovely 3-bedroom, 1780s “vernacular” house. Meticulous attention has been paid to renovations and modern additions that preserve its architectural integrity, accented by art and furniture from the owner's travels. A new split-system A/C has been installed for summer 2025 for your comfort.
The 1st floor offers an open flow to spacious living areas — a library-foyer with working fireplace, large dining room accommodating 8, and a fully-equipped and stocked cook’s kitchen with Bosch/GE/Wolf appliances. The light-filled sunroom opens to a deck designed for entertainment with a flowering pergola, water views, and salt breezes. The original porch is perfect for relaxing, reading, and watching passers-by.
The main bedroom on the 1st floor has a working fireplace and full bathroom. Two bedrooms on the 2nd floor with water views share a full bath: a large bedroom (queen bed) with cross ventilation and a charming guest room (full bed for a single) with skylight.
A patio by the kitchen with flowering arbor, water views, and Weber grill offers additional dining possibilities. The back yard with mature trees and gardens boasts a large lawn, perfect for family games (croquet, badminton), and a fire pit for when the weather gets cooler. An outdoor shower awaits your return from a day at the beach.
Enjoy dining al fresco with freshly caught fish from Southold Fish Market, sweet corn from Latham and Sep's Farms, greens from Sang Lee and Deep Roots Farms. Indulge in bivalves at Little Creek Oyster and artisanal beers at Greenport Harbor Brewery, both steps away on Carpenter Street; and wines from Kontokosta Winery on the Main Road, 5 minutes away by foot, bike, or car.
As a North Fork food-and-wine destination, the village abounds with attractions: the new North Fork Arts Center, Burton’s Bookstore, Mitchell Park and Carousel, boating/fishing tours, restaurants, cafés, bakeries, markets and shops. Public beaches are close by -- 67 Steps & Inlet Pond on Long Island Sound; 4th St, 5th St, Gull Pond & Sandy Beach on Peconic Bay.
Transportation: The Long Island Railroad (LIRR), Hampton Jitney & Long Island Expressway (LIE) all serve Greenport. North Ferry connects the village to Shelter Island & South Ferry to the Hamptons and Montauk on the South Fork. Cross Sound Ferry at Orient Pt, 8 miles away, plies the seas to New England.
Keywords: House
Tucked away in Sterling Harbor in the Historic District on Greenport's most desired street is this lovely 3-bedroom, 1780s “vernacular” house. Meticulous attention has been paid to renovations and modern additions that preserve its architectural integrity, accented by art and furniture from the owner's travels. A new split-system A/C has been installed for summer 2025 for your comfort.
The 1st floor offers an open flow to spacious living areas — a library-foyer with working fireplace, large dining room accommodating 8, and a fully-equipped and stocked cook’s kitchen with Bosch/GE/Wolf appliances. The light-filled sunroom opens to a deck designed for entertainment with a flowering pergola, water views, and salt breezes. The original porch is perfect for relaxing, reading, and watching passers-by.
The main bedroom on the 1st floor has a working fireplace and full bathroom. Two bedrooms on the 2nd floor with water views share a full bath: a large bedroom (queen bed) with cross ventilation and a charming guest room (full bed for a single) with skylight.
A patio by the kitchen with flowering arbor, water views, and Weber grill offers additional dining possibilities. The back yard with mature trees and gardens boasts a large lawn, perfect for family games (croquet, badminton), and a fire pit for when the weather gets cooler. An outdoor shower awaits your return from a day at the beach.
Enjoy dining al fresco with freshly caught fish from Southold Fish Market, sweet corn from Latham and Sep's Farms, greens from Sang Lee and Deep Roots Farms. Indulge in bivalves at Little Creek Oyster and artisanal beers at Greenport Harbor Brewery, both steps away on Carpenter Street; and wines from Kontokosta Winery on the Main Road, 5 minutes away by foot, bike, or car.
As a North Fork food-and-wine destination, the village abounds with attractions: the new North Fork Arts Center, Burton’s Bookstore, Mitchell Park and Carousel, boating/fishing tours, restaurants, cafés, bakeries, markets and shops. Public beaches are close by -- 67 Steps & Inlet Pond on Long Island Sound; 4th St, 5th St, Gull Pond & Sandy Beach on Peconic Bay.
Transportation: The Long Island Railroad (LIRR), Hampton Jitney & Long Island Expressway (LIE) all serve Greenport. North Ferry connects the village to Shelter Island & South Ferry to the Hamptons and Montauk on the South Fork. Cross Sound Ferry at Orient Pt, 8 miles away, plies the seas to New England.
Keywords: House
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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10.0 out of 10, (51 reviews)
House Rules
Check in after 3:00 PM
Check out before 11:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Strip any used beds and gather used towels
Take out the rubbish
Lock the doors and return the keys
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Greenport
Located in Greenport, this holiday home is in a rural area and near theme parks. Camera Obscura and Greenport Carousel are local landmarks, and some of the area's attractions include East End Seaport Maritime Museum and Railroad Museum of Long Island. Norman E. Klipp Marine Park and Shelter Island Whale's Tail are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Greenport, NY
What's nearby
- Eastern Long Island Hospital - 6 min walk - 0.6 km
- Greenport Carousel - 9 min walk - 0.8 km
- Railroad Museum of Long Island - 14 min walk - 1.2 km
- Kontokosta Winery - 16 min walk - 1.4 km
- 67 Steps Beach - 3 min drive - 2.2 km
Getting around
Restaurants
- Aldo's - 12 min walk
- Porto Bello - 3 min drive
- Lucharitos - 11 min walk
- Charlie Boy - 11 min walk
- First And South - 10 min walk
Frequently asked questions
About the host
Hosted by Owner

Languages:
English, French, Spanish
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