Charming historic house, Sterling Harbor water views, walk to village

Top rated by guests
Front of house facing east
Bathroom 2nd floor
Master bedroom - 1st floor, water views & fireplace
2nd floor bedroom (double)
Single guest bedroom, airy with sky light
review stars
10Outstanding
(5 Ratings)
"Our hostess, Ellen, greeted us as soon as we arrived and spent a couple of hours chatting with us. She even helped us bring her luggage into her charming house during a downpour. The kitchen is ideal ..."
Mary Ann S.
Don't miss out! Price and availability may change
10 / 10
Outstanding(5 Ratings)

House in Greenport, NY

5 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Tucked away on 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 character, accentuated by eclectic art, furniture, and cultural artifacts from the owner's travels. A mini split-system A/C has been installed for your comfort.

The 1st floor offers an open flow to spacious living areas — a library-foyer with working fireplace, large dining room, and a fully-equipped, fully-stocked cook’s kitchen with Bosch/GE/Wolf appliances. The light-filled sun room opens to a deck for dining and entertainment, with a flowering pergola, water views, and salt breezes. The original porch has been preserved, perfect for relaxing, reading, watching boats and passers-by.

Bedrooms: On the 1st floor is the main bedroom (queen) with a working fireplace and full bathroom (shower/tub). On the 2nd floor is a large bedroom (queen) with cross ventilation; and a charming guest room with skylight for a single person. Both bedrooms have water views and share a bathroom (tub/European shower system).

A patio by the kitchen, with flowering arbor, water views, and Weber grill, offers additional outdoor dining. The back yard boasts a large lawn, mature trees and gardens, perfect for family games (croquet, badminton). For cooler evenings, there is a fire pit. An outdoor shower awaits one's return from a day at the beach, sailing, or fishing.

Enjoy dining al fresco, freshly caught fish from Southold Fish Market, sweet corn from Latham & Sep's Farms, greens from Sang Lee & Deep Roots Farms. Indulge in bivalves at Little Creek Oyster and artisanal beers at Greenport Harbor Brewery, both steps away on Carpenter Street. Wines from Kontokosta Winery on the Main Road is 5 minutes away.

With the North Fork a food-and-wine destination, the village abounds with attractions: North Fork Arts Center for films and cultural events, Burton’s Bookstore, Mitchell Park (music concerts and Saturday farmers' market) and the Carousel, boating/fishing tours, restaurants, cafés, bakeries, markets and shops. Public beaches are nearby -- 67 Steps & Inlet Pond on the Long Island Sound; 4th St and 5th St beaches, Gull Pond, and Sandy Beach on the Peconic Bay. An added feature is the possibility of renting dock space or slips at the marinas across the street from the house.

Transportation: The Long Island Railroad (LIRR), Hampton Jitney, & Long Island Expressway (LIE) all serve Greenport. North Ferry connects the village to Shelter Island and South Ferry to the Hamptons and Montauk on the South Fork. The Cross Sound Ferry at Orient Pt, 8 miles away, plies the seas to and from New England.

Keywords: House

Amenities at Charming historic house, Sterling Harbor water views, walk to village

Non-smoking
No pets allowed
Family friendly

Map of Greenport, NY

city location on map

Ratings and reviews

10 / 10
Outstanding(5 Ratings)
10 / 10Outstanding·Aug 2025
Our hostess, Ellen, greeted us as soon as we arrived and spent a couple of hours chatting with us. She even helped us bring her luggage into her charming house during a downpour. The kitchen is ideal for me. Everything was located exactly where you would want it as you’re cooking. There is an abundance of dishes, glasses, pots, pans, cutting boards, and utensils. There are many interesting books and artwork. Being across from the harbor lends to the relaxing and calming vibe. And we lucked out on the weather during our day.
10 / 10Outstanding·Jul 2025
Absolutely wonderful and relaxing
10 / 10Outstanding·Jul 2024
We had a lovely stay in this beautiful home. Great location, fully equipped kitchen, lots of room in the house and large backyard for croquet. Ellen was a gracious and responsive host!
5 / 10·Aug 2021
Loved it!

$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Charming historic house, Sterling Harbor water views, walk to village. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Charming historic house, Sterling Harbor water views, walk to village pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Charming historic house, Sterling Harbor water views, walk to village?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.