Charming historic house on Sterling Harbor, water views, 5-min walk to village

Greenport, New York
$612 avg/night Minimum Stay 7 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 5

Max Sleeps

Night 7 nights

Min Stay

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 artifacts from the owner's travels, A mini split-system A/C has recently 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 cook’s kitchen with Bosch/GE/Wolf appliances. The light-filled sun room opens to a deck designed for dining and entertainment, with a flowering pergola, water views, and salt breezes. The original porch has been preserved, perfect for relaxing, reading, and watching boats and passers-by.

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

A patio by the kitchen, with flowering arbor, water views, and Weber grill, offers additional outdoor dining possibilities. The back yard consists of a large lawn, mature trees and gardens, perfect for family games (croquet, badminton). There is a fire pit for cooler evenings. An outdoor shower awaits one's 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 by foot, bike, or car.

A North Fork food-and-wine destination, the village abounds with attractions: the North Fork Arts Center, Burton’s Bookstore, Mitchell Park and the Carousel, boating/fishing tours, restaurants, cafés, bakeries, markets and shops, and a farmers' market on Fridays. Public beaches are nearby -- 67 Steps & Inlet Pond on Long Island Sound; 4th St and 5th St beaches, Gull Pond & Sandy Beach, all 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 and the 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

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Bed Sheets Provided Day Bed
  • GENERAL

    Unit Size: 2000 Sq Ft (186 Sq M)
  • KITCHEN

    Blender Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Fenced Yard Firepit Garden Outdoor Furniture Patio
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English French Spanish
  • THINGS TO DO

    Basketball Nearby Fitness Facilities Nearby Golfing On Site Hiking/biking Trails Nearby Jet Skiing Nearby Marina Nearby Power Boating Nearby Sailing Nearby Scuba Diving Nearby Surfing/body Boarding Nearby Tennis On Site Winery Tours Nearby
  • ENTERTAINMENT

    Books DVD Player Music Library Stereo Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Playground Stair Gate
  • LOCATION HIGHLIGHTS

    In A Rural Location Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Phone
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Rates & Availability

Review Review

  • Mary Ann S.

    Submitted Aug 14, 2025

    Stayed Jul 31, 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.

  • jerry t.

    Submitted Jul 20, 2025

    Stayed Jul 7, 2025

    Absolutely wonderful and relaxing

  • terrence g.

    Submitted Jul 26, 2024

    Stayed Jul 1, 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!

  • Richard R.

    Submitted Dec 7, 2015

    Stayed Dec 31, 1969

    Two weeks in this beautiful but spacious cottage flew by. Breakfast each morning on the deck, under the pergola, with a view of the inlet; nights in a four-poster bed; swordfish on the gas grill and dinners prepared in the fully equipped country kitchen; plenty of room for visiting adult children in the two extra bedrooms; a house full of light, charm, and tchotchkes from the owner's travels. The house is on a quiet street a 10-minute stroll along similarly sleepy streets to Greenport's bustling business district, restaurants, movie theater. You're not far from beaches, gorgeous bike rides, vineyards, and just 10 minutes from Shelter Island. Moreover, Greenport itself is a quaint haven of an historic whaling village, with not a Starbucks or fast-food franchise in sight. An ideal escape.

  • Gail B.

    Submitted Feb 20, 2015

    Stayed Dec 31, 1969

    My husband and I rented this incredibly charming home for the month of August last year. It's nestled on a very quiet road with beautiful harbor views and is a few minutes walk from all the activities and amenites of Greenport village. The home is very spacious and has great outdoor living/dining spaces. We most definitely enjoyed our time her and would highly recommend it.

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Total

Includes taxes and fees
$612+
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