Entire home

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

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

Front of house facing east
Front porch with rocking chairs
Street view of property
Side yard with sunlight and shade
Kitchen

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 52000 sq ft

Popular amenities

  • Beach view
  • Dryer
  • Washer
  • Fireplace
  • Kitchen
  • Parking available

Explore the area

Map
Greenport, NY
  • Greenport Carousel
    ‪13 min walk‬
  • Kontokosta Winery
    ‪16 min walk‬
  • 67 Steps Beach
    ‪2 min drive‬
  • East Hampton, NY (HTO)
    ‪70 min drive‬

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

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 that preserve its architectural integrity and charm while expanding the home’s lay-out with modern additions, accented by art and furniture from the owner's travels. A new A/C split-system is being installed in time 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, fully-stocked cook’s kitchen with Bosch/GE/Wolf appliances. The light-filled sunroom opens to a deck designed for entertainment, with flowering pergola, water views, and salt breezes. The original porch is perfect for reading, relaxing, and watching passers-by.

The main bedroom on the 1st floor has a working fireplace and full bathroom. Two additional bedrooms on the 2nd floor -- a large room with cross ventilation (queen bed) and a charming guest room with a skylight (full bed for a single person) -- share a full bath and water views.

Off the kitchen, a patio with flowering arbor, water views, and Weber grill, offers additional dining possibilities. The back yard is private, with mature trees and gardens, a fire pit, and large lawn perfect for family games. An outdoor shower awaits your return from the beach, boating, or fishing.

Enjoy dining al fresco with freshly caught fish from Southold Fish Market, sweet corn from Latham and Sep's Farms, assorted greens from Sang Lee and Deep Roots Farms. Indulge in bivalves at Little Creek Oyster and artisanal beers at Greenport Harbor Brewery, both on Carpenter Street, and wines from Kontokosta Winery on the Main Road -- all 5 minutes away by foot, bike, or car.

Attractions abound in the village: North Fork Arts Center, Burton’s Bookstore, Mitchell Park and Carousel, boating/fishing tours, restaurants, cafés, bakeries, and shops, as Greenport has become a food-and-wine destination on the North Fork. Enjoy public beaches on the Long Island Sound (67 Steps, Inlet Pond) and Peconic Bay (4th and 5th Streets, Gull Pond, and Sandy Beach), all close-by.

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

Keywords: House

Property manager

Owner

Languages

English, French, Spanish

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Outdoor Space
Parking available

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House Rules

Check in after 3:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the neighborhood

Greenport

Located in Greenport, this vacation 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. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Map
Greenport, NY

What's nearby

  • Eastern Long Island Hospital - 8 min walk - 0.7 km
  • Greenport Carousel - 13 min walk - 1.1 km
  • Kontokosta Winery - 16 min walk - 1.4 km
  • Railroad Museum of Long Island - 17 min walk - 1.5 km
  • 67 Steps Beach - 2 min drive - 1.8 km

Getting around

  • Greenport Station - 16 min walk
  • East Hampton, NY (HTO) - 70 min drive

Restaurants

  • ‪Sterlington Deli - ‬15 min walk
  • ‪Billy's By The Bay - ‬3 min drive
  • ‪Lucharitos - ‬11 min walk
  • ‪Aldo's - ‬12 min walk
  • ‪Crazy Beans - ‬10 min walk

Frequently asked questions

Is Charming historic house on Sterling Harbor, water views, 5-min walk to village pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Charming historic house on Sterling Harbor, water views, 5-min walk to village?

Check-in begins at 3:00 PM.

What time is check-out at Charming historic house on Sterling Harbor, water views, 5-min walk to village?

Check-out is at 11:00 AM.

Where is Charming historic house on Sterling Harbor, water views, 5-min walk to village located?

Situated in a rural location, this vacation home is within a 10-minute walk of Eastern Long Island Hospital and Stony Brook Eastern Long Island Hospital. Greenport Farmers' Market and Camera Obscura are also within 15 minutes. Greenport Station is 16 minutes by foot.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

terrence g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Greenport Gem

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!
Stayed 12 nights in Jul 2024
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Richard R., New York City

Ideal

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.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Gail B.

Charming home in great location!!

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.

About the host

Hosted by Owner

Host profile image

Languages:

English, French, Spanish