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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Bedrooms 4
Half Baths1
Property type house
Minimum Stay 1 - 3 nights


About the property

Pristine with private gardens, great for family reunions

Relax in one of America's most beautiful seaside villages, historic Greenport. Walk to the village and within minutes to vineyards, Lavender farm, golf and beaches also Shelter Island and Orient Point Ferries. Take the Hampton Jitney or LIRR from the city and walk to our breathtaking home.

Elegant and located on Captains Row in the Greenport Historic District. Elegantly built for the wealthiest banker on the North Fork. Largest property in National Historic District in Greenport Village. The backyard is truly special, private with pergola and outdoor grill perfect for dining under the stars and our new giant chess set is sure to please.

Lovingly restored to its original elegance and authentic Classic Queen Anne Victorian. This is a complete modern home with new kitchen and bathrooms. This home has been the subject of many artists!

Enter this home and feel the impeccable carpentry work with its rich patina. Magnificent 5 foot single pocket siding doors that separate the formal rooms that will glide with your fingertips. Top of the line kitchen appliances. New luxury linens, mattresses and romantic brass and iron beds. Feel the elegance of the bygone era. There is even a maids room should you travel with yours. All lighting is exquisitely original, restored and sets the mood.

WE DO NOT ALLOW ANY PARTIES OR GATHERINGS AT THE OUR HOME. Any celebrations are to be enjoyed by our overnight renters only. A home of this age could not sustain the wear and tear that comes with the hosting of social events, so please do not plan any such events with our property in mind.

We are compliant with local laws and there are minimum stay requirements.

We have minimum stay requirements but please email us for special consideration. Weekend rates apply to holidays.

We will try our best to accommodate you!

More Details

Property Manager
Member since: 2015
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english, spanish, greek
Response time:
Within an hour
Response rate:
Calendar last updated:
September 18, 2018

About Sofia

We love restoring historic homes and returning all aspects back to the original period design. Part of the process includes researching the previous owners and documenting the unique property features. Our mission is to share with our friends the bygone periods of elegance and excellent craftsmanship and meld the 21st century to make our home the best out there!

Why Sofia chose Greenport

This property is the most well preserved home in the area. It was custom built by the wealthiest man at the turn of the 1900's. The location is prime, walking distance to all of Greenport shops, restaurants and tours. Many vineyards close by. Rent a bicycle and forget about enjoy the outdoors by visiting the marina and nearby beaches.....

What makes this house unique

Historic district centrally located and within walking distance to LIRR, Hampton Jitney, restaurants, shopping and yoga studio.


Greenport House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 8
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed ...
  • Non smoking only ...
Location Type:
  • Downtown ...
  • Near The Ocean ...
  • Village ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Fitness Room / Equipment ...
  • Garage
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 8 people
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , combination tub/shower
    Bathroom 2 - toilet , sink
    Bathroom 3 -
  • 4 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 queen , Lovely romantic queen brass iron bed
    Bedroom 1 - 1 king , Lovely bright and sunny king bedroom
    Bedroom 1 - 1 queen , Feel like you are in the clouds in this lovely room
    Bedroom 1 - 1 queen , Historically accurate bedroom colors
  • Books
  • Satellite / Cable
  • Television ...
  • Balcony
  • Deck / Patio
  • Golf ...
  • Lanai / Gazebo ...
  • Lawn / Garden
  • Outdoor Grill
  • Long-term Renters Welcome
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • marina
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • ice skating
  • jet skiing
  • pier fishing
  • sailing
  • sound/bay fishing
  • swimming
  • tennis


Exceptional! 5/5 -
(9 traveler reviews)

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Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
average rating of 5.0 based on 9 reviews

Gorgeous Home in Greenport!

  • 5 of 5

The house is absolutely gorgeous! The online pics do not do the house justice. There were more bedrooms than we thought, the bathrooms were pretty, and there were so many gorgeous details around the house. The backyard is also very nice as is the front porch. Sofia even set up a snack box for us, and was accessible when we had questions about local beaches. We rented the house for my sister’s bachelorette, and very happy to have rented this particular house.

  • Submitted: Jul 26, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
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Stunning and Pristine!!

  • 5 of 5

If you're looking for the perfect spot for your girls weekend this is it! Sofia, the owner of this gorgeous home was nothing less but perfection. She greeted us with wine and snacks galore! I have to say one of the most accommodating hostesses I have ever had the pleasure to correspond with. As for the house, well...if you love vintage everything this is your dream home. Just stunning! Spacious, pristine, clean! Plenty of parking, privacy and most importantly, close to everything the Northfork has to offer! Loved it!!!

  • Submitted: Feb 15, 2018
  • Stayed: February 2018
  • Source: HomeAway
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Great house, great town!!

  • 5 of 5

Beautiful house with a nicely done interior and a great yard. Would definitely stay here again

  • Submitted: Sep 4, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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World Class accommodations with that "at home" feel and all the amenities of a luxury property.

  • 5 of 5

What a fabulous property that has been maintained and updated to continue the legacy of this Superior building structure. Our hosts Sofia and her son Nick greeted us after our arrival and gave us some history of the property and the updates that have been done since their purchase. The pictures posted on the website can't describe the warm feeling you get when you walk through the door. We were a party of eight and we had plenty of room for all. With an inviting front porch sitting area and a magnificent rear yard patio and portico there were ample outdoor spaces to relax, socialize or just veg-out. The close proximity to the town center made walking to and from a pleasurable easy stroll. We will definitely be coming back and would happily recommend this property for those individuals seeking classy accommodations with old world charm incorporated in every detail.

  • Submitted: Aug 6, 2017
  • Stayed: August 2017
  • Source: HomeAway
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Amazing house--would make a yearly trip here in a heartbeat!

  • 5 of 5

I honestly cannot say enough nice things about the house, location, property and Sofia!

The house is beautiful with tons of hidden nooks and crannies. With all orginial fixtures it was truly a Victorian experience. The rooms were spacious and stocked with blankets, pillows, and plenty of towels. The kitchen had almost anything you could need, along with the staples Sofia left for our arrival (milk, juice, snacks). There were 7 of us staying over and definitely had room to spare for extra guests.plenty of amenities with new appliances and washer/dryer that made it feel like home.

Location was PERFECT less than a mile to the town making it easier to walk for shopping and eating. We went to a Sound beach, vineyards and lavender farms with very short drives.

I would love to return to this house every year!!! It was an amazing experience and felt like our own home away from home

  • Submitted: Jul 26, 2017
  • Stayed: July 2017
  • Source: HomeAway
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Perfect stay in GreenPort

  • 5 of 5

This is the perfect house in greenport, and it looks even prettier in person. Sophia has taken care of every detail in the house, and it was absolutely stunning. She was very kind and communicated constantly during our stay. We loved the Victorian decor and how modern/ clean/ new everything was.

Thanks a lot. We will be back!

  • Submitted: May 29, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
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Nearest Ferry
0.25 Miles
Shelter Island Ferry and Cross Sound Ferry
Nearest Golf
0.5 Miles
Islands End Country Club- Public
Nearest Train
0.25 Miles
Long Island Rail Road- last stop
Nearest Beach
0.25 Miles
so many to choose from...67 steps is closest
Car: not necessary


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $300
Refundable Damage Deposit $1,000

Manager's Cancellation Policy

  • 50% refund if canceled at least 30 days before arrival date.
  • 100% refund if canceled at least 60 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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