This is my home on Shelter Island: a four-seasons-ready remodeled mid-century home on a rolling, landscaped acre. It's neatly appointed with original art and treasures collected locally and from my travels around the globe (I also live part time in Mexico City and Portugal, as well as NYC.) There are three comfortable bedrooms and two full bathrooms. The primary bedroom also has a lovely standing tub from which you can watch deer, turkey, groundhogs, and songbirds in the rear garden through the picture window.

Downstairs, there's a movie theater room with a projector, Apple TV, and real AMC theater seats (+ popcorn machine), a gym with free weights + a Tonal machine (comes with your rental), a cozy study with working wood stove (amazing for the cooler months) and a 1930s burl wood waterfall writing desk + sitting area + my personal library, as well as an office with two desks and two chairs ideal for a couple to work together but separately (the office has a door that closes for privacy - I do a lot of my work upstairs at the dining table.)

Much of the furniture is authentic mid century - a rare set of 6 lemon meringue coloured Eames shell dining chairs, a Knudd Nielsen buffet and hutch, two Hans Brattrud Scandia chairs, a pair of Thonet armchairs, and much more.

The quietest and loveliest beach in New York is 4 minutes away by bike (we have 4 of them available to use) and there are also two inflatable stand up paddle boards, as well as more beach towels than you can count and a set of 4 beach chairs + umbrella.

In the back garden we just installed a 4 person barrel sauna which is easy to operate and really wonderful paired with a dip in the sea just before or after.

Why I'm Renting on TLP

We rent heavily via Airbnb and return rentals over the summer, which is peak season for both demand and dollars. I try to use the house as often as I can in the fall (my favorite season to be there, by far) but my dual jobs as an art fair director and filmmaker prevent me from being there as much as I'd like. The rates we're charging are an offset to our costs and enable the house to be used by people who appreciate. They are much less than what we have to charge on Airbnb to offset all of the fees and uncertainty that come with the platform. In the winter (Jan, Feb, Mar) I am in Mexico City and California for work, so I can't use the house at all. *BUT* for 3 years I did, and those were some of the most peaceful, get-stuff-done winters I've ever had. So don't overlook the opportunity for tranquility, it's worth it!

The beaches are swimmable temperature up until late October (I surf Montauk year round - with a wet suit - and will dip without one in every month except Jan/Feb/Mar - but that's just me!) and September/October are balmy.

About the Island:

Geographically the size of Manhattan, you can cross Shelter Island in any direction in under 10 minutes. It's reachable from either Greenport on the North Fork, or Sag Harbor/North Haven in the South Fork, by a car ferry that runs regularly 365 days a year and does not require appointment (do pay attention to the schedule especially in winter.)

There are several amazing restaurants and a great coffee shop on Shelter Island. Many stay open year round but you'll want to check updated hours if staying in the winter. There is an IGA grocery shop open year round. As well, Sag Harbor and Greenport are both year round towns. Each has a charming cinema, great restaurants, excellent shopping, and its own unique delights. When I've stayed in the winter, a highlight for me is taking the ferry over to Sag, having happy hour at the American Hotel, then catching a movie.

We are dog friendly :)

Available dates and rates:

September 24-October 1 (2025) - $1500 + 250 cleaning
October 17-October 24 (2025) - $1500 + 250 cleaning
October 27-November 24 (2025) - $5,000 + 250 cleaning (this is a $1000 discount for the whole month - if broken into weeks, it would be the $1500/week. Between 1 week and 1 month, let's talk!)
December 1-December 8 (2025) - $1500 + 250 cleaning
January 3-April 4 (2026) - all three months open at $4,500/month + 250 cleaning | $12,000 for all 3 months together***

***during the winter months (Jan, Feb, Mar) we have to charge separately for electricity since the house is electric-heated. The first $300 of electric per month is included in the rental, and you're responsible for the rest. We can go over some ways of limiting that cost (the wood stove is a great way, properly utilized!) but it's just the reality of having an electric-heated home in winter in the northeast.

I would prefer to find either a renter for all three winter months, or rent them as 1 month blocks. This is because it becomes quite difficult to assign electric use during these chillier months, and because I won't be in the country/region, flipping the house becomes more difficult. We have an on island property manager but she travels as well sometimes. However, if you'd like a large block of time during the winter, please just ask and we'll see what we can do.

My goal here is to find people who will appreciate such a special place during seasons when it isn't so clearly a commodity. This doesn't make the space or the island any less extraordinary, and my hope is that the TLP community finds Shelter Island in all its seasons as glorious as I do :)

About This Lister

I'm a go-getter and world traveler with more jobs than I care to admit. Principally, I'm the co-founder and acting director of a major art fair outside of the US, but I've been transitioning a lot of my energy to film over the last several years. I've produced feature and short films, offer paid strategic consulting to filmmakers on their fundraising and distribution strategy, and just directed my first film, a documentary about Miami Beach's coral reef system and the friends protecting it. I also sit on the boards of several film and arts organizations (including the advisory board of our own North Fork Arts Center, just across the Peconic from Shelter Island, in Greenport.)

I'm a tidy person but a collector so I love objects of significance and aesthetic beauty. Everything you'll find in the house means something to me, and I hope you enjoy it too! I'm a voracious reader and a movie nut, and love art as I'm sure you'll be able to tell

I'm your direct contact as the owner of this house, but our on-island property manager Kim will likely be the one welcoming you and letting you in.