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What $900K buys you in Shelter Island

Curbed Comparisons heads a little north


Curbed Comparisons explores what one can buy in the Hamptons for a certain price. Today, we’re moving a bit north and off the South Fork to Shelter Island to see what a $900,000 budget will get you.

25 Great Circle Drive

The 1986 home at 25 Great Circle Drive has three bedrooms and two-and a-half bathrooms in 2,187-square-feet on 0.9 acres. The most expensive home that we’re looking at today is asking $899,000—just under our $900,000 budget.

Located close to Hay Beach Point, this post-and-beam features a full wall of western facing windows, exposed beams, a built-in platform bed in the master suite, and an entertainment deck.

The downside to this space is that it needs some updating. The home itself is a good size, the wall of windows is a huge bonus, and the pool and deck are huge and great for entertaining. But the kitchen looks like it needs to be gutted and tile floors throughout the main level could be swapped out for hardwood.

40 North Ferry Road

Our largest home featured, this five-bedroom, four-bath home is actually a three-unit rental house with 2,900-square-feet on 0.74 acres with B1 zoning. There are two one-bedroom, one-bath units, and one two-bedroom, one-and a-half bath unit.

Outside, there’s a large blacktop driveway with a lot of parking space and a detached barn with garage and lofted storage space—which, for three tenants, is a good feature to have.

The structure was built in 1925 and was most recently listed for sale with Corcoran Group Real Estate for $895,000.

16 Glynn Drive

The least expensive home we’re looking at today is also the smallest. The post modern at 16 Glynn Drive is just 1,977-square-feet with an asking price of $855,000. Inside, there are three bedrooms, two-and a-half bathrooms, fireplace in the living room, eat-in kitchen, master suite with private bathroom and deck, and central air conditioning.

This is also the most recently updated-looking home. There are hardwood floors throughout the space, an outdoor deck, breezeway, manicured lawn, and water views from the backyard.


Which Shelter Island home would you snag for under $900K?

This poll is closed

  • 39%
    25 Great Circle Drive
    (96 votes)
  • 0%
    40 North Ferry Drive
    (2 votes)
  • 59%
    16 Glynn Drive
    (143 votes)
241 votes total Vote Now