A thoughtfully designed retreat offering peace, privacy, and understated luxury. Tucked away on a private drive in the island's center, you're close enough to bike to all of the island's beaches or restaurants. The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a striking silhouette against the natural canopy. That hammock strung between two trees? Exactly where you'll spend Sunday mornings with coffee and a good read. Inside, the design philosophy is clear: let the outside take the stage. White walls, black accents, and a massive window wall make the front yard feel like your living room's best feature. The newly installed Ortal 110 TS fireplace anchors the open space, a sculptural centerpiece that warms the kitchen, dining, and living areas. Ascoli smart lighting throughout means you can set the color temperature to exactly your liking and automate it to match the rhythms of your day. The kitchen features Robern cabinets, a Thermador gas range, a double oven, and a refrigerator, plus a generous island for preparing all that local fish and farmstand produce. Upstairs, three bedrooms include a primary with an ensuite walk-in shower, a second bedroom with queen-sized built-in bunk beds and clever storage nooks, and a third with expansive windows overlooking the rolling front lawn. A second full bathroom with a tub serves the floor. Downstairs, heated floors make winter mornings civilized. The spacious bathroom features Robern cabinets and heated towel rack, while walk-in closets are generous enough that you and your partner won't need to negotiate territory treaties. Every detail considered, nothing overdone. The fully fenced backyard is its own retreat. Your dog thinks it's paradise. Your green thumb agrees. The newly built backyard office/art studio/yoga sanctuary, properly insulated with new windows and doors, offers a legitimate reason to "work from home" that doesn't involve your kitchen table. Whether it becomes your creative sanctuary, your focus zone, or just where you hide from houseguests, it's ready. The house comes with complete pool plans designed by Glenn Lawton at Spatial Arts. Modern amenities where they matter: EV charger, bike and board storage, without sacrificing the serenity that brought you to Shelter Island in the first place. Even the entrance makes a statement with its sculptural fountain and thoughtfully designed wood and bluestone steps.
For sale
$1,845,000
73 N Midway Rd, Shelter Island, NY 11964
4beds
2,296sqft
Single Family Residence
Built in 1976
0.88 Acres Lot
$1,764,200 Zestimate®
$804/sqft
$-- HOA
What's special
Private driveExpansive lawn
- 243 days |
- 348 |
- 16 |
Zillow last checked:
Listed by:
Daniel Gale Sotheby's International Realty 631-764-3847,
JoAnn Wind - Real Estate Sales Person 631-764-3847
Source: Out East,MLS#: 391824
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Laundry, Office
Cooling
- Central Air
Features
- Basement: Yes
- Has fireplace: Yes
Interior area
- Total structure area: 2,296
- Total interior livable area: 2,296 sqft
Video & virtual tour
Property
Parking
- Parking features: None
Features
- Stories: 2
- Pool features: Room for a Pool
Lot
- Size: 0.88 Acres
Details
- Parcel number: 0700014000300035005
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Condition
- New construction: No
- Year built: 1976
Community & HOA
Location
- Region: Shelter Island
Financial & listing details
- Price per square foot: $804/sqft
- Tax assessed value: $1,698,000
- Date on market: 11/1/2025
- Lease term: Contact For Details
Estimated market value
$1,764,200
$1.68M - $1.85M
$6,843/mo
Price history
| Date | Event | Price |
|---|---|---|
| 3/28/2026 | Price change | $1,845,000-2.6%$804/sqft |
Source: | ||
| 11/1/2025 | Listed for sale | $1,895,000+16.5%$825/sqft |
Source: | ||
| 6/7/2022 | Sold | $1,627,000+26.6%$709/sqft |
Source: Public Record Report a problem | ||
| 5/13/2020 | Listing removed | $1,285,000$560/sqft |
Source: Corcoran - EE Shelter Island #258308 Report a problem | ||
| 11/6/2019 | Price change | $1,285,000-1.2%$560/sqft |
Source: Corcoran Group #258308 Report a problem | ||
| 8/25/2019 | Listed for sale | $1,300,000+55.7%$566/sqft |
Source: Corcoran Group #258308 Report a problem | ||
| 11/1/2018 | Listing removed | $835,000$364/sqft |
Source: The Corcoran Group #34734 Report a problem | ||
| 9/30/2018 | Listed for sale | $835,000$364/sqft |
Source: Corcoran Group #34734 Report a problem | ||
| 3/27/2018 | Listing removed | $30,000$13/sqft |
Source: The Corcoran Group #79833 Report a problem | ||
| 2/7/2018 | Listed for rent | $30,000$13/sqft |
Source: The Corcoran Group #79833 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $1,698,000 +90.8% |
| 2024 | -- | $890,000 |
| 2023 | -- | $890,000 |
| 2022 | -- | $890,000 |
| 2021 | -- | $890,000 +1.7% |
| 2020 | -- | $875,000 +61.1% |
| 2019 | -- | $543,000 +4.2% |
| 2018 | -- | $521,000 +3.2% |
| 2017 | $4,461 | $505,000 +3.5% |
| 2016 | -- | $488,000 +3.6% |
| 2015 | -- | $471,000 |
| 2014 | -- | $471,000 |
Find assessor info on the county website
Monthly payment
Estimated monthly payment$1,822
All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 11964
Nearby schools
GreatSchools rating
- 6/10Shelter Island SchoolGrades: PK-12Distance: 0.7 mi
A local agent can set up tours, give advice and negotiate with sellers.
- New York
- Suffolk County
- Shelter Island
- 11964
- 73 N Midway Rd







