A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property offers remarkable versatility to fit your lifestyle.The welcoming ranch-style main home offers a comfortable living space with 3 bedrooms and two full bathrooms. A spacious kitchen with abundant cabinetry flows seamlessly into the dining area, creating an inviting setting for everyday living and entertaining. The living room, anchored by a wood-burning fireplace, provides a warm and cozy gathering place throughout the seasons.Step outside to the expansive rear deck, complete with a hot tub overlooking a large, private backyard with room for a pool, an ideal setting for entertaining, relaxing, or enjoying peaceful evenings. A welcoming front porch, an attached one-car garage, and a carport.Privately positioned toward the rear of the property, the stunning barn-style home feels like a secluded retreat. Overlooking a tranquil pond, this approx. The residence is filled with warmth, character, and natural light. The dramatic main room features soaring vaulted ceilings with exposed beams, a gas fireplace, and an impressive wall of windows that captures beautiful views while flooding the home with sunshine. French doors that open onto an expansive 500 square foot mahogany deck with built-in storage, creating the perfect place to enjoy morning coffee, outdoor dining, or simply unwind.The barn home also features two spacious bedrooms, two full bathrooms, a large loft, and a well-appointed kitchen. The oversized lower-level garage offers exceptional storage for vehicles, recreational equipment, bicycles, tools, and more, while additional facilities and energy-efficient solar panels further enhance the homes appeal.The beautifully landscaped .95 acre property provides an uncommon sense of privacy while remaining just minutes from the Shelter Island beaches, marinas, restaurants, shops, farm stands, and nature preserve. 64A North Midway Road offers possibilities that are rarely available on Shelter Island.
For sale
$2,199,000
64 N Midway Rd, Shelter Island, NY 11964
5beds
2,646sqft
Other
Built in 1977
0.95 Acres Lot
$2,064,000 Zestimate®
$831/sqft
$-- HOA
What's special
Gas fireplaceLarge loftTwo spacious bedroomsAttached one-car garagePicturesque pond next doorStunning barn-style homeExpansive rear deck
- 73 days
- 76
- 3
Zillow last checked:
Listed by:
Douglas Elliman 631-354-8100,
Christine Beckwith
Source: Douglas Elliman,MLS#: 424469
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 4
Features
- Has basement: No
Interior area
- Total structure area: 2,646
- Total interior livable area: 2,646 sqft
Property
Lot
- Size: 0.95 Acres
Details
- Parcel number: 0700014000400007003
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other
- Property subtype: Other
Condition
- Year built: 1977
Community & HOA
Community
- Subdivision: Shelter Island
Location
- Region: Shelter Island
Financial & listing details
- Price per square foot: $831/sqft
- Tax assessed value: $697,600
- Date on market: 7/21/2026
- Lease term: Contact For Details
Estimated market value
$2,064,000
$1.96M - $2.17M
$8,401/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/21/2026 | Listed for sale | $2,199,000+149.9%$831/sqft |
Source: | ||
| 2/1/2022 | Sold | $880,000-3.8%$333/sqft |
Source: Public Record Report a problem | ||
| 9/1/2021 | Contingent | $915,000$346/sqft |
Source: | ||
| 7/3/2021 | Listed for sale | $915,000+81.2%$346/sqft |
Source: | ||
| 11/4/2009 | Sold | $505,000+2%$191/sqft |
Source: Public Record Report a problem | ||
| 12/19/2005 | Sold | $495,000+115.2%$187/sqft |
Source: Public Record Report a problem | ||
| 3/25/2002 | Sold | $230,000$87/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $697,600 +153.7% |
| 2024 | -- | $275,000 -13.9% |
| 2023 | -- | $319,400 -41.5% |
| 2022 | -- | $546,000 |
| 2021 | -- | $546,000 +1.5% |
| 2020 | -- | $538,000 +0.2% |
| 2019 | -- | $537,000 +0.4% |
| 2018 | -- | $535,000 +2.5% |
| 2017 | $3,173 | $522,000 +3.4% |
| 2016 | -- | $505,000 +3.9% |
| 2015 | -- | $486,000 +1.3% |
| 2014 | -- | $480,000 +2.1% |
| 2013 | -- | $470,000 -0.4% |
| 2012 | -- | $472,000 -4.6% |
| 2011 | -- | $495,000 +0.9% |
| 2010 | -- | $490,400 -1.7% |
| 2009 | -- | $499,000 -1.7% |
| 2008 | -- | $507,700 +8.5% |
| 2007 | $2,389 +53.5% | $467,800 +101.8% |
| 2005 | $1,557 +14.7% | $231,800 +23.1% |
| 2004 | $1,357 -2.1% | $188,300 +0.5% |
| 2003 | $1,386 +697.5% | $187,300 +23.2% |
| 2002 | $174 | $152,000 |
| 2001 | -- | $152,000 |
| 2000 | $1,603 | $152,000 |
Find assessor info on the county website





